700033P

5β,6β-epoxycholestanol

Avanti Polar Lipids

• Synonym(s): 110805
• Empirical Formula (Hill Notation): C₂₇H₄₆O₂
• CAS Number: 4025-59-6
• Molecular Weight: 402.65
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• description: cholestanol, 5β,6β-epoxy
• Assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 5 mg (700033P-5mg)
• manufacturer/tradename: Avanti Polar Lipids
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: C[C@]12CC[C@H]([C@](CC[C@H](O)C3)(C)[C@]3(O4)[C@H]4C5)[C@@H]5[C@@H]1CC[C@@H]2[C@H](C)CCCC(C)C
• InChI: 1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
• InChI key: PRYIJAGAEJZDBO-DTLXENBRSA-N

Description

General description

5β,6β-epoxycholestanol (5β,6β-EC) is generated by cholesterol epoxidation and is a diastereoisomer of 5α,6α-epoxycholestanol (5α,6α-EC).

Application

5β,6β-epoxycholestanol may be used as a oxy-mix component in treating human colorectal adenocarcinoma CaCo-2 cells to test its effect on toll-like receptor (TLR) expression, in the preparation of langmuir monolayers for isotherm studies, as an internal standard for gas chromatography-mass spectrometry (GC–MS) chromatograms

Biochem/physiol Actions

5β,6β-epoxycholestanol (5β,6β-EC) is associated with human carotid plaques and is not down-regulated by apolipoprotein A1 (apoA-I) protein. 5,6β-EC along with 5α,6α-epoxycholesterol and other oxysterols are reported to be associated with Alzheimer′s disease. It is catabolized by the enzyme cholesterol-5,6-epoxide hydrolase (ChEH) enzyme to 3β,5α,6β-triol. 5β,6β-EC elicits cytotoxic and inflammatory properties.

Packaging

5 mL PTFE Vial with Screw Cap (700033P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable