Skip to main content
SpringerLink
Log in

Process optimization and kinetic evaluation for biosynthesis of d-isoascorbyl stearate

  • Original Paper
  • Published:
Bioprocess and Biosystems Engineering Aims and scope Submit manuscript

Abstract

The synthesis of d-isoascorbyl stearate from d-isoascorbic acid and stearic acid with immobilized lipase (Novozym®435) as catalyst was studied. Response surface methodology and Box-Behnken design with six variables and three levels were employed to evaluate the effects of processing conditions on the conversion of d-isoascorbic acid. The results confirmed that the response surface method and statistical analysis were proved to be useful in developing optimal conditions for d-isoascorbyl stearate synthesis. The optimum conditions were predicted as follows: reaction temperature 48 °C, reaction time 17.7 h, immobilized lipase amount 50.0 % (w/w, of d-isoascorbic acid), substrate molar ratio 9:1 (stearic acid to d-isoascorbic acid), d-isoascorbic acid concentration 0.14 mol/L (based on solvent), 4A molecular sieve addition 200 g/L (based on solvent), and the optimal conversion was 90.6 %. Through the kinetics model fitting of the esterification, it was considered that the esterification conformed to a Ping–Pong bi–bi kinetic model with d-isoascorbic acid inhibition, and the obtained kinetic constants showed that the inhibition of d-isoascorbic acid and the enzyme affinity to substrate were abate with the increase of the reaction temperature.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Andersen FA (2005) Final report of the safety assessment of l-ascorbic acid, calcium ascorbate, magnesium ascorbate, magnesium ascorbyl phosphate, sodium ascorbate, and sodium ascorbyl phosphate as used in cosmetics. Int J Toxicol 24:51–111

    CAS  Google Scholar 

  2. Chang SW, Yang CJ, Chen FY, Akoh CC, Shieh CJ (2009) Optimized synthesis of lipase-catalyzed l-ascorbyl laurate by Novozym®435. J Mol Catal B-Enzym 56:7–12

    Article  CAS  Google Scholar 

  3. Liu XY, Guo FL, Wu LM, Liu YC, Liu ZL (1996) Remarkable enhancement of antioxidant activity of vitamin C in an artificial bilayer by making it lipo-soluble. Chem Phys Lipids 83:39–43

    Article  CAS  Google Scholar 

  4. Zheng DG, Xiao ZP, Ye HD (2008) Synthesis of saturated alkanoyl-6-O-d-isoascorbates. Chin J Synth Chem 16:99–101

    CAS  Google Scholar 

  5. Zheng DG, Ye HD, Wu T, Liu F, Xiao ZP (2007) Synthesis of d-isoascorbyl myristate. Chem Res Appl 19:104–105

    CAS  Google Scholar 

  6. Zheng DG, Ye HD, Ye Q, Liu F, Wu T (2007) Synthesis of d-isoascorbyl caprate and its solubility test. Chem Reag 29:157–158

    CAS  Google Scholar 

  7. Sun WJ, Zhao HX, Cui FJ, Li YH, Yu SL, Zhou Q, Qian JY, Dong Y (2013) d-isoascorbyl palmitate: lipase-catalyzed synthesis, structural characterization and process optimization using response surface methodology. Chem Cent J 7:114–126

    Article  Google Scholar 

  8. Zhang XL, Zhu XH, Zheng DG, Yu SL (2013) Lipase-catalyzed synthesis of d-isoascorbyl laurate. Chem World 54:293–296

    CAS  Google Scholar 

  9. Lerin LA, Richetti A, Dallago R, Treichel H, Mazutti MA, Oliveira JV, Antunes OAC, Oestreicher EG, De OD (2012) Enzymatic synthesis of ascorbyl palmitate in organic solvents: process optimization and kinetic evaluation. Food Bioprocess Tech 5:1068–1076

    Article  CAS  Google Scholar 

  10. Burham H, Gafoor RA, Rasheed A, Noor NM, Badruddin S, Sidek H (2009) Enzymatic synthesis of palm-based ascorbyl esters. J Mol Catal B-Enzym 58:153–157

