Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z, 9Z)-5,9-eicosadienoic acid through a common synthetic route

Citation
Nm. Carballeira et al., Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z, 9Z)-5,9-eicosadienoic acid through a common synthetic route, CHEM PHYS L, 100(1-2), 1999, pp. 33-40
Citations number
18
Categorie Soggetti
Biochemistry & Biophysics
Journal title
CHEMISTRY AND PHYSICS OF LIPIDS
ISSN journal
00093084 → ACNP
Volume
100
Issue
1-2
Year of publication
1999
Pages
33 - 40
Database
ISI
SICI code
0009-3084(199907)100:1-2<33:FSF(A(>2.0.ZU;2-U
Abstract
The Delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-non adecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercial ly available 2-(2-bromoethyl)-1,3-dioxoiane. The synthetic approach provide d enough material to corroborate the structure and stereochemistry of (5Z,9 Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2 -[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl -2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthe sized from commercially available L-alpha-phosphatidylcholine (egg yolk) an d characterized by positive ion electrospray mass spectrometry. These are t he first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-l position and Delta 5,9 fatty acids at the sn-2 position. (C) 1 999 Elsevier Science Ireland Ltd. All rights reserved.