D-isoascorbyl palmitate: lipase-catalyzed synthesis, structural characterization and process optimization using response surface methodology

Chemistry Central Journal

Wen-Jing Sun¹  Hong-Xia Zhao²  Feng-Jie Cui³  Yun-Hong Li²  Si-Lian Yu¹  Qiang Zhou¹  Jing-Ya Qian²  Ying Dong² 

[1] Parchn Sodium Isovitamin C Co. Ltd, Dexing 334221, P.R. China

[2] School of Food and Biological Engineering, Jiangsu University, Zhenjiang 212013, P.R. China

[3] Jiangxi Provincial Engineering and Technology Center for Food Additives Bio-production, Dexing 334221, P.R. China

关键词: Optimization;    Response surface methodology;    Structural characteristic;    Enzymatic synthesis;    Isoascorbyl palmitate;   

Others  :  787879
DOI  :  10.1186/1752-153X-7-114

 received in 2013-05-09, accepted in 2013-07-04,  发布年份 2013

【 摘 要 】

Background

Isoascorbic acid is a stereoisomer of L-ascorbic acid, and widely used as a food antioxidant. However, its highly hydrophilic behavior prevents its application in cosmetics or fats and oils-based foods. To overcome this problem, D-isoascorbyl palmitate was synthesized in the present study for improving the isoascorbic acid’s oil solubility with an immobilized lipase in organic media. The structural information of synthesized product was clarified using LC-ESI-MS, FT-IR, ¹H and ¹³C NMR analysis, and process parameters for high yield of D-isoascorbyl palmitate were optimized by using One–factor-at-a-time experiments and response surface methodology (RSM).

Results

The synthesized product had the purity of 95% and its structural characteristics were confirmed as isoascorbyl palmitate by LC-ESI-MS, FT-IR, ¹H, and ¹³C NMR analysis. Results from “one–factor-at-a-time” experiments indicated that the enzyme load, reaction temperature and D-isoascorbic-to-palmitic acid molar ratio had a significant effect on the D-isoascorbyl palmitate conversion rate. 95.32% of conversion rate was obtained by using response surface methodology (RSM) under the the optimized condition: enzyme load of 20% (w/w), reaction temperature of 53°C and D- isoascorbic-to-palmitic acid molar ratio of 1:4 when the reaction parameters were set as: acetone 20 mL, 40 g/L of molecular sieves content, 200 rpm speed for 24-h reaction time.

Conclusion

The findings of this study can become a reference for developing industrial processes for the preparation of isoascorbic acid ester, which might be used in food additives, cosmetic formulations and for the synthesis of other isoascorbic acid derivatives.

【 授权许可】

   
2013 Sun et al.; licensee Chemistry Central Ltd.

【 图 表 】

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