H6891
7β-Hydroxycholesterol
≥95%
Synonym(s):
5-Cholestene-3β,7β-diol
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About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Product Name
7β-Hydroxycholesterol, ≥95%
form
powder
assay
≥95%
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
SMILES string
[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 key
OYXZMSRRJOYLLO-UHFFFAOYSA-N
functional group
hydroxyl
shipped in
ambient
storage temp.
room temp
Quality Level
Related Categories
Application
7β-hydroxycholesterol was used to study oxysterol-induced apoptosis in human endothelial cells.
Biochem/physiol Actions
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.
Preparation Note
7β-Hydroxycholesterol yields clear, colorless to faint yellow solution in ethanol, with or without heating.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_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
G Lizard et al.
Arteriosclerosis, thrombosis, and vascular biology, 19(5), 1190-1200 (1999-05-14)
Oxidized low density lipoproteins (LDLs) play a central role in atherosclerosis, and their toxicity is due, at least in part, to the formation of oxysterols that have been shown to induce apoptosis in various cell types. As 7beta-hydroxycholesterol and 7-ketocholesterol
W T Wong et al.
Nutrition, metabolism, and cardiovascular diseases : NMCD, 21(3), 157-164 (2009-12-17)
Oxidized low-density lipoprotein (ox-LDL) causes atherosclerosis and endothelial dysfunction. No study up to the present date has examined the relative contribution of all the oxidized components in ox-LDL to inhibition on vascular function. Our aim was to investigate the effects
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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