D-erythro sphingomyelines (SM) having a defined acyl chain were synthesized with sphingosylphosphorylcholine as a starting material,
and both a structural property and its relating phase transition phenomenon were compared between a symmetric chain length
SM (palmitoyl-SM: C16-SM) and asymmetric chain length SMs (behenoyl-SM: C22-SM, lignoceryl-SM: C24-SM). Furthermore, effect
of increasing a content of asymmetric chain SMs in the mixture systems of C22-SM/C16-SM, and C24-SM/C16-SM was investigated.
The present calorimetric and electron microscopic studies revealed that (1) The main transition enthalpy is smaller for the
asymmetric chain SMs than for the symmetric chain SM by about 3 kJ mol−1, although the acyl chain length is longer for the former than for latter; (2) Relatively small size vesicles (100∼200 nm
diameters) surrounded by one or more lamellae are observed for the asymmetric chain SMs, in contrast to large multilamellar
vesicles (1500∼2500 nm diameters) having at least fifteen stained lamellae for the symmetric chain SM and (3) The coexisting
asymmetric chain SMs cause the decrease in size and multiplicity for the MLV of the symmetric chain SM, simultaneously with
a decrease in the main transition enthalpy.