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

• ChemBase ID: 1976
• Molecular Formular: C15H12O7
• Molecular Mass: 304.25158
• Monoisotopic Mass: 304.05830272
• SMILES: O[C@@H]1[C@H](Oc2cc(O)cc(O)c2C1=O)c1ccc(O)c(O)c1
• Canonical SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O
• InChI: InChI=1S/C15H12O7/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/t14-,15+/m0/s1
• InChIKey: CXQWRCVTCMQVQX-LSDHHAIUSA-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
• IUPAC Traditional name: (2s,3s)-trans-dihydroquercetin; (+)-taxifolin
• Synonyms: (2s,3s)-Trans-Dihydroquercetin; (2R,3R)-3,3′,4′,5,7-Pentahydroxyflavanone; (2R,3R)-Dihydroquercetin; Taxifolin; Dihydroquercetin; Taxifoliol; Distylin; Catechin hydrate; (+)-Taxifolin; trans-Dihydroquercetin; (+)-Dihydroquercetin; Taxifolin; DIHYDROQUERCETIN; 3,3',4',5,7-Pentahydroxyflavanone; (2R,3R)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-1-benzopyran-4-one; (+)-(2R,3R)-Dihydroquercetin; (2R,3R)-(+)-Taxifolin; (2R,3R)-3,3',4',5,7-Pentahydroxyflavanone; 3,5,7,3',4'-Pentahydroxyflavanone; Diquertin; Lariksin; Lavitol; Taxifolin; (+)-trans Taxifolin; 3,3’,4’,5,7-Pentahydroxyflavanone; (+/-)-trans Taxifolin; (2R,3R)-二氢槲皮素; (2R,3R)-3,3′,4′,5,7-五羟基黄烷酮; 花旗松素

Database IDs

• CAS Number: 24198-97-8; 480-18-2
• EC Number: 207-543-4
• MDL Number: MFCD00006845
• Beilstein Number: 5299277
• PubChem SID: 24887336; 160965431; 46508033
• PubChem CID: 439533
• CHEMBL: 66
• Wikipedia Title: Taxifolin

CALCULATED PROPERTIES

JChem

• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 7.742827
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.813926
• LogD (pH = 7.4): 1.6518341
• Log P: 1.8163843
• Molar Refractivity: 74.6089 cm^3
• Polarizability: 28.610525 Å^3

ALOGPS 2.1

• Solubility (Water): 1.16e+00 g/l
• Log P: 1.07
• LOG S: -2.42

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: brown powder; Off-White to Pale Yellow Solid; Powder; Yellow Solid
• Melting Point: <225°C (dec.); 216-220°C
• Hydrophobicity(logP): 0.95 [PERRISSOUD,D & TESTA,B (1986)]

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

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

Product Information

• Purity: ≥85% (HPLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C15H12O7
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05203990

MP Biomedicals Rare Chemical collection

DrugBank - DB02224

Drug information: experimental

Sigma Aldrich - 78666

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 78666.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - T010005

An antioxidant flavenoid.

Toronto Research Chemicals - T010000

An antioxidant flavenoid.

REFERENCES

• Dixon, D., et al.: J. Biol. Chem., 285, 36322 (2010)
• Sheu, M., et al.: Chem. Pharm. Bull., 58, 1187 (2010)