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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:12:45 UTC
Update Date2022-03-07 02:55:34 UTC
HMDB IDHMDB0037944
Secondary Accession Numbers
  • HMDB37944
Metabolite Identification
Common Name(-)-Epicatechin 3-O-gallate
Description(-)-Epicatechin 3-O-gallate, also known as 3-O-galloylepicatechin or ECG, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin (-)-Epicatechin 3-O-gallate is a bitter tasting compound (-)-Epicatechin 3-O-gallate is found, on average, in the highest concentration within a few different foods, such as red tea, herbal tea, and green tea and in a lower concentration in german camomiles (Matricaria recutita), peppermints (Mentha X piperita), and teas (Camellia sinensis) (-)-Epicatechin 3-O-gallate has also been detected, but not quantified in, several different foods, such as pears (Pyrus communis), lettuces (Lactuca sativa), olives (Olea europaea), brussel sprouts (Brassica oleracea var. gemmifera), and apricots (Prunus armeniaca). This could make (-)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods (-)-Epicatechin 3-O-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 small amount of articles have been published on (-)-Epicatechin 3-O-gallate.
Structure
Thumb
Synonyms
Chemical FormulaC22H18O10
Average Molecular Weight442.376
Monoisotopic Molecular Weight442.08999678
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(-)-epicatechin 3-O-gallate
CAS Registry Number1257-08-5
SMILES
OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChI KeyLSHVYAFMTMFKBA-TZIWHRDSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechin gallates
Alternative Parents
Substituents
  • Catechin gallate
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Catechol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point257 - 258 °CNot Available
Boiling Point861.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility36.86 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.670 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available202.902http://allccs.zhulab.cn/database/detail?ID=AllCCS00001419
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 128 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 128 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 IDNot Available
FooDB IDFDB017114
KNApSAcK IDC00008866
Chemspider ID97034
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpicatechin_gallate
METLIN IDNot Available
PubChem Compound107905
PDB IDNot Available
ChEBI ID70255
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1680971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .