(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-5-(2H3)methyl-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 163559
• Molecular Formular: C28H48O
• Molecular Mass: 400.68012
• Monoisotopic Mass: 400.37051616
• 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)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCC(C(C)C)C)C)C)C1)C
• InChI: InChI=1S/C28H48O/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/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19?,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
• InChIKey: SGNBVLSWZMBQTH-QGOUJLTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-5-(^2H₃)methyl-6-methylheptan-2-yl]tetracyclo[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)-2,15-dimethyl-14-[(2R)-5-(^2H₃)methyl-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: 5-Cholesten-24(RS)-methyl-d3-3β-ol; Campesterol-d3 (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162257694
• PubChem CID: 57369256

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.399908
• LogD (pH = 7.4): 7.399908
• Log P: 7.399908
• Molar Refractivity: 125.1651 cm^3
• Polarizability: 49.824352 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 151-153°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C155362

Labelled Campesterol (C155360). A phytosterol, which may inhibit the intestinal absorption of cholesterol.

REFERENCES

• Fransen, H., et al.: J. Nut., 140, 1062 (2010)
• Kojoma, M., et al.: Plant Biotechnol., 27, 59 (2010)
• Orozco-Solano, M., et al.: J. Agric. Food Chem., 58, 7539 (2010)