Skip to main content
SpringerLink
Log in

Optimal production and structural characterization of erythorbyl laurate obtained through lipase-catalyzed esterification

  • Research Article
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

Erythorbic acid, a stereoisomer of L-ascorbic acid, has been extensively used as an antioxidant but cannot be applied to lipid-based foods due to its poor lipophilicity. For this reason, synthesis of erythorbyl laurate (6-O-lauroyl-erythorbate) was achieved in acetonitrile using an immobilized lipase from Candida antarctica as a biocatalyst to increase its lipophilicity. Response surface methodology was used to optimize the erythorbyl laurate synthesis conditions in terms of enzyme content (1,000–5,000 propyl laurate unit, PLU), molar ratio of lauric acid to erythorbic acid (5–25), and reaction temperature (25–65°C). The central composite experimental results showed the conditions for maximum molar conversion yield were as follows: enzyme content, 2,994 PLU; lauric acid to erythorbic acid molar ratio, 24.23; and reaction temperature, 53.03°C. The maximum molar conversion yield reached 77.81%, which was in agreement with the predicted value (76.92%). The erythorbyl laurate was purified and identified by Fourier transform-infrared spectroscopy (FT-IR). This research could help to develop an economical method of synthesizing erythorbyl laurate for use as a novel foodgrade emulsifier with antioxidative activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Sherwin ER. Antioxidants for food fats and oils. J. Am. Oil Chem. Soc. 49: 468–472 (1972)

    Article  CAS  Google Scholar 

  2. Kochhar SP, Rossell JB. Detection, estimation, and evaluation of antioxidants in food systems. pp. 19–64. In: Food Antioxidants. Hudson BJF (ed). Elsevier, New York, NY, USA (1990)

    Chapter  Google Scholar 

  3. Pratt DE, Hudson BJF. Natural antioxidants not exploited commercially. pp. 171–191. In: Food Antioxidants. Hudson BJF (ed). Elsevier, New York, NY, USA (1990)

    Chapter  Google Scholar 

  4. Shahidi F, Janitha PK, Wanasundara PD. Phenolic antioxidants. Crit. Rev. Food Sci. 32: 67–103 (1992)

    Article  CAS  Google Scholar 

  5. Schuler P. Natural antioxidants exploited commercially. pp. 99–170. In: Food Antioxidants. Hudson BJF (ed). Elsevier, New York, NY, USA (1990)

    Chapter  Google Scholar 

  6. Wang XY, Seib PA, Ra KS. L-Ascorbic acid and its 2-phosphorylated derivatives in selected foods: Vitamin C fortification and antioxidant properties. J. Food Sci. 60: 1295–1300 (1995)

    Article  CAS  Google Scholar 

  7. Chang S-W, Yang C-J, Chen F-Y, Akoh CC, Shieh C-J. Optimized synthesis of lipase-catalyzed L-ascorbyl laurate by Novozym® 435. J. Mol. Catal. B-Enzym. 56: 7–12 (2009)

    Article  CAS  Google Scholar 

  8. Humeau C, Girardin M, Coulon D, Miclo A. Synthesis of 6-Opalmitoyl L-ascorbic acid catalyzed by Candida antartica lipase. Biotechnol. Lett. 17: 1091–1094 (1995)

    Article  CAS  Google Scholar 

  9. Kuwabara K, Watanabe Y, Adachi S, Nakanishi K, Matsuno R. Continuous production of acyl L-ascorbates using a packed-bed reactor with immobilized lipase. J. Am. Oil Chem. Soc. 80: 895–899 (2003)

    Article  CAS  Google Scholar 

  10. Karmee SK. Biocatalytic synthesis of ascorbyl esters and their biotechnological applications. Appl. Microbiol. Biot. 81: 1013–1022 (2009)

    Article  CAS  Google Scholar 

  11. Burham H, Rasheed RAGA, Noor NM, Badruddin S, Sidek H. Enzymatic synthesis of palm-based ascorbyl esters. J. Mol. Catal. BEnzym. 58: 153–157 (2009)

    Article  CAS  Google Scholar 

  12. Bradoo S, Saxena RK, Gupta R. High yields of ascorbyl palmitate by thermostable lipase-mediated esterification. J. Am. Oil Chem. Soc. 76: 1291–1295 (1999)

    Article  CAS  Google Scholar 

  13. Swern D, Stirton AJ, Turer J, Wells PA. Fatty acid monoesters of Lascorbic acid and D-isoascorbic acid. J. Am. Oil Chem. Soc. 20: 224–226 (1943)

    CAS  Google Scholar 

  14. Fidler MC, Davidsson L, Zeder C, Hurrell RF. Erythorbic acid is a potent enhancer of nonheme-iron absorption. Am. J. Clin. Nutr. 79: 99–102 (2004)

    CAS  Google Scholar 

  15. Park K-M, Lee DE, Sung H, Lee J, Chang P-S. Lipase-catalyzed synthesis of erythorbyl laurate in acetonitrile. Food Chem. 129: 59–63 (2011)

    Article  CAS  Google Scholar 

  16. Song Q-X, Wei D-Z. Study of vitamin C ester synthesis by immobilized lipase from Candida sp. J. Mol. Catal. B-Enzym. 18: 261–266 (2002)

    Article  CAS  Google Scholar 

  17. Myers RH, Montgomery DC, Anderson-Cook CM. Response Surface Methodology: Process and Product Optimization Using Designed Experiments. John Wiley & Sons, Hoboken, NJ, USA (2009)

    Google Scholar 

  18. Box GEP, Wilson KB. On the experimental attainment of optimum conditions. J. Roy. Stat. Soc. B Met. 13: 1–45 (1951)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Agricultural Biotechnology, Seoul National University, Seoul, 151-742, Korea

    Da Eun Lee, Kyung Min Park & Pahn-Shick Chang

  2. Department of Food Science and Technology, Seoul National University of Science and Technology, Seoul, 139-743, Korea

    Seung Jun Choi

  3. Center for Food Safety and Toxicology, Center for Agricultural Biomaterials, and Research Institute for Agriculture and Life Sciences, Seoul National University, Seoul, 151-742, Korea

    Pahn-Shick Chang

Authors
  1. Da Eun Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kyung Min Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seung Jun Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pahn-Shick Chang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Pahn-Shick Chang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lee, D.E., Park, K.M., Choi, S.J. et al. Optimal production and structural characterization of erythorbyl laurate obtained through lipase-catalyzed esterification. Food Sci Biotechnol 21, 1209–1215 (2012). https://doi.org/10.1007/s10068-012-0158-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-012-0158-2

Keywords

Search

Navigation