1,3-O-Benzylidene-2-linoleoyl-(rac)-glycerol (CAS 56648-80-7)

1,3-O-Benzylidene-2-linoleoyl-(rac)-glycerol, with the CAS number 56648-80-7, is a chemically modified derivative of glycerol in which the hydroxyl groups at the first and third positions are protected by a benzylidene acetal linkage, while the second position features an ester linkage to linoleic acid, an important polyunsaturated fatty acid. This compound serves as a specialized reagent in synthetic organic chemistry, particularly useful for the study and synthesis of more complex glyceride structures which are pivotal in understanding lipid behavior and assembly. The benzylidene acetal protection strategy is crucial as it stabilizes the glycerol molecule against unwanted reactions at the 1 and 3 positions, directing reactivity selectively at the 2 position. This selective reactivity is exploited in research to synthesize tailored glycerides that mimic natural structures or to create novel molecules with specific properties. For instance, in lipidomics research, 1,3-O-Benzylidene-2-linoleoyl-(rac)-glycerol can be employed to investigate the roles and dynamics of unsaturated fats in cellular lipidomes, helping to explain how these fats influence membrane fluidity and lipid signaling pathways. Moreover, the controlled deprotection of the benzylidene group allows researchers to reconstruct glycerides in a stepwise fashion, thereby studying the impact of various fatty acid compositions on lipid function and organization.