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C8667

Cholesterol

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
NACRES:
NA.77
PubChem Substance ID:
24893094
eCl@ss:
39023139
UNSPSC Code:
12352111
EC Number:
200-353-2
MDL number:
MFCD00003646
Beilstein/REAXYS Number:
1915888
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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)

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.

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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

胆固醇生物合成

胆固醇的生物合成通常发生在肝细胞的内质网中，并以乙酰辅酶A开始，乙酰辅酶A主要来源于线粒体中的氧化反应。乙酰辅酶A和乙酰乙酰辅酶A由HMG-辅酶A合成酶转化为3-羟基-3-甲基戊二酰辅酶A（HMG-辅酶A）。

Cholesterol Biosynthesis

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