Glyceridic esters of p‐methoxycinnamic acid. A new sunscreen of the cinnamate class

Abstract

The aim of this work was to investigate whether a 1,3-diacylglycerol moiety can act as enhancer of the photoprotecting action of a new sunscreen of the cinnamate class, owing to its affinity with skin constituents and lower susceptibility to hydrolysis at C-2. The sun protection factors (SPF) for 1,2,3-propanetriol 1,3-dipalmitate-2-p-methoxycinnamate and 1,2,3-propanetriol 1,3-dioctanoate-2-p-methoxy-cinnamate (2.0, 4.5 and 7.5%) were determined. The sunscreen preparations presented SPF values between 4.7 and 16. The results show that although glyceridic esters present higher lipophilicity and are more stable towards enzymatic hydrolysis in vitro, the synthesized triacylglycerols and the standard sunscreen 2-ethylhexyl p-methoxycinnamoyl (EHPM) showed equivalent SPF values for both methods.

Kinetics of enzymatic synthesis of monoferuloyl glycerol and diferuloyl glycerol by transesterification in [BMIM]PF6

“…Feruloyl glycerols (FGs) are the natural derivatives of FA, which are widely used as UV absorbers and antioxidants in many commercial applications (such as, cosmetics, pharmaceuticals, and food industries) [5][6][7]. However, it is difficult to separate FGs from natural raw materials since the contents of monoferuloyl glycerol (MFG) and diferuloyl glycerol (DFG) are very low (<0.1%) [8], which made FGs synthesis very interesting [9][10][11][12].…”

Kinetics of Cinnamoyl Glycerol Formation

“…Cinnamoyl esters are commonly used as organic ultraviolet (UV) filters in sunscreens and cosmetic formulations [4,5]. Compounds such as octyl methoxycinnamate (OMC) and 2-ethylhexyl-p-methoxycinnamate are typical and the esters of longer chain fatty acids, hydroxy fatty acids, and epoxy fatty acids have also been prepared [6][7][8].…”

Preparation and Characterization of 4‐Methoxy Cinnamoyl Glycerol

“…Derivatives of cinnamic acid such as octyl methoxycinnamate (OMC) and 2-ethylhexyl-p-methoxycinnamate find use as organic UV filters in sunscreens and cosmetic formulations [1,2]. These cinnamates and the related esters formed by combining p-methoxy cinnamic acid or ferulic acids with long chain acylglycerides exhibit predominantly lipophilic characteristics [3][4][5]. However, for certain applications it would be advantageous to have a UV filter with more hydrophilic character, e.g., to limit the penetration of a topical formulation into the skin [6][7][8].…”