cis-Vaccenoyl chloride (CAS 95548-26-8)

Cis-vaccenoyl chloride, identified by CAS number 95548-26-8, is a specialized chemical reagent primarily used in organic synthesis and biochemical research. This compound is a derivative of vaccenic acid, a naturally occurring trans-monounsaturated fatty acid, but in its cis form and further modified with a chloride group to increase its reactivity. In synthetic chemistry, cis-vaccenoyl chloride is valued for its ability to introduce the cis-vaccenoyl functional group into other molecules, thereby enabling the synthesis of complex lipid structures with specific geometric configurations. This functionality is particularly important for the study of lipid membranes and lipid-protein interactions within cellular models, as the cis configuration can significantly influence the physical properties of membranes, such as fluidity and phase behavior. Researchers utilize cis-vaccenoyl chloride in the preparation of phospholipid analogues and other lipid-containing assemblies, which are critical for examining the dynamics and roles of lipids in various biological systems. Moreover, its use extends to the creation of labeled molecules where the cis-vaccenoyl moiety acts as a probe or marker for tracking and analyzing lipid distribution and metabolism in non-medical experimental studies, providing insights into fundamental biochemical processes and material science applications.