C9523

Sodium cholesteryl sulfate

• Synonym(s): 5-Cholesten-3β-ol sulfate sodium salt, Cholesterol 3-sulfate sodium salt, Cholesteryl sodium sulfate, Cholesteryl sulfate sodium salt
• Empirical Formula (Hill Notation): C₂₇H₄₅NaO₄S
• CAS Number: 2864-50-8
• Molecular Weight: 488.70
• Beilstein/REAXYS Number: 3899884
• MDL number: MFCD00079091
• UNSPSC Code: 41141804
• eCl@ss: 39023139
• PubChem Substance ID: 24893166
• NACRES: NA.77

Properties

• biological source: synthetic
• description: anionic
• assay: ≥98% (TLC)
• form: powder
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [H][C@@]([C@H](C)CCCC(C)C)([C@@]1(C)CC[C@@]23[H])CC[C@]1([C@](CC=C4C[C@H](CC[C@]34C)OS([O-])(=O)=O)2[H])[H].[Na+]
• InChI: 1S/C27H46O4S.Na/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5;/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30);/q;+1/p-1/t19-,21+,22+,23-,24+,25+,26+,27-;/m1./s1
• InChI key: LMPVQXVJTZWENW-KPNWGBFJSA-M

Description

Application

Sodium cholesteryl sulfate was used as the source of cholesterol in the preparation of Edgar′s growth medium used for embryology experiments. It was used as a standard for the separation of human stratum corneum lipids by thin layer chromatography.

Biochem/physiol Actions

Cholesteryl sulfate is a natural constituent of human spermatozoa and has major role in the maturation of sperms. It could also be involved in the capacitation of sperms and enables ovum penetration. Low concentrations of cholesteryl sulfate inhibits acrosin, the proteinase present in sperm acrosome that facilitates ovum penetration.

Preparation Note

Sodium cholesteryl sulfate yields clear, colorless solution in chloroform-methanol (1:1) mixture at 10 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)