Journal of Japan Oil Chemists' Society
Online ISSN : 1884-1996
Print ISSN : 1341-8327
ISSN-L : 1341-8327
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
Takahiro TADAMasato NOMURAToshiaki SAKAKIYAMAYoshihito FUJIHARAKenji SHIMOMURAKoichi IIDAYukihisa YAMABE
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1997 Volume 46 Issue 8 Pages 891-897,938

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Abstract

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%.

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