(1R)-3-[(E)-2-[(1R,3aR,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol

• ChemBase ID: 176916
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: C1[C@@H](CCC(=C1/C=C/C1=CCC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C)O
• Canonical SMILES: O[C@@H]1CCC(=C(C1)/C=C/C1=CCC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C
• InChI: InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h8-10,12-13,19-20,22,25-27,29H,7,11,14-18H2,1-6H3/b10-9+,13-12+/t20-,22+,25+,26+,27-,28+/m0/s1
• InChIKey: XQFJZHAVTPYDIQ-LOHZHOGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-3-[(E)-2-[(1R,3aR,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
• IUPAC Traditional name: (1R)-3-[(E)-2-[(1R,3aR,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
• Synonyms: (3β,6Z,22E)-9,10-Secoergosta-5(10),6,8,22-tetraen-3-ol; Preergocalciferol; Previtamin D; Previtamin D2

Database IDs

• CAS Number: 21307-05-1
• PubChem SID: 164232826
• PubChem CID: 20838734

CALCULATED PROPERTIES

• Acid pKa: 18.314426
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.9926243
• LogD (pH = 7.4): 6.9926248
• Log P: 6.9926248
• Molar Refractivity: 129.9622 cm^3
• Polarizability: 49.86576 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P713500

The main decomposition product of Vitamin D2. Ergosterol photoisomerization product.

REFERENCES

• Mermet-Bouvier, R., et al.: J. Pharma. Sci., 62, 891 (1973)
• Reeve, J., et al.: Appl. Microbiol. Biotechnol., 33, 161 (1973)