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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=C(O)C(O)=CC=C1

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
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV.
2001 Nov
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 Dec
Quantitative structure toxicity relationships for catechols in isolated rat hepatocytes.
2004 Apr 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 Dec 5
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 Aug 1
The oxidation of apocynin catalyzed by myeloperoxidase: proposal for NADPH oxidase inhibition.
2007 Jan 15
Prevention of estrogen-DNA adduct formation in MCF-10F cells by resveratrol.
2008 Jul 15
Urine biomarkers of risk in the molecular etiology of breast cancer.
2009 Jan 6
A previously uncultured, paper mill Propionibacterium is able to degrade O-aryl alkyl ethers and various aromatic hydrocarbons.
2009 Jun
Oxidative stress and vascular function: implications for pharmacologic treatments.
2010 Jun
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 Fri Dec 15 19:13:59 GMT 2023
Edited
by admin
on Fri Dec 15 19:13:59 GMT 2023
Record UNII
IC13U5393C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-METHOXYCATECHOL
Systematic Name English
2,3-DIHYDROXYANISOLE
Systematic Name English
NSC-66525
Code 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 Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
CAS
934-00-9
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
PUBCHEM
13622
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID4020826
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
MESH
C066344
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
FDA UNII
IC13U5393C
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
NSC
66525
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-276-4
Created by admin on Fri Dec 15 19:13:59 GMT 2023 , Edited by admin on Fri Dec 15 19:13:59 GMT 2023
PRIMARY