Isomerization of Anacardic Acid: A Possible Route to the Synthesis of an Unsaturated Benzolactone and a Kairomone

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dc.creatorMgaya, James E.
dc.creatorMubofu, Egid B.
dc.creatorMgani, Quintino A.
dc.creatorCordes, David B.
dc.creatorSlawin, Alexandra M. Z.
dc.creatorCole‐Hamilton, David J.
dc.date2016-06-15T20:50:22Z
dc.date2016-06-15T20:50:22Z
dc.date2014-09
dc.descriptionFull text can be accessed at http://onlinelibrary.wiley.com/doi/10.1002/ejlt.201400268/full
dc.descriptionCrystalline unsaturated lactone, 8-hydroxy-3-tridecyl-1H-isochromen-1-one (6) has been synthesized by isomerization of anacardic acid having heterogeneous alkyl side chains (a mixture of mono-, di-, and tri-unsaturated anacardic acid) (1). Hydrogenation of 8-hydroxy-3-tridecyl-1H-isochromen-1-one produced a saturated lactone, 8-hydroxy-3-tridecyl-3,4-dihydroisochromen-1-one (7). Isomerization of monoene anacardic acid resulted in a crystalline isoanacardic acid, (E)-2-hydroxy-6-(pentadec-1-enyl)benzoic acid (8) as a major product. This was then metathesized with 2-butene to give 3-prop-1-enylphenol (10). Both isomerization reactions used a 1,2-bis(ditertiarybutylphosphinomethyl)benzene modified palladium catalyst. The two products, 8-hydroxy-3-tridecyl-1H-isochromen-1-one and (E)-2-hydroxy-6-(pentadec-1-enyl)benzoic acid have been crystallographically characterized.
dc.identifierMgaya, J.E., Mubofu, E.B., Mgani, Q.A., Cordes, D.B., Slawin, A.M. and Cole‐Hamilton, D.J., 2015. Isomerization of anacardic acid: A possible route to the synthesis of an unsaturated benzolactone and a kairomone. European Journal of Lipid Science and Technology, 117(2), pp.190-199.
dc.identifierhttp://hdl.handle.net/20.500.11810/2455
dc.identifier10.1002/ejlt.201400268
dc.languageen
dc.publisherWiley
dc.subjectAnacardic acid
dc.subjectBenzolactone
dc.subjectDouble bond isomerisation
dc.subjectIsoanacardic acid
dc.subjectKairomone
dc.titleIsomerization of Anacardic Acid: A Possible Route to the Synthesis of an Unsaturated Benzolactone and a Kairomone
dc.typeJournal Article

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