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C8667

Sigma-Aldrich

Cholesterol

Sigma Grade, ≥99%

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Synonym(s):
3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol
Empirical Formula (Hill Notation):
C27H46O
CAS Number:
Molecular Weight:
386.65
Beilstein:
1915888
EC Number:
MDL number:
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.77

biological source

sheep wool

Quality Level

grade

Sigma Grade

Assay

≥99%

form

powder

bp

360 °C (lit.)

mp

147-149 °C (lit.)

solubility

water: soluble 0.00003 g/L at 20 °C

density

1.067 g/mL at 25 °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[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

Gene Information

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This Item
2673214606H6167
Cholesterol Sigma Grade, ≥99%

Sigma-Aldrich

C8667

Cholesterol

Cholesterol from lanolin, ≥99.0% (GC)

Sigma-Aldrich

26732

Cholesterol

Cholesterol tested according to Ph. Eur.

Sigma-Aldrich

14606

Cholesterol

Cholesterol from sheep wool, Controlled origin, meets USP/NF testing specifications

SAFC

H6167

Cholesterol

grade

Sigma Grade

grade

-

grade

-

grade

-

assay

≥99%

assay

≥99.0% (GC)

assay

-

assay

-

form

powder

form

powder

form

powder

form

powder

bp

360 °C (lit.)

bp

360 °C (lit.)

bp

360 °C (lit.)

bp

360 °C (lit.)

mp

147-149 °C (lit.)

mp

147-149 °C (lit.), 148-150 °C

mp

147-149 °C (lit.)

mp

147-149 °C (lit.)

Application

Cholesterol was used to prepare immune-stimulating complexes to enhance cellular and humoral responses. It was incorporated in animal feed to study the effect of cholesterol-rich diet.
Standard for chromatography

Biochem/physiol Actions

Cholesterol is a lipid that makes up about 20-25% of the structural components of the cell membranes. It determines the fluidity and permeability of the membrane, making it permeable to water but not to ions and protons. Cholesterol also regulates the functions of the transporters and signaling proteins present on the plasma membrane. The major sites of cholesterol synthesis are small intestine and liver.
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

Preparation Note

Cholesterol monohydrate yields a clear, colorless to faint yellow solution in hot alcohol. It is also soluble in acetone, dioxane, ethyl acetate, benzene, petroleum ether, oils, fats, and in aqueous solutions of bile salts. Solutions should be protected from light.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Effects of 2 or 5 consecutive exercise days on adipocyte area and lipid parameters in Wistar rats
Guerra RL et al
Lipids in Health and Disease, 6, doi: 10-doi: 10 (2007)
Anja Helgeby et al.
Journal of immunology (Baltimore, Md. : 1950), 176(6), 3697-3706 (2006-03-07)
The cholera toxin A1 (CTA1)-DD/QuilA-containing, immune-stimulating complex (ISCOM) vector is a rationally designed mucosal adjuvant that greatly potentiates humoral and cellular immune responses. It was developed to incorporate the distinctive properties of either adjuvant alone in a combination that exerted
Effects of probiotic bacteria, isoflavones and simvastatin on lipid profile and atherosclerosis in cholesterol-fed rabbits: a randomized double-blind study
Cavallini DC et al
Lipids in Health and Disease, 8, doi: 10-doi: 10 (2009)
Jeffrey Buter et al.
Nature chemical biology, 15(9), 889-899 (2019-08-21)
Mycobacterium tuberculosis (Mtb) is the world's most deadly pathogen. Unlike less virulent mycobacteria, Mtb produces 1-tuberculosinyladenosine (1-TbAd), an unusual terpene nucleoside of unknown function. In the present study 1-TbAd has been shown to be a naturally evolved phagolysosome disruptor. 1-TbAd
John M Dietschy et al.
Journal of lipid research, 45(8), 1375-1397 (2004-07-16)
Unesterified cholesterol is an essential structural component of the plasma membrane of every cell. During evolution, this membrane came to play an additional, highly specialized role in the central nervous system (CNS) as the major architectural component of compact myelin.

Articles

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

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