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Succinic Anhydride Modification

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Physicochemical and Enzymatic Modification of Gums

Abstract

.Polysaccharides are biocompatible substances produced from natural origins which their inherent hydrophilic nature makes them suitable to offer many functionalities such as swelling, gelling, and film forming abilities as well as enhanced viscosity. However, the backbone of polysaccharides consists of different reactive functional groups (e.g., hydroxyl, carboxyl, phosphate, and sulfate groups), which can react chemically with halogen, epoxide, carboxylic acids, and isocyanate derivatives to develop hydrophobic modified polysaccharides. In such modification, hydrophobic groups are attached randomly to the different sites of the hydrophilic structure of polysaccharides, leading to enhanced dispersibility and homogeneity in a hydrophobic medium, and hence developing new functional properties. Alkyl succinic anhydrides (ASAs), particularly octenyl succinic anhydride (OSA) and dodecenyl succinic anhydride (DSA), as inexpensive and abundant reagents, have gained more attention among other esterifying modifiers for hydrophobic modification of polysaccharides recently. Therefore, the purpose of this chapter is to provide a comprehensive study on the synthesis of OSA- and DSA-hydrophobic modified gums, their characterizations in terms of physicochemical, rheological, interfacial properties, and their potential applications in different fields, mainly the food industry.

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References

  1. Abdul Hadi N, Wiege B, Stabenau S, Marefati A, Rayner M. Comparison of three methods to determine the degree of substitution of quinoa and rice starch acetates, propionates, and butyrates: direct stoichiometry, FTIR, and 1H-NMR. Foods. 2020;9:83.

    Article  CAS  PubMed Central  Google Scholar 

  2. Al-Assaf S, Phillips GO, Aoki H, Sasaki Y. Characterization and properties of Acacia senegal (L.) Willd. var. senegal with enhanced properties (Acacia (sen) SUPER GUM™): part 1—Controlled maturation of Acacia senegal var. senegal to increase viscoelasticity, produce a hydrogel form and convert a poor into a good emulsifier. Food Hydrocoll. 2007;21:319–28.

    Article  CAS  Google Scholar 

  3. Alghooneh A, Razavi SM. Transient and dynamic rheological properties of emerging hydrocolloids. In: Emerging natural hydrocolloids: rheology and functions; 2018.

    Google Scholar 

  4. Altuna L, Herrera ML, Foresti ML. Synthesis and characterization of octenyl succinic anhydride modified starches for food applications. A review of recent literature. Food Hydrocoll. 2018;80:97–110.

    Article  CAS  Google Scholar 

  5. Amid BT, Mirhosseini H, Poorazarang H, Mortazavi SA. Implications of partial conjugation of whey protein isolate to durian seed gum through maillard reactions: foaming properties, water holding capacity and interfacial activity. Molecules. 2013;18:15110–25.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Bai Y, Shi Y-C, Herrera A, Prakash O. Study of octenyl succinic anhydride-modified waxy maize starch by nuclear magnetic resonance spectroscopy. Carbohydr Polym. 2011;83:407–13.

    Article  CAS  Google Scholar 

  7. Behrouzian F, Razavi SM. Steady shear rheological properties of emerging hydrocolloids. In: Emerging natural hydrocolloids: Rheology and functions. Wiley; 2018. p. 81–100.

    Google Scholar 

  8. Biswas A, Cheng H, Kim S, Alves CR, Furtado RF. Hydrophobic modification of cashew gum with alkenyl succinic anhydride. Polymers. 2020;12:514.

    Article  CAS  PubMed Central  Google Scholar 

  9. Caldwell CG, Wurzburg OB. Polysaccharide derivatives of substituted dicarboxylic acids. Google Patents; 1953.

    Google Scholar 

  10. Carvalho A, Curvelo A, Gandini A. Surface chemical modification of thermoplastic starch: reactions with isocyanates, epoxy functions and stearoyl chloride. Ind Crop Prod. 2005;21:331–6.

    Article  CAS  Google Scholar 

  11. Chen M, Yin T, Chen Y, Xiong S, Zhao S. Preparation and characterization of octenyl succinic anhydride modified waxy rice starch by dry media milling. Starch-Stärke. 2014;66:985–91.

    Article  CAS  Google Scholar 

  12. Chi H, Xu K, Xue D, Song C, Zhang W, Wang P. Synthesis of dodecenyl succinic anhydride (DDSA) corn starch. Food Res Int. 2007;40:232–8.

