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C8667

Cholesterol

Sigma Grade, ≥99%

Synonym(s):

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

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$56.80

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$71.90

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$124.00

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$410.00

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$1,310.00

$56.80

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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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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

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

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.)

shipped in

ambient

storage temp.

−20°C

Quality Level

200

Gene Information

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

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1 of 4

This Item
22811147127-U1.03672
Cholesterol Sigma Grade, ≥99%

Sigma-Aldrich

C8667

Cholesterol

Cholesterol, Highly Purified Suitable for use in liposome preparations.

Sigma-Aldrich

228111

Cholesterol, Highly Purified

Cholesterol solution certified reference material, 10 mg/mL in chloroform

Supelco

47127-U

Cholesterol solution

Cholesterol from wool fat extra pure, powdered

SAFC

1.03672

Cholesterol from wool fat

assay

≥99%

assay

≥90% (HPLC)

assay

-

assay

-

biological source

sheep wool

biological source

-

biological source

-

biological source

-

grade

Sigma Grade

grade

-

grade

certified reference material, TraceCERT®

grade

-

storage temp.

−20°C

storage temp.

10-30°C

storage temp.

-10 to -25°C

storage temp.

15-25°C

form

powder

form

powder

form

liquid

form

powder

shipped in

ambient

shipped in

ambient

shipped in

-

shipped in

-

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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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
0000538994
0000531214
0000531217
0000531217
0000531216

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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 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)
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 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)
R R Grummer et al.
Journal of animal science, 66(12), 3160-3173 (1988-12-01)
Cholesterol utilized for steroid synthesis by ovarian tissue may be derived from de novo synthesis or cellular uptake of lipoprotein cholesterol. The majority of blood cholesterol is transported by either low (LDL) or high (HDL) density lipoproteins, depending on the
View All Related Papers

Articles

Cholesterol Biosynthesis

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

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