Ent-25-hydroxycholesterol

Ent-25-hydroxycholesterol (unnatural enantiomer)

Ent-25-Hydroxycholesterol is an enantiomer of the cholesterol derivative 25-hydroxycholesterol.

Enantiomers, also called optical isomers, antipodes, or optical antipodes, are two stereoisomers that are non-superimposable mirror images of one another. These are molecules containing a chiral (asymmetrical) carbon atom.

25-Hydroxycholesterol is a 25-hydroxy steroid and an oxysterol. It derives from cholesterol and has a role as a human metabolite. The compound naturally occurs in Homo sapiens, Rissoella verruculosa and Bombyx mori.

The derivative is obtained from cholesterol through a process of binding an additional hydroxyl group at C25. The process is catalyzed by the enzyme cholesterol-25-hydroxylase, which belongs to a small family of enzymes, located in the endoplasmic reticulum and expressed in different types of tissues, especially in macrophage cells.

25-Hydroxycholesterol is found to play a role in a range of important biological processes, including regulation of cholesterol homeostasis, apoptosis, immune system functions, pathogenesis of atherosclerosis and viral infections, and more.

25-Hydroxycholesterol has been proven to suppress cholesterol synthesis in the body by preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi complex. SREBPs are membrane-bound transcription factors that activate and regulate the endogenous production of cholesterol.

The metabolite has also been shown to have apoptosis-inducing abilities, but the underlying mechanism remains unknown. Still, it is believed that 25-HC-induced apoptosis is aided by caspase-dependent signaling through a FasL-induced death receptor-mediated extrinsic pathway and mitochondria-dependent intrinsic apoptosis in FaDu cells (cells with epithelial morphology).

25-Hydroxycholesterol has been investigated in relation to coronavirus 2 (SARS-CoV-2) infection. Studies provide evidence that the compound inhibits replication of the virus and reduces viral RNA accumulation in the trachea and lungs in mouse models of SARS-CoV-2 infection. Thus, it acts as a potent protector against severe acute respiratory syndrome.

25-hydroxycholesterol enantiomer, Ent-25-Hydroxycholesterol, is an important compound to study and analyze for further insight and details into the mechanisms of the potent bioactive lipid 25-hydroxycholesterol.

Avanti’s Ent-25-Hydroxycholesterol is a high-quality product suitable for a range of research developments.

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• 3D Structure
• Structure
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