3-(15-Hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one and its effect on neuropeptide secretion

Bioorg Med Chem Lett. 2000 Nov 20;10(22):2537-9. doi: 10.1016/s0960-894x(00)00508-4.


The aim of the present study was to describe the synthesis of a trimethyl cyclohexenonic long chain fatty alcohol (t-CFA), and analyze its biological activity. Specifically, 3-(15-hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one, the t-CFA containing 15 carbon atoms on the side chain (t-CFA n = 15) stimulated arginine vasopressin secretion in nerve terminals of the neurohypophysis. This effect was inhibited by extracellular calcium depletion, which suggests that t-CFA n = 15 stimulates neuropeptide secretion through a calcium-dependent exocytosis mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arginine Vasopressin / biosynthesis*
  • Cyclohexanones / chemistry
  • Cyclohexanones / pharmacology*
  • Fatty Alcohols
  • Male
  • Mice
  • Pituitary Gland / drug effects
  • Pituitary Gland / metabolism


  • 3-(15-hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one
  • Cyclohexanones
  • Fatty Alcohols
  • Arginine Vasopressin