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3-Methoxy-4-hydroxy-cinnamic acid

PubChem CID
709
Structure
3-Methoxy-4-hydroxy-cinnamic acid_small.png
3-Methoxy-4-hydroxy-cinnamic acid_3D_Structure.png
Molecular Formula
Synonyms
  • (E/Z)-ferulic acid
  • DTXSID5040673
  • Spectrum_001256
  • SpecPlus_000547
  • Spectrum2_001394
Molecular Weight
194.18 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
See also: Ferulic acid (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3-Methoxy-4-hydroxy-cinnamic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

KSEBMYQBYZTDHS-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

COC1=C(C=CC(=C1)C=CC(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H10O4
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
194.18 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
1.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
194.05790880 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
194.05790880 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
66.8 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
224
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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
1
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 2011.04.04)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian A-60D
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
View All
Authors
Ara T, Morishita Y, Shibata D, Kazusa DNA Research Institute
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
DB-17MS
Retention Time
1035.41 sec
Top 5 Peaks

323 999

308 923

338 811

249 706

293 588

Thumbnail
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License
CC BY-SA
2 of 6
View All
Authors
Ara T, Morishita Y, Shibata D, Kazusa DNA Research Institute
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
DB-17MS
Retention Time
996.528 sec
Top 5 Peaks

249 999

338 922

89 794

308 763

323 736

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License
CC BY-SA

4.2.2 LC-MS

1 of 42
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
10 V
Precursor m/z
193
Precursor Adduct
[M-H]-
Top 5 Peaks

193.4 999

134 31

149.3 31

96.8 27

59.2 21

Thumbnail
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License
CC BY-NC-SA
2 of 42
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
20 V
Precursor m/z
193
Precursor Adduct
[M-H]-
Top 5 Peaks

133.9 999

178.4 229

193.1 134

149.3 121

117.1 59

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License
CC BY-NC-SA

4.2.3 Other MS

1 of 3
View All
Authors
ENDO K, PHARMACEUTICAL INST., TOHOKU UNIV.
Instrument
HITACHI M-52
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 25 eV
Top 5 Peaks

194 999

150 188

179 188

133 156

135 116

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License
CC BY-NC-SA
2 of 3
View All
Authors
YAMAMOTO M, DEP. CHEMISTRY, FAC. SCIENCE, NARA WOMEN'S UNIV.
Instrument
HITACHI M-2500
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

194 999

179 207

133 178

195 117

177 90

Thumbnail
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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Biochemical Reactions

8 Use and Manufacturing

8.1 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

9 Literature

9.1 Consolidated References

9.2 Springer Nature References

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Pathways

12 Biological Test Results

12.1 BioAssay Results

13 Taxonomy

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

14 Classification

14.1 EPA CPDat Classification

14.2 NORMAN Suspect List Exchange Classification

14.3 EPA DSSTox Classification

14.4 LOTUS Tree

14.5 EPA Substance Registry Services Tree

14.6 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. 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/
    2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, homopolymer
    https://commonchemistry.cas.org/detail?cas_rn=97274-61-8
  2. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. ChEBI
    3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:193350
  4. 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/
    3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid
    https://www.wikidata.org/wiki/Q51617501
  5. 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
  6. EPA Chemical and Products Database (CPDat)
  7. Natural Product Activity and Species Source (NPASS)
    3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid
    https://bidd.group/NPASS/compound.php?compoundID=NPC272471
  8. MassBank Europe
  9. SpectraBase
    3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoicacid
    https://spectrabase.com/spectrum/73IAWICj6Op
    4-Hydroxy-3-methoxycinnamic acid
    https://spectrabase.com/spectrum/AY76VsaXW6L
    4-hydroxy-3-methoxycinnamic acid
    https://spectrabase.com/spectrum/DhUveIZA0nO
    CINNAMIC ACID, 4-HYDROXY-3-METHOXY-,
    https://spectrabase.com/spectrum/3fRzy51eAfe
  10. Springer Nature
  11. Wikidata
  12. PubChem
  13. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. EPA Substance Registry Services
  15. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  16. PATENTSCOPE (WIPO)
CONTENTS