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Merck
CN

20808

Cholesterol

meets analytical specification of NF

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H46O
CAS Number:
Molecular Weight:
386.65
UNSPSC Code:
12352200
PubChem Substance ID:
eCl@ss:
39023139
EC Number:
200-353-2
Beilstein/REAXYS Number:
1915888
MDL number:
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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

optical activity

[α]20/D −38 to −34°, c = 2% in dioxane

quality

meets analytical specification of NF

ign. residue

≤0.1% (as SO4)

loss

≤0.3% loss on drying, 60 °C, 4 h (vacuum)

bp

360 °C (lit.)

mp

147-149 °C (lit.), 147-150 °C

solubility

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

density

1.067 g/mL at 25 °C (lit.)

Gene Information

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Biochem/physiol Actions

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

Storage Class

13 - Non Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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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
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
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.
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
Zhan Ye et al.
Infection and immunity, 77(9), 3791-3806 (2009-07-08)
YopM, a protein toxin of Yersinia pestis, is necessary for virulence in a mouse model of systemic plague. We previously reported YopM-dependent natural killer (NK) cell depletion from blood and spleen samples of infected mice. However, in this study we

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