An official website of the United States government

Phenylacetic Acid

PubChem CID
999
Structure
Phenylacetic Acid_small.png
Phenylacetic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • PHENYLACETIC ACID
  • 2-Phenylacetic acid
  • Benzeneacetic acid
  • 103-82-2
  • Phenylethanoic acid
Molecular Weight
136.15 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Phenylacetic acid is a monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. It has a role as a toxin, a human metabolite, an Escherichia coli metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite, an EC 6.4.1.1 (pyruvate carboxylase) inhibitor, an Aspergillus metabolite, a plant growth retardant, an allergen and an auxin. It is a monocarboxylic acid, a member of benzenes and a member of phenylacetic acids. It is functionally related to an acetic acid. It is a conjugate acid of a phenylacetate.
Phenylacetic acid is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a disagreeable odor. Because it is used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China.
Benzeneacetic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Phenylacetic Acid.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-phenylacetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

WLJVXDMOQOGPHL-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC=C(C=C1)CC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H8O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C8H8O2

C6H5CH2CO2H

2.3 Other Identifiers

2.3.1 CAS

103-82-2
51146-16-8

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DEA Code Number

8791 (DEA list I chemical)

2.3.8 DrugBank ID

2.3.9 DSSTox Substance ID

2.3.10 FEMA Number

2.3.11 HMDB ID

2.3.12 ICSC Number

2.3.13 JECFA Number

1007

2.3.14 KEGG ID

2.3.15 Metabolomics Workbench ID

2.3.16 NCI Thesaurus Code

2.3.17 Nikkaji Number

2.3.18 NSC Number

2.3.19 RXCUI

2.3.20 Wikidata

2.3.21 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • phenylacetate
  • phenylacetic acid
  • phenylacetic acid, ammonium salt
  • phenylacetic acid, calcium salt
  • phenylacetic acid, cesium salt
  • phenylacetic acid, lithium salt
  • phenylacetic acid, mercury salt
  • phenylacetic acid, potassium salt
  • phenylacetic acid, rubidium salt
  • phenylacetic acid, sodium salt
  • phenylacetic acid, sodium salt , carboxy-(11)C-labeled cpd
  • sodium phenylacetate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
136.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
136.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
136.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
114
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Shiny white solid with a floral odor; [Hawley] White crystalline solid; [MSDSonline]
Solid
WHITE-TO-YELLOW CRYSTALS OR FLAKES WITH PUNGENT ODOUR.
Glistening white crystalline solid with leafy crystals; sweet animal honey-like odour

3.2.2 Color / Form

Leaflets on distillation in-vacuo; plates, tablets from petroleum ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1352
Shiny, white plate crystals
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1061
White to yellow crystals or flakes
CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: https://www.cdc.gov/niosh/ipcs/default.html

3.2.3 Odor

Floral odor
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1061
Disagreeable odor of geranium
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V5: 3562
Has a sweet honey-like odor when diluted; the odor of the concentrated solution is suffocating and unpleasant.
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA19: 403

3.2.4 Taste

Sweet honey-like flavor at high levels; at low levels, it is a sweetner
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1657

3.2.5 Boiling Point

265.5 deg at 760 mm Hg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1352
Liquid, BP: 215 °C /Phenylacetic acid methyl ester/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1352
265.5 °C

3.2.6 Melting Point

76.7 °C
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-34
76.5 °C

3.2.7 Flash Point

132 °C (270 °F)
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
>212 °F (>100 °C) (closed cup)
National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-97
132 °C c.c.

3.2.8 Solubility

In water, 1.73X10+4 mg/L at 25 °C
Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 478
In water, 1.66X10+4 mg/L at 20 °C
Chio CT et al; Environ Sci Technol 11: 475-8 (1977)
Soluble in alcohol and ether; Soluble 4.422 moles/L in chloroform at 25 °C; 1.842 moles/L in carbon tetrachloride at 25 °C; 4.513 moles/L in acetylene tetrachloride at 25 °C; 3.29 moles/L in trichlorethylene at 25 °C; 1.558 moles/L in tetrachlorethylene at 25 °C; 3.252 moles/L in pentachloroethane at 25 °C
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V5: 3652
Very soluble in ethanol, ethyl ether, carbon disulfide; soluble in acetone; slightly soluble in chloroform; insoluble in ligroin
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 583
16.6 mg/mL
Solubility in water, g/100ml at 20 °C: 0.16
Slightly soluble in water; soluble in oils
Soluble at room temperature (in ethanol)

3.2.9 Density

1.091 at 77 °C/4 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1352
Density (at 77 °C): 1.09 g/cm³

3.2.10 Vapor Pressure

0.0038 [mmHg]
3.8X10-3 mm Hg at 25 °C (extrapolated)
Perry RH, Green D; Perry's Chemical Engineer's Handbook 6th ed New York, NY: McGraw-Hill, Inc p. 3-59 (1984)
Vapor pressure at 20 °C: negligible

3.2.11 LogP

log Kow = 1.41
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 41
1.41
HANSCH,C ET AL. (1995)

3.2.12 Stability / Shelf Life

Stable under recommended storage conditions.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html

3.2.13 Autoignition Temperature

543 °C

3.2.14 Decomposition

Hazardous decomposition products formed under fire conditions: Carbon oxides
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
When heated to decomposition it emits acrid smoke and irritating fumes.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895

3.2.15 Heat of Combustion

-3896.7 to -3910 kJ/mol
NIST; NIST Chemistry WebBook. Phenylacetic Acid (103-82-2). NIST Standard Reference Database No. 69, Feb 2015 Release. Washington, DC: US Sec Commerce. Available from, as of June 9, 2017: https://webbook.nist.gov

3.2.16 Heat of Vaporization

79.1 kJ/mol
NIST; NIST Chemistry WebBook. Phenylacetic Acid (103-82-2). NIST Standard Reference Database No. 69, Feb 2015 Release. Washington, DC: US Sec Commerce. Available from, as of June 9, 2017: https://webbook.nist.gov

3.2.17 pH

Aqueous solutions of phenyl acetic acid are weakly acidic.
CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: https://www.cdc.gov/niosh/ipcs/default.html

3.2.18 Odor Threshold

Malodorous substance. Off site odor is the primary environmental concern. The odor threshold is undoubtedly very low but is not quantified.
European Chemicals Bureau; IUCLID Dataset, Phenylacetic acid (103-82-2) (2000 CD-ROM edition).

3.2.19 Dissociation Constants

pKa = 4.31
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 5-100

3.2.20 Relative Evaporation Rate

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C
CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: https://www.cdc.gov/niosh/ipcs/default.html

3.2.21 Kovats Retention Index

Standard non-polar
1251 , 1240 , 1269 , 1252 , 1233 , 1230 , 1236 , 1212 , 1236 , 1236 , 1236.8 , 216.16
Semi-standard non-polar
1246.2 , 1265.9 , 1254 , 1276 , 1262 , 1248 , 1262 , 1263 , 1255 , 1265 , 1246 , 1248 , 1256 , 1265 , 1274 , 1267 , 1263 , 1265 , 1265 , 1263 , 1262 , 1269 , 1269 , 1269 , 1268 , 1270 , 1262 , 1262 , 1252 , 1262 , 1262 , 1276 , 1279 , 1251 , 1257 , 1257 , 1257 , 1262 , 1249 , 1249 , 1249 , 1249 , 1262 , 1264 , 1262
Standard polar
2561 , 2565 , 2585 , 2540 , 2554 , 2543 , 2569 , 2582 , 2581 , 2556 , 2561 , 2569 , 2578 , 2581 , 2589 , 2590 , 2548 , 2574 , 2557 , 2519 , 2540 , 2570 , 2570 , 2578 , 2555 , 2569 , 2530 , 2568 , 2570 , 2569 , 2573 , 2595 , 2550 , 2550 , 2521 , 2568 , 2528 , 2545 , 2560 , 2553 , 2560 , 2574 , 2551 , 2519 , 2564 , 2566 , 2551 , 2577 , 2539 , 2550 , 2550 , 2578 , 2553 , 2553 , 2548 , 2592 , 2601 , 2601 , 2551 , 2585 , 2585 , 2575 , 2597 , 2548 , 2548 , 2585 , 2571 , 2565 , 2571 , 2569 , 2546 , 2534 , 2534 , 2550 , 2568 , 2568 , 2568 , 2538 , 2610 , 2555

3.2.22 Other Experimental Properties

Aqueous solution saturated at 25 °C is 0.131N
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1352
Enthalpy of sublimation = 98.6 kJ/mol (305-321 deg K); Enthalpy of fusion = 349.2-350.8 kJ/mol
NIST; NIST Chemistry WebBook. Phenylacetic Acid (103-82-2). NIST Standard Reference Database No. 69, Feb 2015 Release. Washington, DC: US Sec Commerce. Available from, as of June 9, 2017: https://webbook.nist.gov
Liquid. Pleasant odor. Density: 1.033 at 20 °C/4 °C. BP: 226 °C at 760 mm Hg, 135 °C at 32 mm Hg, 121 °C at 20 mm Hg. Index of refraction: 1.49921 at 18.5 °C/D /Phenylacetic acid ethyl ester/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1352

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Organic Acids

3.4.1 Drugs

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
S58 | PSYCHOCANNAB | Synthetic Cannabinoids and Psychoactive Compounds | DOI:10.5281/zenodo.3247723
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.4.2 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Food
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

