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C6012 Sigma

Cholesta-3,5-diene

≥93% (HPLC)

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Properties

Related Categories Biochemicals and Reagents, Cholesterol and Derivatives, Lipids, Sterol Lipids
assay   ≥93% (HPLC)
mp   78-80 °C(lit.)
storage temp.   −20°C

Description

Preparation Note

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

Application

Cholesta-3,5-diene was used as standard in HPLC in quality analysis of different types of olive oils1 and edible fats.2

Biochem/physiol Actions

Cholesta-3,5-diene is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis.3 The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation.4 Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.3

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
22
Safety Statements (Europe) 
36
WGK Germany 
3
RTECS 
FZ5600000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. 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 J. Am. Oil Chem. Soc. 75, 527-30, (1998)

2. Determination of Edible Fat Refining by HPLC of δ 3, 5‐Steradienes Schulte E Eur. J. Lipid Sci. Technol. 96, 124-8, (1994)

3. Oxysterols as non-genomic regulators of cholesterol homeostasis Bielska AA et al Trends Endocrinol. Metab. 23, 99-106, (2012)

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4. Oxysterols: modulators of cholesterol metabolism and other processes Schroepfer GJ Jr Physiol. Rev. 80, 361-554, (2000)

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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, Kenttämaa HI. Int. J. Mass Spectrometry and Ion Processes 301, 234-239, (2011)

Gas- and particulate-phase specific tracer and toxic organic compounds in environmental tobacco smoke. Bi X, Sheng G, Feng Y, et al. Chemosphere 61, 1512-1522, (2005)

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Docosahexaenoic acid supplementation fully restores fertility and spermatogenesis in male β-6 desaturase-null mice. Roqueta-Rivera M, Stroud CK, et al. J. Lipid Res. 51, 360-367, (2010)

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The Liebermann-Burchard reaction: sulfonation, desaturation, and rearrangment of cholesterol in acid. Xiong Q, Wilson WK, Pang J. Lipids 42, 87-96, (2007)

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Cholesterylene, a newly recognized tissue lipid, found at high levels in the cornea. Cenedella RJ, Linton LL, and Moore CP Biochem. Biophys. Res. Commun. 186(3), 1647-55, (1992)

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Beil. 5,III,1429

FT-IR 2 (3), 4216:B / FT-NMR 1 (3), 563:B / RegBook 1 (2), 2853:B / Sigma FT-IR 1 (1), 1204:C / Structure Index 1, 457:B:1

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