    Article  CAS  Google Scholar 

  13. Davies ER. Computer and machine vision: theory, algorithms, practicalities. Academic; 2012.

    Google Scholar 

  14. Deshpande AP. Oscillatory shear rheology for probing nonlinear viscoelasticity of complex fluids: large amplitude oscillatory shear. In: Rheology of complex fluids. Springer; 2010. p. 87–110.

    Chapter  Google Scholar 

  15. Dickinson E. Hydrocolloids at interfaces and the influence on the properties of dispersed systems. Food Hydrocoll. 2003;17:25–39.

    Article  CAS  Google Scholar 

  16. Dickinson E. Hydrocolloids as emulsifiers and emulsion stabilizers. Food Hydrocoll. 2009;23:1473–82.

    Article  CAS  Google Scholar 

  17. Dokić P, Dokić L, Dapčević T, Krstonošić V. Colloid characteristics and emulsifying properties of OSA starches. In: Colloids for nano-and biotechnology. Springer; 2008. p. 48–56.

    Chapter  Google Scholar 

  18. Eenschooten C, Guillaumie F, Kontogeorgis GM, Stenby EH, Schwach-Abdellaoui K. Preparation and structural characterisation of novel and versatile amphiphilic octenyl succinic anhydride–modified hyaluronic acid derivatives. Carbohydr Polym. 2010;79:597–605.

    Article  CAS  Google Scholar 

  19. Gahruie HH. Chemical modification of basil seed gum to improve interfacial properties. Ph.D. thesis; Department of Food Science and Technology, Shiraz University, Iran 2019.

    Google Scholar 

  20. Gahruie HH, Eskandari MH, Van der Meeren P, Hosseini SMH. Study on hydrophobic modification of basil seed gum-based (BSG) films by octenyl succinate anhydride (OSA). Carbohydr Polym. 2019;219:155–61.

    Article  Google Scholar 

  21. Gahruie HH, Eskandari MH, Khalesi M, Van der Meeren P, Hosseini SMH. Rheological and interfacial properties of basil seed gum modified with octenyl succinic anhydride. Food Hydrocoll. 2020;101:105489.

    Article  CAS  Google Scholar 

  22. George A, Sanjay M, Sriusk R, Parameswaranpillai J, Siengchin S. A comprehensive review on chemical properties and applications of biopolymers and their composites. Int J Biol Macromol. 2020;154:329–38.

    Article  CAS  PubMed  Google Scholar 

  23. Ghiasi F, Eskandari MH, Golmakani M-T, Hosseini SMH. Development of highly stable colloidal dispersions of gelled-oil nanoparticles loaded with cuminaldehyde. J Colloid Interface Sci. 2019;541:65–74.

    Article  CAS  PubMed  Google Scholar 

  24. Ghiasi F, Golmakani M-T, Eskandari MH, Hosseini SMH. A new approach in the hydrophobic modification of polysaccharide-based edible films using structured oil nanoparticles. Ind Crop Prod. 2020;154:112679.

    Article  CAS  Google Scholar 

  25. Hansen NM, Plackett D. Synthesis and characterization of birch wood xylan succinoylated in 1-n-butyl-3-methylimidazolium chloride. Polym Chem. 2011;2:2010–20.

    Article  CAS  Google Scholar 

  26. Hermanson GT. Bioconjugate techniques. Academic; 2013.

    Google Scholar 

  27. Higiro J, Herald T, Alavi S, Bean S. Rheological study of xanthan and locust bean gum interaction in dilute solution: effect of salt. Food Res Int. 2007;40:435–47.

    Article  CAS  Google Scholar 

  28. Hui R, Qi-He C, Ming-liang F, Qiong X, Guo-qing H. Preparation and properties of octenyl succinic anhydride modified potato starch. Food Chem. 2009;114:81–6.

    Article  CAS  Google Scholar 

  29. Jahanbin K, Moini S, Gohari AR, Emam-Djomeh Z, Masi P. Isolation, purification and characterization of a new gum from Acanthophyllum bracteatum roots. Food Hydrocoll. 2012;27:14–21.

    Article  CAS  Google Scholar 

  30. Klaochanpong N, Puncha-arnon S, Uttapap D, Puttanlek C, Rungsardthong V. Octenyl succinylation of granular and debranched waxy starches and their application in low-fat salad dressing. Food Hydrocoll. 2017;66:296–306.

    Article  CAS  Google Scholar 

  31. Koocheki A, Taherian AR, Bostan A. Studies on the steady shear flow behavior and functional properties of Lepidium perfoliatum seed gum. Food Res Int. 2013;50:446–56.

