Lauryl laurate is a medium-chain saturated wax ester synthesized from lauric acid (C12:0) and lauryl alcohol (C12H25OH), representing an early member of the simple wax lipid series with properties bridging emollients and lubricants. Derived from coconut and palm kernel oils, this low-molecular-weight monoester offers superior spreadability compared to longer-chain homologs such as cetyl palmitate or behenyl behenate.
Chemical Structure
Lauryl laurate features the molecular formula C24H48O2 and a molecular weight of 368.64 g/mol, with the IUPAC name dodecyl dodecanoate (CH3(CH2)10COO(CH2)11CH3). Its symmetric linear ester linkage provides 22 rotatable bonds, no hydrogen bond donors, a TPSA of 26.3 Ų, and high lipophilicity (LogP 10.98), forming flexible β-lamellar crystals despite its compact chain length.
Physical Properties
White to pale yellow waxy solid or semi-solid (melting point 23–30°C, boiling point 226°C at reduced pressure, density 0.860 g/cm³), lauryl laurate exhibits low viscosity when molten and is insoluble in water but shows excellent solubility in oils, ethanol, and chloroform. Fluid at skin temperature, it delivers dry, non-greasy occlusion unlike heavier esters.
Synthesis and Production
Produced via acid-catalyzed esterification of lauric acid and 1-dodecanol (both sourced from coconut fractionation), followed by vacuum distillation (>99% purity). Enzymatic routes using Candida antarctica lipase can achieve higher yields when vegetable feedstocks are used.