3.4.3 Fragrances

Fragrance Ingredient (Phenylacetic acid) -> IFRA transparency List

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
MAX ABSORPTION (ALCOHOL): 247.5, 258.5 & 267.5 NM (SHOULDER) (LOG E= 2.05, 2.26 & 1.85); SADTLER REFERENCE NUMBER: 1655 (IR, PRISM); 474 (UV); 117 (NMR)
1D NMR Spectra
1H NMR: 117 (Sadtler Research Laboratories spectral collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
View All
Spectra ID
Instrument Type
Varian
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
7.29:37.69, 7.38:11.10, 7.30:8.61, 7.31:8.82, 7.36:21.66, 7.38:4.80, 7.36:5.54, 7.37:23.40, 3.53:100.00, 7.28:29.20
Thumbnail
Thumbnail
2 of 4
View All
Spectra ID
Instrument Type
Bruker
Solvent
D2O
pH
7.4
Shifts [ppm]:Intensity
7.37:6.61, 7.30:4.50, 7.39:2.66, 7.28:6.62, 3.52:20.69, 7.35:7.35, 7.29:10.46
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 6
View All
Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
47.12:12.83, -0.00:1.14, 131.30:19.00, 140.02:1.70, 183.58:1.60, 131.82:18.18, 129.07:11.67
Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Frequency
400 MHz
Solvent
H2O
Shifts [ppm]
129.07, 140.02, 183.58, 131.82, 131.30, 47.12
Thumbnail
Thumbnail

4.1.3 17O NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
3.53:47.17:1.00, 7.30:129.15:0.35, 7.29:131.85:0.80, 7.37:131.51:0.50
Thumbnail
Thumbnail

4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 13
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

91.0 99.99

136.0 30.07

92.0 20.12

65.0 15.59

39.0 11.11

Thumbnail
Thumbnail
Notes
instrument=HITACHI M-80B
2 of 13
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

91.0 1

164.0 0.58

193.0 0.40

89.0 0.39

90.0 0.38

Thumbnail
Thumbnail

4.3.2 MS-MS

1 of 9
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

91.04054 100

119.03525 43.10

137.04553 8.90

95.03539 3.30

81.05661 2.60

Thumbnail
Thumbnail
2 of 9
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

65.02634 100

77.02516 41.30

66.03442 28.20

51.01075 25.20

63.01134 19.20

Thumbnail
Thumbnail

4.3.3 LC-MS

1 of 4
View All
Authors
Evans A M, Mitchell M, DeHaven C D, Barrett T, Milgram E, Metabolon Inc.
Instrument
LTQ XL, Thermo Finnigan
Instrument Type
LC-ESI-IT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
135.1
Precursor Adduct
[M-H]-
Top 5 Peaks

91.1 999

135.2 3

91.9 2

Thumbnail
Thumbnail
License
CC BY-NC-ND
2 of 4
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
135.1
Instrument
LTQ XL, Thermo Finnigan
Instrument Type
LC-ESI-IT
Ionization
ESI
Ionization Mode
negative
Collision Energy
40
Top 5 Peaks

91.1 100

135.2 0.30

91.9 0.20

Thumbnail
Thumbnail
License
CC BY-NC-ND

4.3.4 Other MS

1 of 5
View All
Other MS
MASS: 21060 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
2 of 5
View All
Authors
SODA AROMATIC CO., LTD.
Instrument
HITACHI M-80B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

91 999

136 301

92 201

65 156

39 111

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.4 UV Spectra

UV: 474 (Sadtler Research Laboratories spectral collection)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 583

4.5 IR Spectra

IR Spectra
IR: 320 (Coblentz Society spectral collection)

4.5.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: MELT
Source of Sample
Fritzsche Brothers, Inc., New York, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
KBr WAFER
Source of Sample
Eastman Kodak Company, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
116138
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
P16621
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
P16621
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.6 Raman Spectra

1 of 3
View All
Raman Spectra
Raman: 806 (Sadtler Research Laboratories spectral collection)
2 of 3
View All
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
116138
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle.

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.3 Biomarker Information

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FEMA Flavor Profile

Caramel, Floral, Flower, Honey

8.3 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
2878
GRAS Number
3, 25
JECFA Flavor Number
1007

8.4 Associated Foods

8.5 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

1 of 3
Chemical Name
alpha-TOLUIC ACID
Evaluation Year
2002
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
2 of 3
Chemical Name
PHENYLACETIC ACID
Evaluation Year
2002
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
3 of 3
Chemical Name
BENZYLCARBOXYLIC ACID
Evaluation Year
2002
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic
Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

9.2 FDA Pharmacological Classification

FDA UNII
ER5I1W795A
Active Moiety
PHENYLACETIC ACID
Pharmacological Classes
Mechanisms of Action [MoA] - Ammonium Ion Binding Activity
Pharmacological Classes
Established Pharmacologic Class [EPC] - Nitrogen Binding Agent
FDA Pharmacology Summary
Phenylacetic acid is a Nitrogen Binding Agent. The mechanism of action of phenylacetic acid is as an Ammonium Ion Binding Activity.

9.3 Absorption, Distribution and Excretion

Volume of Distribution
19.2 ± 3.3 L.
... Although exhaled volatile organic compound (VOC) patterns change in obstructive sleep apnea (OSA) patients, individual VOC profiles are not fully determined. The primary outcome was VOC characterizations; secondary outcomes included their relationships with sleep and clinical parameters in OSA patients. We prospectively examined 32 OSA patients with an apnea-hypopnea index (AHI) >/= 15 by full polysomnography, and 33 age- and sex-matched controls without obvious OSA symptoms. Nine severe OSA patients were examined before and after continuous positive airway pressure (CPAP) treatment. By applying a method which eliminates environmental VOC influences, exhaled VOCs were identified by gas chromatography (GC)-mass spectrometry, and their concentrations were determined by GC. Exhaled aromatic hydrocarbon concentrations (toluene, ethylbenzene, p-xylene, and phenylacetic acid) in the severe OSA groups (AHI >/= 30) and exhaled saturated hydrocarbon concentrations (hexane, heptane, octane, nonane, and decane) in the most severe OSA group (AHI >/= 60) were higher than those in the control group. Exhaled isoprene concentrations were increased in all OSA groups (AHI >/= 15); acetone concentration was increased in the most severe OSA group. Ethylbenzene, p-xylene, phenylacetic acid, and nonane concentrations were increased according to OSA severity, and correlated with AHI, arousal index, and duration of percutaneous oxygen saturation (SpO2)
Aoki T et al; Toxicol Sci 156 (2): 362-374 (2017)
The dose limiting toxicity and pharmacokinetics of phenylacetic acid (phenylacetate) were studied in 17 patients with advanced solid tumors who received single iv bolus doses followed by a 14 day continuous iv infusion of the drug in a phase I trial. Phenylacetic acid displayed nonlinear pharmacokinetics with evidence for induction of drug clearance. Ninety-nine percent of phenylacetic acid elimination was accounted for by conversion to phenylacetylglutamine which was excreted in the urine...
Thibault A et al; Cancer Res 54: 1690-94 (1994)
Phenylacetic acid... /is/ rapidly absorbed from human buccal tissues or membranes.
National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 754
Man excreted 93%...as glutamine conjugate... . New world monkeys excreted conjugates of glutamine, glycine and taurine, while old world species excreted large proportion of free acid and only glutamine and taurine conjugates. Non-primate species excreted only glycine connjugate.
The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 569
Distribution of conjugates in 24 hr urine samples showed marked species variation.
The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 569