    Article  CAS  Google Scholar 

  32. Lai L-S, Chiang H-F. Rheology of decolorized hsian-tsao leaf gum in the dilute domain. Food Hydrocoll. 2002;16:427–40.

    Article  CAS  Google Scholar 

  33. Li X, Fang Y, Al-Assaf S, Phillips GO, Nishinari K, Zhang H. Rheological study of gum arabic solutions: interpretation based on molecular self-association. Food Hydrocoll. 2009;23:2394–402.

    Article  CAS  Google Scholar 

  34. Liang R-H, Wang L-H, Chen J, Liu W, Liu C-M. Alkylated pectin: synthesis, characterization, viscosity and emulsifying properties. Food Hydrocoll. 2015;50:65–73.

    Article  Google Scholar 

  35. Mahmood K, Alamri MS, Abdellatif MA, Hussain S, Qasem AAA. Wheat flour and gum cordia composite system: pasting, rheology and texture studies. Food Sci Technol. 2018;38:691–7.

    Article  Google Scholar 

  36. Meng F, Zheng L, Wang Y, Liang Y, Zhong G. Preparation and properties of konjac glucomannan octenyl succinate modified by microwave method. Food Hydrocoll. 2014;38:205–10.

    Article  CAS  Google Scholar 

  37. Mitura S, Sionkowska A, Jaiswal A. Biopolymers for hydrogels in cosmetics. J Mater Sci Mater Med. 2020;31:1–14.

    Article  Google Scholar 

  38. Mohammadi S, Abbasi S, Scanlon M. Development of emulsifying property in Persian gum using octenyl succinic anhydride (OSA). Int J Biol Macromol. 2016;89:396–405.

    Article  CAS  PubMed  Google Scholar 

  39. Nahm S, Cheng H. Transition-state geometry and stereochemistry of the ene reaction between olefins and maleic anhydride. J Org Chem. 1986;51:5093–100.

    Article  CAS  Google Scholar 

  40. Nesterenko A, Alric I, Silvestre F, Durrieu V. Influence of soy protein’s structural modifications on their microencapsulation properties: α-tocopherol microparticle preparation. Food Res Int. 2012;48:387–96.

    Article  CAS  Google Scholar 

  41. Niakousari M, Damueh M, Gahruie HH, Bekhit A, Greiner R, Roohiejad S. Conventional emulsions. In: Roohinejad S, et al., editors. Emulsion-based systems for delivery of food active compounds: formation, application, health and safety. 1st ed. Croydon: Wiley; 2018. p. 1–27.

    Google Scholar 

  42. Nie S-P, Wang C, Cui SW, Wang Q, Xie M-Y, Phillips GO. The core carbohydrate structure of Acacia seyal var. seyal (Gum arabic). Food Hydrocoll. 2013;32:221–7.

    Article  CAS  Google Scholar 

  43. Oppolzer W, Snieckus V. Intramolecular ene reactions in organic synthesis. Angew Chem Int Ed Engl. 1978;17:476–86.

    Article  Google Scholar 

  44. Padil VVT, Senan C, Černík M. Dodecenylsuccinic anhydride derivatives of gum karaya (Sterculia urens): preparation, characterization, and their antibacterial properties. J Agric Food Chem. 2015;63:3757–65.

    Article  CAS  PubMed  Google Scholar 

  45. Pan J, Yang L, Qiu D. Optimization of a synthesis process for octenylsuccinic anhydride modified gum arabic. Food Sci Biotechnol. 2015;24:7–13.

    Article  CAS  Google Scholar 

  46. Rafe A, Razavi SM. Dynamic viscoelastic study on the gelation of basil seed gum. Int J Food Sci Technol. 2013;48:556–63.

    Article  CAS  Google Scholar 

  47. Rashid F, Ahmed Z, Hussain S, Huang J-Y, Ahmad A. Linum usitatissimum L. seeds: flax gum extraction, physicochemical and functional characterization. Carbohydr Polym. 2019;215:29–38.

    Article  CAS  PubMed  Google Scholar 

  48. Sarkar S, Singhal RS. Esterification of guar gum hydrolysate and gum Arabic with n-octenyl succinic anhydride and oleic acid and its evaluation as wall material in microencapsulation. Carbohydr Polym. 2011;86:1723–31.

