(2R,3R)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 177766
• Molecular Formular: C25H22O10
• Molecular Mass: 482.43618
• Monoisotopic Mass: 482.1212969
• SMILES: c1c(c(cc(c1)C1Oc2c(OC1CO)ccc(c2)[C@H]1Oc2c(C(=O)[C@@H]1O)c(cc(c2)O)O)OC)O
• Canonical SMILES: OCC1Oc2ccc(cc2OC1c1ccc(c(c1)OC)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
• InChI: InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20?,23-,24?,25+/m0/s1
• InChIKey: SEBFKMXJBCUCAI-DBMPWETRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2R,3R)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one
• Synonyms: (2R,3R)-2-[2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one; Silybin A,B (mixture)

Database IDs

• CAS Number: 802918-57-6
• PubChem SID: 164233676
• PubChem CID: 3086637

CALCULATED PROPERTIES

• Acid pKa: 7.811773
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.6272182
• LogD (pH = 7.4): 2.4878588
• Log P: 2.629316
• Molar Refractivity: 120.2939 cm^3
• Polarizability: 46.884537 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Methanol
• Apperance: Beige Solid
• Melting Point: 152-153°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S465850

Hepatoprotectant. In nature, the flavonolignan Silybin occurs as a mixture of two diastereomers, Silybin A and Silybin B.

REFERENCES

• Xu, P., et al.: Int. J. Biol. Macromol., 47, 654 (2010)
• Ravichandran, K., et al.: Clin. Canc. Res., 16, 4595 (2010)
• Derbre, S., et al.: Anal. Bioanal. Chem., 398, 1747 (2010)