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3-O-methyl gallic acid
benzoic acid, 3,4-dihydroxy-5-methoxy-

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Name:3,4-dihydroxy-5-methoxybenzoic acid
CAS Number: 3934-84-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:223-512-8
FDA UNII: 8JA4OZ7166
Nikkaji Web:J217.773K
Beilstein Number:2695762
MDL:MFCD00016518
XlogP3:0.70 (est)
Molecular Weight:184.14776000
Formula:C8 H8 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
3,4-Dihydroxy-5-methoxy-benzoic acid 95%
Carbosynth
For experimental / research use only.
3,4-Dihydroxy-5-methoxybenzoic acid
ExtraSynthese
For experimental / research use only.
3-O-Methylgallic Acid
Santa Cruz Biotechnology
For experimental / research use only.
3,4-Dihydroxy-5-methoxy-benzoic Acid ≥97%
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for 3-O-methyl gallic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 3-O-methyl gallic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :19829
National Institute of Allergy and Infectious Diseases:Data
3,4-dihydroxy-5-methoxybenzoic acid
Chemidplus:0003934847
 
References:
 3,4-dihydroxy-5-methoxybenzoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):19829
Pubchem (sid):134985356
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C05616
HMDB (The Human Metabolome Database):HMDB13635
FooDB:FDB012009
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 wine red wine
Search Picture
 
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
 

Articles:

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.
 
Notes:
Present in hydrolysed soy protein and oak aged wines and brandies
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