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Details

Stereochemistry ACHIRAL
Molecular Formula C7H9NO
Molecular Weight 123.1525
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-AMINO-2-HYDROXYTOLUENE

SMILES

CC1=CC=C(N)C=C1O

InChI

InChIKey=DBFYESDCPWWCHN-UHFFFAOYSA-N
InChI=1S/C7H9NO/c1-5-2-3-6(8)4-7(5)9/h2-4,9H,8H2,1H3

HIDE SMILES / InChI

Molecular Formula C7H9NO
Molecular Weight 123.1525
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

4-Amino-2-Hydroxytoluene is a substituted aromatic compound used in the formulation of permanent hair dyes, colors and tints. 4-Amino-2-Hydroxytoluene is used as a coupler in cosmetic hair dye formulations. The compound has a low oral toxicity in animals and has no significant mutagenic or teratogenic effects. The compound, at most, is a weak skin and eye irritant and, at most, a weak sensitizer. Carcinogenic skin painting studies of hair dyes containing this compound were negative. A variety of epidemio-logic studies have given no indication of a carcinogenic effect from the use of hair dyes.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Determination of 4-amino-m-cresol and 5-amino-o-cresol by high performance liquid chromatography and fluorescence derivatization using fluorescamine.
2004 Oct 29
Contact dermatitis to 4-amino-2-hydroxytoluene in hair dye.
2009 Feb
Skin metabolism of aminophenols: human keratinocytes as a suitable in vitro model to qualitatively predict the dermal transformation of 4-amino-2-hydroxytoluene in vivo.
2009 Feb 15
Metabolite screening of aromatic amine hair dyes using in vitro hepatic models.
2009 Nov
Patents

Sample Use Guides

Rats, 4 per sex/dose were administered 4-Amino-2-Hydroxytoluene via gavage in dose levels of 0, 0.4, 1, 2.5 or 6.4 g/kg bw. To determine the median lethal dose more precisely dosing was extended to a larger group, and additional groups of 5 rats per dose/sex, were administered the test substance via gavage in dose levels of 0, 1.6, 2.5, 4.0 or 6.4 g/kg bw. Shortly after dosing clinical signs observed were lethargy, piloerection and decreased respiration rate. Above 1.6 g/kg these signs were accompanied by ataxia, and in rats dosed above 2.5 mg/kg also fine body tremors and increased lacrimation was observed. The acute median lethal oral dose of 4-amino-2-hydroxytoluene in rats was calculated to be 3.6 (95% confidence limits: 3.1-4.0) g/kg bw.
Route of Administration: Oral
A genotoxic potential of 4-Amino-2-Hydroxytoluene was observed after 48 hours of incubation with V79 cells starting at the lowest concentration tested (10 ug/ml), while DNA damage in both V79NAT1*4 and HaCaT cells started at substantially higher concentrations, 100 and 31,6 ug/ml, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:01:08 GMT 2023
Edited
by admin
on Fri Dec 15 17:01:08 GMT 2023
Record UNII
UBB8XEB10B
Record Status Validated (UNII)
Record Version
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Name Type Language
4-AMINO-2-HYDROXYTOLUENE
INCI  
INCI  
Official Name English
5-AMINO-2-METHYLPHENOL
Systematic Name English
4-AMINO-2-HYDROXY-1-METHYLBENZENE
Systematic Name English
4-AMINO-2-HYDROXYTOLUENE [INCI]
Common Name English
5-AMINO-O-CRESOL [HSDB]
Common Name English
3-HYDROXY-4-METHYLANILINE
Systematic Name English
2-HYDROXY-4-AMINOTOLUENE
Systematic Name English
2-METHYL-5-AMINOPHENOL
Systematic Name English
PHENOL, 5-AMINO-2-METHYL-
Systematic Name English
3-HYDROXY-P-TOLUIDINE
Common Name English
1-METHYL-2-HYDROXY-4-AMINOBENZENE
Systematic Name English
Code System Code Type Description
FDA UNII
UBB8XEB10B
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
220-618-6
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
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PUBCHEM
17818
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
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DAILYMED
UBB8XEB10B
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
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HSDB
7152
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
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RXCUI
1740236
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
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CAS
2835-95-2
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
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EPA CompTox
DTXSID9024489
Created by admin on Fri Dec 15 17:01:08 GMT 2023 , Edited by admin on Fri Dec 15 17:01:08 GMT 2023
PRIMARY