ContaminantDB: 4-Aminophenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-11-11 22:18:18 UTC

Update Date

2026-03-27 01:00:36 UTC

Accession Number

CHEM002576

Identification

Common Name

4-Aminophenol

Class

Small Molecule

Description

4-Aminophenol is an amphoteric molecule and a reducing agent. Aminophenols are intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. 4-aminophenol is considered a minor nephrotoxic metabolite of phenacetin and acetaminophen (paracetamol) in man. 4-Aminophenol can undergo autoxidations and metal-catalyzed and enzymatic oxidations in man to produce reactive oxygen species. (2) (15)

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Aromatic Hydrocarbon
Cosmetic Toxin
Food Toxin
Household Toxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-Aminobenzenol	ChEBI
4-Hydroxyaniline	ChEBI
p-Aminophenol	ChEBI
p-Hydroxyaniline	ChEBI
4-Aminophenol conjugate monoacid	MeSH
4-Aminophenol hydrochloride	MeSH
4-Aminophenol monopotassium salt	MeSH
4-Aminophenol monosodium salt	MeSH
4-Aminophenol sulfate	MeSH
4-Aminophenol sulfate (2:1)	MeSH
4-Aminophenol, 18O-labeled	MeSH
4-Aminophenol, 3H-labeled	MeSH
4-Aminophenol, ion(1+)	MeSH
p-Aminophenol phosphate	MeSH
Para-aminophenol	MeSH
1-amino-4-Hydroxybenzene	HMDB
4-amino-1-Hydroxybenzene	HMDB
Activol	HMDB
Aminophenol	HMDB
Energol	HMDB
Fouramine P	HMDB
P-Hydroxyphenylamine	HMDB
Paramidophenol	HMDB
Paranol	HMDB
4-Aminophenol	KEGG

Chemical Formula

C₆H₇NO

Average Molecular Mass

109.126 g/mol

Monoisotopic Mass

109.053 g/mol

CAS Registry Number

123-30-8

IUPAC Name

4-aminophenol

Traditional Name

aminophenol

SMILES

NC1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

PLIKAWJENQZMHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

P-aminophenol
Aniline or substituted anilines
Aminophenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aminophenol (CHEBI:17602 )
a phenol (CPD-259 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Epidermis
Spleen

Pathways

Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

White powder. (16)

Experimental Properties

Property	Value
Melting Point	187.5°C
Boiling Point	187.5°C
Solubility	16 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	121 g/L	ALOGPS
logP	0.47	ALOGPS
logP	0.84	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	10.4	ChemAxon
pKa (Strongest Basic)	5.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32.74 m³·mol⁻¹	ChemAxon
Polarizability	11.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-9c5bfea7a6ff3c845001	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pe9-9300000000-8ff47e2157f6fbfe6754	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f79-1890000000-c8247060f46131c693d1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-1927000000-b873199d9ac85605a4df	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-9c5bfea7a6ff3c845001	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pe9-9300000000-8ff47e2157f6fbfe6754	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f79-1890000000-c8247060f46131c693d1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-1927000000-b873199d9ac85605a4df	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5900000000-e64da39e73e3c0ea696c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-060r-6900000000-2c6cd652b49e26ce3fce	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-3900000000-906f96b14dfdad2310de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-d56be0077647bc66e962	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-937794addf5b73c988e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-2900000000-1d20b6ad92e8fe4dcb55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-2900000000-5950ca2352822bea4a01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-02tc-9300000000-3524fecaa931f284564b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-da3b2114d9298a0363e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-b43943b1e137b2912b0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-9000000000-8ca8655366b90d8f42df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-28f35dbe83fee57d4a70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-6aa4cd1a9d2a859fa70b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-9300000000-177dcaf10b9e95cb409c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-c89e2460dc3caf4abe05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9100000000-b0a8e0715ece78a9716d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-9000000000-aed714f11873786e9c3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-875d8abd6f6773a40634	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-875d8abd6f6773a40634	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9200000000-17afc5bcee8bb56bc9e8	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9700000000-00bffb48fd955696bccc	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (13) ; inhalation (13)

Mechanism of Toxicity

4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl then form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4). It is also though that the mode of action involves metabolic activation by N-hydroxylation, followed by N-esterification leading to the formation of a reactive electrophile, which binds covalently to DNA, principally to deoxyguanosine, leading to an increased rate of DNA mutations and ultimately to the development of cancer. In humans and dogs, the urinary bladder urothelium is the target organ, whereas in mice it is the bladder and liver; in other species, other tissues can be involved. Differences in organ specificity are thought to be due to differences in metabolic activation versus inactivation (12).

Metabolism

Not Available

Toxicity Values

LD50: 375 mg/kg (Oral, Rat) (17)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

4-Aminophenol is commonly used as a developer in black and white film, marketed under the name Rodinal. Aminophenols are also intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (15, 16)

Minimum Risk Level

Not Available

Health Effects

4-Aminophenol may act as a skin sensitizer and cause contact dermatitis. In addition, inhalation of large amounts can cause methemoglobinemia and bronchial asthma. (18)

Symptoms

4-Aminophenol may cause contact dermatitis. Signs and symptoms of methemoglobinemia may include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia can result in dysrhythmias, seizures, coma, and death. (18, 14)

Treatment

Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (14)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001169

FooDB ID

FDB022462

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-259

METLIN ID

6051

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Zhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang. Method for preparation of p-aminophenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304127

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1395635

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7179289

5. Zhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang. Method for preparation of p-aminophenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.

6. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.

7. Zhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang. Method for preparation of p-aminophenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.

8. Lampinen M, Bondesson U, Fredriksson E, Hedeland M: Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 15;789(2):347-54.

9. Clark PM, Clark JD, Wheatley T: Urine discoloration after acetaminophen overdose. Clin Chem. 1986 Sep;32(9):1777-8.