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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)

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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Die Dokumentenbibliothek aufrufen

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
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)
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
Dmitri Svistounov et al.
PloS one, 7(9), e46134-e46134 (2012-10-03)
Fenestrations are transcellular pores in endothelial cells that facilitate transfer of substrates between blood and the extravascular compartment. In order to understand the regulation and formation of fenestrations, the relationship between membrane rafts and fenestrations was investigated in liver sinusoidal

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