African elephant sesquiterpenes. II. Identification and synthesis of new derivatives of 2,3-dihydrofarnesol.
A search for potential semiochemicals revealed nerolidol (6), albicanol (7), and the new 2,3-dihydrofarnesol derivatives 8-10 in the temporal gland secretions of African elephants. A novel synthesis from (E,E)-farnesol (1) provided compounds 8-10 for GC-MS comparison to the natural products. This study confirms the farnesol family as frequently occurring secondary metabolites in African elephant temporal gland secretions.
D000349:Africa; D000818:Animals; D001050:Apocrine Glands / Q000378:metabolism*; D004606:Elephants / Q000378:metabolism*; D005204:Farnesol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C470355:2,3-dihydrofarnesol; D009281:Naphthalenes; D012717:Sesquiterpenes; D005204:Farnesol; C438910:albicanol; C037055:nerolidol