3,4,6-trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-5H-benzo[7]annulen-5-one

• ChemBase ID: 157220
• Molecular Formular: C29H24O12
• Molecular Mass: 564.49366
• Monoisotopic Mass: 564.12677621
• SMILES: c1c(cc(c(=O)c2c1c(cc(c2O)O)[C@@H]1[C@@H](Cc2c(cc(cc2O1)O)O)O)O)[C@@H]1[C@@H](Cc2c(cc(cc2O1)O)O)O
• Canonical SMILES: Oc1cc2O[C@@H]([C@@H](Cc2c(c1)O)O)c1cc2c(cc(c(c2c(=O)c(c1)O)O)O)[C@H]1Oc2cc(O)cc(c2C[C@H]1O)O
• InChI: InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22-,28-,29-/m1/s1
• InChIKey: IPMYMEWFZKHGAX-ZKSIBHASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4,6-trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-5H-benzo[7]annulen-5-one
• IUPAC Traditional name: theaflavin
• Synonyms: 3,4,5-Trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-2-chromanyl]-6-benzo[7]annulenone; 3,4,6-Trihydroxy-1,8-bis(3α,5,7-trihydroxy-2α-chromanyl)-5H-benzocyclohepten-5-one; Theaflavin; 1,8-Bis[(2R,3R)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-5H-benzocyclohepten-5-one; Theaflavine; (-)-Theaflavin; Theaflavin 1; [2R-[2α(2R*,3R*),3α]]-1,8-Bis(3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-5H-benzocyclohepten-5-one; Theaflavin; 3,4,5-三羟基-1,8-双[(2R,3R)-3,5,7-三羟基-2-苯并二氢吡喃基]-6-苯并[7]环烯酮; 3,4,6-三羟基-1,8-双(3α,5,7-三羟基-2α-苯并二氢吡喃基)-5H-苯并环庚烯-5-酮; 茶黄素

Database IDs

• CAS Number: 4670-05-7
• MDL Number: MFCD03427500
• PubChem SID: 162251357
• PubChem CID: 114777

CALCULATED PROPERTIES

• Acid pKa: 7.9620113
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): 2.8256803
• LogD (pH = 7.4): 2.7221303
• Log P: 2.8282638
• Molar Refractivity: 144.2674 cm^3
• Polarizability: 54.09713 Å^3
• Polar Surface Area: 217.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥90.0% (HPLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C29H24O12

DETAILS

Toronto Research Chemicals - T340200

Theaflavin is a polyphenolic compound found in black tea. Theaflavin derivatives show anti-HIV-1 activity by targeting gp41. Theaflavin is a potent inhibitor of amyloid-β (Aβ) and α-synuclein (αS) fibrillogenesis. Theaflavin also shows potent anti-tumor a

REFERENCES

• Grelle, G. et al.: Biochemistry, 50, 10624 (2011)
• Liu, S. et al.: Biochim. Biophys. Acta, 1723, 270 (2011)
• Leone, M. et al.: Cancer, Res., 63, 8118 (2011)
• Letchoumy, P.V. et al.: Arch. Med. Sci., 3, 330 (2011)