2-aminophenol (CHEBI:18112)

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CHEBI:18112 - 2-aminophenol

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ChEBI Name	2-aminophenol

ChEBI ID	CHEBI:18112

Definition	The aminophenol which has the single amino substituent located ortho to the phenolic -OH group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:39779, CHEBI:11527, CHEBI:1023, CHEBI:19476

Supplier Information	ChemicalBook:CB8309112, eMolecules:477080, ZINC000000157526

Download	Molfile XML SDF

more structures >>

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15 15 0 0 0 0 999 V2000

0.8564 -0.6285 0.0220 C 0 0 0 0 0 0 0 0 0 1 0 0

-0.5578 -0.6239 -0.0414 C 0 0 0 0 0 0 0 0 0 2 0 0

-1.2506 0.6053 0.0110 C 0 0 0 0 0 0 0 0 0 3 0 0

-0.5424 1.8194 0.0684 C 0 0 0 0 0 0 0 0 0 4 0 0

0.8642 1.8136 0.0808 C 0 0 0 0 0 0 0 0 0 5 0 0

1.5609 0.5915 0.0703 C 0 0 0 0 0 0 0 0 0 6 0 0

1.5169 -1.6992 0.0402 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2380 -1.7427 -0.1630 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.2740 0.6292 0.0032 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0485 2.7078 0.0972 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3788 2.6970 0.1013 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5842 0.6009 0.0987 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1122 -2.4812 0.0411 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1720 -1.7269 -0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7904 -2.5625 -0.2168 H 0 0 0 0 0 0 0 0 0 0 0 0

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Wikipedia	License
2-Aminophenol is an organic compound with the formula C6H7NO. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds. Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallized from hot water.
Read full article at Wikipedia

Formula

C6H7NO

Net Charge

Average Mass

109.12592

Monoisotopic Mass

109.05276

InChI

InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2

InChIKey

CDAWCLOXVUBKRW-UHFFFAOYSA-N

SMILES

Nc1ccccc1O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	2-aminophenol (CHEBI:18112) has role bacterial metabolite (CHEBI:76969) 2-aminophenol (CHEBI:18112) is a aminophenol (CHEBI:28829)

Incoming	2-acetamidophenol sulfate (CHEBI:133562) has functional parent 2-aminophenol (CHEBI:18112) 2-aminophenyl hydrogen sulfate (CHEBI:133186) has functional parent 2-aminophenol (CHEBI:18112)

IUPAC Name

2-aminophenol

Synonyms	Sources
2-Aminobenzenol	KEGG COMPOUND
2-Aminophenol	KEGG COMPOUND
2-AMINOPHENOL	PDBeChem
2-aminophenol	UniProt
2-Hydroxyaniline	KEGG COMPOUND
o-Aminophenol	KEGG COMPOUND
o-hydroxyaniline	NIST Chemistry WebBook

Manual Xrefs	Databases
2-Aminophenol	Wikipedia
2AF	PDBeChem
C00007533	KNApSAcK
C01987	KEGG COMPOUND
c0316	UM-BBD
DB01726	DrugBank
View more database links

Registry Numbers	Types	Sources
26978	Gmelin Registry Number	Gmelin
606075	Gmelin Registry Number	Gmelin
606075	Reaxys Registry Number	Reaxys
95-55-6	CAS Registry Number	KEGG COMPOUND
95-55-6	CAS Registry Number	ChemIDplus
95-55-6	CAS Registry Number	NIST Chemistry WebBook

Citations

Capello MC, Broquier M, Ishiuchi S, Sohn WY, Fujii M, Dedonder-Lardeux C, Jouvet C, Pino GA (2014)
Fast nonradiative decay in o-aminophenol.
The journal of physical chemistry. A 118, 2056-2062 [PubMed:24571346]
[show Abstract]

Chirino B, Strahsburger E, Agulló L, González M, Seeger M (2013)
Genomic and functional analyses of the 2-aminophenol catabolic pathway and partial conversion of its substrate into picolinic acid in Burkholderia xenovorans LB400.
PloS one 8, e75746 [PubMed:24124510]
[show Abstract]

Wulferink M, González J, Goebel C, Gleichmann E (2001)
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
Chemical research in toxicology 14, 389-397 [PubMed:11304127]
[show Abstract]
The most basic arylamine, aniline, belongs to a class of compounds notorious for inducing allergic and autoimmune reactions. In 1981 in Spain, many people succumbed to toxic oil syndrome (TOS), a disease caused by ingestion of cooking oil contaminated with aniline. Indirect evidence points toward an immune pathogenesis of TOS driven by T lymphocytes, but it is unclear to which antigens these cells could react. Here, using the popliteal lymph node (PLN) assay in mice, we analyzed the sensitizing potential of aniline, its metabolites, and some of the aniline-coupled lipids detected in the contaminated cooking oil. Whereas aniline itself and its non-protein-reactive metabolites nitrobenzene, p-aminophenol and N-acetyl-p-aminophenol, failed to elicit PLN responses, its reactive metabolites nitrosobenzene and N-hydroxylaniline did. The aniline-coupled lipids, namely, linoleic anilide and linolenic anilide, and a mixture of fatty acid esters of 3-(N-phenylamino)-1,2-propanediol, all implicated in TOS, induced significant PLN responses, whereas the respective aniline-free lipids, linoleic acid, linolenic acid, and triolein, did not. Hence, the aniline moiety plays a crucial role in the immunogenicity of the aniline-coupled lipids of TOS. PLN responses to the reactive aniline metabolites and the one aniline-coupled lipid that was tested, linolenic anilide, were T-cell-dependent. Secondary PLN responses to nitrosobenzene were detectable not only after priming with nitrosobenzene but, in some experiments, also after priming with linolenic anilide. This suggests that the aniline moiety was cleaved from the aniline-coupled lipid and metabolized to the intermediate nitrosobenzene that generated the prospective neoantigens. Consistent with this, in lymphocyte proliferation tests in vitro, T cells primed to nitrosobenzene reacted in anamnestic fashion to white bone marrow cells (WBMCs) pulsed with aniline. Hence, we propose that aniline is a prohapten that can be metabolized by WBMCs, which form neoantigens that are recognized by T cells. The possible significance of these findings for the pathogenesis of TOS is discussed.

Takenaka S, Murakami S, Shinke R, Aoki K (1998)
Metabolism of 2-aminophenol by Pseudomonas sp. AP-3: modified meta-cleavage pathway.
Archives of microbiology 170, 132-137 [PubMed:9683650]
[show Abstract]

Basketter DA, Lidén C (1992)
Further investigation of the prohapten concept: reactions to benzene derivatives in man.
Contact dermatitis 27, 90-97 [PubMed:1395635]
[show Abstract]

Last Modified

03 October 2016

CHEBI:18112 - 2-aminophenol

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