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

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  • TADA Takahiro
    Research and Department Division, Mikimoto pharmaceutical & Co., Ltd.
  • NOMURA Masato
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University
  • SAKAKIYAMA Toshiaki
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University
  • FUJIHARA Yoshihito
    Department of Industrial Chemistry, Faculty of Engineering, Kinki University
  • SHIMOMURA Kenji
    Research and Department Division, Mikimoto pharmaceutical & Co., Ltd.
  • IIDA Koichi
    Research and Department Division, Mikimoto pharmaceutical & Co., Ltd.
  • YAMABE Yukihisa
    Research and Department Division, Mikimoto pharmaceutical & Co., Ltd.

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Other Title
  • 3- [(8<I>Z</I>) -8-ペンタデセニル] フェノールおよび3- [(8<I>Z</I>, 11<I>Z</I>) -8, 11, 14-ペンタデカトリエニル] フェノールと数種のインドール化合物との縮合反応ならびに美白効果
  • 3 8Z 8 ペンタデセニル フェノール オヨビ 3 8Z 11Z 8 11

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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.<BR>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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