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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:37 UTC
Update Date2020-11-09 23:20:24 UTC
HMDB IDHMDB0033836
Secondary Accession Numbers
  • HMDB33836
Metabolite Identification
Common NameEthyl gallate
DescriptionEthyl gallate, also known as ethyl gallic acid, belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. A gallate ester obtained by the formal condensation of gallic acid with ethanol. Ethyl gallate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ethyl gallate is found, on average, in the highest concentration within grape wines and vinegars. Ethyl gallate has also been detected, but not quantified in, fruits and guava. This could make ethyl gallate a potential biomarker for the consumption of these foods.
Structure
Data?1570205367
Synonyms
ValueSource
Ethyl gallic acidGenerator
Ethyl 3,4,5-trihydroxybenzoateMeSH
e313ChEMBL, HMDB
3,4,5-Trihydroxybenzoic acid ethyl esterHMDB
EthylgallateHMDB
Gallic acid ethyl esterHMDB
NIPA 48HMDB
Nipagallin aHMDB
PhyllemblinHMDB
Progallin aHMDB
Ethyl gallateHMDB
Chemical FormulaC9H10O5
Average Molecular Weight198.174
Monoisotopic Molecular Weight198.052823422
IUPAC Nameethyl 3,4,5-trihydroxybenzoate
Traditional Nameethyl gallate
CAS Registry Number831-61-8
SMILES
CCOC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3
InChI KeyVFPFQHQNJCMNBZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and 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
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point160 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.30Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.42 g/LALOGPS
logP1.48ALOGPS
logP1.42ChemAxon
logS-1.8ALOGPS
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 Count3ChemAxon
Refractivity48.77 m³·mol⁻¹ChemAxon
Polarizability19.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0291200000-d1ec8193d3b49ff9e32e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0291200000-d1ec8193d3b49ff9e32e2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-4b5fba46d4a66277f0c42017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00ba-3009000000-48f27e32e6f1e91e75fc2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-af60a1c80c1290575d0b2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-c1205d52b04ae343a22d2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0900000000-092da9b1eda49f7f42df2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v6s-4900000000-8569bd2257b09b6bb0802015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-15e325cfb82bcc5051ab2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-1900000000-2e8046390a06b057aaad2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-4900000000-196c0eeac6ec036a79fc2015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-668193ba8df755614ff12021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0900000000-1d1ddf3b0fe1b2fe7dcf2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016u-9600000000-a4a2896002a0a5d002582021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0127 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.105 +/- 0.137 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID439
FooDB IDFDB012004
KNApSAcK IDC00030222
Chemspider ID12693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl gallate
METLIN IDNot Available
PubChem Compound13250
PDB IDNot Available
ChEBI ID87247
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mori T, Chang C, Maurtua D, Hammond GB: Isolation of the active compound in Mauria heterophylla, a Peruvian plant with antibacterial activity. Phytother Res. 2006 Feb;20(2):160-1. [PubMed:16444672 ]
  2. Paulino N, Pizollatti MG, Yunes RA, Filho VC, Creczynski-Pasa TB, Calixto JB: The mechanisms underlying the relaxant effect of methyl and ethyl gallates in the guinea pig trachea in vitro: contribution of potassium channels. Naunyn Schmiedebergs Arch Pharmacol. 1999 Sep;360(3):331-6. [PubMed:10543436 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .