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H6891

Sigma-Aldrich

7β-Hydroxycholesterol

≥95%

Synonym(e):

5-Cholestene-3β,7β-diol

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About This Item

Empirische Formel (Hill-System):
C27H46O2
CAS-Nummer:
566-27-8
Molekulargewicht:
402.65
MDL-Nummer:
MFCD00058406
UNSPSC-Code:
12352211
PubChem Substanz-ID:
24895774
NACRES:
NA.77
Preise und Verfügbarkeit sind derzeit nicht verfügbar.

Qualitätsniveau

200

Assay

≥95%

Form

powder

Funktionelle Gruppe

hydroxyl

Versandbedingung

ambient

Lagertemp.

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

InChIKey

OYXZMSRRJOYLLO-UHFFFAOYSA-N

Anwendung

7β-hydroxycholesterol was used to study oxysterol-induced apoptosis in human endothelial cells.[1]

Biochem./physiol. Wirkung

7β-Hydroxycholesterol is an oxysterol, the enzymatic or non-enzymatic product of cholesterol oxidation.[2] 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.[3] Increased levels of 7β-Hydroxycholesterol correlates with increased risk of cardiovascular diseases including atherosclerosis.[4]

Angaben zur Herstellung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000139118
0000139118
0000265588
0000264060
0000220019

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Die Dokumentenbibliothek aufrufen

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
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
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
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
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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