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H6891

Sigma-Aldrich

7β-Hydroxycholesterol

≥95%

Synonym(s):

5-Cholestene-3β,7β-diol

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
566-27-8
Molecular Weight:
402.65
MDL number:
MFCD00058406
UNSPSC Code:
12352211
PubChem Substance ID:
24895774
NACRES:
NA.77

Quality Level

200

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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