CAS 3371-27-5|(2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol|@epigallocatechin|Epigallocatechin|(-)-Gallocatechin|(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-ben...

General Information

Structure

Molecular Formula

C₁₅H₁₄O₇

Molecular Mass

306.26746

Exact Mass

306.07395279

Charge

InChI

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-DOMZBBRYSA-N

Canonic Smiles

Oc1cc2O[C@@H](c3cc(O)c(c(c3)O)O)[C@@H](Cc2c(c1)O)O

Isomeric Smiles

O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c(O)c1

Calculated Properties

JChem

LogD (pH = 7.4)

1.47

LogD (pH = 5.5)

1.49

Log P

1.49

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

8.75

Polar Surface Area

130.61

Polarizability

29.36

Molar Refractivity

75.98

LOG S

-1.29

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC name

(2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

IUPAC Traditional name

@epigallocatechin epigallocatechin (-)-gallocatechin

Synonyms

Epigallocatechin(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol(-)-Gallocatechinl-Gallocatechin(-)-Gallocatechin(2S,3R)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol(2S-trans)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol(-)-Gallocatechol(2S,3R)-flavan-3,3',4',5,5',7-hexol(2S,3R)-(-)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol(2S,3R)-gallocatechin(-)-gallocatechin(2S,3R)-flavan-3,5,7,3',4',5'-hexolent-gallocatechin

Names and Identifiers

Registration numbers

MDL Number

MFCD01632616

CAS Number

3371-27-5

PubChem SID

2489526646506265160966905160646133

PubChem CID

9882981

BRENDA Database

3.1.1.201.17.1.31.3.1.1121.1.1.1461.3.1.775.6.2.1

NMRShiftDB Database

60016314

MetaboLights Database

MTBLS494MTBLS1405MTBLS403MTBLS519MTBLS784MTBLS353MTBLS4099MTBLS3769MTBLS3657

SureChEMBL Database

SCHEMBL1742127

BKMS React Database

126759

BRENDA Ligand Database

CHEMBL

BindingDB Database

Chemspider ID

CHEBI ID

CompTox Database

Wikipedia Title

Registration numbers

Properties

Physical Property

Solubility

H2O: soluble5 mg/mL (with brief sonication)

alcohol: soluble

Product Information

Purity

≥98% (HPLC)

≥97.0% (HPLC)

Empirical Formula (Hill Notation)

C15H14O7

Shelf Life

(limited shelf life, expiry date on the label)

Grade

analytical standard

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB03823

Drug information: experimental

Sigma Aldrich

G6657

Other Notes
Polyphenolic compound found in green tea. An epimer of (-)-epigallocatechin.
Biochem/physiol Actions
Possesses free radical scavenging ability. Inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

TRC

G188990

An antioxidant with free radical scavenging ability; a potential cancer chemopreventive agent. It inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells. An epimer of (-)-Epigallocatechin (E588940).

ChEBI

CHEBI:71225

A a gallocatechin that has (2S,3R)-configuration.

Molecule Details

References

PubChem Literature

From Data Sources

• Sakanaka, S. et al.: Biosci. Biotechnol. Biochem., 60, 745 (1999)

• Guo, Q. et al.: Biochim. Biophys. Acta, 1427, 13 (1999)

References

Bioactivity

PubChem BioAssay