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Merck

14606

Cholesterol

tested according to Ph. Eur.

Synonym(s):

Cholesterolum, 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:
41141804
NACRES:
NA.21
PubChem Substance ID:
329750548
EC Number:
200-353-2
Beilstein/REAXYS Number:
1915888
MDL number:
MFCD00003646

Key Documents

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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

Quality Level

100

Gene Information

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

agency

tested according to Ph. Eur.

form

powder

bp

360 °C (lit.)

mp

147-149 °C (lit.)

solubility

chloroform: soluble 1 gm in 4.5 ml, diethyl ether: soluble 1 gm in 2.8 ml, pyridine: soluble 1 gm in 1.5 ml, H2O: insoluble, acetone: soluble, alcohol: slightly soluble, alcohol: very soluble (Hot), benzene: soluble, dioxane: soluble, ethyl acetate: soluble, hexane: soluble, oil: soluble, petroleum ether: soluble

density

1.067 g/mL at 25 °C (lit.)

application(s)

pharmaceutical (small molecule)

storage temp.

2-8°C

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Biochem/physiol Actions

Major component of all biological membranes; ~25% of total brain lipid is cholesterol.
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.

Application

Cholesterol was used for preparing ISCOMS containing ovalbumin (OVA) for studying whether the incorporation of the protein antigen ovalbumin (OVA) in lipophilic immune-stimulating complexes (ISCOMS) induces very strong primary immune responses. It was incorporated in animal feed to study the effect of cholesterol-rich diet.

Storage Class

11 - Combustible Solids

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
BCCK5493
BCCG1852
BCCF4488
BCCC9091
BCCC1761

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Daniela C U Cavallini et al.
Lipids in health and disease, 8, 1-1 (2009-01-09)
Much attention has been drawn to different alternative strategies for cardiovascular disease prevention. The aim of the present study was to observe and compare the effects of Enterococcus faecium CRL183 (probiotic microorganism), an isoflavones mixture and simvastatin (drug used to
Ricardo L F Guerra et al.
Lipids in health and disease, 6, 16-16 (2007-07-04)
Exercise has been prescribed in the treatment and control of dyslipidemias and cholesterolemia, however, lipid responses to different training frequencies in hypercholesterolemic men have been inconsistent. We sought to verify if different frequencies of continuous moderate exercise (2 or 5
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
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.
Peter Libby et al.
Immunity, 38(6), 1092-1104 (2013-07-03)
According to the traditional view, atherosclerosis results from a passive buildup of cholesterol in the artery wall. Yet, burgeoning evidence implicates inflammation and immune effector mechanisms in the pathogenesis of this disease. Both innate and adaptive immunity operate during atherogenesis
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