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700088P

Avanti

Atheronal A

Avanti Research™ - A Croda Brand

Synonym(s):

3β-hydroxy-5-oxo-5,6-seco-cholestan-6-al

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About This Item

Empirical Formula (Hill Notation):
C27H46O3
Molecular Weight:
418.65
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700088P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−70°C

SMILES string

C[C@]1(CC2)C(CCC1C(CCCC(C)C)C)C(C2[C@](CC[C@H](O)C3)(C)C3=O)CC=O

General description

Atheronal A is a product of cholesterol ozonolysis.[1] It is produced in the neutrophils post oxidative burst. Atheronal A displays higher hydrophilicity than cholesterol.[2]
Atheronal molecules may be a  new association, in the already complex inter-relationship, between inflammation, cholesterol oxidation, the tissue macrophage, and atherosclerosis.

Biochem/physiol Actions

Atheronal A favors apoptosis and is implicated in atherosclerosis. It promotes neuronal cell death, β- amyloid aggregation[2] and chemotaxis in macrophages.[1] Atheronal A modulates phosphatidylethanolamine membrane structure[2] and MAPKs (mitogen activated protein kinase) functionality.[3]

Packaging

5 mL Amber Glass Screw Cap Vial (700088P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available

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D Bach et al.
Chemistry and physics of lipids, 161(2), 95-102 (2009-08-05)
The effect of an oxidized form of cholesterol, 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al on the thermotropic and structural properties of phospholipid membranes was investigated by differential scanning calorimetry and X-ray diffraction and compared with that of cholesterol. The phospholipids studied included 1-palmitoyl-2-oleoylphosphatidylserine, dipalmitoleoylphosphatidylethanolamine, 1-palmitoyl-2-oleoylphosphatidylethanolamine
D Bach et al.
Chemistry and physics of lipids, 164(7), 672-679 (2011-07-19)
An oxidized form of cholesterol, atheronal, is a form found in vivo that has been associated with human pathologies. We have studied mixtures of this oxidized sterol with the phospholipids phosphatidylethanolamine and phosphatidylcholine. We used phospholipids either with palmitoyl and
Cindy Takeuchi et al.
Biochemistry, 45(23), 7162-7170 (2006-06-07)
The proatherogenic properties of the cholesterol 5,6-secosterols (atheronal-A and atheronal-B), recently discovered in atherosclerotic arteries, have been investigated in terms of their effects on monocyte/macrophage function. A fluorescent analogue of atheronal-B (1) (50 microM), when cultured in either aqueous buffer
Natalie K Cygan et al.
Biochemistry, 50(12), 2092-2100 (2011-02-15)
Myelin degradation in the central nervous system (CNS) is a clinical hallmark of multiple sclerosis (MS). A reduction in the net positive charge of myelin basic protein (MBP) via deimination of arginine to citrulline has been shown to correlate strongly

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