Resolution of d,l-menthol by interesterification with triacetin using the free and immobilized lipase of Candida cylindracea

Summary

Interesterification in isooctane with triacetin as an acyl donor was found to be a new and effective method of racemic resolution of d,l-menthol, when using the free and immobilized lipase of Candida cylindracea. No water was produced by this highly stereoselective type of reaction in contrast to ester synthesis with acetic acid as an acyl donor. Even with diacetin no possible back reaction occurred and the enzyme was easily separated from the reaction solution as opposed to ester hydrolysis in aqueous systems. Inhibition of interesterification was caused by increasing concentrations of the acyl donor triacetin by more than 10 mmol·l-1 on the one hand, and especially by diacetin on the other hand. The reaction product menthyl acetate had no influence. By adding water the interesterification activity of the lipase was reduced significantly. An alteration of the acyl donor triacetin to longerchained triglycerides caused changes in higher specific activities but poor enantioselectivities of the products, as in the case of ester synthesis starting from longer-chained organic acids.

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Correspondence to Christoph Syldatk.

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Dedicated to Prof. Dr. Fritz Wagner on the occasion of his 60th birthday

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Lokotsch, W., Fritsche, K. & Syldatk, C. Resolution of d,l-menthol by interesterification with triacetin using the free and immobilized lipase of Candida cylindracea . Appl Microbiol Biotechnol 31, 467–472 (1989). https://doi.org/10.1007/BF00270778

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Keywords

  • Lipase
  • Triglyceride
  • Candida
  • Isooctane
  • Interesterification Activity