Type I natural ceramide derivative and method for producing same
View Patent ↗The present invention aims to provide a novel type I natural ceramide derivative having a structure more similar to that of a type I natural ceramide composed of sphingosine and an ω-acyloxy long-chain carboxylic acid; and a method for producing the same. The derivative is provided by reacting an ω-acyloxy long-chain fatty acid derivative with dihydrosphingosine or a salt thereof. The thus produced novel type I natural ceramide derivative, when combined with other ceramides, can significantly improve the compatibility of ceramides, which facilitates preparation of a composition containing ceramides, such as a moisturizer or a cosmetic, and also increases the storage stability of the composition.
1. A novel type I natural ceramide derivative represented by formula (1):
wherein R 3 represents a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C7 to C20 aralkyl group.
2. A composition comprising the novel type I natural ceramide derivative according to claim 1 .
3. The composition according to claim 2 , further comprising at least one other ceramide.
4. The composition according to claim 3 , wherein a weight ratio of the novel type I natural ceramide derivative to the at least one other ceramide is 1:99 to 20:80.
5. The composition according to claim 4 , wherein the weight ratio of the novel type I natural ceramide derivative to the at least one other ceramide is 5:95 to 20:80.
6. The composition according to claim 3 , wherein the at least one other ceramide is a natural ceramide.
7. The composition according to claim 6 , wherein the natural ceramide is a type II natural ceramide and/or a type III natural ceramide.
8. The composition according to claim 7 , wherein the natural ceramide is a type II natural ceramide.
9. An external preparation for skin, comprising the composition according to claim 2 .
10. A moisturizer comprising the composition according to claim 2 .
11. A method for producing the novel type I natural ceramide derivative according to claim 1 , comprising
reacting an ω-acyloxy long-chain fatty acid derivative represented by formula (2):
wherein R l represents a substituted or unsubstituted C1 to C18 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C7 to C20 aralkyl group, or hydrogen, and R 3 represents a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C7 to C20 aralkyl group,
with dihydrosphingosine represented by formula (3):
or a salt thereof.
12. The composition according to claim 4 , wherein the at least one other ceramide is a natural ceramide.
13. The composition according to claim 5 , wherein the at least one other ceramide is a natural ceramide.
14. An external preparation for skin, comprising the composition according to claim 3 .
15. An external preparation for skin, comprising the composition according to claim 4 .
16. An external preparation for skin, comprising the composition according to claim 5 .
17. An external preparation for skin, comprising the composition according to claim 6 .
18. An external preparation for skin, comprising the composition according to claim 7 .
19. An external preparation for skin, comprising the composition according to claim 8 .
20. A moisturizer comprising the composition according to claim 3 .