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Merck
CN

700015P

Avanti

7-ketocholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

7-oxocholesterol; 7-oxo-5-cholesten-3β-ol-7-one; 5-cholesten-3β-ol-7-one; 3β-hydroxycholest-5-en-7-one; 110806

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About This Item

Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
566-28-9
Molecular Weight:
400.64
MDL number:
MFCD00010474
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

7-ketocholesterol, Avanti Research™ - A Croda Brand

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

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

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>

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.

General description

7-ketocholesterol is a major oxidation product of cholesterol.

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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Certificates of Analysis (COA)

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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)
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
7-Ketocholesterol
Lyons MA and Brown AJ
The International Journal of Biochemistry & Cell Biology, 31(3-4), 369-375 (1999)
Raku Shinkyo et al.
The Journal of biological chemistry, 286(38), 33021-33028 (2011-08-05)
7-Ketocholesterol is a bioactive sterol, a potent competitive inhibitor of cytochrome P450 7A1, and toxic in liver cells. Multiple origins of this compound have been identified, with cholesterol being the presumed precursor. Although routes for formation of the 7-keto compound
Samantha A Hutchinson et al.
Nutrients, 11(11) (2019-11-07)
Interventions that alter cholesterol have differential impacts on hormone receptor positive- and negative-breast cancer risk and prognosis. This implies differential regulation or response to cholesterol within different breast cancer subtypes. We evaluated differences in side-chain hydroxycholesterol and liver X nuclear

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