Synthesis of cocoa butter substitutes from Cinnamomum camphora seed oil and fully hydrogenated palm oil by enzymatic interesterification

  • Xiaoyu Ma
  • Zhenying Hu
  • Jinyuan Mao
  • Yuxi Xu
  • Xuemei ZhuEmail author
  • Hua Xiong
Original Article


Cinnamomum camphora trees have a vast range of distribution in southern China and the seed oil has unique fatty acid (FA) properties and various bio-activities. In this work, Cinnamomum camphora seed oil (CCSO) was utilized to synthesize value-added cocoa butter substitute (CBS) by enzymatic interesterification. The synthesis was conducted in a solvent-free system by blending CCSO with fully hydrogenated palm oil under the catalysis of Lipozyme RM IM. The reacted products were assessed with physicochemical properties, i.e. FA composition, slip melting point (SMP), triacylglycerol (TAG), crystal polymorphism, microstructure, melting and crystallization properties and solid fat content (SFC). It showed that MCFAs (capric acid plus lauric acid) was the main fatty acid in products, accounting for over 45%. Comparing to physical blends, some novel TAG species such as LaLaLa and LaMLa/LaLaM were observed after enzymatic interesterification whereas SSS TAGs were reduced. IP presented a ball-like, well-distributed and nearly round crystal microstructure and a smaller crystal size. Moreover, it should be mentioned that SFC of IP ranging from 31.85 to 38.47% at 25 °C with most β′ crystal forms, was beneficial to improve the spreadability in term of confectionery products and baked goods. The SMP of the interesterified products was 35.75–36.15 °C which closed to the commercial CBS. Hence, the products synthesized can be used to as CBS, and the results in this study also showed CCSO have value-added applications.


Cocoa butter substitute Cinnamomum camphora seed oil Enzymatic interesterification Lipozyme RM IM 



This work was supported by the Natural Science Foundation of China (31460427, 31660470) and Young Scientists of Jiangxi Province (20171BCB23025).


  1. Adhikari P, Shin JA, Lee JH, Hu JN, Zhu XM, Akoh CC, Lee KT (2010a) Production of trans-free margarine stock by enzymatic interesterification of rice bran oil, palm stearin and coconut oil. J Sci Food Agric 90:703–711. CrossRefPubMedGoogle Scholar
  2. Adhikari P et al (2010b) Scaled-up production of zero-trans margarine fat using pine nut oil and palm stearin. Food Chem 119:1332–1338. CrossRefGoogle Scholar
  3. Adhikari P, Shin JA, Lee JH, Kim HR, Kim IH, Hong ST, Lee KT (2012) Crystallization, physicochemical properties, and oxidative stability of the interesterified hard fat from rice bran oil, fully hydrogenated soybean oil, and coconut oil through lipase-catalyzed reaction. Food Bioprocess Technol 5:2474–2487. CrossRefGoogle Scholar
  4. Aini IN, Miskandar MS (2007) Utilization of palm oil and palm products in shortenings and margarines. Eur J Lipid Sci Technol 109:422–432. CrossRefGoogle Scholar
  5. Alvarez CA, Akoh CC (2015) Enzymatic synthesis of infant formula fat analog enriched with capric acid. J Am Oil Chem Soc 92:1003–1014. CrossRefGoogle Scholar
  6. Bahari A, Akoh CC (2018) Synthesis of a cocoa butter equivalent by enzymatic interesterification of illipe butter and palm midfraction. J Am Oil Chem Soc 95:547–555. CrossRefGoogle Scholar
  7. Biswas N, Cheow YL, Tan CP, Kanagaratnam S, Siow LF (2017) Cocoa butter substitute (CBS) produced from palm mid-fraction/palm kernel oil/palm stearin for confectionery fillings. J Am Oil Chem Soc 94:235–245. CrossRefGoogle Scholar
  8. Borhan RH, Said M, Sahri MM (2011) Enzymatic interesterification of palm products for producing low calorie cocoa butter substitutes. J Appl Sci 11:3750–3754. CrossRefGoogle Scholar
  9. Braipson-Danthine S, Deroanne C (2006) Determination of solid fat content (SFC) of binary fat blends and use of these data to predict SFC of selected ternary fat blends containing low-erucic rapeseed oil. J Am Oil Chem Soc 83:571–581. CrossRefGoogle Scholar
  10. de Oliveira GM, Ribeiro APB, dos Santos AO, Cardoso LP, Kieckbusch TG (2015) Hard fats as additives in palm oil and its relationships to crystallization process and polymorphism. Lwt-Food Sci Technol 63:1163–1170. CrossRefGoogle Scholar
  11. Dian NLHM, Sundram K, Idris NA (2007) Effect of chemical interesterification on triacylglycerol and solid fat contents of palm stearin, sunflower oil and palm kernel olein blends. Eur J Lipid Sci Tech 109:147–156. CrossRefGoogle Scholar
  12. Dsouza V, Deman JM, Deman L (1990) Short spacings and polymorphic forms of natural and commercial solid fats—a review. J Am Oil Chem Soc 67:835–843. CrossRefGoogle Scholar
  13. Farmani J, Hamedi M, Safari M, Madadlou A (2007) Trans-free Iranian vanaspati through enzymatic and chemical transesterification of triple blends of fully hydrogenated soybean, rapeseed and sunflower oils. Food Chem 102:827–833. CrossRefGoogle Scholar
  14. Gold IL, Ukhun ME, Akoh CC (2011) Characteristics of eutectic compositions of restructured palm oil olein, palm kernel oil and their mixtures. J Am Oil Chem Soc 88:1659–1667. CrossRefGoogle Scholar
  15. Hu JN et al (2011) Characterization of medium-chain triacylglycerol (MCT)-enriched seed oil from Cinnamomum camphora (Lauraceae) and its oxidative stability. J Agric Food Chem 59:4771–4778. CrossRefPubMedGoogle Scholar
  16. Jiang H, Wang J, Song L, Cao XS, Yao X, Tang F, Yue YD (2016) GCxGC-TOFMS analysis of essential oils composition from leaves, twigs and seeds of Cinnamomum camphora L. Presl and their insecticidal and repellent activities. Molecules. CrossRefPubMedPubMedCentralGoogle Scholar
  17. Karabulut I, Turan S, Ergin G (2004) Effects of chemical interesterification on solid fat content and slip melting point of fat/oil blends. Eur Food Res Technol 218:224–229. CrossRefGoogle Scholar
  18. Limbardo RP, Santoso H, Witono JR (2017) The effect of coconut oil and palm oil as substituted oils to cocoa butter on chocolate bar texture and melting point. In: American Institute of Physics Conference Series, pp 7–17.
  19. Liu CH, Mishra AK, Tan RX, Tang C, Yang H, Shen YF (2006) Repellent and insecticidal activities of essential oils from Artemisia princeps and Cinnamomum camphora and their effect on seed germination of wheat and broad bean. Bioresour Technol 97:1969–1973. CrossRefPubMedGoogle Scholar
  20. Mayamol PN, Balachandran C, Samuel T, Sundaresan A, Arumughan C (2009) Zero trans shortening using rice bran oil, palm oil and palm stearin through interesterification at pilot scale. Int J Food Sci Technol 44:18–28. CrossRefGoogle Scholar
  21. Mcgauley SE, Marangoni AG, Marangoni AG, Narine SS (2002) Static crystallization behavior of cocoa butter and its relationship to network microstructure. Phys Prop Lipids 10:150. CrossRefGoogle Scholar
  22. Mohamed IO (2015) Enzymatic synthesis of cocoa butter equivalent from olive oil and palmitic-stearic fatty acid mixture. Appl Biochem Biotech 175:757–769. CrossRefGoogle Scholar
  23. Papamandjaris AA, MacDougall DE, Jones PJH (1998) Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications. Life Sci 62:1203–1215. CrossRefPubMedGoogle Scholar
  24. Petrauskaite V, De Greyt W, Kellens M, Huyghebaert A (1998) Physical and chemical properties of trans-free fats produced by chemical interesterification of vegetable oil blends. J Am Oil Chem Soc 75:489–493. CrossRefGoogle Scholar
  25. Ribeiro APB, Grimaldi R, Gioielli LA, Goncalves LAG (2009) Zero trans fats from soybean oil and fully hydrogenated soybean oil: physico-chemical properties and food applications. Food Res Int 42:401–410. CrossRefGoogle Scholar
  26. Soares FASD, da Silva RC, da Silva KCG, Lourenco MB, Soares DF, Gioielli LA (2009) Effects of chemical interesterification on physicochemical properties of blends of palm stearin and palm olein. Food Res Int 42:1287–1294. CrossRefGoogle Scholar
  27. Solis-Fuentes JA, Hernandez-Medel MD, Duran-de-Bazua MD (2005) Determination of the predominant polymorphic form a of mango (Mangifera indica) almond fat by differential scanning calorimetry and X-ray diffraction. Eur J Lipid Sci Technol 107:395–401. CrossRefGoogle Scholar
  28. Takeuchi H, Sekine S, Kojima K, Aoyama T (2008) The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation. Asia Pac J Clin Nutr 17:320–323PubMedGoogle Scholar
  29. Tang L, Hu JN, Zhu XM, Luo LP, Lei L, Deng ZY, Lee KT (2012) Enzymatic interesterification of palm stearin with Cinnamomum camphora seed oil to produce zero-trans medium-chain triacylglycerols-enriched plastic fat. J Food Sci 77:C454–C460CrossRefGoogle Scholar
  30. Xu YX, Zhu XM, Ma XY, Xiong H, Zeng ZL, Peng HL, Hu JN (2018) Enzymatic production of trans-free shortening from coix seed oil, fully hydrogenated palm oil and Cinnamomum camphora seed oil. Food Biosci 22:1–8. CrossRefGoogle Scholar
  31. Yamoneka J, Malumba P, Lognay G, Bera F, Blecker C, Danthine S (2018) Enzymatic inter-esterification of binary blends containing Irvingia gabonensis seed fat to produce cocoa butter substitute. Eur J Lipid Sci Technol 120:10. CrossRefGoogle Scholar
  32. Zaidul ISM, Norulaini NAN, Omar AKM, Smith RL (2007) Blending of supercritical carbon dioxide (SC-CO2) extracted palm kernel oil fractions and palm oil to obtain cocoa butter replacers. J Food Eng 78:1397–1409. CrossRefGoogle Scholar
  33. Zhang X, Li L, Xie H, Liang ZL, Su JY, Liu GQ, Li B (2014) Effect of temperature on the crystalline form and fat crystal network of two model palm oil-based shortenings during storage. Food Bioprocess Technol 7:887–900. CrossRefGoogle Scholar
  34. Zhu XM et al (2012) Physiochemical and oxidative stability of interesterified structured lipid for soft margarine fat containing Delta 5-UPIFAs. Food Chem 131:533–540. CrossRefGoogle Scholar
  35. Zhu TW, Zhao YL, Zong MH, Li B, Zhang X, Wu H (2017) Improvement of physical properties of palm stearin and soybean oil blends by enzymatic interesterification and their application in fast frozen food. RSC Adv 7:34435–34441. CrossRefGoogle Scholar

Copyright information

© Association of Food Scientists & Technologists (India) 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Food Science and TechnologyNanchang UniversityNanchangPeople’s Republic of China

Personalised recommendations