Journal of the American Oil Chemists' Society

, Volume 83, Issue 2, pp 93–99 | Cite as

Enrichment of CLA isomers by selective esterification with l-menthol using Candida rugosa lipase

  • Takashi Kobayashi
  • Toshihiro Nagao
  • Yomi Watanabe
  • Yoshie Yamauchi-Sato
  • Satoshi Negishi
  • Vuji Shimada
Articles

Abstract

Commercially available preparations of CLA are composed of almost equal amounts of 9-cis,11-trans (9c,11t)-CLA and 10-trans,12-cis (10t,12c)-CLA. Each isomer was fractionated and enriched, for availability as a food supplement, by a process comprising selective esterification with l-menthol by Candida rugosa lipase, distillation, and n-hexane extraction. The first selective esterification of CLA isomers was conducted with an equimolar amount of l-menthol of 30°C. The oil phase of the reaction mixture was fractionated into an l-menthyl ester fraction (9c,11t-CLA rich) and an FFA fraction (10t,12c-CLA rich) by distillation. The FFA fraction was esterified again with an equimolar amount of l-menthol to enrich 10t,12c-CLA. The 10t,12c-CLA preparation was obtained as the resulting FFA fraction by distillation. 10t,12c-CLA was enriched to 91% with 40% recovery. To enrich 9c,11t-CLA, the l-menthyl ester fraction in the first esterification was chemically hydrolyzed, and the resulting FFA were esterified again with an equimolar amount of l-menthol. The 9c, 11t-CLA preparation was obtained by chemical hydrolysis of the resulting l-methyl ester fraction, followed by n-hexane extraction. 9c,11t-CLA was enriched to 94% with 42% recovery. This effective process for purification of CLA isomers using l-methol is applicable to the production of food supplements.

Key Words

Candida rugosa lipase CLA l-menthol purification selective esterification 

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Copyright information

© AOCS Press 2006

Authors and Affiliations

  • Takashi Kobayashi
    • 2
  • Toshihiro Nagao
    • 2
  • Yomi Watanabe
    • 2
  • Yoshie Yamauchi-Sato
    • 1
  • Satoshi Negishi
    • 1
  • Vuji Shimada
    • 2
  1. 1.Nisshin OilliO Group, Ltd.Japan
  2. 2.Osaka Municipal Technical Research InstituteOsakaJapan

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