Abstract
We have demonstrated the potential ofVernonia galamensis seed oil as a source of hydroxy alkoxy fatty esters. Reaction of the oil with various alcohols (methanol, ethanol, 1-propanol and 2-propanol), under acidic conditions, resulted in transesterification as well as epoxy ring opening in all cases. The major products, the hydroxy alkoxy fatty esters, constituted approximately 80% of the product mixtures, of which the 12-hydroxy-13-alkoxy isomers were the major constituents. These derivatives were isolated by solvent extraction and/or column chromatography to afford 78–80% of pure isomers. Alcoholysis with butanol resulted in a poor yield of the hydroxy butoxy esters. A discussion of the isolation and mass-spectrometric characterization of these new esters is provided.
Similar content being viewed by others
References
Perdue, R.E., Jr., K.D. Carlson and M.G. Gilbert,Econ. Bot. 40:54 (1986).
Aziz, A., S.A. Khan and A.W. Sabir,Pakistan J. Sci. Ind. Res. 27:215 (1984).
Carlson, K.D., W.J. Schneider, C.P. Chang and L.H. Princen, inNew Sources of Fats and Oils, edited by E.H. Pryde, L.H. Princen and K.D. Mukherjee, American Oil Chemists’ Society, Champaign, 1981, p. 297.
Ayorinde, F.O., J. Clifton, Jr., O.A. Afolabi and R.L. Shepard,J. Am. Oil Chem. Soc. 65:942 (1988).
Kleiman, R., G.F. Spencer and F.R. Earle,Lipids 4:118 (1969).
Kleiman, R., and G.F. Spencer,J. Am. Oil Chem. Soc. 50:31 (1973).
Spencer, G.F., R.D. Plattner and R.W. Miller,Phytochemistry 16:766 (1977).
Morrison, R.T., and R. Boyd,Organic Chemistry, 5th edn., Allyn and Bacon, Inc., Boston, 1987.
Baker, A.D., and R. Engel,Organic Chemistry, 1st edn., West Publishing Co., St. Paul, 1992.
Author information
Authors and Affiliations
About this article
Cite this article
Bryant, K.A.A., Nwaonicha, C.P., Anderson, M.A. et al. Acid-catalyzed alcoholysis ofVernonia galamensis oil. J Am Oil Chem Soc 69, 1023–1026 (1992). https://doi.org/10.1007/BF02541070
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02541070