9.4 Metabolism / Metabolites

Phenylacetate esterases found in the human liver cytosol. Human plasma esterase also hydrolyze phenylacetate. Phenylacetate hydrolysis involved arylesterase in plasma, both arylesterase and carboxylesterase in liver microsomes and carboxylesterase in liver cytosol. Plasma hydrolysis is less important and overall esterase activity is lower in humans than in the rat.
Although there has been increasing interest in the use of high protein diets, little is known about dietary protein related changes in the mammalian metabolome. We investigated the influence of protein intake on selected tryptophan and phenolic compounds, derived from both endogenous and colonic microbial metabolism. Furthermore, potential inter-species metabolic differences were studied. For this purpose, 29 healthy subjects were allocated to a high (n = 14) or low protein diet (n = 15) for 2 weeks. In addition, 20 wild-type FVB mice were randomized to a high protein or control diet for 21 days. Plasma and urine samples were analyzed with liquid chromatography-mass spectrometry for measurement of tryptophan and phenolic metabolites. In human subjects, we observed significant changes in plasma level and urinary excretion of indoxyl sulfate (P 0.004 and P 0.001), and in urinary excretion of indoxyl glucuronide (P 0.01), kynurenic acid (P 0.006) and quinolinic acid (P 0.02). In mice, significant differences were noted in plasma tryptophan (P 0.03), indole-3-acetic acid (P 0.02), p-cresyl glucuronide (P 0.03), phenyl sulfate (P 0.004) and phenylacetic acid (P 0.01). Thus, dietary protein intake affects plasma levels and generation of various mammalian metabolites, suggesting an influence on both endogenous and colonic microbial metabolism. Metabolite changes are dissimilar between human subjects and mice, pointing to inter-species metabolic differences with respect to protein intake.
Poesen R et al; PLoS One 10 (10): e0140820 (2015)
Burkholderia heleia PAK1-2 is a potent biocontrol agent isolated from rice rhizosphere, as it prevents bacterial rice seedling blight disease caused by Burkholderia plantarii. Here, we isolated a non-antibacterial metabolite from the culture fluid of B. heleia PAK1-2 that was able to suppress B. plantarii virulence and subsequently identified as indole-3-acetic acid (IAA). IAA suppressed the production of tropolone in B. plantarii in a dose-dependent manner without any antibacterial and quorum quenching activity, suggesting that IAA inhibited steps of tropolone biosynthesis. Consistent with this, supplementing cultures of B. plantarii with either L-[ring-(2)H5]phenylalanine or [ring-(2)H2~5]phenylacetic acid revealed that phenylacetic acid (PAA), which is the dominant metabolite during the early growth stage, is a direct precursor of tropolone. Exposure of B. plantarii to IAA suppressed production of both PAA and tropolone. These data particularly showed that IAA produced by B. heleia PAK1-2 disrupts tropolone production during bioconversion of PAA to tropolone via the ring-rearrangement on the phenyl group of the precursor to attenuate the virulence of B. plantarii. B. heleia PAK1-2 is thus likely a microbial community coordinating bacterium in rhizosphere ecosystems, which never eliminates phytopathogens but only represses production of phytotoxins or bacteriocidal substances.
Wang M et al; Sci Rep 6: 22596 doi: 10.1038/srep22596 (2016)
2-phenylethylamine is an endogenous constituent of the human brain and is implicated in cerebral transmission. This bioactive amine is also present in certain foodstuffs such as chocolate, cheese and wine and may cause undesirable side effects in susceptible individuals. Metabolism of 2-phenylethylamine to phenylacetaldehyde is catalyzed by monoamine oxidase B but the oxidation to its acid is usually ascribed to aldehyde dehydrogenase and the contribution of aldehyde oxidase and xanthine oxidase, if any, is ignored. The objective of this study was to elucidate the role of the molybdenum hydroxylases, aldehyde oxidase and xanthine oxidase, in the metabolism of phenylacetaldehyde derived from its parent biogenic amine. Treatments of 2-phenylethylamine with monoamine oxidase were carried out for the production of phenylacetaldehyde, as well as treatments of synthetic or enzymatic-generated phenylacetaldehyde with aldehyde oxidase, xanthine oxidase and aldehyde dehydrogenase. The results indicated that phenylacetaldehyde is metabolized mainly to phenylacetic acid with lower concentrations of 2-phenylethanol by all three oxidizing enzymes. Aldehyde dehydrogenase was the predominant enzyme involved in phenylacetaldehyde oxidation and thus it has a major role in 2-phenylethylamine metabolism with aldehyde oxidase playing a less prominent role. Xanthine oxidase does not contribute to the oxidation of phenylacetaldehyde due to low amounts being present in guinea pig. Thus aldehyde dehydrogenase is not the only enzyme oxidizing xenobiotic and endobiotic aldehydes and the role of aldehyde oxidase in such reactions should not be ignored.
Panoutsopoulos GI et al; Basic Clin Pharmacol Toxicol 95 (6): 273-9 (2004)
Phenylacetic acid, the major metabolite of phenylethylamine, has been identified and quantitated in rat brain regions by capillary column high-resolution gas chromatography mass spectrometry. Its distribution is heterogeneous and correlates with that of phenylethylamine. The values obtained were (ng/g +/- SEM): whole brain, 31.2 +/- 2.7; caudate nucleus, 64.6 +/- 6.5; hypothalamus, 60.1 +/- 7.4; cerebellum, 31.3 +/- 2.9; brainstem, 33.1 +/- 3.3, and the "rest," 27.6 +/- 3.0.
Durden DA, Boulton AA; J Neurochem 38 (6): 1532-6 (1982)
For more Metabolism/Metabolites (Complete) data for Phenylacetic acid (9 total), please visit the HSDB record page.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

9.5 Human Metabolite Information

9.5.1 Metabolite Pathways

Phenylalanine metabolism

9.6 Biochemical Reactions

9.7 Transformations

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Naturally occurs in some essential oils, honeys, and teas; Used to make penicillin G, penicillin derivatives, and its esters; Also used as a fungicide, flavoring agent, lab reagent, and starting material for synthetic perfumes; [HSDB] A metabolite of phenylalanine and may cause some of the neurotoxic effects of maternal phenylketonuria; [REPROTOX]
REPROTOX - Scialli AR, Lione A, Boyle Padgett GK. Reproductive Effects of Chemical, Physical, and Biological Agents. Baltimore: The Johns Hopkins University Press, 1995.
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
This is a DEA List 1 chemical substance.
21 CFR 1310.02(a) (8) (USDEA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 5, 2017: https://www.ecfr.gov
List I chemical means a chemical specifically designated by the Administrator in section 1310.02(a) of this chapter that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance.
21 CFR 1300.02 (USDEA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2017: https://www.ecfr.gov
Used in production of drugs of abuse.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895
Used in perfume, precursor in manufacture of penicillin G, fungicide, flavoring, laboratory reagent.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1061
For more Uses (Complete) data for Phenylacetic acid (7 total), please visit the HSDB record page.
Naturally produced by the body (endogenous).

10.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index

10.1.2 DEA Listed Chemicals

Name
Phenylacetic acid, its esters, and its salts
List I Chemical
A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance.

10.2 Methods of Manufacturing

Made by refluxing benzyl cyanide with diluted sulfuric acid or hydrochloric acid.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1351
From benzyl cyanide refluxed with dilute hydrochloric acid.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1061
In the presence of suitable catalysts, benzyl chloride reacts with carbon monoxide to produce phenylacetic acid.
Seper KW; Benzyl Chloride, Benzal Chloride, and Benzotrichloride. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2017). John Wiley & Sons, Inc. Online Posting Date: April 16, 2001
By the treatment of benzyl cyanide with dilute sulfuric acid and other processes.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1657
A catalytic process for the synthesis of phenylacetic acid from benzyl chloride uses Ni(CO)4 as catalyst. The product is formed with a selectivity of 95% at 60 bar and 80 °C.
Bertleff W et al; Carbonylation. Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2016). NY, NY: John Wiley & Sons. Online Posting Date: July 15, 2007

10.3 Formulations / Preparations

Grades: technical; FCC.
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1061

10.4 U.S. Production

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI
(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI
(1985) Not reported
USITC. SYN ORG CHEM-U.S. PROD/SALES 1985 p.125
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
>10 thousand - 500 thousand
Year
1990
Production Range (pounds)
No Reports
Year
1994
Production Range (pounds)
>10 thousand - 500 thousand
Year
1998
Production Range (pounds)
No Reports
Year
2002
Production Range (pounds)
No Reports
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Benzeneacetic acid (103-82-2). Available from, as of May 1, 2007: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
For more U.S. Production (Complete) data for Phenylacetic acid (6 total), please visit the HSDB record page.

10.5 U.S. Imports

(1977) 3.24X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI
(1979) 7.49X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI

10.6 General Manufacturing Information

EPA TSCA Commercial Activity Status

11 Identification

11.1 Analytic Laboratory Methods

Spectrophotometric determination of phenylacetic acid at 390 nm.
Fisel S et al; Rev Chim (Bucharest) 29 (5): 476 (1978)

11.2 Clinical Laboratory Methods

Endoplasmic reticulum (ER) stress is associated with various human diseases. Phenylbutyric acid (PBA) is a well-known chemical chaperone that regulates ER stress. The main objective of this study was to develop a simple, rapid, and sensitive method for the simultaneous determination of phenylbutyric acid and its metabolite, phenylacetic acid (PAA). A LC-MS/MS analysis using negative electrospray ionization was used. Samples were analyzed by multiple reaction monitoring (MRM) in 15 min of total run time, using d11-PBA and d7-PAA as internal standards. The limit of quantification was 1 ug/g for tissue and 0.8 ug/mL for plasma. Recoveries for plasma and tissues were higher than 81% for both PBA and PAA. The inter-day and intra-day accuracy and precision were within +/-15%. We then further successfully validated this method by applying it to determine the tissue distribution of PBA and its metabolite PAA after i.p. injection of PBA at a dose of 500 mg/kg in mice. The maximum concentrations of PBA and PAA in plasma and tissues were seen at 15 min and 45 min, respectively. The PBA plasma concentration was 15-fold higher than the concentration in the kidney, whereas the PAA plasma concentration was 6-fold higher than the concentration in the liver. The area under the curve decreased in the order of plasma > kidney > liver > heart > muscle > lung for PBA and plasma > liver > kidney > heart > muscle > lung for PAA. The tissue to plasma ratio ranged from 0.007 to 0.063 for PBA and 0.016 to 0.109 for PAA. In summary, the LC-ESI-MS method developed in this study is simple, sensitive and reliable.
Marahatta A et al; J Chromatogr B Analyt Technol Biomed Life Sci 903: 118-25 (2012)
Phenyl acetic acid, a metabolite of 2-phenyl ethylamine, acts as a neuromodulator in the nigrostriatal dopaminergic pathway stimulating the release of dopamine. The evaluation of phenyl acetic acid concentration in the biological fluid reflects phenyl ethylamine levels thus allowing the assessment of the modulatory role of this endogenous substance. Changes in biological fluids levels of 2-phenylethylamine and/or in its metabolite have been reported in affective disorders, such as depression and schizophrenia. Recently, the occurrence of the "attention deficit hyperactivity syndrome" has been frequently reported in childhood population and involvement of dopaminergic dysfunction in this disease has been suspected. A fast, reliable and reproducible method for the determination of phenyl acetic acid in human blood, is therefore needed in order to have a screening tool for monitoring both healthy childhood population and suspected "attention deficit hyperactivity syndrome" patients. The gas chromatographic-mass spectrometric method here described makes use of a deuterated internal standard in order to overcome problems related to the lack of reproducibility often encountered when a derivatization step is performed.
Mangani G et al; Ann Chim 94 (9-10): 715-9 (2004)
NO prevents atherogenesis and inflammation in vessel walls by inhibition of cell proliferation and cytokine-induced endothelial expression of adhesion molecules and proinflammatory cytokines. Reduced NO production due to inhibition of either eNOS or iNOS may therefore reinforce atherosclerosis. Patients with end-stage renal failure show markedly increased mortality due to atherosclerosis. In the present study we tested the hypothesis that uremic toxins are responsible for reduced iNOS expression. LPS-induced iNOS expression in mononuclear leukocytes was studied using real-time PCR. The iNOS expression was blocked by addition of plasma from patients with end-stage renal failure, whereas plasma from healthy controls had no effect. Hemofiltrate obtained from patients with end-stage renal failure was fractionated by chromatographic methods. The chromatographic procedures revealed a homogenous fraction that inhibits iNOS expression. Using gas chromatography/mass spectrometry, this inhibitor was identified as phenylacetic acid. Authentic phenylacetic acid inhibited iNOS expression in a dose-dependent manner. In healthy control subjects, plasma concentrations were below the detection level, whereas patients with end-stage renal failure had a phenylacetic acid concentration of 3.49 +/- 0.33 mmol/L (n = 41). It is concluded that accumulation of phenylacetic acid in patients with end-stage renal failure inhibits iNOS expression. That mechanism may contribute to increased atherosclerosis and cardiovascular morbidity in patients with end-stage renal failure.
Jankowski J et al; J Clin Invest 112 (2): 256-64 (2003)
Conjugated and unconjugated phenylacetic acid and m- and p-hydroxyphenylacetic acid have been determined in the plasma of normal, healthy subjects after fasting, consumption of a meal and ingestion of deuterium labelled amine precursors, by high-resolution gas chromatography--high resolution mass spectrometry with selected ion monitoring of their trifluoroethyl-pentafluoropropionyl derivatives. We observed that all three conjugated acids are higher in fasting than in non-fasting subjects, and unconjugated phenylacetic acid was lower. Ingestion of deuterium-labelled amine precursors resulted in the appearance in the blood of the correspondingly labelled acids, a peak in the concentrations being reached about 1 hr after consumption. Conjugated and unconjugated acids as expected increased following the consumption of a meal. Unconjugated phenylacetic acid was significantly higher in females than in males. Most values tended to increase with age, with male unconjugated and conjugated m-hydroxyphenylacetic acid and female conjugated phenylacetic and m-hydroxyphenylacetic acids increasing significantly.
Davis BA et al; J Chromatogr 230 (2): 219-30 (1982)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 2
View All
Note
Pictograms displayed are for > 99.9% (1843 of 1844) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1844) of reports.
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H318 (14.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (85.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes

