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C6012

Sigma-Aldrich

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:
747-90-0
Molecular Weight:
368.64
EC Number:
212-021-4
MDL number:
MFCD00009939
UNSPSC Code:
12352211
PubChem Substance ID:
24892827
NACRES:
NA.77

biological source

natural (organic)

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Quanbo Xiong et al.
Lipids, 42(1), 87-96 (2007-03-30)
In the Liebermann-Burchard (LB) colorimetric assay, treatment of cholesterol with sulfuric acid, acetic anhydride, and acetic acid elicits a blue color. We studied the reactivity of cholesterol under LB conditions and provide definitive NMR characterization for approximately 20 products, whose
R J Cenedella et al.
Biochemical and biophysical research communications, 186(3), 1647-1655 (1992-08-14)
In the course of measuring the concentration of cholesterol in an opacified dog cornea by gas-chromatography, relatively large amounts of an unidentified non-saponifiable lipid were recognized. When the unknown lipid was subjected to gas chromatographic-mass spectral analysis it displayed a
Determination of Edible Fat Refining by HPLC of δ 3, 5?Steradienes
Schulte E
European Journal of Lipid Science and Technology, 96, 124-128 (1994)
Agata A Bielska et al.
Trends in endocrinology and metabolism: TEM, 23(3), 99-106 (2012-01-17)
Tight regulation of cellular and plasma cholesterol is crucial to proper cellular functioning because excess free cholesterol is toxic to cells and is associated with atherosclerosis and heart disease. Cellular cholesterol homeostasis is regulated by enzymatically formed oxygenated cholesterol derivatives
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