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

• ChemBase ID: 127523
• 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-IUODEOHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: epigallocatechin
• Synonyms: (2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol; Epigallocatechol; l-Gallocatecholl); (-)-3,3',4',5,5',7-Flavanhexol; (-)-Epigallocatechol; (-)-epi-Gallocatechin; (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychroman; 1-epi-3',4',5',5,7-Pentahydroxy-3-flavanol; 3,3',4',5,5',7-Flavanhexol; Antiscurvy factor C2; EGC; Galloepicatechin; L-Epigallocatechin; NSC 674039; Sunphenon EGC; epi-Gallocatechin; l-Epigallocatechol; (-)-Epigallocatechin; epigallocatechin; (+)-gallocatechin; Gallocatechol; (-)-cis-3,3′,4′,5,5′,7-Hexahydroxyflavane; (-)-Epigallocatechin; (-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; Epigallocatechin; (-)-cis-2-(3,4,5-三羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7-三醇; (-)-表没食子儿茶素

Database IDs

• CAS Number: 970-74-1; 1617-55-6
• MDL Number: MFCD00075939
• PubChem SID: 24846148; 24894529; 162221842
• PubChem CID: 72277; 65084
• CHEMBL: 47386
• MeSH Name: Gallocatechol
• Wikipedia Title: Gallocatechol

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥90% (HPLC); ≥95% (HPLC); 98.0
• Grade: analytical standard
• Biological Source: from green tea
• Empirical Formula (Hill Notation): C15H14O7

DETAILS

Sigma Aldrich - 08108

Biochem/physiol Actions
Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - E3768

Biochem/physiol Actions
Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.
抗氧化剂
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Toronto Research Chemicals - E588490

A natural constituent of green tea. It is an antioxidant and a potential cancer chemopreventive agent. An epimer of (-)-Gallocatechin (G188990).

REFERENCES

• Kalaivani, M. et al.: J. Pharm. Res., 3, 2901 (2010)
• Letchoumy, P.V. et al.: Arch. Med. Sci., 3, 330 (2010)
• Zhu, N. et al.: J. Food Lipids, 7, 275 (2010)