P264+P265, P280, P305+P351+P338, P305+P354+P338, P317, and P337+P317

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 1844 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 1844 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 15 notifications provided by 1843 of 1844 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

12.1.2 Hazard Classes and Categories

Eye Dam. 1 (14.6%)

Eye Irrit. 2 (85.3%)

12.1.3 NFPA Hazard Classification

NFPA 704 Diamond
2-1-0
NFPA Health Rating
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
NFPA Fire Rating
1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

12.1.4 Fire Hazards

Combustible.

12.1.5 Hazards Summary

An eye and mild skin irritant; [ICSC] A reproductive effector and moderate eye irritant; [RTECS] Emergency medical treatment: irritants; [HSDB] Safe when used as a flavoring agent in food; [WHO JEFCA] An irritant; [MSDSonline]

12.1.6 Fire Potential

Combustible liquid
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895

12.1.7 Skin, Eye, and Respiratory Irritations

Inhalation: cough, sore throat. Skin: redness. Eyes: redness, pain
International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Phenylacetic acid (June 2006). Available from, as of June 27, 2017: https://www.inchem.org/pages/icsc.html

12.2 Safety and Hazard Properties

12.2.1 Critical Temperature & Pressure

Critical temperature: 766 deg K, critical pressure: 3.9 MPa
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 6-69

12.3 First Aid Measures

Inhalation First Aid
Fresh air, rest.
Skin First Aid
Rinse skin with plenty of water or shower.
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth. Give one or two glasses of water to drink.

12.4 Fire Fighting

Use water spray, powder, foam, carbon dioxide.

12.4.1 Fire Fighting Procedures

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Powder, water spray, foam, carbon dioxide.
International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Phenylacetic acid (June 2006). Available from, as of June 27, 2017: https://www.inchem.org/pages/icsc.html

12.5 Accidental Release Measures

12.5.1 Spillage Disposal

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers.

12.5.2 Cleanup Methods

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures. Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Do NOT let this chemical enter the environment. Sweep spilled substance into containers.
International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Phenylacetic acid (June 2006). Available from, as of June 27, 2017: https://www.inchem.org/pages/icsc.html

12.5.3 Disposal Methods

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html

12.5.4 Preventive Measures

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures. Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
For more Preventive Measures (Complete) data for Phenylacetic acid (6 total), please visit the HSDB record page.

12.6 Handling and Storage

12.6.1 Safe Storage

Separated from strong oxidants, strong bases and strong reducing agents. Store in an area without drain or sewer access.

12.6.2 Storage Conditions

Keep container tightly closed in a dry and well-ventilated place.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
/Store/ separated from strong oxidants, strong bases and strong reducing agents. Store in an area without drain or sewer access.
International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Phenylacetic acid (June 2006). Available from, as of June 27, 2007: https://www.inchem.org/pages/icsc.html

12.7 Exposure Control and Personal Protection

12.7.1 Inhalation Risk

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

12.7.2 Effects of Short Term Exposure

The substance is irritating to the eyes. The substance is mildly irritating to the skin.

12.7.3 Personal Protective Equipment (PPE)

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Skin protection: Handle with gloves.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html
Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html

12.7.4 Preventions

Fire Prevention
NO open flames.
Inhalation Prevention
Use local exhaust or breathing protection.
Skin Prevention
Protective gloves.
Eye Prevention
Wear safety goggles.
Ingestion Prevention
Do not eat, drink, or smoke during work.

12.8 Stability and Reactivity

12.8.1 Hazardous Reactivities and Incompatibilities

Incompatible materials: Strong oxidizing agents, strong bases, strong reducing agents.
Sigma-Aldrich; Safety Data Sheet for Phenylacetic acid. Product Number: P16621, Version 4.6 (Revision Date 04/12/2017). Available from, as of June 26, 2017: https://www.sigmaaldrich.com/safety-center.html

12.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
DEA Listed Chemicals
List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance.
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Phenylacetic acid: Does not have an individual approval but may be used under an appropriate group standard

12.9.1 FDA Requirements

Phenylacetic acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
21 CFR 172.515 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 5, 2017: https://www.ecfr.gov
The following chemical has been specifically designated by the Administrator of the Drug Enforcement Administration as subject to the provisions of this part and parts 1309 and 1313 of this chapter. Phenylacetic acid, its esters and its salts are List 1 chemicals; DEA Code: 8791.
21 CFR 1310.02(a) (8) (USDEA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of July 5, 2017: https://www.ecfr.gov

12.10 Other Safety Information

Chemical Assessment

IMAP assessments - Benzeneacetic acid: Environment tier I assessment

IMAP assessments - Benzeneacetic acid: Human health tier I assessment

13 Toxicity

13.1 Toxicological Information

13.1.1 Toxicity Summary

IDENTIFICATION AND USE: Phenylacetic acid forms white to yellow crystals or flakes. It is used in perfume, as a precursor in manufacture of penicillin G, fungicide, flavoring, and laboratory reagent. It is also used in production of drugs of abuse. HUMAN STUDIES: Inhalation exposure leads to cough, sore throat. Skin exposure leads to redness. Eyes exposure leads to redness, pain. ANIMAL STUDIES: Acute oral toxicity in rats is low. In study of acute effects in mice, ip injection of 300 mg/kg was toxic. Phenylacetic acid did not promote tumor formation when given to rabbits iv and sc for 40 days. In vitro phenylacetic acid induced dose-related embryotoxicity above 0.3 mg/mL. In teratogenic study with rats, administration of 3.2 mg/kg phenylacetic acid on 12th day of embryogenesis affected body weight, retarded skeletal ossification, and caused embryos to be resorbed at twice rate of controls. Phenylacetic acid inhibits activity of coenzyme A.
Uremic toxins such as phenylacetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869)
A7868: Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. PMID:25041433
A7869: Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. PMID:22419041

13.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

13.1.3 Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

13.1.4 Exposure Routes

Endogenous, Ingestion, Dermal (contact)

13.1.5 Symptoms

Inhalation Exposure
Cough. Sore throat.
Skin Exposure
Redness.
Eye Exposure
Redness. Pain.
As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

13.1.6 Acute Effects

13.1.7 Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

13.1.8 Antidote and Emergency Treatment

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 176
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize, because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 176-7
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary. Start IV administration of D5W TKO. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 177

