Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2018-05-28 23:02:31 UTC
Primary IDFDB000663
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl gallate
DescriptionMethyl gallate, also known as methyl 3 or methyl galloic acid, is a member of the class of compounds known as galloyl esters. Galloyl esters are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. Methyl gallate is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Methyl gallate can be found in peach and pomegranate, which makes methyl gallate a potential biomarker for the consumption of these food products. Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid .
CAS Number99-24-1
Structure
Thumb
Synonyms
SynonymSource
Methyl 3ChEMBL
45-TrihydroxybenzoateChEMBL
Methyl galloateChEMBL
345-Trihydroxy-benzoic acid methyl esterChEMBL
Methyl gallic acidGenerator
45-Trihydroxybenzoic acidGenerator
Methyl galloic acidGenerator
345-Trihydroxy-benzoate methyl esterGenerator
Gallic acid, methyl esterMeSH
Methyl 3,4,5-trihydroxybenzoateMeSH
3,4,5-Trihydroxy-benzoic acid methyl esterbiospider
Benzoic acid, 3,4,5-trihydroxy-, methyl esterbiospider
Gallic acid methyl esterbiospider
Gallicin?db_source
Methyl gallatedb_source
Methylgallatebiospider
Predicted Properties
PropertyValueSource
Water Solubility4.11 g/LALOGPS
logP1.01ALOGPS
logP1.07ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.03 m³·mol⁻¹ChemAxon
Polarizability16.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H8O5
IUPAC namemethyl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
InChI KeyFBSFWRHWHYMIOG-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
Classification
DescriptionThis compound belongs to the class of chemical entities known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentGalloyl esters
Alternative Parents
Substituents
  • Galloyl ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.18%; H 4.38%; O 43.44%DFC
Melting PointMp 157°DFC
Boiling PointNot Available
Experimental Water Solubility10.6 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.86HANSCH,C ET AL. (1995)
Experimental pKapKa1 7.88 (25°, 0.1M KNO3)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data283 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-401d71dbf57a34ddc235View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-51202d68563eee1bdab2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvj-5900000000-b7c5629192d45e0d9cb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-90389cc7f792df061dc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-50a11e1df989b937ae23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-5900000000-59e6084d7e7bb182a1a7View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7428
Pubchem Substance IDNot Available
ChEBI ID551062
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:BFL36-J
EAFUS IDNot Available
Dr. Duke IDMETHYL-GALLATE
BIGG IDNot Available
KNApSAcK IDC00030754
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti allergenic50857 A drug used to treat allergic reactions.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
Gram(+)icide33282 A substance that kills or slows the growth of bacteria.DUKE
Gram(-)icide33282 A substance that kills or slows the growth of bacteria.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
reverse transcriptase inhibitor59897 An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need to reproduce.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.