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About This Item
Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
Molecular Weight:
400.64
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
description
3β-hydroxy-5-cholestene-7-one
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 100 mg (700015P-100mg), pkg of 1 × 5 mg (700015P-5mg), pkg of 1 × 50 mg (700015P-50mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
shipped in
dry ice
storage temp.
−20°C
SMILES string
O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CCCC(C)C)C)(CC3)C)C(=O)C=C2C1)C
InChI
1S/C27H44O2/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/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
InChI key
YIKKMWSQVKJCOP-ABXCMAEBSA-N
General description
7-ketocholesterol is a major oxidation product of cholesterol.
Application
<ul>
<li><strong>Cytoprotective effects of linolenic acid on 7-ketocholesterol-induced damage:</strong> This study highlights how specific fatty acids can mitigate the toxic effects of 7-ketocholesterol in neural and vascular cells, emphasizing potential therapeutic applications for neurodegenerative and cardiovascular diseases (Yammine et al., 2024).</li>
</ul>
<li><strong>Cytoprotective effects of linolenic acid on 7-ketocholesterol-induced damage:</strong> This study highlights how specific fatty acids can mitigate the toxic effects of 7-ketocholesterol in neural and vascular cells, emphasizing potential therapeutic applications for neurodegenerative and cardiovascular diseases (Yammine et al., 2024).</li>
</ul>
Biochem/physiol Actions
7-ketocholesterol is a strong inhibitor of cytochrome P450 7A1. It modulates cholesterol homeostasis, cytotoxicity and apoptosis. 7-ketocholesterol stimulates inflammation, growth inhibition and vascular endothelial growth factor. Cellular accumulation of 7-ketocholesterol enhances oxidative stress, endoplasmic reticulum stress and apoptosis in macrophages.
Packaging
5 mL Amber Glass Screw Cap Vial (700015P-100mg)
5 mL Amber Glass Screw Cap Vial (700015P-50mg)
5 mL Amber Glass Screw Cap Vial (700015P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Association of plasma 7-ketocholesterol with cardiovascular outcomes and total mortality in patients with coronary artery disease
Song J, et al.
Circulation Research, 120(10), 1622-1631 (2017)
7-Ketocholesterol
Lyons MA and Brown AJ
The International Journal of Biochemistry & Cell Biology, 31(3-4), 369-375 (1999)
Jesse A Rudd-Schmidt et al.
Nature communications, 10(1), 5396-5396 (2019-11-30)
Killer T cells (cytotoxic T lymphocytes, CTLs) maintain immune homoeostasis by eliminating virus-infected and cancerous cells. CTLs achieve this by forming an immunological synapse with their targets and secreting a pore-forming protein (perforin) and pro-apoptotic serine proteases (granzymes) into the
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 700015P-5MG | 04061835383245 |
| 700015P-100MG | 04061835383221 |
| 700015P-50MG | 04061835383238 |