Synthesis of trans-10,cis-12 conjugated linoleic acid-enriched triacylglycerols via two-step lipase-catalyzed esterification

Ingu Kang, Hyo Jeong Bang, In-Hwan Kim, Hee Don Choi, Byung Hee Kim

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

This study aimed to synthesize trans-10,. cis-12 conjugated linoleic acid (t10,. c12-CLA)-enriched triacylglycerols (TAGs) with potential anti-obesity effects via a two-step lipase-catalyzed reaction. Commercial CLA isomer mixtures, containing 33.3g/100g t10,. c12-CLA, were esterified with dodecan-1-ol to selectively enrich the t10,. c12-CLA in a free fatty acid (FFA) fraction. The reaction was performed in a recirculating packed bed reactor using Candida rugosa lipase (immobilized on Immobead 150) as the biocatalyst. An FFA fraction containing 54.7g/100g t10,. c12-CLA was produced in a yield of 21.8g/100g initial t10,. c12-CLA under the optimal conditions, i.e., temperature, 20°C; CLA mixtures-to-dodecan-1-ol molar ratio, 1:1; water content, zero (no added water); reaction time, 36h. A t10,. c12-CLA-enriched FFA fraction was esterified with glycerol to prepare t10,. c12-CLA-enriched TAGs. The reaction was performed in a stirred batch reactor using Candida antarctica lipase B (immobilized on macroporous acrylic resin) as the biocatalyst. The optimal combination of temperature, glycerol-to-FFA fraction molar ratio, enzyme loading, reaction time, and vacuum level was 60°C, 1:3, 10g/100g (based on total substrates), 12h, and 0.4kPa, respectively. Under these conditions, the TAG content reached 93.7g/100g and t10,. c12-CLA was evenly distributed throughout the glycerol backbone of the TAG.

Original languageEnglish
Pages (from-to)249-256
Number of pages8
JournalLWT - Food Science and Technology
Volume62
Issue number1
DOIs
Publication statusPublished - 2015 Jun 1

Fingerprint

Esterification
esterification
conjugated linoleic acid
Lipase
Nonesterified Fatty Acids
free fatty acids
Triglycerides
triacylglycerols
Glycerol
glycerol
synthesis
Enzymes
Candida rugosa
Pseudozyma antarctica
Conjugated Linoleic Acids
Acrylic Resins
Temperature
Water
Vacuum
Candida

Keywords

  • Esterification
  • Lipase
  • Recirculating packed bed reactor
  • Trans-10,cis-12 conjugated linoleic acid
  • Triacylglycerol

ASJC Scopus subject areas

  • Food Science

Cite this

Synthesis of trans-10,cis-12 conjugated linoleic acid-enriched triacylglycerols via two-step lipase-catalyzed esterification. / Kang, Ingu; Bang, Hyo Jeong; Kim, In-Hwan; Choi, Hee Don; Kim, Byung Hee.

In: LWT - Food Science and Technology, Vol. 62, No. 1, 01.06.2015, p. 249-256.

Research output: Contribution to journalArticle

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abstract = "This study aimed to synthesize trans-10,. cis-12 conjugated linoleic acid (t10,. c12-CLA)-enriched triacylglycerols (TAGs) with potential anti-obesity effects via a two-step lipase-catalyzed reaction. Commercial CLA isomer mixtures, containing 33.3g/100g t10,. c12-CLA, were esterified with dodecan-1-ol to selectively enrich the t10,. c12-CLA in a free fatty acid (FFA) fraction. The reaction was performed in a recirculating packed bed reactor using Candida rugosa lipase (immobilized on Immobead 150) as the biocatalyst. An FFA fraction containing 54.7g/100g t10,. c12-CLA was produced in a yield of 21.8g/100g initial t10,. c12-CLA under the optimal conditions, i.e., temperature, 20°C; CLA mixtures-to-dodecan-1-ol molar ratio, 1:1; water content, zero (no added water); reaction time, 36h. A t10,. c12-CLA-enriched FFA fraction was esterified with glycerol to prepare t10,. c12-CLA-enriched TAGs. The reaction was performed in a stirred batch reactor using Candida antarctica lipase B (immobilized on macroporous acrylic resin) as the biocatalyst. The optimal combination of temperature, glycerol-to-FFA fraction molar ratio, enzyme loading, reaction time, and vacuum level was 60°C, 1:3, 10g/100g (based on total substrates), 12h, and 0.4kPa, respectively. Under these conditions, the TAG content reached 93.7g/100g and t10,. c12-CLA was evenly distributed throughout the glycerol backbone of the TAG.",
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