    Article  CAS  Google Scholar 

  49. Sarkar S, Gupta S, Variyar PS, Sharma A, Singhal RS. Hydrophobic derivatives of guar gum hydrolyzate and gum Arabic as matrices for microencapsulation of mint oil. Carbohydr Polym. 2013;95:177–82.

    Article  CAS  PubMed  Google Scholar 

  50. Sav AK, Fule RA, Ali MT, Amin P. Synthesis and evaluation of octenyl succinate anhydride derivative of fenugreek gum as extended release polymer. J Pharm Investig. 2013;43:417–29.

    Article  CAS  Google Scholar 

  51. Shah NN, Soni N, Singhal RS. Modification of proteins and polysaccharides using dodecenyl succinic anhydride: synthesis, properties and applications—a review. Int J Biol Macromol. 2018;107:2224–33.

    Article  CAS  PubMed  Google Scholar 

  52. Sharif HR, Abbas S, Majeed H, Safdar W, Shamoon M, Khan MA, Shoaib M, Raza H, Haider J. Formulation, characterization and antimicrobial properties of black cumin essential oil nanoemulsions stabilized by OSA starch. J Food Sci Technol. 2017;54:3358–65.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Shi Y, Li C, Zhang L, Huang T, Ma D, Tu Z-C, Wang H, Xie H, Zhang N-H, Ouyang B-L. Characterization and emulsifying properties of octenyl succinate anhydride modified Acacia seyal gum (gum arabic). Food Hydrocoll. 2017;65:10–6.

    Article  CAS  Google Scholar 

  54. Song X, He G, Ruan H, Chen Q. Preparation and properties of octenyl succinic anhydride modified early indica rice starch. Starch-Stärke. 2006;58:109–17.

    Article  CAS  Google Scholar 

  55. Soni N, Shah NN, Singhal RS. Dodecenyl succinylated guar gum hydrolysate as a wall material for microencapsulation: synthesis, characterization and evaluation. J Food Eng. 2019;242:133–40.

    Article  CAS  Google Scholar 

  56. Tomasik P, Wang Y, Jane JL. Facile route to anionic starches. Succinylation, maleination and phthalation of corn starch on extrusion. Starch-Stärke. 1995;47:96–9.

    Article  CAS  Google Scholar 

  57. Tømmeraas K, Eenschooten C. Aryl/alkyl succinic anhydride hyaluronan derivatives. Google Patents; 2012.

    Google Scholar 

  58. Tournier C, Grass M, Zope D, Salles C, Bertrand D. Characterization of bread breakdown during mastication by image texture analysis. J Food Eng. 2012;113:615–22.

    Article  Google Scholar 

  59. Viswanathan A. Effect of degree of substitution of octenyl succinate starch on the emulsification activity on different oil phases. J Environ Polym Degrad. 1999;7:191–6.

    Article  CAS  Google Scholar 

  60. Wang H, Williams PA, Senan C. Synthesis, characterization and emulsification properties of dodecenyl succinic anhydride derivatives of gum Arabic. Food Hydrocoll. 2014;37:143–8.

    Article  Google Scholar 

  61. Wang C, He X, Fu X, Luo F, Huang Q. High-speed shear effect on properties and octenylsuccinic anhydride modification of corn starch. Food Hydrocoll. 2015;44:32–9.

    Article  Google Scholar 

  62. Wei Y, Lin Y, Xie R, Xu Y, Yao J, Zhang J. The flow behavior, thixotropy and dynamical viscoelasticity of fenugreek gum. J Food Eng. 2015;166:21–8.

    Article  Google Scholar 

  63. Xu Y, Huang Q, Fu X, Jane, J.-L. Modification of starch octenylsuccinate by β-amylase hydrolysis in order to increase its emulsification properties. Food Hydrocoll. 2015;48:55–61.

    Article  CAS  Google Scholar 

  64. Xu T, Gao C, Feng X, Wu D, Meng L, Cheng W, Zhang Y, Tang X. Characterization of chitosan based polyelectrolyte films incorporated with OSA-modified gum arabic-stabilized cinnamon essential oil emulsions. Int J Biol Macromol. 2020;150:362–70.

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Fatemeh Ghiasi .

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Ghiasi, F., Hashemi Gahruie, H., Eskandari, M.H., Golmakani, MT., Mousavi Khaneghah, A. (2021). Succinic Anhydride Modification. In: Gahruie, H.H., Eskandari, M.H., Mousavi Khaneghah, A., Ghiasi, F. (eds) Physicochemical and Enzymatic Modification of Gums. Springer, Cham. https://doi.org/10.1007/978-3-030-87996-9_2

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