3-O-methyl gallic acid

benzoic acid, 3,4-dihydroxy-5-methoxy-

CAS: 3934-84-7 C8 H8 O5 MW: 184.14776000

Identification

Name3-O-methyl gallic acid
IUPAC3,4-dihydroxy-5-methoxybenzoic acid
CAS Number3934-84-7
EINECS223-512-8
FDA UNII8JA4OZ7166
Molecular FormulaC8 H8 O5
Molecular Weight184.14776000
MDL NumberMFCD00016518
Nikkaji NumberJ217.773K
Beilstein2695762
XlogP30.70 (est)

Regulatory

Physical Properties

Food Chemicals Codex Listed No
Boiling Point 433.70 °C. @ 760.00 mm Hg (est)
Flash Point 362.00 °F. TCC ( 183.60 °C. ) (est)
logP (o/w) 1.190 (est)
Soluble in water, 1.229e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for 3-O-methyl gallic acid usage levels up tonot for fragrance use.
Recommendation for 3-O-methyl gallic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

wine red wine

Synonyms

benzoic acid, 3,4-dihydroxy-5-methoxy- 3,4- dihydroxy-5-methoxybenzoic acid 4,5- dihydroxy-m-anisic acid 4,5- dihydroxy-meta-anisic acid 3-O- methylgallic acid PubMed: Studies on cytotoxic constituents from the leaves of Elaeagnus oldhamii Maxim. in non-small cell lung cancer A549 cells. PubMed: Synthesis of 3-O-methylgallic acid a powerful antioxidant by electrochemical conversion of syringic acid. PubMed: Phenolic acid concentrations in plasma and urine from men consuming green or black tea and potential chemopreventive properties for colon cancer. PubMed: The anthocyanin metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals. PubMed: Isolation of methyl syringate as a specific aflatoxin production inhibitor from the essential oil of Betula alba and aflatoxin production inhibitory activities of its related compounds. PubMed: Methyl-3-O-methyl gallate and gallic acid from the leaves of Peltiphyllum peltatum: isolation and comparative antioxidant, prooxidant, and cytotoxic effects in neuronal cells. PubMed: Gut metabolites of anthocyanins, gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde, inhibit cell proliferation of Caco-2 cells. PubMed: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. PubMed: Anti-ischemic activity and endothelium-dependent vasorelaxant effect of hydrolysable tannins from the leaves of Rhus coriaria (Sumac) in isolated rabbit heart and thoracic aorta. PubMed: Synthesis of (-)-epicatechin 3-(3-O-methylgallate) and (+)-catechin 3-(3-O-methylgallate), and their anti-inflammatory activity. PubMed: Identification of Cabernet Sauvignon anthocyanin gut microflora metabolites. PubMed: Resonant two-photon ionization mass spectrometry of jet-cooled phenolic acids and polyphenols. PubMed: Degradation of 3-O-methylgallate in Sphingomonas paucimobilis SYK-6 by pathways involving protocatechuate 4,5-dioxygenase. PubMed: Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. PubMed: A tetrahydrofolate-dependent O-demethylase, LigM, is crucial for catabolism of vanillate and syringate in Sphingomonas paucimobilis SYK-6. PubMed: [Studies on chemical constituents in fruits of Tibetan medicine Phyllanthus emblica]. PubMed: Antioxidant activity of phenolic and related compounds: a density functional theory study on the O-H bond dissociation enthalpy. PubMed: Characterization of the 3-O-methylgallate dioxygenase gene and evidence of multiple 3-O-methylgallate catabolic pathways in Sphingomonas paucimobilis SYK-6. PubMed: A novel tetrahydrofolate-dependent O-demethylase gene is essential for growth of Sphingomonas paucimobilis SYK-6 with syringate. PubMed: Gallic acid metabolites are markers of black tea intake in humans. PubMed: Degradation of substituted mandelic acids by meta fission reactions. PubMed: Interactions of natural phenols with macromolecules. PubMed: Aerobic and Anaerobic Catabolism of Vanillic Acid and Some Other Methoxy-Aromatic Compounds by Pseudomonas sp. Strain PN-1. PubMed: 2-pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species. PubMed: Bacterial degradation of 3,4,5-trimethoxycinnamic acid with production of methanol. PubMed: Studies in vitro on the involvement of O-sulphate esters in the formation of O-methylated 3,4-dihydroxybenzoic acid by rat liver. PubMed: Production of methanol from aromatic acids by Pseudomonas putida. PubMed: Alternative routes of aromatic catabolism in Pseudomonas acidovorans and Pseudomonas putida: gallic acid as a substrate and inhibitor of dioxygenases.