« Previous Abstract"Synthesis of [14,14,14-2H3] 12-hydroxytetradecanoic acid and [13,14-2H2] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis"    Next Abstract[Studies on volatile vegetable matter; on the trivial nomenclature of ironies] »

Lipids

Title:		Possible fatty acyl pheromone precursors in Spodoptera littoralis. Search for 11- and 12-hydroxytetradecanoic acids in the pheromone gland
Author(s):		Navarro I; Fabrias G; Camps F;
Address:		"Departamento de Quimica Organica Biologica, Centro de Investigacion y Desarrollo, Consejo Superior de Investigaciones Cientificas, Barcelona, Spain"
Journal Title:		Lipids
Year:		1997
Volume:		32
Issue:		4
Page Number:		407 - 412
DOI:		10.1007/s11745-997-0052-x
ISSN/ISBN:		0024-4201 (Print) 0024-4201 (Linking)
Abstract:		"Lipid extracts of Spodoptera littoralis pheromone glands submitted to acid methanolysis using: (i) sulfuric acid/methanol/benzene (0.1:4:2, by vol) at 90 degrees C for 1 h; (ii) 12 N HCI/methanol (1:2, vol/vol) at 90 degrees C for 1 h, or (iii) 14% BF3-MeOH at 90 degrees C for 1 h did not reveal the presence of either 11- or 12-hydroxytetradecanoic acid in the extracts, as concluded from the gas chromatography-mass spectrometry analyses. Under the above methanolysis conditions, a synthetic sample of methyl (14, 14, 14-2H3) 12-hydroxytetradecanoate remained unaltered. These results may indicate that formation of (E)-11-tetradecenoic acid from tetradecanoic acid does not occur in the pheromone gland by dehydration of an intermediate hydroxyacid. Acid methanolysis of a lipidic extract using BF3-MeOH led to the formation of a mixture of methoxy fatty acid methyl esters, identified by gas chromatography-mass spectrometry. These methoxy derivatives should arise from BF3-catalyzed addition of methanol to the double bond of the natural monounsaturated fatty acyl derivatives present in the gland. Thus, under the same conditions, a synthetic sample of methyl (Z)-11-tetradecenoate was partially transformed into methyl 11-methoxytetradecanoate and methyl 12-methoxytetradecanoate. This reaction might be a useful alternative procedure to obtain methoxy derivatives of olefins, which are very helpful for the structural characterization of the parent alkenes"
Keywords:		Animals Gas Chromatography-Mass Spectrometry Hydroxylation Myristates/*analysis Pheromones/*chemistry/metabolism Spodoptera;
Notes:		"MedlineNavarro, I Fabrias, G Camps, F eng Research Support, Non-U.S. Gov't 1997/04/01 Lipids. 1997 Apr; 32(4):407-12. doi: 10.1007/s11745-997-0052-x"