C6012
Cholesta-3,5-diene
≥93% (HPLC)
Synonym(s):
Δ3,5-Cholestadiene, Cholesterilene
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About This Item
Empirical Formula (Hill Notation):
C27H44
CAS Number:
Molecular Weight:
368.64
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
EC Number:
212-021-4
MDL number:
biological source
natural (organic)
Quality Level
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
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.
signalword
Warning
hcodes
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
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Characterization of Nonpolar Lipids and Selected Steroids by Using Laser-Induced Acoustic Desorption/Chemical Ionization, Atmospheric Pressure Chemical Ionization, and Electrospray Ionization Mass Spectrometry.
Jin Z, Daiya S, Kenttamaa HI.
International Journal of Mass Spectrometry and Ion Processes, 301, 234-239 (2011)
Jie Gao et al.
Journal of immunology (Baltimore, Md. : 1950), 203(5), 1131-1141 (2019-07-25)
The myeloid differentiation factor 2 (MD-2)-related lipid-recognition (ML) domain is found in multiple proteins, including MD-2, MD-1, Niemann-Pick disease type C2, and mite major allergen proteins. The significance of ML proteins in antibacterial signal transduction and in lipid metabolism has
Separation of stigmasta-3, 5-diene, squalene lsomers, and wax esters from olive oils by single high-performance liquid chromatography run
Amelio M et al
Journal of the American Oil Chemists' Society, 75, 527-530 (1998)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| C6012-100MG | 04061833076033 |
| C6012-25MG | 04061833503010 |