    Article  CAS  Google Scholar 

  11. Xu FJ, Tan TW (2005) Biological synthesis of l-ascorbyl palmitate. Chin J Biotechnol 21:988–992

    CAS  Google Scholar 

  12. Zhang DH, Li C, Xie LL, Yuwen LX (2013) Enzymatic synthesis of l-ascorbyl laurate in DMSO-acetone mixed solvent. Ind Eng Chem Res 52:11875–11879

    Article  CAS  Google Scholar 

  13. Gao J, Jiang YJ, Huang ZH, Zhou LY (2007) Evaluation of kinetic parameters for enzymatic interesterification synthesis of l-ascorbyl lactate by response surface methodology. Appl Biochem Biotech 136:153–164

    Article  CAS  Google Scholar 

  14. Huang ZL, He BR, Mo C (2004) Study on the synthesis of l-ascorbyl benzoate and its property. Food Sci 25:87–90

    CAS  Google Scholar 

  15. Bezbradica D, Stojanović M, Veličković D, Dimitrijević A, Carević M, Mihailović M, Milosavić N (2013) Kinetic model of lipase-catalyzed conversion of ascorbic acid and oleic acid to liposoluble vitamin C ester. Biochem Eng J 71:89–96

    Article  CAS  Google Scholar 

  16. Kuwabara K, Watanabe Y, Adachi S, Nakanishi K, Matsuno R (2003) Synthesis of 6-O-unsaturated acyl l-ascorbates by immobilized lipase in acetone in the presence of molecular sieve. Biochem Eng J 16:17–22

    Article  CAS  Google Scholar 

  17. Song QX, Zhao Y, Xu WQ, Zhou WY, Wei DZ (2006) Enzymatic synthesis of l-ascorbyl linoleate in organic media. Bioprocess Biosyst Eng 28:211–215

    Article  CAS  Google Scholar 

  18. Watanabe Y, Sawahara Y, Nosaka H, Yamanaka K, Adachi S (2008) Enzymatic synthesis of conjugated linoleoyl ascorbate in acetone. Biochem Eng J 40:368–372

    Article  CAS  Google Scholar 

  19. Zhang DH, Li C, Zhi GY (2013) Kinetic and thermodynamic investigation of enzymatic l-ascorbyl acetate synthesis. J Biotechnol 168:416–420

    Article  CAS  Google Scholar 

  20. Hans M, Keul H, Moeller M (2009) Ring-opening polymerization of DD-lactide catalyzed by novozyme 435. Macromol Biosci 9:239–247

    Article  CAS  Google Scholar 

  21. Tamayo JJ, Ladero M, Santos VE, Garcia-Ochoa F (2012) Esterification of benzoic acid and glycerol to alpha-monobenzoate glycerol in solventless media using an industrial free Candida antarctica lipase B. Process Biochem 47:243–250

    Article  CAS  Google Scholar 

  22. Gayot S, Santarelli X, Coulon D (2003) Modification of flavonoid using lipase in non-conventional media: effect of the water content. J Biotechnol 101:29–36

    Article  CAS  Google Scholar 

  23. Srinivasan K, Devi KV (2010) Characterization of l-ascorbic acid single crystals grown from solution with different solvents. Cryst Res Technol 45:946–952

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was financially supported by Technology Breakthrough Major Project in Henan Province (Grant No: 112101210200).

Author information

Authors and Affiliations

  1. School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou, 450001, China

    Zhenfeng Liu, Yanmin Shen, Weiwei Li, Wen Zhang, Tao Li & Baozeng Ren

  2. School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, 450001, China

    Yanmin Shen

Authors
  1. Zhenfeng Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yanmin Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Weiwei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wen Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tao Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Baozeng Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Tao Li or Baozeng Ren.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 167 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, Z., Shen, Y., Li, W. et al. Process optimization and kinetic evaluation for biosynthesis of d-isoascorbyl stearate. Bioprocess Biosyst Eng 38, 833–839 (2015). https://doi.org/10.1007/s00449-014-1326-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00449-014-1326-y

Keywords

Search

Navigation