Photostabilization of resveratrol with alkoxycrylene compounds
View Patent ↗The photostabilizing electronic excited state energy—particularly singlet state energy from resveratrol compounds—has been found to be readily transferred to (accepted by) α-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R 1 and R 2 is a straight or branched chain C 1 -C 30 alkoxy radical, preferably C 1 -C 8 , more preferably methoxy, and the non-alkoxy radical R 1 or R 2 is hydrogen; and R 3 is a straight or branched chain C 1 -C 30 alkyl radical, preferably C 2 -C 20 . The alkoxycrylene compounds of formula (I) significantly increase the photostability of resveratrol compounds in a composition by at least 3-fold and as much as 10-fold or greater. The ability of the alkoxycrylene compounds to stabilize the resveratrol compound is concentration dependent, with the amount of resveratrol photostabilization increasing with the concentration of the alkoxycrylene compound.
1. A method of protecting a trans-resveratrol compound from isomerization to cis-resveratrol in a sunscreen or dermatological composition when exposed to UV radiation from UV-induced photodegradation comprising combining said trans-resveratrol compound with a compound of formula (I) in an amount of at least 0.1% based on the total weight of the composition,
wherein one of R 1 and R 2 is a straight or branched chain C 1 -C 30 alkoxy radical, and the non-alkoxy R 1 and R 2 is hydrogen; and R 3 is a straight or branched chain C 1 -C 30 alkyl radical, thereby photostabilizing the trans-resveratrol compound.
2. The method of claim 1 , wherein R 1 is methoxy and R 2 is hydrogen.
3. The method of claim 1 , wherein R 1 is hydrogen and R 2 is methoxy.
4. The method of claim 1 , wherein R 3 is a C 12 -C 24 straight chain or branched alkyl.
5. The method of claim 4 , wherein R 3 is a 2-butyloctyl radical.
6. The method of claim 4 , wherein R 3 is an 2-ethylhexyl radical.
7. The method of claim 1 , wherein the compound of formula (I) is present in an amount in the weight range of about 0.1% to about 20%, based on the total weight of the composition.
8. The method of claim 7 , wherein the compound of formula (I) is present in an amount in this weight range of about 0.1% to about 10%, based on the total weight of the composition.
9. The method of claim 7 , wherein the compound of formula (I) is present in an amount in this weight range of about 0.1% to about 5%, based on the total weight of the composition.
10. The method of claim 1 , wherein the resveratrol compound is present in an amount in the weight range of about 0.001% to about 5%, based on the total weight of the composition.
11. The method of claim 10 , wherein the resveratrol compound is present in this weight range of about 0.005% to about 1%, based on the total weight of the composition.
12. The method of claim 10 , wherein the resveratrol compound is present in this weight range of about 0.01% to about 0.5%, based on the total weight of the composition.
13. The method of claim 1 , wherein a molar ratio of the resveratrol compound to the compound of formula (I) is about 0.001 to about 1.
14. The method of claim 13 , wherein the molar ratio of the resveratrol compound to the compound of formula (I) is about 0.005 to about 0.1.
15. The method of claim 13 , wherein the molar ratio of the resveratrol compound to the compound of formula (I) is about 0.01 to about 0.06.