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C6012

Cholesta-3,5-diene

≥93% (HPLC)

Synonym(s):

Δ3,5-Cholestadiene, Cholesterilene

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$595.00

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About This Item

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

Key Documents

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Product Name

Cholesta-3,5-diene, ≥93% (HPLC)

InChI key

RLHIRZFWJBOHHD-HKQCOZBKSA-N

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

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

biological source

natural (organic)

assay

≥93% (HPLC)

form

powder

mp

78-80 °C (lit.)

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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1 of 4

This Item
T751730800C4151
Cholesta-3,5-diene ≥93% (HPLC)

Sigma-Aldrich

C6012

Cholesta-3,5-diene

Glyceryl tridecanoate ≥99% (GC)

Sigma-Aldrich

T7517

Glyceryl tridecanoate

7-Dehydrocholesterol ≥95.0% (HPLC)

Sigma-Aldrich

30800

7-Dehydrocholesterol

Sodium decanoate ≥98%

Sigma-Aldrich

C4151

Sodium decanoate

biological source

natural (organic)

biological source

-

biological source

synthetic

biological source

natural (organic)

assay

≥93% (HPLC)

assay

≥99% (GC)

assay

≥95.0% (HPLC)

assay

≥98%

shipped in

ambient

shipped in

ambient

shipped in

-

shipped in

ambient

form

powder

form

powder

form

powder or crystals

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

mp

78-80 °C (lit.)

mp

-

mp

148-152 °C (lit.)

mp

-

Application

Cholesta-3,5-diene was used as standard in HPLC in quality analysis of different types of olive oils[1] 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]

Preparation Note

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
0000483014
0000483013
0000483013
0000483014
0000481097

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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
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
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)
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
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