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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8O3
Molecular Weight 140.1366
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-METHOXYCATECHOL

SMILES

COC1=CC=CC(O)=C1O

InChI

InChIKey=LPYUENQFPVNPHY-UHFFFAOYSA-N
InChI=1S/C7H8O3/c1-10-6-4-2-3-5(8)7(6)9/h2-4,8-9H,1H3

HIDE SMILES / InChI

Molecular Formula C7H8O3
Molecular Weight 140.1366
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

3-methoxycatechol is a derivative of catchol. Despite initial interest in its antioxidant properties, 3-methoxycatechol has demonstrated carcinogenic properties in rat models both in vitro and in vivo.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Oxidative stress and vascular function: implications for pharmacologic treatments.
2010-06
A previously uncultured, paper mill Propionibacterium is able to degrade O-aryl alkyl ethers and various aromatic hydrocarbons.
2009-06
Urine biomarkers of risk in the molecular etiology of breast cancer.
2009-01-06
Prevention of estrogen-DNA adduct formation in MCF-10F cells by resveratrol.
2008-07-15
The reactivity of ortho-methoxy-substituted catechol radicals with sulfhydryl groups: contribution for the comprehension of the mechanism of inhibition of NADPH oxidase by apocynin.
2007-08-01
The oxidation of apocynin catalyzed by myeloperoxidase: proposal for NADPH oxidase inhibition.
2007-01-15
Alanine 101 and alanine 110 of the alpha subunit of Pseudomonas stutzeri OX1 toluene-o-xylene monooxygenase influence the regiospecific oxidation of aromatics.
2005-12-05
Quantitative structure toxicity relationships for catechols in isolated rat hepatocytes.
2004-04-15
Vibrational analysis of substituted phenols: part I. Vibrational spectra, normal coordinate analysis and transferability of force constants of some formyl-, methoxy-, formylmethoxy-, methyl- and halogeno-phenols.
2002-12
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV.
2001-11
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001-02
Effects of combined treatment with phenolic compounds and sodium nitrite on two-stage carcinogenesis and cell proliferation in the rat stomach.
1994-01
Effects of sodium nitrite and catechol or 3-methoxycatechol in combination on rat stomach epithelium.
1990-09
Patents

Sample Use Guides

Multi-organ cancer was induced in rats by application of 100 mg/kg of body weight diethylnitrosamine intraperitoneal injection, 4 times intraperitoneal injection of 20 mg/kg of body weight N-methylnitrosourea, 4 times subcutaneous injection of 40 mg/kg of body weight dimethylhydrazine, 0.05% oral N-butyl-N-(4-hydroxybutyl)nitrosamine in the drinking water for the first 2 weeks and 0.1% oral 2,2'-dihydroxy-di-n-propylnitrosamine in the drinking water for the next 2 weeks. Starting 3 days after completion of these carcinogen treatments animals were given diets containing 2% butylated hydroxyanisole, 0.8% catechol, 2% 3-methoxycatechol, or basal diet either alone or in combination with 0.3% sodium nitrite until week 28 when a complete autopsy was performed. The combination of NaNO2 with 3-methoxycatechol inhibited glandular stomach lesions with or without carcinogen exposure. However, 3-Methoxycatechol promoted esophageal carcinogenesis either with or without NaNO2.
Route of Administration: Oral
Hepatocytes were isolated from rats by collagenase perfusion of the liver. Isolated hepatocytes were suspended in Krebs-Henseleit buffer (pH 7.4) containing HEPES (12.5 mM) in continuous rotation at 37 deg-C under a 5% CO2 atmosphere. After 30 min an aliquot of 3-methoxycatechol was added and the hepatocytes were incubated for another 2 hours. The concentration at which the compound caused 50% cell death was determined by counting the number of cells that excluded trypan blue. 3-methoxychatechol demonstrated an LD50 of 240 micro-M after 2 hours.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:38:58 GMT 2025
Edited
by admin
on Mon Mar 31 19:38:58 GMT 2025
Record UNII
IC13U5393C
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-66525
Preferred Name English
3-METHOXYCATECHOL
Systematic Name English
2,3-DIHYDROXYANISOLE
Systematic Name English
PYROGALLOL 1-METHYL ETHER
Common Name English
6-METHOXYCATECHOL
Systematic Name English
1,2-BENZENEDIOL, 3-METHOXY-
Systematic Name English
1,2-DIHYDROXY-3-METHOXYBENZENE
Systematic Name English
1-O-METHYLPYROGALLOL
Systematic Name English
3-METHOXYPYROCATECHOL
Systematic Name English
PYROCATECHOL, 3-METHOXY-
Systematic Name English
Code System Code Type Description
CHEBI
141700
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
PRIMARY
CAS
934-00-9
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
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PUBCHEM
13622
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
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EPA CompTox
DTXSID4020826
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
PRIMARY
MESH
C066344
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
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FDA UNII
IC13U5393C
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
PRIMARY
NSC
66525
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-276-4
Created by admin on Mon Mar 31 19:38:58 GMT 2025 , Edited by admin on Mon Mar 31 19:38:58 GMT 2025
PRIMARY