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C8667

Cholesterol

Name: Cholesterol
Brand: SIGMA

Sigma Grade, ≥99%

Synonym(s):

3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₄₆O

CAS Number:

57-88-5

Molecular Weight:

386.65

UNSPSC Code:

12352111

EC Number:

200-353-2

NACRES:

NA.77

PubChem Substance ID:

24893094

eCl@ss:

39023139

MDL number:

MFCD00003646

Beilstein/REAXYS Number:

1915888

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Properties

biological source

sheep wool

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.)

application(s)

advanced drug delivery

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

human ... POLA1(5422), TOP2A(7153)
rat ... Ar(24208), Polb(29240)

Description

Application

Standard for chromatography

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.

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Articles

Cholesterol Biosynthesis

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Global Trade Item Number

SKU	GTIN
C8667-100G	04061835543601
C8667-5G	04061835543632
C8667-1G	04061835543618
C8667-25G	04061835521746
C8667-500MG	04061835543625