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

• ChemBase ID: 157529
• Molecular Formular: C26H24O9
• Molecular Mass: 480.46336
• Monoisotopic Mass: 480.14203235
• SMILES: Cc1ccc(cc1OC)C1[C@H](Oc2ccc(cc2O1)[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O)CO
• Canonical SMILES: OC[C@H]1Oc2ccc(cc2OC1c1ccc(c(c1)OC)C)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
• InChI: InChI=1S/C26H24O9/c1-12-3-4-13(7-18(12)32-2)25-21(11-27)33-17-6-5-14(8-19(17)34-25)26-24(31)23(30)22-16(29)9-15(28)10-20(22)35-26/h3-10,21,24-29,31H,11H2,1-2H3/t21-,24+,25?,26-/m1/s1
• InChIKey: GDVGLBLNDLCLFY-AQUAXTIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3,5,7-trihydroxy-2-[(2R)-2-(hydroxymethyl)-3-(3-methoxy-4-methylphenyl)-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-[(2R)-2-(hydroxymethyl)-3-(3-methoxy-4-methylphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one
• Synonyms: (2R,3R)-3,5,7-Trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin-6-yl]chroman-4-one; Silibinin; Silybin; (2R,3R)-3,5,7-三羟基-2-[(2R,3R)-3-(4-羟基-3-甲氧基苯基)-2-羟甲基-2,3-二氢苯并[1,4]二噁英-6-基]苯并二氢吡喃-4-酮; 西利马林; 水飞蓟宾

Database IDs

• CAS Number: 802918-57-6
• EC Number: 245-302-5
• PubChem SID: 162251666
• PubChem CID: 71312535

CALCULATED PROPERTIES

• Acid pKa: 7.8152657
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 3.4442217
• LogD (pH = 7.4): 3.3061824
• Log P: 3.446303
• Molar Refractivity: 123.3542 cm^3
• Polarizability: 47.991497 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: DJ2981770
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Grade: primary reference standard
• Quality: mixture of Silybin A and B
• Empirical Formula (Hill Notation): C25H22O10

DETAILS

Sigma Aldrich - 02000585

Application
Reference standard in the analysis of herbal medicinal products.
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate