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

• ChemBase ID: 3466
• Molecular Formular: C15H14O7
• Molecular Mass: 306.26746
• Monoisotopic Mass: 306.07395279
• SMILES: O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c(O)c1
• Canonical SMILES: Oc1cc2O[C@@H](c3cc(O)c(c(c3)O)O)[C@@H](Cc2c(c1)O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: @epigallocatechin; epigallocatechin
• Synonyms: Epigallocatechin; (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; (-)-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; l-Gallocatechin; (-)-Gallocatechin

Database IDs

• CAS Number: 3371-27-5
• MDL Number: MFCD01632616
• PubChem SID: 46506265; 24895266; 160966905
• PubChem CID: 9882981

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.728533
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 1.4912869
• LogD (pH = 7.4): 1.4716134
• Log P: 1.4915417
• Molar Refractivity: 75.9806 cm^3
• Polarizability: 29.079527 Å^3
• Polar Surface Area: 130.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.71
• LOG S: -2.55
• Solubility (Water): 8.71e-01 g/l

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; H2O: soluble5 mg/mL (with brief sonication)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); ≥98% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H14O7

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

Toronto Research Chemicals - 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).

REFERENCES

• Guo, Q. et al.: Biochim. Biophys. Acta, 1427, 13 (1999)
• Sakanaka, S. et al.: Biosci. Biotechnol. Biochem., 60, 745 (1999)