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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:37 UTC
Update Date2022-03-07 02:53:52 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. Ethyl gallate is found, on average, in the highest concentration within grape wine and vinegar. Ethyl gallate has also been detected, but not quantified in, fruits and guavas (Psidium guajava). This could make ethyl gallate a potential biomarker for the consumption of these foods. Ethyl gallate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Ethyl gallate.
Structure
Data?1570205367
Synonyms
ValueSource
Ethyl gallic acidGenerator
e313ChEMBL, HMDB
3,4,5-Trihydroxybenzoic acid ethyl esterHMDB
Ethyl 3,4,5-trihydroxybenzoateHMDB, MeSH
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility74390 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.30Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.95231661259
DarkChem[M-H]-143.50531661259
DeepCCS[M+H]+144.64830932474
DeepCCS[M-H]-142.2930932474
DeepCCS[M-2H]-176.33730932474
DeepCCS[M+Na]+151.15530932474
AllCCS[M+H]+142.832859911
AllCCS[M+H-H2O]+138.732859911
AllCCS[M+NH4]+146.632859911
AllCCS[M+Na]+147.732859911
AllCCS[M-H]-141.032859911
AllCCS[M+Na-2H]-141.632859911
AllCCS[M+HCOO]-142.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl gallateCCOC(=O)C1=CC(O)=C(O)C(O)=C12963.8Standard polar33892256
Ethyl gallateCCOC(=O)C1=CC(O)=C(O)C(O)=C11871.8Standard non polar33892256
Ethyl gallateCCOC(=O)C1=CC(O)=C(O)C(O)=C11740.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethyl gallate,1TMS,isomer #1CCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C)=C11869.4Semi standard non polar33892256
Ethyl gallate,1TMS,isomer #2CCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O)=C11863.2Semi standard non polar33892256
Ethyl gallate,2TMS,isomer #1CCOC(=O)C1=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C11926.1Semi standard non polar33892256
Ethyl gallate,2TMS,isomer #2CCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11903.2Semi standard non polar33892256
Ethyl gallate,3TMS,isomer #1CCOC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11954.1Semi standard non polar33892256
Ethyl gallate,1TBDMS,isomer #1CCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12130.9Semi standard non polar33892256
Ethyl gallate,1TBDMS,isomer #2CCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C12125.2Semi standard non polar33892256
Ethyl gallate,2TBDMS,isomer #1CCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12378.7Semi standard non polar33892256
Ethyl gallate,2TBDMS,isomer #2CCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12359.5Semi standard non polar33892256
Ethyl gallate,3TBDMS,isomer #1CCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12607.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl gallate GC-MS (3 TMS)splash10-001i-0291200000-d1ec8193d3b49ff9e32e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl gallate GC-MS (Non-derivatized)splash10-001i-0291200000-d1ec8193d3b49ff9e32e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl gallate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-4b5fba46d4a66277f0c42017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl gallate GC-MS (3 TMS) - 70eV, Positivesplash10-00ba-3009000000-48f27e32e6f1e91e75fc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl gallate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 10V, Positive-QTOFsplash10-0002-0900000000-c1205d52b04ae343a22d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 20V, Positive-QTOFsplash10-0udj-0900000000-092da9b1eda49f7f42df2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 40V, Positive-QTOFsplash10-0v6s-4900000000-8569bd2257b09b6bb0802015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 10V, Negative-QTOFsplash10-0002-0900000000-15e325cfb82bcc5051ab2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 20V, Negative-QTOFsplash10-0f92-1900000000-2e8046390a06b057aaad2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 40V, Negative-QTOFsplash10-0fb9-4900000000-196c0eeac6ec036a79fc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 10V, Positive-QTOFsplash10-0002-0900000000-15db75971e9343b075ff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 20V, Positive-QTOFsplash10-0udj-0900000000-cc2f820b6106f40a6b342021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 40V, Positive-QTOFsplash10-0uxr-9800000000-acb201bce395e18354e62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 10V, Negative-QTOFsplash10-0002-0900000000-668193ba8df755614ff12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 20V, Negative-QTOFsplash10-0udj-0900000000-1d1ddf3b0fe1b2fe7dcf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl gallate 40V, Negative-QTOFsplash10-016u-9600000000-a4a2896002a0a5d002582021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView 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
Good Scents IDrw1697681
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.. .