Skip to content

Research at St Andrews

Isomerization of anacardic acid: a possible route to the synthesis of an unsaturated benzolactone and a kairomone

Research output: Contribution to journalArticle

DOI

Author(s)

James E. Mgaya, Egid B. Mubofu, Quintino A. Mgani, David B. Cordes, Alexandra M. Slawin, David J. Cole-Hamilton

School/Research organisations

Abstract

Crystalline 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.
Practical applications: Unsaturated lactones are structural elements often found in natural products, which have medicinal value. Benzolactones derived from anacardic acid reported in this work have some structural similarity with lactones such as massoia lactone having medicinal value. Therefore with this idea in mind, the unsaturated benzolactones reported in this work will be tested for their anti pathogenic activity. 3-Propylphenol is used in combination with racemic 1-octen-3-ol and p-cresol to prepare a kairomone for tsetse fly traps. Results from this work describe the suitability of anacardic acid for synthesizing 3-propylphenol. The fact that 3-propylphenol can be synthesized from anacardic acid, a component of cashew nut shell liquid is of particular interest since most of the areas affected with tsetse flies are suitable for growing cashew plants. This means the raw materials (CNSL) for synthesis of 3-propylphenol will be obtained from within the same region where the kairomone is to be applied, although we appreciate that specialized facilities would be required for the types of transformation described.

Close

Details

Original languageEnglish
Pages (from-to)190-199
Number of pages10
JournalEuropean Journal of Lipid Science and Technology
Volume117
Issue number2
Early online date30 Jan 2015
DOIs
StatePublished - 6 Feb 2015

    Research areas

  • Anacardic acid, Benzolactone, Double bond isomerisation, Isoanacardic acid, Kairomone, Nut-shell liquid, Fatty-acids, Cashew, Cardanol, Occidental, Constituents, Esters, Oils

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Homochiral emissive Λ8- andΔ8-[Ir8Pd4]16+ supramolecular cages

    Rota Martir, D., Escudero, D., Jacquemin, D., Cordes, D., Slawin, A., Fruchtl, H., Warriner, S. & Zysman-Colman, E. 12 Oct 2017 In : Chemistry - A European Journal. 23, 57, p. 14358–14366

    Research output: Contribution to journalArticle

  2. Phosphorus-sulfur heterocycles incorporating an O-P(S)-O or O-P(S)-S-S-P(S)-O scaffold: one-pot synthesis and crystal structure study

    Hua, G., Davidson, K., Cordes, D. B., Du, J., Slawin, A. M. Z. & Woollins, J. D. 10 Oct 2017 In : Molecules. 22, 10, 14 p., 1687

    Research output: Contribution to journalArticle

  3. Coordination of trivalent lanthanides with bismalonamide ligands: implications for liquid-liquid extraction

    Tyumentsev, M., Foreman, M. R. S. J., Slawin, A. M. Z., Cordes, D. B., Savolainen, O., Ylmén, R., Steenari, B-M. & Ekberg, C. Oct 2017 In : European Journal of Inorganic Chemistry. 2017, 37, p. 4285-4298

    Research output: Contribution to journalArticle

  4. Near-infrared fluorescence of silicon phthalocyanine carboxylate esters

    Pal, A. K., Varghese, S., Cordes, D. B., Slawin, A. M. Z., Samuel, I. D. W. & Zysman-Colman, E. 25 Sep 2017 In : Scientific Reports. 7, 14 p., 12282

    Research output: Contribution to journalArticle

Related by journal

  1. Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

    Mmongoyo, J. A., Mgani, Q. A., Mdachi, S. J. M., Pogorzelec, P. J. & Cole-Hamilton, D. J. Oct 2012 In : European Journal of Lipid Science and Technology. 114, 10, p. 1183-1192 10 p.

    Research output: Contribution to journalArticle

ID: 176499706