(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-1(17),7,9-trien-5-ol

• ChemBase ID: 133153
• Molecular Formular: C28H42O
• Molecular Mass: 394.63248
• Monoisotopic Mass: 394.32356596
• SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC=C1C2=CC=C2[C@@]1(CC[C@@H](C2)O)C)C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC=C3C2=CC[C@]2([C@H]3CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C1)C
• InChI: InChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1
• InChIKey: QSVJYFLQYMVBDR-CMNOFMQQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(17),7,9-trien-5-ol
• IUPAC Traditional name: (2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(17),7,9-trien-5-ol
• Synonyms: Dehydroergosterol; Ergosta-5,7,9(11),22-tetraen-3β-ol

Database IDs

• CAS Number: 516-85-8
• MDL Number: MFCD00083319
• PubChem SID: 24894479; 162227430
• PubChem CID: 6436660

CALCULATED PROPERTIES

• Acid pKa: 18.33725
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.2268276
• LogD (pH = 7.4): 6.2268276
• Log P: 6.2268276
• Molar Refractivity: 127.9817 cm^3
• Polarizability: 49.12357 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 40
• Safety Statements: 36/37
• Storage Temperature: -20°C

Product Information

• Purity: ~96% (HPLC)

DETAILS

Sigma Aldrich - E2634

Application
A fluorescent cholesterol analog useful as a probe in membrane research.