A new sunscreen of the cinnamate class: synthesis and enzymatic hydrolysis evaluation of glyceryl esters of p-methoxycinnamic acid.
Glyceryl esters of p-methoxycinnamic acid, 1,3-dipalmitoyl-2-p-methoxycinnamoyl-1,2,3-propanetriol and 1,3-dioctanoyl-2-p-methoxycinnamoyl-1,2,3-propanetriol were synthesised in an attempt to increase substantivity and decrease eventual undesirable effects of sunscreens of this class. To assess if the glyceryl esters could present a higher stability towards hydrolysis by lipases in the stratum corneum, hydrolysis rates were determined in vitro using a commercial fungal lipase from Rhizomucor miehei. Results presented herein show that the glyceryl esters have similar lambda(max) and epsilon values to sunscreens of the cinnamate class. The ester 1,3-dipalmitoyl-2-p-methoxycinnamoyl-1,2,3-propanetriol presented a 2.8 times lower hydrolysis rate by lipase, in vitro, than the commercial sunscreen 2-ethylhexyl-p-methoxycinnamate (alkyl ester). This finding suggests that this triacylglycerol can possibly have a longer retention time in the skin and consequently promote a more intense and effective antisolar action than the commercial sunscreen.
de Freitas
Zaida Maria Faria
ZM
Departamento de Medicamentos, Universidade Federal do Rio de Janeiro, CCS bloco K, 2 andar, sala 50, Ilha do Fundão, CEP 21941-590, Rio de Janeiro, Brazil. zaidaff@terra.com.br
dos Santos
Elisabete Pereira
EP
da Rocha
João Ferreira
JF
Dellamora-Ortiz
Gisela Maria
GM
Gonçalves
José Carlos Saraiva
JC
D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D012867:Skin / Q000378:metabolism; D013473:Sunscreening Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D014280:Triglycerides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D002934:Cinnamates; D013473:Sunscreening Agents; D014280:Triglycerides; D008049:Lipase