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

Key Documents

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Product Name

Cholesterol, Sigma Grade, ≥99%

InChI key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

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

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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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

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)

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The combined CTA1-DD/ISCOM adjuvant vector promotes priming of mucosal and systemic immunity to incorporated antigens by specific targeting of B cells.

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)

A review of lipoprotein cholesterol metabolism: importance to ovarian function.

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

Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal.

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.

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)

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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.

Cholesterol

Sigma Grade, ≥99%

Select a Size

About This Item

Key Documents

Properties

Product Name

InChI key

InChI

SMILES string

biological source

grade

assay

form

bp

mp

solubility

density

shipped in

storage temp.

Quality Level

Gene Information

Related Categories

Description

Application

Biochem/physiol Actions

Preparation Note

Safety Information

Storage Class

wgk

flash_point_f

flash_point_c

ppe

Documentation

Certificates of Analysis (COA)

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Peer Reviewed Papers

Protocols and Articles

Articles

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