NOVEL SHOGAOL COMPOUND AND TYROSINASE ACTIVITY INHIBITOR COMPRISING THE COMPOUND

摘要

The present invention provides a compound more highly active in tyrosinase activity inhibition and the like than shogaol and gingerol, which is of the same class as shogaol and gingerol useful in the fields of foods, medicines, quasi-drugs, cosmetics, etc. The invention is a compound represented by the following formula (1):
wherein R 1 is a hydrogen atom, a lower alkyl group, or a protective group of a phenolic hydroxyl group, R 2 is a hydrogen atom or a protective group of a phenolic hydroxyl group, A is an alkylene group having 1 to 4 carbon atoms, B is an alkylene group having 1 to 12 carbon atoms, R 3 is -COOR 4 (wherein R 4 is a protective group of a carboxyl group), a carboxyl group, or -CH 2 OH, and Z is -CO-CH=CH-, -CHOH-CH=CH-, -CHOH-1,2-epoxy-, -CO-CH 2 CH 2 -, -CHOH-CH 2 CH 2 -, -CO-CH 2 CHOH-, -CHOH-CH 2 CHOH-, -CO-CH 2 CHOR 5 -, -CHOH-CH 2 CHOR 5 -, a ketal derivative of -CO-CH=CH-, or a ketal derivative of -CO-CH 2 CH 2 - and R 5 is a lower alkyl group when R 3 is a -COOR 4 group, Z is -CO-CH=CH-, -CHOH-CH=CH-, -CHOH-1,2-epoxy-, -CHOH-CH 2 CH 2 -, -CHOH-CH 2 CHOH-, -CO-CH 2 CHOR 5 -, -CHOH-CH 2 CHOR 5 -, a ketal derivative of -CO-CH=CH-, or a ketal derivative of -CO-CH 2 CH 2 - and R 5 is a lower alkyl group when R 3 is a carboxyl group, or Z is -CHOH-CH=CH-, -CHOH-1,2-epoxy-, -CHOH-CH 2 CHOH-, -CO-CH 2 CHOR 5 -, -CHOH-CH 2 CHOR 5 -, a ketal derivative of -CO-CH=CH-, or a ketal derivative of -CO-CH 2 CH 2 - and R 5 is a lower alkyl group when R 3 is a -CH 2 OH.