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Merck
CN

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:
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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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

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
0000483014
0000483013
0000481097

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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
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)
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
Manuel Roqueta-Rivera et al.
Journal of lipid research, 51(2), 360-367 (2009-08-20)
Delta-6 desaturase-null mice ((-/-)) are unable to synthesize highly unsaturated fatty acids (HUFAs): arachidonic acid (AA), docosahexaenoic acid (DHA), and n6-docosapentaenoic acid (DPAn6). The (-/-) males exhibit infertility and arrest of spermatogenesis at late spermiogenesis. To determine which HUFA is
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)
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