(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl 3-phenylprop-2-enoate

• ChemBase ID: 156462
• Molecular Formular: C24H30O11
• Molecular Mass: 494.4884
• Monoisotopic Mass: 494.17881178
• SMILES: C[C@@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)OC(=O)/C=C/c1ccccc1
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@](C)(OC(=O)/C=C/c2ccccc2)C[C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
• InChIKey: KVRQGMOSZKPBNS-WEXCICBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl 3-phenylprop-2-enoate
• IUPAC Traditional name: (1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,5H,6H,7aH-cyclopenta[c]pyran-7-yl 3-phenylprop-2-enoate
• Synonyms: Harpagoside; 哈巴俄苷

Database IDs

• CAS Number: 19210-12-9
• EC Number: 242-881-6
• MDL Number: MFCD00017415
• PubChem SID: 162250600
• PubChem CID: 5281542

CALCULATED PROPERTIES

• Acid pKa: 12.119163
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -0.88667643
• LogD (pH = 7.4): -0.8866846
• Log P: -0.8866763
• Molar Refractivity: 118.7716 cm^3
• Polarizability: 47.646107 Å^3
• Polar Surface Area: 175.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard; primary reference standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C24H30O11

DETAILS

Sigma Aldrich - 00420580

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