13.1.9 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Inhalation: cough, sore throat. Skin: redness. Eyes: redness, pain
International Program on Chemical Safety/Commission of the European Communities; International Chemical Safety Card on Phenylacetic acid (June 2006). Available from, as of June 27, 2017: https://www.inchem.org/pages/icsc.html
/ALTERNATIVE and IN VITRO TESTS/ Tumor necrosis factor (TNF)-alpha and oxidative stress are considered to play crucial roles in atherosclerosis and vascular calcification. "Uremic toxins" detected in patients with chronic kidney disease (CKD) could cause impaired signal transduction and dysfunction in many organs. Since phenylacetic acid (PAA), identified as one of the uremic toxins, has an inhibiting property of monocytes as well as osteoblastic cells, we examined the effects of PAA on TNF-alpha secretion and oxidative stress in vascular endothelial cells. In human aortic endothelial cells, TNF-alpha secretion was assessed after treatment with PAA using an ELISA kit and following the manufacturer's instructions. For determination of reactive oxygen species (ROS), 8-hydroxydeoxyguanosine (8-OHdG) in the culture medium was measured in the presence or absence of PAA. Treatment with PAA in aortic endothelial cells for 24 hr significantly stimulated TNF-alpha secretion in a dose-dependent manner ranging between 0.5 and 5 mM. On the other hand, the 8-OHdG level in the culture medium was significantly increased in the cells incubated with 1 mM PAA for 12 hr. To determine if PAA-induced TNF-alpha secretion is mediated by ROS production, the effect of free radical scavenger 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPOL) was examined. It was found that PAA-induced TNF-alpha secretion was significantly inhibited by TEMPOL. Our findings indicate that PAA stimulates TNF-alpha secretion at least in part through ROS production in aortic endothelial cells. The plasma PAA level was reported to be approximately 3.5 mM in end-stage CKD patients, whereas it was <5 uM in healthy subjects; thus, PAA could be involved in the pathological changes of the vasculature in CKD.
Morita M et al; Ther Apher Dial 15 (2): 147-50 (2011)
/OTHER TOXICITY INFORMATION/ ... In this study, inhibitors of Ca2+ ATPase were isolated from ultrafiltrate of patients with end-stage renal failure. They were identified as dimethylguanosine, phenylethylamine, and phenylacetic acid by chromatography and mass spectrometry. Ca2+ ATPase activity was measured spectrophotometrically as the difference in hydrolysis of ATP in the presence and absence of Ca2+ with different concentrations of ATP and the isolated substances. All of the identified compounds are sufficiently lipophilic to penetrate the blood-brain barrier and to accumulate in cerebral tissue. The inhibitory effects of these agents were additive. The apparent K(m) values for ATP and Ca2+ were not altered by these substances, suggesting a noncompetitive mechanism of inhibition. In plasma of healthy subjects, the substances were not detectable.
Jankowski J et al; J Am Soc Nephrol 9 (7): 1249-57 (1998)
/OTHER TOXICITY INFORMATION/ Phenylacetic acid (PAA) is the active moiety in sodium phenylbutyrate (NaPBA) and glycerol phenylbutyrate (GPB, HPN-100). Both are approved for treatment of urea cycle disorders (UCDs) - rare genetic disorders characterized by hyperammonemia. PAA is conjugated with glutamine in the liver to form phenylacetyleglutamine (PAGN), which is excreted in urine. PAA plasma levels >/= 500 ug/dL have been reported to be associated with reversible neurological adverse events (AEs) in cancer patients receiving PAA intravenously. Therefore, we have investigated the relationship between PAA levels and neurological AEs in patients treated with these PAA pro-drugs as well as approaches to identifying patients most likely to experience high PAA levels. The relationship between nervous system AEs, PAA levels and the ratio of plasma PAA to PAGN were examined in 4683 blood samples taken serially from: [1] healthy adults [2], UCD patients of >/= 2 months of age, and [3] patients with cirrhosis and hepatic encephalopathy (HE). The plasma ratio of PAA to PAGN was analyzed with respect to its utility in identifying patients at risk of high PAA values. Only 0.2% (11) of 4683 samples exceeded 500 ug/mL. There was no relationship between neurological AEs and PAA levels in UCD or HE patients, but transient AEs including headache and nausea that correlated with PAA levels were observed in healthy adults. Irrespective of population, a curvilinear relationship was observed between PAA levels and the plasma PAA:PAGN ratio, and a ratio>2.5 (both in ug/mL) in a random blood draw identified patients at risk for PAA levels>500 ug/mL. The presence of a relationship between PAA levels and reversible AEs in healthy adults but not in UCD or HE patients may reflect intrinsic differences among the populations and/or metabolic adaptation with continued dosing. The plasma PAA:PAGN ratio is a functional measure of the rate of PAA metabolism and represents a useful dosing biomarker.
Mokhtarani M et al; Mol Genet Metab 110 (4): 446-53 (2013)

13.1.10 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Acute oral toxicity in rats is low. Its acute effect on skin is slight irritation. /from table/
Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1839
/LABORATORY ANIMALS: Acute Exposure/ In study of acute effects in mice, ip injection of 300 mg/kg proved toxic; 11 of 15 experimental animals died. Time to death varied from 10 min to 10 days.
National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 754
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity: Initiation-Promotion/ /It is/ reported that phenylacetic acid did not promote tumor formation when... given to rabbits iv and sc for 40 days.
National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 754
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... the possible embryotoxicity of ...and phenylacetic acid /was studied/ in the postimplantation whole embryo culture system. Day 10 rat embryos (4 or 8 somites) were cultured in rat serum to which tested compounds were added. After 26 hr of culture, embryos were scored morphologically. ... and /phenylacetic acid/ induced dose-related embryotoxicity above 0.3 mg/mL. These results suggest a possible role for PKU-related phe-metabolites in the induction of congenital malformations.
Hamers AE et al; Reprod Toxicol 5 (3): 266 (1991)
For more Non-Human Toxicity Excerpts (Complete) data for Phenylacetic acid (11 total), please visit the HSDB record page.

13.1.11 Non-Human Toxicity Values

LD50 Rat oral 2250 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895
LD50 Mouse oral 2250 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895
LD50 Mouse sc 1500 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895
LD50 Mouse ip 2270 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 2895
For more Non-Human Toxicity Values (Complete) data for Phenylacetic acid (6 total), please visit the HSDB record page.

13.1.12 Ongoing Test Status

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of July 28, 2017: http://actor.epa.gov/dashboard/]

13.2 Ecological Information

13.2.1 Ecotoxicity Values

EC50; Species: Xenopus laevis (African clawed frog) embryo; Conditions: freshwater, renewal, pH 7.0-7.8; Concentration: 801900 ug/L for 96 hr (95% confidence interval: 761000-845000 ug/L); Effect: developmental changes (craniofacial defects, abnormal gut coiling) /> or = 98% purity/
Dawson DA et al; Teratog Carcinog Mutagen 16 (2): 109-24 (1996) Available from, as of July 25, 2017
LC50; Species: Xenopus laevis (African clawed frog) embryo; Conditions: freshwater, renewal, pH 7.0-7.8; Concentration: 1273700 ug/L for 96 hr (95% confidence interval: 1252000-1296000 ug/L) /> or = 98% purity/
Dawson DA et al; Teratog Carcinog Mutagen 16 (2): 109-24 (1996) Available from, as of July 25, 2017
EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static, pH 8; Concentration: 11 mg/L for 24 hr; Effect: behavior, equilibrium
Bringmann G, Kuhn R; Zeitschrift fuer Wasser und Abwasser Forschung 15 (1): 1-6 (1982) Available from, as of July 25, 2017

13.2.2 Ecotoxicity Excerpts

/OTHER TOXICITY INFORMATION/ In Pseudomonas aeruginosa, quorum sensing (QS) autoinducer known as acyl homoserine lactone (AHL) acts as a key regulator in the expression of pathogenic characters. In this work, the efficiency of phenylacetic acid (PAA) in reducing the production of AHL-dependent factors in P. aeruginosa PAO1 was studied. PAA at a concentration of 200 ug/mL displayed significant reduction in QS-dependent pyocyanin, exopolysaccharide, and protease and elastase production in PAO1. In swimming inhibition assay, PAA-treated PAO1 cells exhibited poor motility in swimming agar plate. In in vivo analysis, PAO1-preinfected Caenorhabditis elegans showed enhanced survival when treated with PAA. PAA at the QS inhibitory concentration showed no growth inhibitory activity on PAO1. Results of the present study revealed the potential of PAA as antipathogenic compound to prevent QS-dependent pathogenicity of P. aeruginosa.
Musthafa KS et al; Curr Microbiol 65 (5): 475-80 (2012)

13.2.3 ICSC Environmental Data

The substance is harmful to aquatic organisms.

13.2.4 Environmental Fate / Exposure Summary

Phenylacetic acid's production and use as a starting material in the manufacture of synthetic perfumes and cosmetics, in the manufacture of penicillin G, and as a perfume, flavoring agent, and lab reagent may result in its release to the environment through various waste streams. Phenylacetic acid is on the US DEA (Drug Enforcement Administration) list of surveillance chemicals used in clandestine drug manufacture. Phenylacetic acid occurs in tobacco smoke and emissions from wood combustion. It occurs in various essential oils, tobacco, orange flowers, cocoa, guava, papaya, raspberry, strawberry, tomato, pepper, passion fruit, starfruit, mango, and mushroom. If released to air, a vapor pressure of 3.8X10-3 mm Hg at 25 °C indicates phenylacetic acid will exist solely as a vapor in the atmosphere. Vapor-phase phenylacetic acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 3.6 days. Phenylacetic acid does not absorb UV light at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, phenylacetic acid is expected to have very high mobility based upon Koc values of 26, 28 and 31. The pKa of phenylacetic acid is 4.31, indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Utilizing an unadapted soil suspension, biodegradation of 90% in 3 days was reported, indicating that biodegradation may be an important environmental fate process in soil and water. If released into water, phenylacetic acid is not expected to adsorb to suspended solids and sediment based upon the Koc values. Under anaerobic conditions, phenylacetic acid biodegraded >90% in 60 days using municipal sewage waste water. The pKa indicates that phenylacetic acid will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to phenylacetic acid may occur through inhalation and dermal contact with this compound at workplaces where phenylacetic acid is produced or used. Monitoring data indicate that the general population may be exposed to phenylacetic acid via inhalation of tobacco and wood smoke, ingestion of food and drinking water, and dermal contact with consumer products containing phenylacetic acid. (SRC)

13.2.5 Natural Pollution Sources

Phenylacetic acid occurs in Japanese peppermint oil, neroli oil, and in trace amounts in rose oils(1). Phenylacetic acid was found as a volatile component in yellow box honey at 0.2 mg/kg and blue gum honey at 0.1 mg/kg(2). Phenylacetic acid was identified as a flavor compound in pine sprout tea and pine needle tea(3). It is reportedly found in various essential oils, tobacco, orange flowers, cocoa, guava, papaya, raspberry, strawberry, tomato, pepper, passion fruit, starfruit, mango, and mushroom(4).
(1) Panten J; Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds. Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2017). New York, NY: John Wiley & Sons. Online Posting Date: 28 Jan 2016.
(2) Darcy BR et al; J Agric Food Chem 45: 1834-43 (1997)
(3) Kim KY, Chung HJ; J Agric Food Chem 48: 1269-72 (1997)
(4) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p. 1657 (2010)

