Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:56 UTC
Primary IDFDB012004
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEthyl gallate
DescriptionEthyl gallate, also known as ethyl gallic acid or E313, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 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.
CAS Number831-61-8
Structure
Thumb
Synonyms
SynonymSource
Ethyl gallic acidGenerator
Ethyl 3,4,5-trihydroxybenzoateHMDB
e313HMDB
3,4,5-Trihydroxybenzoic acid ethyl esterHMDB
EthylgallateHMDB
Gallic acid ethyl esterHMDB
NIPA 48HMDB
Nipagallin aHMDB
PhyllemblinHMDB
Progallin aHMDB
Ethyl gallateHMDB
Progallin Abiospider
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O5
IUPAC nameethyl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=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
Isomeric SMILESCCOC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight198.174
Monoisotopic Molecular Weight198.052823422
Classification
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:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionC 54.55%; H 5.09%; O 40.37%DFC
    Melting PointMp 160-162° (anhyd.)DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP1.30HANSCH,C ET AL. (1995)
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0291200000-d1ec8193d3b49ff9e32eJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0291200000-d1ec8193d3b49ff9e32eJSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-4b5fba46d4a66277f0c4JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00ba-3009000000-48f27e32e6f1e91e75fcJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-c1205d52b04ae343a22dJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0900000000-092da9b1eda49f7f42dfJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v6s-4900000000-8569bd2257b09b6bb080JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-15e325cfb82bcc5051abJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-1900000000-2e8046390a06b057aaadJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-4900000000-196c0eeac6ec036a79fcJSpectraViewer
    ChemSpider ID12693
    ChEMBL IDCHEMBL453196
    KEGG Compound IDNot Available
    Pubchem Compound ID13250
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID439
    DrugBank IDNot Available
    HMDB IDHMDB33836
    CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:HCL73-L
    EAFUS IDNot Available
    Dr. Duke IDGALLIC-ACID-ETHYL-ESTER
    BIGG IDNot Available
    KNApSAcK IDC00030222
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID439
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti methicillin-resistant Staphylococcus aureus33282 A substance that kills or slows the growth of bacteria.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).
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.