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
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
| 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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolite screening of aromatic amine hair dyes using in vitro hepatic models. | 2009-11 |
|
| 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. | 2009-02-15 |
|
| Contact dermatitis to 4-amino-2-hydroxytoluene in hair dye. | 2009-02 |
|
| Metabolism and disposition of [14C]5-amino-o-cresol in female F344 rats and B6C3F1 mice. | 2008-02 |
|
| Comparison of flow cytometry- and microscopy-based methods for measuring micronucleated reticulocyte frequencies in rodents treated with nongenotoxic and genotoxic chemicals. | 2008-01-08 |
|
| Vibrational spectroscopy investigation using ab initio and density functional theory analysis on the structure of 5-amino-o-cresol. | 2007-11 |
|
| Function of surfactants in hair dyeing by oxidation dyes 2. Effect on formation of oxidation dyes by p-aminophenol and 5-amino-o-cresol in dye bath(1). | 2007-08 |
|
| Fading of artificial hair colour and its prevention by photofilters. | 2006-06 |
|
| Fading of artificial hair color and its prevention by photofilters. | 2005-08-09 |
|
| Determination of 4-amino-m-cresol and 5-amino-o-cresol by high performance liquid chromatography and fluorescence derivatization using fluorescamine. | 2004-10-29 |
|
| Determination of 4-amino-m-cresol and 5-amino-o-cresol and metabolites in human keratinocytes (HaCaT) by high-performance liquid chromatography with DAD and MS detection. | 2004-10-29 |
|
| Final report on the safety assessment of 6-Amino-m-Cresol, 6-Amino-o-Cresol, 4-Amino-m-Cresol, 5-Amino-4-Chloro-o-Cresol, 5-Amino-6-Chloro-o-Cresol, and 4-Chloro-2-Aminophenol. | 2004 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24275315
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
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Edited
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UBB8XEB10B
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Validated (UNII)
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