(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-5-thiol

• ChemBase ID: 150977
• Molecular Formular: C27H46S
• Molecular Mass: 402.71914
• Monoisotopic Mass: 402.33202247
• SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CC[C@@H](C2)S)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)S)C)C
• InChI: InChI=1S/C27H46S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: QGVQZRDQPDLHHV-DPAQBDIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5-thiol
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-ene-5-thiol
• Synonyms: 5-Cholestene-3β-thiol; Cholesteryl mercaptan; Thiocholesterol; 5-胆甾烯-3β-硫醇; 胆甾烯基硫醇; 巯基胆固醇

Database IDs

• CAS Number: 1249-81-6
• EC Number: 215-003-4
• MDL Number: MFCD00003647
• PubChem SID: 162245136; 24848256
• PubChem CID: 65075

CALCULATED PROPERTIES

• Acid pKa: 10.029759
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 8.2604685
• LogD (pH = 7.4): 8.259537
• Log P: 8.260481
• Molar Refractivity: 126.6943 cm^3
• Polarizability: 50.444527 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 97-99 °C(lit.)
• Optical Rotation: [α]20/D -23°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95%
• Empirical Formula (Hill Notation): C27H46S

DETAILS

Sigma Aldrich - T3256

Packaging
Sealed ampule.

Sigma Aldrich - 136115

Packaging
1 g in glass bottle
Application
Used in biological cross-linking1 and membrane2 studies.