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C2394

Sigma-Aldrich

5-Cholesten-3β-ol-7-one

≥90%

Synonym(s):

3β-Hydroxy-5-cholesten-7-one, 7-Ketocholesterol

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About This Item

Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
566-28-9
Molecular Weight:
400.64
MDL number:
MFCD00010474
UNSPSC Code:
41141804
PubChem Substance ID:
24892324
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥90%

form

powder

functional group

ketone

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@@]([C@](CC[C@H](O)C3)(C)C3=CC4=O)([H])[C@]4([H])[C@]1([H])CC[C@]2([H])[C@]([H])(C)CCCC(C)C

InChI

1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1

InChI key

YIKKMWSQVKJCOP-ABXCMAEBSA-N

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Application

5-Cholesten-3β-ol-7-one was used as a standard in the determination of cholesterol derivatives by GC-MS and HPLC.

Biochem/physiol Actions

5-Cholesten-3β-ol-7-one is a cholesterol derivative that decreases the membrane potential of lipid bilayers. It reportedly accumulates in atherosclerotic plaques that leads to apoptosis of vascular cells.

Preparation Note

5-Cholesten-3β-ol-7-one yields clear to slightly hazy, colorless to faint yellow solution in chloroform at 250 mg/5 ml.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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E Boselli et al.
Journal of chromatography. A, 917(1-2), 239-244 (2001-06-14)
Pressurized liquid extraction (PLE, ASE) was compared with the Folch procedure (a solid-liquid extraction with chloroform/methanol 2:1, v/v) for the lipid extraction of egg-containing food; the accuracy of PLE for the quantitative determination of oxysterols in whole egg powder was
C Adcox et al.
Journal of agricultural and food chemistry, 49(4), 2090-2095 (2001-04-20)
The cytotoxicity of cholesterol and a mixture of beta-sitosterol/campesterol (50%/40%) and their oxides was examined in a cultured-derived macrophage cell line, C57BL/6. Cell numbers, lactate dehydrogenase (LDH) leakage, protein content, lipid uptake, and mitochondria dehydrogenase activity were determined after exposure
Rapid analysis of oxidized cholesterol derivatives by high-performance liquid chromatography combined with diode-array ultraviolet and evaporative laser light-scattering detection
Osada K et al
Journal of the American Oil Chemists' Society, 76, 863-871 (1999)
Thomas Starke-Peterkovic et al.
Biophysical journal, 90(11), 4060-4070 (2006-03-04)
The effect of cholesterol removal by methyl-beta-cyclodextrin on the dipole potential, psi(d), of membrane vesicles composed of natural membrane lipids extracted from the kidney and brain of eight vertebrate species was investigated using the voltage-sensitive fluorescent probe di-8-ANEPPS. Cyclodextrin treatment
Vesa M Olkkonen
Current opinion in lipidology, 23(5), 462-470 (2012-07-21)
To offer a comprehensive review on the roles that oxysterols synthesized or engulfed by macrophages, or oxysterol-binding proteins in these cells, play in the development and progression of atherosclerotic lesions. Oxysterols abundant within the plaque have the capacity to potentiate
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