Basic information
- CAS
970-74-1- Standard SMILES
Oc1cc(O)c2c(c1)O[C@H](c1cc(O)c(O)c(O)c1)[C@H](O)C2- InChIKey
XMOCLSLCDHWDHP-IUODEOHRSA-N- Molecular formula
- C15H14O7
- Average molar mass
- 306.27 g/mol
- Monoisotopic mass
- 306.07395279
Overview
(-)-epigallocatechin is a flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration. It has a role as an antioxidant, a plant metabolite and a food component. It is a catechin and a flavan-3,3',4',5,5',7-hexol. It is an enantiomer of a (+)-epigallocatechin.
Names & identifiers
- Preferred name
- Epigallocatechin
- IUPAC
- (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
- English name
- (-)-Epigallocatechin
- Molecular formula
- C15H14O7
- Molecular weight
- 306.27
Names & synonyms
(-)-EpigallocatechinEpigallocatechin970-74-1EpigallocatecholL-Epigallocatechinepi-GallocatechinAntiscurvy factor C2(-)-EpigallocatecholGalloepicatechin3,3',4',5,5',7-Flavanhexol(-)-epi-GallocatechinSunphenon EGC
Show more names
epi-l-Epigallocatechol(-)-EGC, ≥98%(HPLC)(+)-Epigallocatechin(2R)-3,4-Dihydro-2α-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triolTFPI1(-)-EGCNSC 674039
(-)-3,3',4',5,5',7-Flavanhexol2,3-cis-epigallocatechin(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol7Z197MG6QLNSC-674039(2R,3R)-2-(3,4,5-trihydroxyphenyl)chroman-3,5,7-triolCHEBI:42255DTXSID40891550
Database identifiers
- CAS
970-74-1- PubChem CID
- 72277
- DTXSID
DTXSID40891550- ChEMBL
CHEMBL47386- ChEBI
CHEBI:42255- UNII
- 7Z197MG6QL
- EC Number
- 619-254-4
- Nikkaji
- J277.681B
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 131 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 380
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavans, Flavanols and Leucoanthocyanidins [PK1202]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point219 - 221 °C
Physical DescriptionSolid
Collision Cross Section
165.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
152.21 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 208 · 208-210°C
- alpha
- -50 · -50 º (c=0.04, EtOH)
- Boiling point
- 685.6 · 685.6±55.0 °C(Predicted)
- Density
- 1.695 · 1.695±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.02 · 9.02±0.15(Predicted)
- color
- White to Light Beige
- biological source
- green tea
- λmax
- 278 nm · 278nm(MeOH)(lit.)
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- 1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
- InChIKey
- XMOCLSLCDHWDHP-IUODEOHRSA-N
- SMILES
- O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3cc(O)c(O)c(O)c3
- LogP
- -0.1 · -0.100 (est)
- CAS DataBase Reference
- 970 · 970-74-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 Z197MG6QL · 7Z197MG6QL
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- RTECS
- 5100000 · KB5100000
- F
- 3 · 3-10
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 75% (3 of 4) of all reports.
Warning
H315 (25%): 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 4 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (25%)
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- KB5100000
- hs_code
- 29329990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolism/Metabolites(-)-Epigallocatechin has known human metabolites that include (-)-Epigallocatechin, 3p-hydroxy-glucuronide.
Cellular LocationsCytoplasm
Applications
Usesantineoplastic
UsesA natural constituent of green tea. It is an antioxidant and a potential cancer chemopreventive agent. An epimer of (-)-Gallocatechin (G188990).
UsesA natural product from green tea that induces apoptosis
General Description()-Epigallocatechin (EGC) belongs to the tea catechins group of polyphenols.
Suppliers100 total
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Additional notes
DefinitionChEBI: (-)-epigallocatechin is a flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration. It has a role as an antioxidant, a plant metabolite and a food component. It is a flavan-3,3',4',5,5',7-hexol and a catechin. It is an enantiomer of a (+)-epigallocatechin.
Related reactions
1 records
Compound notes
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