Journal of the Korean Society of Food Science and Nutrition (한국식품영양과학회지)

The Korean Society of Food Science and Nutrition (한국식품영양과학회)
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The Base Catalyzed Synthesis of Sucrose Ester Containing Omega-3 Fatty Acids

오메가 3 지방산을 함유한 Sucrose Ester의 합성

  • Shin, Jung-Ah (Dept. of Food Science and Technology, Chungnam National University) ;
  • Jang, Ji-Sun (Dept. of Food Science and Technology, Chungnam National University) ;
  • Hong, Jang-Hwan (Neomega Corp.) ;
  • Lee, Ki-Teak (Dept. of Food Science and Technology, Chungnam National University)
  • Published : 2006.09.01
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Abstract

Sucrose esters were synthesized by transesterification of sucrose with docosahexaenoic acid ethylester mixture (DHAEE). Potassium carbonate as a base catalyst was used in the presence of dimethylsulfoxide (DMSO) for the reactions. The reactions were performed with the different reaction times and molar ratios of substrates in the presence of surfactant in vacuum. Among the reaction conditions in this study, SE#4～7 showed the relatively high conversion rate (>96%) of DHAEE, leading to the high yield of sucrose esters. In addition, the product composition was changed from sucrose mono ester to di/tri/polyesters after the prolonged reaction time while the increased molar ratio of DHAEE also resulted in the composition changes of sucrose mono ester to the sucrose di/tri/polyesters. From the reaction (SE#7), conversion ratio was 98.5% in which 87.3% mono ester and 13.7% di/tri/polyester were found, resulting in the highest content of mono ester. Therefore, the sucrose ester containing various rates of mono and di/tri/polyesters, which effects on hydrophilic lipophilic balance (HLB) values, can be manipulatively synthesized using the reaction conditions reported in this study.

고급불포화지방산인 docosahexaenoic acid ethylester (DHAEE)와 sucrose를 transesterification반응을 하여 sucrose ester를 기질 및 촉매의 비율, 반응시간, 용매사용 및 기압 등을 달리하여 합성하고, 합성율을 살펴보았고, 특히, 섭취 시 인체 내에서 이용 가능한 DHA를 함유하고 있으며, hydrophilic한 유화제로써 sucrose fatty acid mono ester의 합성율을 높이는 합성조건을 연구하였다. 무용매 상태에서의 sucrose ester의 합성율이 낮았기 때문에 반응용매로써 dimethyl sulfoxide(DMSO)를 사용하여 몰비율과 반응시간에 따른 합성을 실시하였다. 여러 반응조건 중 DHAEE의 전환율(%)은 sucrose:DHAEE의 몰비율이 1:0.98, 1:0.60, 1:0.40, 1:0.20인 SE#4, SE#5, SE#6, SE#7에서 모두 96% 이상을 나타내었다. 특히, SE#6(1:0.4 mole)에서 반응시간에 따른 전환율과 sucrose ester의 조성변화를 살펴본 결과, 반응시간 1시간일 때 55.3%의 전환율(mono ester 91.6%)을 보였고, 이후 반응 3.5시간일 때에는 97.1%(mono ester 66%)의 전환율을 보였다. 따라서 반응초기에 대부분의 sucrose ester가 합성되며, 특히 반응시간이 길어짐에 따라 mono ester에서 di-, tri- 및 polyester로 그 조성이 점차 변화됨을 확인하였고, 기질 중 DHAEE의 비율이 증가할수록 sucrose mono ester의 생성은 감소한 반면에, sucrose di-, tri- 및 polyester의 생성은 증가함을 확인하였다. 연구된 합성조건 중 sucrose mono ester의 합성은 1:0.2(sucrose:DHAEE)의 몰비율로 2.5시간동안 반응(SE#7)하였을 때 98.5%의 높은 전환율을 보이면서 그 조성은 87.3%로 가장 높게 합성되었다.

Keywords

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