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Key Documents

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H6891

Sigma-Aldrich

7β-Hydroxycholesterol

≥95%

Sinónimos:

5-Cholestene-3β,7β-diol

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About This Item

Fórmula empírica (notación de Hill):
C27H46O2
Número de CAS:
566-27-8
Peso molecular:
402.65
Número MDL:
MFCD00058406
Código UNSPSC:
12352211
ID de la sustancia en PubChem:
24895774
NACRES:
NA.77

Nivel de calidad

200

Análisis

≥95%

formulario

powder

grupo funcional

hydroxyl

Condiciones de envío

ambient

temp. de almacenamiento

room temp

cadena SMILES

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

InChI

1S/C27H46O2/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/h16-18,20-25,28-29H,6-15H2,1-5H3

Clave InChI

OYXZMSRRJOYLLO-UHFFFAOYSA-N

Aplicación

7β-hydroxycholesterol was used to study oxysterol-induced apoptosis in human endothelial cells.

Acciones bioquímicas o fisiológicas

7β-Hydroxycholesterol is an oxysterol, the enzymatic or non-enzymatic product of cholesterol oxidation. Oxysterols are cytotoxic and induce death in monocytes, smooth muscle cells and endothelial cells. The mechanism of apoptosis induced by oxysterols may involve caspases or DNA fragmentation. Increased levels of 7β-Hydroxycholesterol correlates with increased risk of cardiovascular diseases including atherosclerosis.

Nota de preparación

7β-Hydroxycholesterol yields clear, colorless to faint yellow solution in ethanol, with or without heating.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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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G Lizard et al.
FEBS letters, 419(2-3), 276-280 (1998-01-15)
The oxysterols, 7beta-hydroxycholesterol and 7-ketocholesterol, are involved in the cytotoxicity of oxidized LDL. To elucidate their molecular mechanisms, the human promonocytic leukemia cells U937 and U4 were used. U4 cells overexpressing Bcl-2 were obtained by transfection of U937 cells. 7Beta-hydroxycholesterol
Raymond C S Seet et al.
Free radical research, 47(4), 283-290 (2013-01-25)
The purpose of this study was to evaluate the use of Framingham risk scores (FRRs) to identify high-risk individuals with biochemical evidence of increased oxidative damage, who may benefit from antioxidant therapies. A bimodal change in plasma F2-isoprostane levels was
Ludovic Clarion et al.
Biochemical pharmacology, 83(1), 37-46 (2011-10-11)
7β-Hydroxycholesterol cytotoxicity has been shown in vivo and in vitro to be dependent on the accumulation of its esters. We show in our study, using a detergent-free raft preparation and LC/MS lipid content analysis, that membrane microdomains isolated from 7β-hydroxycholesterol-treated
B Ziedén et al.
Arteriosclerosis, thrombosis, and vascular biology, 19(4), 967-971 (1999-04-09)
The mortality in coronary heart disease among 50- to 54-year-old men is 4 times higher in Lithuania than in Sweden. It was recently suggested that traditional risk factors could not explain this mortality difference. LDL of Lithuanian men showed, however
Paola Gamba et al.
Aging cell, 10(3), 403-417 (2011-01-29)
All three cholesterol oxidation products implicated thus far in the pathogenesis of Alzheimer's disease, 7β-hydroxycholesterol, 24-hydroxycholesterol, and 27-hydroxycholesterol, markedly enhance the binding of amyloid-beta (Aβ) to human differentiated neuronal cell lines (SK-N-BE and NT-2) by up-regulating net expression and synthesis
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