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:
Quality Level
assay
≥95%
form
powder
functional group
hydroxyl
shipped in
ambient
storage temp.
room temp
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
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
InChI key
OYXZMSRRJOYLLO-UHFFFAOYSA-N
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| H6891-1MG | 04061833802427 |
| H6891-10MG | 04061833076538 |
| H6891-5MG | 04061833802533 |