3,5-dihydroxy-4-methoxybenzoic acid
3,5-dihydroxy-p-anisic acid
 
Notes:
catechol methyltransferase inhibitor; n1 same as nm. 4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792 4-O-methylgallic acid (4-OMGA), a major metabolite of gallic acid abundant in red wine. 4-OMGA inhibited the expression of intercellular adhesion molecule-1(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha), resulting in the suppression of leukocyte adhesion to HUVECs. PMID: 17027748 [HMDB]
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      Product(s):
      4319-02-2 3,5-DIHYDROXY-4-METHOXYBENZOIC ACID 95%
       
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CAS Number: 4319-02-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 224-346-9
FDA UNII: 0XW32QVU6J
Nikkaji Web: J205.704B
MDL: MFCD00016521
XlogP3: 1.00 (est)
Molecular Weight: 184.14776000
Formula: C8 H8 O5
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 423.40 °C. @ 760.00 mm Hg (est)
Flash Point: 354.00 °F. TCC ( 179.10 °C. ) (est)
logP (o/w): 0.760 (est)
Soluble in:
 water, 1.229e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
3,5-DIHYDROXY-4-METHOXYBENZOIC ACID 95%
Carbosynth
For experimental / research use only.
3,5-Dihydroxy-4-methoxybenzoic Acid
ExtraSynthese
For experimental / research use only.
4-O-Methylgallic acid (HPLC) ≥95%
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 3,5-dihydroxy-4-methoxybenzoic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 3,5-dihydroxy-4-methoxybenzoic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 4319-02-2
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 78016
National Institute of Allergy and Infectious Diseases: Data
 3,5-dihydroxy-4-methoxybenzoic acid
Chemidplus: 0004319022
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References:
 3,5-dihydroxy-4-methoxybenzoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 78016
Pubchem (sid): 135036026
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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
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB13198
FooDB: FDB001960
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 date palm stem
Search Trop  Picture
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Synonyms:
 benzoic acid, 3,5-dihydroxy-4-methoxy-
3,5-dihydroxy-p-anisic acid
3,5-dihydroxy-para-anisic acid
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Articles:
PubMed: Chemical constituents from the roots of Leea thorelii Gagnep.
PubMed: [Study on the chemical constituents in the fruit of Harrisonia perforata].
PubMed: Antinociceptive properties of bergenin.
PubMed: Conjugates of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) as cancer chemopreventive agents.
PubMed: [Chemical constituents from Myricaria alopecuroides].
PubMed: Interaction of polyphenolic metabolites with human serum albumin: a circular dichroism study.
PubMed: [Studies on chemical constituentsfrom leaves of Acer truncatum].
PubMed: Identification of two polyphenolic compounds with antioxidant activities in longan pericarp tissues.
PubMed: Acute effects of tea on fasting and non-fasting plasma total homocysteine concentrations in human subjects.
PubMed: 4-O-methylgallic acid down-regulates endothelial adhesion molecule expression by inhibiting NF-kappaB-DNA-binding activity.
PubMed: 4-O-Methylgallic acid suppresses inflammation-associated gene expression by inhibition of redox-based NF-kappaB activation.
PubMed: Drinking tea is associated with lower plasma total homocysteine in older women.
PubMed: Is reversal of endothelial dysfunction by tea related to flavonoid metabolism?
PubMed: Antiangiogenic activity of 4-O-methylgallic acid from Canavalia gladiata, a dietary legume.
PubMed: Two pyranocoumarins from the seeds of Calophyllum polyanthum.
PubMed: Phenolic acid metabolites as biomarkers for tea- and coffee-derived polyphenol exposure in human subjects.
PubMed: Tea intake is inversely related to blood pressure in older women.
PubMed: Can black tea influence plasma total homocysteine concentrations?
PubMed: Method for analysis of tannic acid and its metabolites in biological samples: application to tannic acid metabolism in the rat.
PubMed: Acute effects of ingestion of black tea on postprandial platelet aggregation in human subjects.
PubMed: Regular ingestion of tea does not inhibit in vivo lipid peroxidation in humans.
PubMed: Effects of regular ingestion of black tea on haemostasis and cell adhesion molecules in humans.
PubMed: Red wine polyphenols, in the absence of alcohol, reduce lipid peroxidative stress in smoking subjects.
PubMed: Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans.
PubMed: Acute effects of ingestion of black and green tea on lipoprotein oxidation.
PubMed: Determination of gallic acid and its metabolites in human plasma and urine by high-performance liquid chromatography.
PubMed: Rumen involvement in sheep tannic acid metabolism.
PubMed: Antimicrobial constituents of Rhus glabra.
PubMed: Isolation and cytotoxicity of two new flavonoids from Chrysosplenium grayanum and related flavonols.
PubMed: Toxic interaction between narcotic analgesics and inhibitors of catechol-O-methyltransferase.
PubMed: Catechol-O-methyltransferase. II. A new class of inhibitors of catechol-o-methyltransferase; 3,5-dihydroxy-4-methoxybenzoic acid and related compounds.
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