Skip to Content
Merck
CN

Key Documents

View All Documentation

C6012

Cholesta-3,5-diene

≥93% (HPLC)

Synonym(s):

Δ3,5-Cholestadiene, Cholesterilene

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

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
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

biological source

natural (organic)

Quality Level

200

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

Related Categories

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000546562
0000546562
0000483014
0000483013
0000483014

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
View All Related Papers

Global Trade Item Number

SKUGTIN
C6012-100MG04061833076033
C6012-25MG04061833503010

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service