Basic information
- Standard SMILES
O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1ccc(O)c(O)c1)c1cc(O)c(O)c(O)c1- InChIKey
LSHVYAFMTMFKBA-TZIWHRDSSA-N- Molecular formula
- C22H18O10
- Average molar mass
- 442.4 g/mol
- Monoisotopic mass
- 442.08999678
Overview
(-)-epicatechin-3-O-gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. It has a role as a metabolite, an EC 3.2.1.1 (alpha-amylase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a catechin, a polyphenol and a gallate ester. It is functionally related to a gallic acid and a (-)-epicatechin.
Names & identifiers
- Preferred name
- Epicatechin Gallate
- IUPAC
- [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Names & synonyms
Epicatechin gallate92587OVD8ZEpicatechin-3-galloyl esterDTXSID70925231NSC-636594RefChem:590910DTXCID101354061863-03-6(-)-Epicatechin gallate1257-08-5(-)-epicatechingallate(-)-Epicatechin-3-O-gallate
Show more names
(-)-Epicatechin-3-gallateL-Epicatechin gallateepicatechin monogallateTeatanninECG(-)-Epicatechin 3-O-gallateEpicatechol, gallate3-O-Galloylepicatechin
Database identifiers
- CAS
1257-08-5- PubChem CID
- 107905
- DTXSID
DTXSID70925231- ChEMBL
CHEMBL36327- ChEBI
CHEBI:70255- UNII
- 92587OVD8Z
- EC Number
- 603-088-4
- Nikkaji
- J277.682K
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 649
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavans, Flavanols and Leucoanthocyanidins [PK1202]
Melting Point257 - 258 °C
Physical DescriptionSolid
Collision Cross Section202.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 40% (2 of 5) of reports.
Warning
H315 (60%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (60%)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Cellular LocationsMembrane
Related reactions
1 records
Linked notes
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