13.2.6 Artificial Pollution Sources

Phenylacetic acid's production and use as a starting material in the manufacture of synthetic perfumes, condensation products with aldehydes(1) and cosmetics(2), in the manufacture of penicillin G, and as a perfume, flavoring agent, and lab reagent(3) may result in its release to the environment through various waste streams(SRC). Phenylacetic acid is on the US DEA (Drug Enforcement Administration) list of surveillance chemicals used in clandestine drug manufacture(4). Phenylacetic acid occurs in tobacco smoke(5) and emissions from wood combustion(6).
(1) O'Neil MJ, ed; The Merck Index. 15 th ed., Cambridge, UK: Royal Society of Chemistry, p. 1352 (2013)
(2) Le Berre C et al; Acetic Acid. Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2017). New York, NY: John Wiley & Sons. Online Posting Date: 26 Mar 2014.
(3) Larranaga MD et al; Hawley's Condensed Chemical Dictionary 16th ed., Hoboken, NJ: John Wiley & Sons, Inc., p 1061 (2016)
(4) DEA; Title 21 Code of Federal Regulations. Part 1310.02, Substances Covered. US Dept of Justice, Drug Enforcement Administration. Available from, as of June 14, 2017: https://www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm
(5) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke 2nd, ed., Baco Raton, FL: CRC Press p. 1236, 2078 (2013)
(6) Fine PM et al; Environ Sci Technol 36: 1442-1451 (2002)

13.2.7 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 31, 26, and 28 from Podzol soil, Alfisol soil, and lake sediment, respectively(2) indicate that phenylacetic acid is expected to have very high mobility in soil(SRC). The pKa of phenylacetic acid is 4.31(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Phenylacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 0.0038 mm Hg at 25 °C(5). Utilizing an unadapted soil suspension, biodegradation of 90% in 3 days was reported(6), indicating that biodegradation may be an important environmental fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) von Oepen B et al; Chemosphere 22: 285-304 (1991)
(3) Haynes WM, ed; CRC Handbook of Chemistry and Physics. 95th ed., Boca Raton, FL: CRC Press LLC, p. 5-100 (2014)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Perry RH, Green D; Perry's Chemical Engineer's Handbook 6th ed NY, NY: McGraw-Hill, Inc p. 3-59 (1984)
(6) Leidner H et al; Xenobiotica 10: 47-56 (1980)
AQUATIC FATE: Based on a classification scheme(1), Koc values of 31, 26 and 28, determined from Podzol soil, Alfisol soil, and lake sediment, respectively(2) indicate that phenylacetic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.31(3) indicates phenylacetic acid will exist almost entirely in the anion form at pH values of 5 to 9(4) and, therefore, volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3(SRC), from a log Kow of 1.41(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing an unadapted soil suspension, biodegradation of 90% in 3 days was reported(8), suggesting that biodegradation may be an important environmental fate process in water(SRC). Under anaerobic conditions, phenylacetic acid biodegraded >90% in 60 days using municipal sewage waste water(9). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(4).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) von Oepen B et al; Chemosphere 22: 285-304 (1991)
(3) Haynes WM. ed; CRC Handbook of Chemistry and Physics. 95th ed., Boca Raton, FL: CRC Press LLC, p. 5-100 (2014)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 41 (1995)
(7) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of June 12, 2017: https://www2.epa.gov/tsca-screening-tools
(8) Leidner H et al; Xenobiotica 10: 47-56 (1980)
(9) Hofmann K, Hammer E; Chemosphere 38: 2561-8 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenylacetic acid, which has a vapor pressure of 3.8X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase phenylacetic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.6 days(SRC), calculated from its rate constant of 4.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Phenylacetic acid does not absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Perry RH, Green D; Perry's Chemical Engineer's Handbook 6th ed New York, NY: McGraw-Hill, Inc pg 3-59 (1984)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of June 12, 2017: https://www2.epa.gov/tsca-screening-tools
(4) Dahab AA; RSC Advances 4(Issue 13): 6624 (2014)

13.2.8 Environmental Biodegradation

AEROBIC: Phenylacetic acid, as the source of carbon, was readily biodegraded using an unadapted mixed culture (soil suspension): primary degradation was 100 percent in 2 days (in mixture), primary degradation was 100 percent in three days (by GLC), and total degradation was 90 percent in about 3 days (by dissolved organic carbon measurement)(1). Oxygen consumption was approximately 6 ug/mL after six days when phenylacetic acid was degraded in Hudson Collamer silt loam(2). A diverse range of microorganisms (66 different isolates) capable of growth on phenylacetic acid as the sole source of carbon and energy were isolated from soil(3).
(1) Leidner H et al; Xenobiotica 10: 47-56 (1980)
(2) Subba-Rao RV, Alexander M; J Agric Food Chem 25: 327-9 (1977)
(3) O'Connor KE et al; Chemosphere 61: 965-973 (2005)
ANAEROBIC: Anaerobic degradation in two Maxey Flats trench leachate samples by a mixed culture of bacteria decreased the concentration of phenylacetic acid by 7 and 50% after 30 days(1). Phenylacetic acid, at a concentration of 6.5 mg/L, was biodegraded to 0.5 mg/L in municipal sewage waste water in 60 days at 26 °C in a nitrogen atmosphere(2).
(1) Francis AJ et al; Appl Environ Microbiol 40: 108-113 (1980)
(2) Hofmann K, Hammer E; Chemosphere 38: 2561-8 (1999)

13.2.9 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of phenylacetic acid with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the estimated OH radical reaction of ionized phenylacetic acid with hydroxyl radicals in aqueous solutions at pH 6-8 is 7.9X10+9 L/mol-sec(2); this corresponds to an aquatic half-life of 102 days at an aquatic concentration of 1X10-17 hydroxyl radicals per liter(3). Phenylacetic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). The UV spectrum of phenylacetic acid shows a log episilon absorbance of only 0.4 at 275 nm(5) and no absorbance at 290-300 nm(6). Therefore, phenylacetic acid is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of June 12, 2017: https://www2.epa.gov/tsca-screening-tools
(2) Buxton GV et al; J Phys Chem Ref Data 17: 513-882 (1988)
(3) Mill T et al; Science 207: 886-887 (1980)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(5) NIST; NIST Chemistry WebBook. Phenylacetic Acid (103-82-2). NIST Standard Reference Database No. 69, Feb 2015 Release. Washington, DC: US Sec Commerce. Available from, as of June 9, 2017: https://webbook.nist.gov
(6) Dahab AA; RSC Advances 4(Issue 13): 6624 (2014)
.../UV irradiation of aqueous solution showed that phenylacetic acid was degraded to benzyl alcohol, benzaldehydes & benzoic acids /which/ appeared entirely analogous to phenoxy acid photolysis
Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 856

13.2.10 Environmental Bioconcentration

An estimated BCF of 3 was calculated in fish for phenylacetic acid(SRC), using a log Kow of 1.41(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 41 (1995)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of June 12, 2017: https://www2.epa.gov/tsca-screening-tools
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

13.2.11 Soil Adsorption / Mobility

Koc values of 31, 26, and 28 were experimentally determined for phenylacetic acid in three specific soils: a Podzol (pH = 2.8, sand = 89.2%, silt = 8.2%, and clay = 2.6%), an alfisol (pH = 6.7, sand = 69.7%, silt = 14.4%, and clay = 15.9%) and sediment from Lake Constance (pH = 7.1, sand = 5.5%, silt = 58.8%, and clay = 35.7%), respectively(1). According to a classification scheme(2), these Koc values suggest that phenylacetic acid is expected to have very high mobility in soil. The pKa of phenylacetic acid is 4.31(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) von Oepen B et al; Chemosphere 22: 285-304 (1991)
(2) Swann RL et al; Res Rev 85: 23 (1983)
(3) Haynes WM, ed; CRC Handbook of Chemistry and Physics. 95th ed., Boca Raton, FL: CRC Press LLC, p. 5-100 (2014)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

13.2.12 Volatilization from Water / Soil

The pKa of phenylacetic acid is 4.31(1), indicating that this compound will exist almost entirely in anion form at pH 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). Phenylacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 0.0038 mm Hg at 25 °C(2).
(1) Haynes WM, ed; CRC Handbook of Chemistry and Physics. 95th ed. Boca Raton, FL: CRC Press LLC, p. 5-100 (2014)
(2) Perry RH, Green D; Perry's Chemical Engineer's Handbook 6th ed New York, NY: McGraw-Hill, Inc p. 3-59 (1984)

13.2.13 Environmental Water Concentrations

GROUND WATER: At a site in Galloway Township, NJ where an underground storage tank filled with gasoline spilled, phenylacetic acid was found at 5 ug/L in ground water 15.5 feet below land surface(1). Phenylacetic acid has been qualitatively identified in ground water contaminated by a landfill in Florida in 1991(2). At a groundwater site contaminated by wood preserving chemicals in Pensacola FL, phenylacetic acid was detected at the following concentrations and depths: 3.94 mg/L at 6.1 m, 1.3 mg/L at 3.3 m, 1.45 mg/L at 5.8 m, and 0.00 mg/L at 11.0 m(3). In a multiple basalt aquifer polluted by organic wastes dumped into unused quarry holes (Werribee Plains, Australia), phenylacetic acid was qualitatively identified(4). Phenylacetic acid was found in ground water samples at 3.3-3.5 mg/L of total organic carbon from superfund sites(5). Ground water samples taken in 1990 from 7 wells down gradient from an oil spill in Bemidji, MN in 1979 had concentrations ranges from <0.015-0.123 uM(6).
(1) Cozzarelli IM et al; Environ Sci Technol 29: 458-69 (1995)
(2) Eckel WP et al; Ground Water 31: 801-4 (1993)
(3) Goerlitz DF; in Environ Sci Pollut Control Ser 4(Groundwater Contamination and Analysis at Hazardous Waste Sites): 295-355 (1992)
(4) Stepan S et al; Australian Water Resources Council Conf Ser 1: 415-24 (1981)
(5) Betowski LD et al; Environ Sci Technol 30: 3558-64 (1996)
(6) Cozzarelli IM et al; Geochim Cosmochim Acta 58: 863-77 (1994)
DRINKING WATER: Phenylacetic acid was found in the drinking water of Ottumwa, Iowa at a concentration of 4 ug/L(1). Phenylacetic acid was listed as a contaminant found in drinking water for a survey of US cities including Cincinnati, OH, New Orleans, LO, Philadelphia, PA, Ottumwa, IA, and Seattle, WA(2). Phenylacetic acid was identified as a ozone disinfection by-product in drinking water(3). Analysis of raw and treated waters at various stages in a Spanish drinking water treatment plant (DWTP) during 2011 and 2012 detected phenylacetic acid at concentrations ranging from 0.8 to 5.6 ug/L(4).
(1) USEPA; Preliminary Assessment of Suspected Carcinogens in Drinking Water. Interim Report to Congress June 1975 Washington, DC (1975)
(2) Lucas SV; GC/MS Anal of Org in Drinking Water Concentrates and Advanced Treatment Concentrates Vol 1 USEPA-600/1-84-020A (NTIS PB85-128239) p. 397 (1984)
(3) Richardson SD et al; Environ Sci Tech 33: 3368-77 (1999)
(4) Jurado-Sanchez B et al; Water Research 51: 186-197 (2014)
Of 10 water supplies surveyed by EPA (1975), only finished water of Seattle, WA contained phenylacetic acid, at 4 ug/L.
National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 754
SURFACE WATER: Phenylacetic acid was qualitatively identified in Lake Michigan's St Joseph River(1). Phenylacetic acid was identified in Dokai Bay, Japan in samples collected in September 1990(2).
(1) Great Lakes Water Quality Board; An Inventory of Chemical Substances Identified in the Great Lakes Ecosystem. Volume I - Summary. Report to the Great Lakes Water Quality Board. Windsor Ontario, Canada 195 pp. (1983)
(2) Terashi A et al; Bull Environ Contam Toxicol 50: 348-55 (1993)

13.2.14 Effluent Concentrations

Phenylacetic acid has been detected in the effluents of the following industries: iron and steel manufacturing (114 ng/uL extract), organics and plastics (42766 ng/uL extract), textile mills (7 ng/uL extract), pulp and paper (61 ng/uL extract), pharmaceuticals (62677 ng/uL extract), electronics (152 ng/uL extract), organic chemicals (4568 ng/uL extract), mechanical products (4396 ng/uL extract), and publicly-owned treatment works (110 ng/uL extract)(1). Phenylacetic acid has been reported at Superfund Sites 181 times(2). Phenylacetic acid has been qualitatively detected in the effluent from a publicly-owned treatment works facility in Addison, IL in 1980(3). Water soluble fractions of soil samples taken from a controlled landfill site contained phenylacetic acid: 20.6%, 18.7%, and 41.1% at 1-1.5 m, 3-3.5 m, and 6.5-7 m deep, respectively(4). Phenylacetic acid has been identified in three leachate samples each from two low-level radioactive waste disposal sites: Maxey Flats, KY Trench Leachate; at 0.56, 1.5 and 3.4 mg/L and West Valley, NY Trench Leachate; 3.8, 7.5 and 6.0 mg/L(5). Phenylacetic acid was detected in primary waste treatment effluent and in the acid fraction of domestic US sewage treatment effluents(6). Phenylacetic acid was listed as a contaminant found in advanced waste treatment water for a survey of US cities including Lake Tahoe, CA, Orange County, CA, Dallas, TX, and Blue Plains, Washington, DC(7). The estimated emission rate of phenylacetic acid to the South coast air basin of California in the late 1980s was 250 kg/day(8).
(1) Bursey JT, Pellizzari ED; Analysis of Industrial Wastewater for Organic Pollutants in Consent Decree Survey. Contract No 68-03-2867 Athens, GA USEPA Env Res Lab pg 167 (1982)
(2) Eckel WP; Amer Chem Soc Div Environ Chem Preprint Ext Abstr 208th ACS Nat Meet Vol 34: 67-9 (1994)
(3) Ellis DD et al; Arch Environ Contam Toxicol 11: 373-82 (1982)
(4) Gonzalez-Vila FJ et al; Chemosphere 31: 2817-25 (1995)
(5) Francis AJ et al; Nuclear Technology 50: 158-63 (1980)
(6) USEPA; Preliminary Assessment of Suspected Carcinogens in Drinking Water. Interim Report to Congress June 1975 Washington, DC (1975)
(7) Lucas SV; GC/MS Anal of Org in Drinking Water Concentrates and Advanced Treatment Concentrates Vol 1 USEPA-600/1-84-020A (NTIS PB85-128239) p. 397 (1984)
(8) Grosjean D et al; Measurements of Organic Acids in the South Coast Air Basin. Final Report September 1988. Research Division, State of California Air Resources Board (NTIS PB89-145411) (1988)
Phenylacetic acid was qualitatively identified in acid fractions of Iona Island, Vancouver, British Columbia, Canada sewage and sludge(1). Phenylacetic acid was detected in only one out of three Swedish municipal landfill leachate samples with a suspected origin of pharmaceuticals, cosmetics, soaps, pesticides, insect repellants, disinfectants, food-, leather, and textile-preservatives, and the degradation of lignin(2). In Woolwich landfill leachate (Waterloo, Ontario), phenylacetic acid was detected at 19.6 and 24.6 meters deep at >10+4 and >10+2 ug/L(3). Phenylacetic acid was found in leachate from landfill for municipal wastes in Japan at 49.9 ug/L(4).
(1) Rogers IH et al; Water Poll Res J Canada 21: 187-204 (1986)
(2) Oman C, Hynning PA; Environmental Pollution 80: 265-71 (1993)
(3) Reinhard M, Goodman NL; Environ Sci Technol 18: 953-61 (1984)
(4) Yasuhara A et al; Kankyo Kagaku 3: 356-7 (1993)

13.2.15 Sediment / Soil Concentrations

SEDIMENT: Phenylacetic acid was detected, not quantified in 5 of 7 sediment samples collected in 1998 from the German Bight; one sample is directly influenced by discharges from the Elbe River, and one from the Weser and Ems rivers. The remaining three sites were situated farther from the coastal areas(1). Sediment samples collected from the Dokai Bay, Japan in September 1990 contained phenylacetic acid(2).
(1) Schwarzbauer J et al; Org Geochem 31: 1713-31 (2000)
(2) Terashi A et al; Bull Environ Contam Toxicol 50: 348-55 (1993)

13.2.16 Atmospheric Concentrations

URBAN/SUBURBAN: Phenylacetic acid was identified as one of the organic acids occurring in air samples collected at a smog receptor site in Glendora, CA in August 1986(1).
(1) Grosjean D et al; Measurements of Organic Acids in the South Coast Air Basin. Final Report September 1988. Research Division, State of California Air Resources Board (NTIS PB89-145411) (1988)

13.2.17 Food Survey Values

Phenylacetic acid was found as a volatile component in yellow box honey at 0.2 mg/kg and blue gum honey at 0.1 mg/kg(1). Phenylacetic acid was identified as a flavor compound in pine sprout tea and pine needle tea(2). Phenylacetic acid was detected in the volatiles of Rambutan fruit and in the juice at a concentration of 131.67 ug/L(3). Phenylacetic acid is reported to occur in guava, papaya, raspberry, strawberry, cooked potatoes, tomato, pepper, passion fruit, starfruit, mango, mushroom, rye bread, cheddar cheese, Swiss cheese, boiled mutton, beer, cognac, cider, sherry, grape wines, white wine, sake, cocoa, tea, honey soy protein, malt, and roasted chicory root(4). Reported food uses of phenylacetic acid include alcoholic beverages, baked goods, frozen dairy, gelatins, puddings and hard candy(4).
(1) Darcy BR et al; J Agric Food Chem 45: 1834-43 (1997)
(2) Kim KY, Chung HJ; J Agric Food Chem 48: 1269-72 (2000)
(3) Ong PKC et al; J Agric Food Chem 46: 611-615 (1998)
(4) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p. 1657 (2010)

13.2.18 Plant Concentrations

Phenylacetic acid is reported to be a constituent in a few essential oils, tobacco, Bulgarian rose, and orange flowers. It is reportedly found in cocoa volatiles, guava, papaya, raspberry, strawberry, tomato, peppermint oil, pepper, passion fruit, starfruit, mango, and mushroom(1).
(1) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p. 1657 (2010)
Phenylacetic acid occurrence in plants(1).
Genus species
Camellia sinensis
Family
Theaceae
Common name(s)
Tea
Part
Leaf
Concn (ppm)
1850-3130
Genus species
Mentha x piperita
Family
Lamiaceae
Common name(s)
Peppermint
Part
Leaf
Concn (ppm)
0.001-0.01
Genus species
Zea mays
Family
Poaceae
Common name(s)
Corn
Part
Pollen or Spore
Concn (ppm)
not reported
Genus species
Polianthes tuberosa
Family
Agavaceae
Common name(s)
Tuberose
Part
Flower
Concn (ppm)
not reported
Genus species
Juglans nigra
Family
Juglandaceae
Common name(s)
Black Walnut
Part
Seed
Concn (ppm)
not reported
Genus species
Citrus aurantium
Family
Rutaceae
Common name(s)
Bitter Orange
Part
Flower; Plant
Concn (ppm)
not reported
Genus species
Ligustrum japonicum
Family
Oleaceae
Common name(s)
Ligustri Fructus
Part
Flower
Concn (ppm)
not reported
Genus species
Piper methysticum
Family
Piperaceae
Common name(s)
Kava-Kava
Part
Rhizome
Concn (ppm)
not reported
Genus species
Prunus dulcis
Family
Rosaceae
Common name(s)
Almond
Part
Flower
Concn (ppm)
not reported
(1) US Dept Agric; US Dept Agric, Agric Res Service. 1992-2017. Dr. Duke's Phytochemical and Ethnobotanical Databases. Phenylacetic-Acid. Available from, as of June 14, 2017: https://phytochem.nal.usda.gov/phytochem/search

