8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

• ChemBase ID: 156465
• Molecular Formular: C27H30O14
• Molecular Mass: 578.5187
• Monoisotopic Mass: 578.16355564
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO)c1c(cc(c2c1oc(cc2=O)c1ccc(cc1)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O
• InChI: InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1
• InChIKey: LYGPBZVKGHHTIE-HUBYJIGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: vitexin 2''-rhamnoside
• Synonyms: 2-O-Rhamnosylvitexin; Vitexin 2-O-rhamnoside; 牧荆葡基黄酮-2''-O-鼠李糖苷; 牡荆素-2-O-鼠李糖苷

Database IDs

• CAS Number: 64820-99-1
• MDL Number: MFCD00143627
• PubChem SID: 162250603; 24879517
• PubChem CID: 5282151

CALCULATED PROPERTIES

• Acid pKa: 6.198727
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -0.85316736
• LogD (pH = 7.4): -1.9767128
• Log P: -0.7745575
• Molar Refractivity: 136.9018 cm^3
• Polarizability: 53.854496 Å^3
• Polar Surface Area: 236.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Grade: analytical standard; primary reference standard
• Empirical Formula (Hill Notation): C27H30O14

DETAILS

Sigma Aldrich - 00660585

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