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Merck
CN

700046P

Avanti

7-ketocholesterol-d7

Avanti Research™ - A Croda Brand

Synonym(s):

3b-hydroxy-5-cholestene-7-one(d7); 7-Oxocholesterol(d7); 7-oxo-5-Cholesten-3b-ol-7-one(d7); 5-cholesten-3 b-ol-7-one(d7); 3b-Hydroxycholest-5-en-7-one(d7)

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About This Item

Empirical Formula (Hill Notation):
C27H37O2D7
CAS Number:
127684-08-6
Molecular Weight:
407.68
MDL number:
MFCD06658677
UNSPSC Code:
12352100
NACRES:
NA.25

Key Documents

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Product Name

7-ketocholesterol-d7, Avanti Research™ - A Croda Brand

SMILES string

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@](C(CC4)[C@@H](CCCC(C([2H])([2H])[2H])(C([2H])([2H])[2H])[2H])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/i1D3,2D3,17D

InChI key

YIKKMWSQVKJCOP-YMQSFMNJSA-N

description

3β-hydroxy-5-cholestene-7-one-d7

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700046P-1mg)
pkg of 1 × 5 mg (700046P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

Application

7-ketocholesterol-d7 has been used:
  • as a deuterated internal standard for spiking plasma samples for liquid chromatography with tandem mass spectrometry (LC-MS-MS) analysis
  • as a deuterated internal standard for spiking aorta and macrophage lipid extract gas chromatography-mass spectrometry (CG/MS)
  • as an internal standard in ultra performance liquid chromatography - tandem mass spectrometer (UPLC-MS/MS) for plasma oxysterol analysis

Biochem/physiol Actions

7-ketocholesterol (7-KC) levels are elevated in cerebrospinal fluid in multiple sclerosis, senile cataracts, in erythrocytes of sickle cell anemia and in hypercholesterolemia. 7-KC favors apoptosis in macrophages and is involved in endoplasmic reticulum stress. 7-KC is also implicated in liver damage and Niemann Pick disease.

General description

7-ketocholesterol-d7 is a deuterated derivative of 7-ketocholesterol. 7-ketocholesterol is a cholesterol autooxidation product.

Packaging

5 mL Amber Glass Screw Cap Vial (700046P-1mg)
5 mL Amber Glass Screw Cap Vial (700046P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Amelia Anderson et al.
Redox biology, 29, 101380-101380 (2020-01-14)
7-Ketocholesterol (7KC) is a toxic oxysterol that is associated with many diseases and disabilities of aging, as well as several orphan diseases. 7KC is the most common product of a reaction between cholesterol and oxygen radicals and is the most
David M van Reyk et al.
Redox report : communications in free radical research, 11(6), 255-262 (2007-01-09)
Oxysterols are the 27-carbon products of cholesterol oxidation by both enzymic and non-enzymic mechanisms. Their roles in cholesterol homeostasis, as well as in diseases in which oxidative damage and lipid peroxidation are implicated (e.g. atherosclerosis), have been investigated extensively. However
Jiayi Song et al.
Circulation research, 120(10), 1622-1631 (2017-04-07)
7-Ketocholesterol (7-KC), a form of cholesterol oxidation product, plays an essential role in the atherogenesis in animal models. We sought to determine the association of circulating 7-KC with clinical cardiovascular outcomes and total mortality in patients with stable coronary artery
Irundika H K Dias et al.
Redox biology, 16, 139-145 (2018-03-04)
Oxysterols (OHC) are biologically active cholesterol metabolites circulating in plasma that may be formed enzymatically (e.g. 24S-OHC, 25-OHC and 27-OHC) or by autoxidative mechanisms (e.g. 7-ketocholesterol, 7β-OHC and 25-OHC). Oxysterols are more soluble than cholesterol and are reported to exert
M Voorink-Moret et al.
Molecular genetics and metabolism, 123(2), 76-84 (2018-01-02)
In patients suspected of a lipid storage disorder (sphingolipidoses, lipidoses), confirmation of the diagnosis relies predominantly on the measurement of specific enzymatic activities and genetic studies. New UPLC-MS/MS methods have been developed to measure lysosphingolipids and oxysterols, which, combined with
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