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H6891

Sigma-Aldrich

7β-Hydroxycholesterol

≥95%

Sinonimo/i:

5-Cholestene-3β,7β-diol

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About This Item

Formula empirica (notazione di Hill):
C27H46O2
Numero CAS:
566-27-8
Peso molecolare:
402.65
Numero MDL:
MFCD00058406
Codice UNSPSC:
12352211
ID PubChem:
24895774
NACRES:
NA.77
Prezzi e disponibilità al momento non sono disponibili

Livello qualitativo

200

Saggio

≥95%

Stato

powder

Gruppo funzionale

hydroxyl

Condizioni di spedizione

ambient

Temperatura di conservazione

room temp

Stringa SMILE

[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
OYXZMSRRJOYLLO-UHFFFAOYSA-N

Categorie correlate

Applicazioni

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

Azioni biochim/fisiol

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]

Nota sulla preparazione

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
0000410708
0000410708
0000139118
0000139118
0000265588

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5-Cholesten-3β-ol-7-one ≥90%

Sigma-Aldrich

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5-Cholesten-3β-ol-7-one

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Supelco

52853

7α-Hydroxy-4-cholesten-3-one

Cholesterol 5β,6β-epoxide ≥98%

Sigma-Aldrich

C2648

Cholesterol 5β,6β-epoxide

7β-hydroxycholesterol-d7 Avanti Research™ - A Croda Brand

Avanti

700044P

7β-hydroxycholesterol-d7

4β-hydroxycholesterol Avanti Research™ - A Croda Brand

Avanti

700036P

4β-hydroxycholesterol

7α,25-Dihydroxycholesterol ≥98% (HPLC)

Sigma-Aldrich

SML0541

7α,25-Dihydroxycholesterol

25-hydroxycholesterol Avanti Research™ - A Croda Brand

Avanti

700019P

25-hydroxycholesterol

22(S)-Hydroxycholesterol

Sigma-Aldrich

H5884

22(S)-Hydroxycholesterol

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
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
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
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