C8003

5-α-Cholestane

≥97.0% (HPLC)

• Synonym(s): NSC 224419
• Empirical Formula (Hill Notation): C₂₇H₄₈
• CAS Number: 481-21-0
• Molecular Weight: 372.67
• Beilstein/REAXYS Number: 2051806
• EC Number: 207-562-8
• MDL number: MFCD00066412
• UNSPSC Code: 12352211
• PubChem Substance ID: 24893005
• NACRES: NA.77

Properties

• Quality Level: 200
• assay: ≥97.0% (HPLC)
• form: powder
• mp: 80-82 °C (lit.)
• SMILES string: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CCCC[C@]4(C)[C@H]3CC[C@]12C
• InChI: 1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21-,22+,23-,24+,25+,26+,27-/m1/s1
• InChI key: XIIAYQZJNBULGD-XWLABEFZSA-N

Description

Application

5-α-Cholestane has been used:

• as an internal standard in gas phase chromatography (GC) and high-performance liquid chromatography (HPLC) to quantify cholesterol in meat products for a comparison study
• to quantify the active compounds in the oils using a gas chromatograph coupled to a mass spectrometer
• as a reference standard in GC analyses to quantify sterol content in the unsaponifiables obtained from oat lipids and different sterol standards like fucosterol, sitosterol, campesterol, and stigmasterol

Biochem/physiol Actions

5α-Cholestane is a sterol produced endogenously from cholesterol and has been isolated from human feces. It is derived from cholesterol by the action of intestinal microorganisms. Derivatives of 5α-cholestane in plants are called brassinosteroids that selectively activate the PPI3K/Akt pathway.

Preparation Note

5α-Cholestane yields clear to slightly hazy, colorless to faint yellow solution in chloroform at 50 mg/ml.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)