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

• ChemBase ID: 133158
• Molecular Formular: C15H14O6
• Molecular Mass: 290.26806
• Monoisotopic Mass: 290.07903817
• SMILES: c1cc(c(cc1[C@H]1[C@@H](Cc2c(cc(cc2O1)O)O)O)O)O
• Canonical SMILES: Oc1cc2O[C@@H](c3ccc(c(c3)O)O)[C@@H](Cc2c(c1)O)O
• InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m1/s1
• InChIKey: PFTAWBLQPZVEMU-HIFRSBDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: α catechin
• Synonyms: (-)-trans-3,3′,4′,5,7-Pentahydroxyflavane; (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; (-)-Catechin; (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; (-)-Catechin

Database IDs

• CAS Number: 18829-70-4
• EC Number: 242-611-7
• MDL Number: MFCD00135997
• PubChem SID: 162227435; 24892260
• PubChem CID: 73160

CALCULATED PROPERTIES

• Acid pKa: 9.004574
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 1.7949721
• LogD (pH = 7.4): 1.784451
• Log P: 1.795107
• Molar Refractivity: 73.9997 cm^3
• Polarizability: 28.420568 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

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 ... BACE1(23621)

Product Information

• Purity: ≥98% (HPLC); ≥98.5% (HPLC)
• Grade: puriss.
• Biological Source: from green tea
• Empirical Formula (Hill Notation): C15H14O6

DETAILS

Toronto Research Chemicals - C217505

A natural phenol antioxidant plant secondary metabolite.

REFERENCES

• Wu, Z., et al.: J. Agric. Food Chem., 59, 10737 (2011)