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H6891

Sigma-Aldrich

7β-Hydroxycholesterol

≥95%

Synonyme(s) :

5-Cholestene-3β,7β-diol

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About This Item

Formule empirique (notation de Hill):
C27H46O2
Numéro CAS:
566-27-8
Poids moléculaire :
402.65
Numéro MDL:
MFCD00058406
Code UNSPSC :
12352211
ID de substance PubChem :
24895774
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥95%

Forme

powder

Groupe fonctionnel

hydroxyl

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne 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

Clé InChI

OYXZMSRRJOYLLO-UHFFFAOYSA-N

Application

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

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Raymond C S Seet et al.
Free radical biology & medicine, 50(12), 1787-1793 (2011-03-23)
Cigarette smoking predisposes to the development of multiple diseases involving oxidative damage. We measured a range of oxidative damage biomarkers to understand which differ between smokers and nonsmokers and if the levels of these biomarkers change further during the act
Cinzia Mascia et al.
Free radical biology & medicine, 49(12), 2049-2057 (2010-10-07)
Cholesterol and its oxidation products, namely oxysterols, have very recently been shown to potentially interfere with homeostasis of the human digestive tract, by promoting and sustaining irreversible damage of the colonic epithelial layer. This report concerns the strong proinflammatory action
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
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
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
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