Fractionated aliphatic alcohols as synthetic precursors of ultra long chain monoacylglycerols for cosmetic applications

Abstract

Background

Xerosis is an abnormally dry and flaky skin condition that is associated with a change in the packing behavior of the lipid matrix in the stratum corneum (SC), the outermost layer of the skin. This skin condition can lead to an increase in transepidermal water loss (TEWL). Since ultralong chain fatty acids have a positive effect on maintaining the packing behavior of the SC lipid matrix, a moisturizer which contains glycerides of ultralong chain fatty acids could act as an semi-occlusive layer on the surface of the skin. This will lower the rate of water evaporation through the epidermis, and consequently help prevent or improve skin xerosis.

Objective

To identify a novel source of ultralong chain lipids and develop monoacylglycerols with mixed fatty acyl chain lengths that have occlusive properties superior to petrolatum.

Methods

Initially, Performacol 425, a mixture of very long chain fatty alcohols, was fractionated using short path distillation to yield a fraction enriched with C22:0-C26:0 fatty alcohols. The fatty alcohol fraction was then oxidized using Jones reagent, and the resulting fatty acids were esterified with glycerol to yield the corresponding monoglycerides using Novozym 435. These were then evaluated using Fourier transform infrared spectroscopy, differential scanning calorimetry and water vapor transmission rate measurements.

Results

The monoacylglycerols enriched with C22:0-C26:0 displayed a melting point of 80 °C and orthorhombic packing; packing behavior mainly present in healthy SC. In addition, a phospholipid-structured emulsion containing 3% of the monoglycerides displayed occlusive properties superior to the vehicle containing 3% petrolatum jelly.

Conclusions

Performacol 425 can be a potential source of fatty alcohols to synthesize monoacylglycerols that can improve the occlusive behavior of phospholipid-structured emulsions.

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