13.2.19 Fish / Seafood Concentrations

Phenylacetic acid was identified as a volatile component of rotten mussels (left out at room temperature for 10 days) at 2.35 ug/g wet weight, but not in fresh mussels(1).
(1) Yashuhara A; Journal of Chromatography 409: 251-58 (1987)

13.2.20 Animal Concentrations

Ants from fungus farming colonies secrete and synthesize phenylacetic acid(1).
(1) Fernandez-Marin H et al; Proc Biol Sci 282(1807): 20150212 (2015)

13.2.21 Other Environmental Concentrations

Phenylacetic acid has been identified as a chemical component of tobacco smoke, tobacco and substitite tobacco smoke(1). Phenylacetic acid was qualitatively found in cigarette smoke condensate(2). Burn emission rates of phenylacetic acid in mg/g of organic carbon were found to be 0.055 for red oak(3), 0.286 for paper birch(3), 0.130 for white pine(3), 0.047 for balsam(1), 0.044 for yellow poplar(2), 0.055 for mockernut hickory(4), 0.171 for loblolly pine(4), and 0.228 for slash pine(4). Phenylacetic acid was also detected in emissions from red maple(1), hemlock(3), balsam fir(3), white ash(4), and sweet gum(4).
(1) Rodgman A, Perfetti TA; The Chemical Components of Tobacco and Tobacco Smoke 2nd, ed., Baco Raton, FL: CRC Press p. 1236, 2078 (2013)
(2) Arnarp J et al; Acta Chemica Scandinavica 43: 381-5 (1989). Available from, as of Jun 14, 2017: https://www.ncbi.nlm.nih.gov/pubmed/?term=2485642
(3) Fine PM et al; Environ Sci Technol 35: 2665-75 (2001)
(4) Fine PM et al; Environ Sci Technol 36: 1442-1451 (2002)
Phenylacetic acid was identified as a biosynthesis product of the bacterium Azospirillum brasilense via phenylalanine or its precursors(1).
(1) Somers E et al; Appl Environ Microbiol 71(4): 1803-1810 (2005)

13.2.22 Probable Routes of Human Exposure

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimates the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of phenylacetic acid (benzeneacetic acid) in the United States may be as low as 100-499 workers and as high as 100-499 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1). According to the 2016 TSCA Inventory Update Reporting data, 1 reporting facility did not report the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of phenylacetic acid (benzeneacetic acid) in the United States(1).
(1) US EPA; Chemical Data Reporting (CDR). Non-confidential 2012 and 2016 Chemical Data Reporting information on chemical production and use in the United States. Available from, as of June 12, 2017: https://www.epa.gov/chemical-data-reporting
NIOSH (NOES Survey 1981-1983) has statistically estimated that 19,331 workers (6,627 of these are female) are potentially exposed to phenylacetic acid in the US(1). Occupational exposure to phenylacetic acid may occur through inhalation and dermal contact with this compound at workplaces where phenylacetic acid is produced or used. Monitoring and use data indicate that the general population may be exposed to phenylacetic acid via inhalation of tobacco and wood smoke, ingestion of food and drinking water, and dermal contact with consumer products containing phenylacetic acid(SRC).
(1) CDC; International Chemical Safety Cards (ICSC) 2012. Atlanta, GA: Centers for Disease Prevention & Control. National Institute for Occupational Safety & Health (NIOSH). Ed Info Div. Available from, as of June 12, 2017: https://www.cdc.gov/niosh/ipcs/default.html

13.2.23 Average Daily Intake

The average Individual (food) intake of phenylacetic acid has been reported as 0.001002 mg/kg/day(1).
(1) Burdock GA, ed; Fenaroli's Handbook of Flavor Ingredients. 6th ed. Boca Raton, FL: CRC Press, p. 1657 (2010)

13.2.24 Body Burden

Phenylacetic acid was present in 47.3% of the 54 samples of normal human expired air from an average concentration of 0.161 ng/L(1). Phenylacetic acid is detected in human faecal samples(2). Phenylacetic acid occurs as a protein-bound uremic compound in humans(3).
(1) Krotoszynski BK et al; J Anal Toxicol 3: 225-34 (1979)
(2) Russell WR et al; Mol Nutr Food Res 57(3): 523-535 (2013)
(3) Brettschneider F et al; Artif Organs 37(4): 409-416 (2013)

14 Associated Disorders and Diseases

Disease
Kidney disease
References
Disease
Leukemia
References
Disease
Uremia
References

PubMed: 11865086, 10509899, 9607216, 7482520, 6520173, 22626821, 21359215, 2026685, 9573551, 24023812, 15353324, 19309105, 8087979, 17132244, 12675874

Merck Manual of Diagnosis and Therapy.

David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971

Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.

Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

National Health and Nutrition Examination Survey (NHANES Survey) 2013

Geigy Scientific Tables, 8th Rev edition, pp. 80-82. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Disease
Irritable bowel syndrome
References
Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Attachment loss
References
PubMed: 31026179
Disease
Missing teeth
References
PubMed: 31026179
Disease
Periodontal Probing Depth
References
PubMed: 31026179
Disease
Prosthesis/Missing teeth
References
PubMed: 31026179
Disease
Supragingival Calculus
References
PubMed: 31026179
Disease
Supragingival Plaque
References
PubMed: 31026179
Disease
Tooth Decay
References
PubMed: 31026179
Disease
Phenylketonuria
References

PubMed: 7333014, 2091926, 12101068, 17574536, 6790852, 466810, 2116554, 19551947, 25964343, 15168722, 4837567

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Wiley References

15.6 Nature Journal References

15.7 Synthesis References

15.8 Chemical Co-Occurrences in Literature

15.9 Chemical-Gene Co-Occurrences in Literature

15.10 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

17.2 Chemical-Target Interactions

17.3 Drug-Drug Interactions

17.4 Pathways

18 Biological Test Results

18.1 BioAssay Results

19 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

20 Classification

20.1 MeSH Tree

20.2 NCI Thesaurus Tree

20.3 ChEBI Ontology

20.4 FDA Pharm Classes

20.5 ChemIDplus

20.6 ChEMBL Target Tree

20.7 UN GHS Classification

20.8 EPA CPDat Classification

20.9 Drug Enforcement Administration (DEA) Classification

20.10 NORMAN Suspect List Exchange Classification

20.11 EPA DSSTox Classification

20.12 EPA TSCA and CDR Classification

20.13 LOTUS Tree

20.14 EPA Substance Registry Services Tree

20.15 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    Benzeneacetic acid, labeled with tritium
    https://commonchemistry.cas.org/detail?cas_rn=17303-65-0
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  6. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  9. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Hazardous Substances Data Bank (HSDB)
  11. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  12. ILO-WHO International Chemical Safety Cards (ICSCs)
  13. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  14. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  15. Drug Enforcement Administration (DEA)
    LICENSE
    Unless otherwise indicated, information on Department of Justice websites is in the public domain and may be copied and distributed without permission. Citation of the Department of Justice as source of the information is appreciated, as appropriate.
    https://www.justice.gov/legalpolicies
    Phenylacetic acid, its esters, and its salts
    https://www.deadiversion.usdoj.gov/chem_prog/34chems.html
    DEA drug and chemical classification
    https://www.dea.gov/drug-information/drug-scheduling
  16. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  17. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  18. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  19. ChEBI
  20. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  21. FDA Pharm Classes
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  22. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  23. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  24. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  25. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Phenylacetic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  26. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  27. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  28. KNApSAcK Species-Metabolite Database
  29. Natural Product Activity and Species Source (NPASS)
  30. EPA Chemical and Products Database (CPDat)
  31. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  32. EU Food Improvement Agents
  33. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  34. FDA Substances Added to Food
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  35. Flavor and Extract Manufacturers Association (FEMA)
  36. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  37. IUPAC Digitized pKa Dataset
  38. NMRShiftDB
  39. MassBank Europe
  40. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  41. SpectraBase
    PHENYLACETIC-ACID;BENZENE-ACETIC-ACID
    https://spectrabase.com/spectrum/Dk4nGtKJdwe
  42. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  43. Japan Chemical Substance Dictionary (Nikkaji)
  44. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  45. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  46. Metabolomics Workbench
  47. Nature Chemistry
  48. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  49. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  50. Protein Data Bank in Europe (PDBe)
  51. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  52. Springer Nature
  53. SpringerMaterials
  54. The University of Alabama Libraries
  55. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  56. Wikidata
  57. Wikipedia
  58. Wiley
  59. PubChem
  60. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Antimetabolites, Antineoplastic
    https://www.ncbi.nlm.nih.gov/mesh/68000964
  61. GHS Classification (UNECE)
  62. EPA Substance Registry Services
  63. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  64. PATENTSCOPE (WIPO)
  65. NCBI
CONTENTS