C6012

Cholesta-3,5-diene

≥93% (HPLC)

• Synonym(s): Δ^3,5-Cholestadiene, Cholesterilene
• Empirical Formula (Hill Notation): C₂₇H₄₄
• CAS Number: 747-90-0
• Molecular Weight: 368.64
• NACRES: NA.77
• PubChem Substance ID: 24892827
• UNSPSC Code: 12352211
• EC Number: 212-021-4
• MDL number: MFCD00009939

Properties

• biological source: natural (organic)
• Quality Segment: 200
• assay: ≥93% (HPLC)
• form: powder
• mp: 78-80 °C (lit.)
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C=CCC[C@]4(C)[C@H]3CC[C@]12C
• InChI: 1S/C27H44/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/h6,11-12,19-20,22-25H,7-10,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1
• InChI key: RLHIRZFWJBOHHD-HKQCOZBKSA-N

Description

Application

Cholesta-3,5-diene was used as standard in HPLC in quality analysis of different types of olive oils and edible fats.

Biochem/physiol Actions

Cholesta-3,5-diene is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis. The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation. Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.

Preparation Note

Cholesta-3,5-diene yields clear, colorless solution in chloroform at 50 mg/ml.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves