Skip to main content
SpringerLink
Log in

Cinnamyl Esters Synthesis By Lipase-Catalyzed Transesterification in a Non-Aqueous System

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Esters of cinnamyl alcohol find many applications in food, cosmetic and pharmaceutical industries as flavor and fragrance compounds. The current work focuses on the synthesis of cinnamyl acetate from cinnamyl alcohol and vinyl acetate, including screening optimization of reaction conditions such as organic solvents, temperature, catalyst loading and mole ratio. Conversion (93%) was achieved after 4 h when transesterification was carried out at vinyl acetate/cinnamyl alcohol 2:1, 4.0 g L−1 of lipase loading, and at 40 °C in hexane as solvent. Also the catalytic behaviors of lipase LipBA for synthesis different carbon chain lengths of cinnamyl esters were determined. Among the different acyl donors employed, vinyl propionate was found to be the best acyl donor which presents a 96% conversion. Enzymatic synthesis of cinnamyl esters is an efficient process vis-à-vis chemical catalysis.

Graphical Abstract

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Geng B, Wang M, Qi W, Su R, He Z (2012) Biotechnol Appl Biochem 59:270–275

    Article  CAS  Google Scholar 

  2. Devulapelli VG, Weng H-S (2009) Catal Commun 10:1638–1642

    Article  CAS  Google Scholar 

  3. Gao W, Wu K, Chen L, Fan H, Zhao Z, Gao B, Wang H, Wei D (2016) Microb Cell Fact 15:41–53

    Article  Google Scholar 

  4. Mahapatra P, Kumari A, Kumar Garlapati V, Banerjee R, Nag A (2009) J Mol Catal B 60:57–63

    Article  CAS  Google Scholar 

  5. Hou M, Wang R, Wu X, Zhang Y, Ge J, Liu Z (2015) Catal Lett 145:1825–1829

    Article  CAS  Google Scholar 

  6. Rosset IG, Cavalheiro MCHT, Assaf EM, Porto ALM (2013) Catal Lett 143:863–872

    Article  CAS  Google Scholar 

  7. Yadav GD, Dhoot SB (2009) J Mol Catal B 57:34–39

    Article  CAS  Google Scholar 

  8. Cai X, Ma J, Wei DZ, Lin JP, Wei W (2014) Antonie Van Leeuwenhoek 106:1049–1060

    Article  CAS  Google Scholar 

  9. Yadav GD, Devendran S (2012) Process Biochem 47:496–502

    Article  CAS  Google Scholar 

  10. Wu Z, Qi W, Wang M, Su R, He Z (2014) J Mol Catal B 110:32–38

    Article  CAS  Google Scholar 

  11. Badgujar KC, Pai PA, Bhanage BM (2016) Bioprocess Biosyst Eng 39:211–221

    Article  CAS  Google Scholar 

  12. Iyer PV, Ananthanarayan L (2008) Process Biochem 43:1019–1032

    Article  CAS  Google Scholar 

  13. Wang R, Hou M, Zhang Y, Ge J, Liu Z (2015) Catal Lett 145:995–999

    Article  CAS  Google Scholar 

  14. Guillaume B, Shareck Fo, Hurtubise Y, Le´pine Fo, Doucet N (2014) PLoS ONE 9:1–10

    Google Scholar 

  15. Huang J, Liu Y, Jin Q, Wu X, Wang X, Song Z (2012) J Am Oil Chem Soc 89:1627–1632

    Article  CAS  Google Scholar 

  16. Malcata FX, Reyes HR, Garcia HS, Hill CG, Amundson CH (1992) Enzyme Microb Technol 14:426–446

    Article  CAS  Google Scholar 

  17. Yong YP, Al-Duri B (1996) J Chem Technol Biot 65:239–248

    Article  CAS  Google Scholar 

  18. Yan H-D, Zhang Q, Wang Z (2014) Catal Commun 45:59–62

    Article  CAS  Google Scholar 

  19. Wolfson A, Atyya A, Dlugy C, Tavor D (2009) Bioprocess Biosyst Eng 33:363–366

    Article  Google Scholar 

  20. Damnjanović JJ, Žuža MG, Savanović JK, Bezbradica DI, Mijin DŽ, Bošković-Vragolović N, Knežević-Jugović ZD (2012) J Mol Catal B 75:50–59

    Article  Google Scholar 

Download references

Acknowledgements

This research was financially supported by the National Natural Science Foundation of China (No. C31570795), the National High Technology Research and Development Program of China (No. 2013AA102109), the Shanghai International Science and Technology Cooperation Project (No. 14520720500), the Minhang District Leading Talent Project (No. 201541), the Shanghai Talent Development Project (No. 201531).

Author information

Authors and Affiliations

  1. State Key Laboratory of Bioreactor Engineering, Newworld Institute of Biotechnology, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, People’s Republic of China

    Xianghai Cai, Wei Wang, Yaling Shen, Wei Wei & Dong-zhi Wei

  2. Research Laboratory for Functional Nanomaterial, National Engineering Research Center for Nanotechnology, Shanghai, 200241, People’s Republic of China

    Lin Lin & Dannong He

  3. Shanghai University of Medicine and Health Sciences, Shanghai, 200093, People’s Republic of China

    Lin Lin & Dannong He

Authors
  1. Xianghai Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lin Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dannong He
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yaling Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Wei Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Dong-zhi Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Yaling Shen or Wei Wei.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cai, X., Wang, W., Lin, L. et al. Cinnamyl Esters Synthesis By Lipase-Catalyzed Transesterification in a Non-Aqueous System. Catal Lett 147, 946–952 (2017). https://doi.org/10.1007/s10562-017-1994-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-017-1994-8

Keywords

Search

Navigation