Condensation Reaction of 3-[(8Z)-8-Pentadecenyl] Phenol and 3-[(8Z, 11Z)-8, 11, 14-Pentadecatrienyl] Phenol with Several Indoles and Their Application to Whitening Effects Utility

Natural materiarl extracts are presently used as cosmetic ingredients. Their physiological effects were examined, using 3- [(8Z) -8-pentadecenyl] phenol (1), 3- [(8Z, 11Z) -8, 11, 14-pentadecatrienyl] phenol (2) from cashew nuts shell oil as starting material.Twenty-eight derivatives were synthesized by condensation using seven different indole carboxylic acids. These derivatives were examined for their use as whitening agents which inhibit tyrosinase activity, scarvenging of superoxygen and hyaluronidase activity. 5-Methoxyindole-2- [3'- [(8Z) -8-pentadecenyl] benzene-1'-yl] ester (1 b), 5-methoxy-2-methylindole-3-ethylene- [3'- [(8Z) -8-pentadecenyl] benzene-1'-yl] ester (1 e), 5-methoxyindole-2- [3'- [(8 Z, 11Z) -8, 11, 14-pentadecatrienyl] benzene-1'-yl] ester (2 b), 5-methoxy-2-methylindole-3-ethylene- [3'-[(8Z, 11Z) -8, 11, 14-pentadecatrienyl] benzene-1'-yl] ester (2 e) and indole-2- (3'-n-pentadecyl benzene-1'-yl) ester (3 f) caused greater inhibition of tyrosinase activity than arbutin, 5-hydroxyindole-2- [3'-[(8 Z) -8-pentadecenyl] benzene-1'-yl] ester (1 a), (1 b), 5-hydroxyindole-3-ethylene- [3'- [(8Z) -8-pentadecenyl] benzene-1'-yl] ester (1 c), (1 e) or (2 e), and to inhibit hyaluronidase activity by more than 96%.