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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

Standard for chromatography
Cholesterol was used to prepare immune-stimulating complexes to enhance cellular and humoral responses.[1] 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.[2] The major sites of cholesterol synthesis are small intestine and liver.[3]
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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This Item
C8503PHR15331131960
Cholesterol Sigma Grade, ≥99%

Sigma-Aldrich

C8667

Cholesterol

Cholesterol from sheep wool, ≥92.5% (GC), powder

Sigma-Aldrich

C8503

Cholesterol

Cholesterol Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1533

Cholesterol

Cholesterol United States Pharmacopeia (USP) Reference Standard

USP

1131960

Cholesterol

biological source

sheep wool

biological source

sheep wool

biological source

-

biological source

sheep

assay

≥99%

assay

≥92.5% (GC)

assay

-

assay

-

grade

Sigma Grade

grade

-

grade

certified reference material, pharmaceutical secondary standard

grade

pharmaceutical primary standard

solubility

water: soluble 0.00003 g/L at 20 °C

solubility

water: soluble 0.00003 g/L at 20 °C

solubility

water: soluble 0.00003 g/L at 20 °C

solubility

-

form

powder

form

powder

form

powder

form

-

storage temp.

−20°C

storage temp.

room temp

storage temp.

-10 to -25°C

storage temp.

−20°C

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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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Certificates of Analysis (COA)

Lot/Batch Number
0000547998
0000548011
0000548012
0000547999
0000548013

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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.

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
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
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Global Trade Item Number

SKUGTIN
C8667-5G04061835543632
C8667-100G04061835543601
C8667-500MG04061835543625
C8667-25G04061835521746
C8667-1G04061835543618