Cholesterol → Cholesteryl Oleate

Participants

Reaction Steps

Esters such as steroid esters are widely used as an oil phase material or base material of cosmetics for the skin or hair, or of ointments. For example, stearic acid ester or oleic acid ester of cholesterol is contained in stick-like cosmetics such as lipstick, eyeshadow and stick pomade as well as in cosmetic cream, ointment, etc. These linear fatty acid esters of cholesterol are excellent in water-embracing or -encapsulating property and emulsifying property, exhibit affinity with the skin, and are not irritative. These properties render the esters desirable for use as an oil phase material or additive of, for example, cosmetics or ointments. However, these esters are undesirably solidified at temperatures near the human skin temperature. For example, cholesteryl stearate has a melting point of 75° to 85° C., with cholesteryl oleate having a melting point of 40° to 45° C., with the result that the cosmetics containing these esters give uncomfortable feel to the user when applied to the skin. It should also be noted that these esters are decomposed into cholesterol and fatty acids under the action of lipase present on the skin.

Provenance & Evidence