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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

Description

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

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.