(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one hydrate

• ChemBase ID: 133112
• Molecular Formular: C15H14O8
• Molecular Mass: 322.26686
• Monoisotopic Mass: 322.06886741
• SMILES: c1cc(c(cc1[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O)O)O.O
• Canonical SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O.O
• InChI: InChI=1S/C15H12O7.H2O/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6;/h1-5,14-19,21H;1H2/t14-,15+;/m0./s1
• InChIKey: DNQPGSVMBPSRIR-LDXVYITESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one hydrate
• IUPAC Traditional name: (+)-taxifolin hydrate
• Synonyms: 3,3′,4′,5,7-Pentahydroxyflavanone hydrate; Dihydroquercetin hydrate; (±)-Taxifolin hydrate

Database IDs

• CAS Number: 24198-97-8(anhydrous)
• MDL Number: MFCD11044454
• PubChem SID: 162227389; 24278739
• PubChem CID: 71308639

CALCULATED PROPERTIES

• Acid pKa: 7.797971
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.8142184
• LogD (pH = 7.4): 1.6695796
• Log P: 1.8163843
• Molar Refractivity: 74.6089 cm^3
• Polarizability: 28.610525 Å^3
• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Hexa(15211)

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - T4512

Biochem/physiol Actions
Flavonoid, antioxidant. Inhibits lipogenesis in cancer cells, most likely by targeting fatty acid synthase activity.