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

Chemistry and Physics of Lipids

Volumn 100, Issue 1-2, 1999, Pages 33-40

  Carballeira, Néstor M ^a   Emiliano, Anastacio ^a   Guzmán, Aikomari ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

(5Z,9Z) 5,9 Eicosadienoic acid; (5Z,9Z) 5,9 Hexadecadienoic acid; (5Z,9Z) 5,9 Nonadecadienoic acid; Fatty acids; Phosphatidylcholine; Synthesis

Indexed keywords

5,9 EICOSADIENOIC ACID; 5,9 HEXADECADIENOIC ACID; 5,9 NONADECADIENOIC ACID; FATTY ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; FATTY ACIDS, UNSATURATED; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; MALVACEAE; PORIFERA; STEREOISOMERISM;

MALVACEAE; MALVAVISCUS ARBOREUS;

EID: 0032773644     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(99)00034-1     Document Type: Article

References (18)

1. Ayanoglu E., Huiting L., Djerassi C., Duzgunes N. Phospholipid studies of marine organisms. Part 17. Unusual sponge phospholipids and their analogs. Synthesis and interactions with conventional phospholipids and cholesterol in model membranes. Chem. Phys. Lipids. 47:1988;165-175.
2. Bergel'son L.D., Bezzubov A.A., Vaver V.A., Shemyakin M.M. Stereospecificity of carbonyl olefination of aldehydes by phosphorylides with unconjugated double bonds. Izv. Akad. Nauk SSSR, Ser. Khim. 11:1968;2558-2563.
3. Bestmann H.J., Koschatzky K.H., Schaetzke W., Suess J., Vostrowsky O. Bausteine zur darstellung zweifach ungesättigter schmetterlings-pheromone. Liebigs Ann. Chem. 9:1981;1705-1720.
4. Carballeira N.M., Cruz C. 5,9-Nonadecadienoic acids in Malvaviscus arboreus and Allamanda cathartica. Phytochemistry. 49:1998;1253-1256.
5. Carballeira N.M., Maldonado L. Identification of 5,9-hexadecadienoic acid in the marine sponge Chondrilla nucula. Lipids. 21:1986;470-471.
6. Carballeira N.M., Negrón V. Identification and characterization of two new methylicosadienoic acids from Erylus formosus. J. Nat. Prod. 54:1991;305-309.
7. Carballeira N.M., Reyes E.D., Sostre A., Rodríguez A.D., Rodríguez J.L., González F.A. Identification of the novel antimicrobial fatty acid (5Z,9Z)-14-methyl-5,9-pentadecadienoic in Eunicea succinea. J. Nat. Prod. 60:1997;502-504.
8. Carballeira N.M., Emiliano A., Hernández-Alonso N., González F.A. Facile synthesis and antimicrobial activity of the marine fatty acids (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid. J. Nat. Prod. 61:1998;1543-1546.
9. Davidoff F., Korn E.D. Lipids of Dictyostelium discoideum; phospholipid composition and the presence of two new fatty acids, cis, cis-5,11-octadecadienoic and cis,cis-5,9-hexadecadienoic acids. Biochem. Biophys. Res. Commun. 9:1962;54-58.
10. Djerassi C., Lam W.-K. Sponge phospholipids. Acc. Chem. Res. 24:1991;69-75.
11. Goodrich B.S., Hesterman E.R., Murray K.E., Mykytowycz R., Stanley G. Identification of behaviorally significant volatile compounds in the anal gland of the rabbit. Oryctolagus cuniculus. J. Chem. Ecol. 4:1978;581-594.
12. 13C nmr spectroscopy. Chem. Phys. Lipids. 78:1995;89-96.
13. 1b with antiulcerogenic activity I. Synthesis of ceramides with optically active α-hydroxypalmitic acids. Tetrahedron. 45:1989;7247-7262.
14. Madrigal R.V., Smith C.R. Taxus baccata seed oil: a new source of cis-5, cis-9-octadecadienoic acid. Lipids. 10:1975;502-504.
15. Mena P.L., Pilet O., Djerassi C. Phospholipid studies of marine organisms. 7. Stereospecific synthesis of (5Z,9Z)-, (5Z,9E)-, (5E,9Z)-, and (5E,9E)-5,9-hexacosadienoic acid. J. Org. Chem. 49:1984;3260-3264.
16. Mori, K., Kinsho, T., 1988. Synthesis of anti-ulcerogenic cerebrosides isolated from Tetragonia tetragonoides. Liebigs Ann. Chem. 1988, 807-814.
17. Rezanka T. Polyunsaturated and unusual fatty acids from slime molds. Phytochemistry. 33:1993;1441-1444.
18. Wolff R.L., Bayard C. Fatty acid composition of some pine seed oils. J. Am. Oil Chem. Soc. 72:1995;1043-1046.