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C2394

Sigma-Aldrich

5-Cholesten-3β-ol-7-one

≥90%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C27H44O2
Número de CAS:
566-28-9
Peso molecular:
400.64
MDL number:
MFCD00010474
UNSPSC Code:
41141804
PubChem Substance ID:
24892324
NACRES:
NA.77

biological source

synthetic (organic)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
Aline Yammine et al.
Molecules (Basel, Switzerland), 25(10) (2020-05-18)
The brain, which is a cholesterol-rich organ, can be subject to oxidative stress in a variety of pathophysiological conditions, age-related diseases and some rare pathologies. This can lead to the formation of 7-ketocholesterol (7KC), a toxic derivative of cholesterol mainly
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