(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-ethyl-6-(2H3)methyl(6,7,7,7-2H4)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 177794
• Molecular Formular: C29H50O
• Molecular Mass: 414.7067
• Monoisotopic Mass: 414.38616622
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCC(C(C)C)CC)C)C)O
• Canonical SMILES: CCC(C(C)C)CC[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)O)C
• InChI: InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21?,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: KZJWDPNRJALLNS-OAIXMFQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-ethyl-6-(^2H₃)methyl(6,7,7,7-^2H₄)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-ethyl-6-(^2H₃)methyl(6,7,7,7-^2H₄)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: 5-Cholesten-24(RS)-ethyl-3β-ol-25,26,26,26,27,27,27-d7; 24(R,S)-Stigmast-5-en-3β-ol; β-Sitosterol-d7 (mixture of diasteromers)

Database IDs

• PubChem SID: 164233704
• PubChem CID: 57347730

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.8444767
• LogD (pH = 7.4): 7.8444767
• Log P: 7.8444767
• Molar Refractivity: 129.7661 cm^3
• Polarizability: 51.670784 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S497052

Labelled Sitosterol (S497050). A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.

REFERENCES

• Tanaka, et al.: J. Biochem., 17, 483 (1933)
• Nigro, N.D., et al.: J. Natl. Cancer Inst., 69, 103 (1933)