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Merck

C2394

Sigma-Aldrich

5-Cholesten-3β-ol-7-on

≥90%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C27H44O2
CAS-Nummer:
Molekulargewicht:
400.64
MDL-Nummer:
UNSPSC-Code:
41141804
PubChem Substanz-ID:
NACRES:
NA.77

Biologische Quelle

synthetic (organic)

Qualitätsniveau

Assay

≥90%

Form

powder

Funktionelle Gruppe

ketone

Versandbedingung

ambient

Lagertemp.

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

InChIKey

YIKKMWSQVKJCOP-ABXCMAEBSA-N

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Verwandte Kategorien

Anwendung

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

Biochem./physiol. Wirkung

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.

Angaben zur Herstellung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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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
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
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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