Journal of the Korean Wood Science and Technology

The Korean Society of Wood Science & Technology (한국목재공학회)
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Structure Determination of Sucrose by Acetylation and Acid Hydrolysis

  • Min, Hee-Jeong (Department of Forest Biomaterials Engineering, College of Forest and Environment Sciences, Kangwon National University) ;
  • Lee, Tae-Seong (Research & Education Institution of World Organic Agriculture and Fisheries) ;
  • Bae, Young-Soo (Department of Forest Biomaterials Engineering, College of Forest and Environment Sciences, Kangwon National University)
  • Received : 2014.01.27
  • Accepted : 2014.03.10
  • Published : 2014.03.25
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Abstract

For the structure determination of D-(+)-sucrose, which consists of ${\alpha}$-D-(+)-glucose and ${\beta}$-D-(+)-fructose, it was acetylated with acetic anhydride and triethyl amine, pyridine, zinc chloride, and sodium acetate as catalysts. The acetylated D-(+)-sucrose was acid-hydrolyzed using sulfuric acid and sodium chloride in methanolic solution. The structures of the reaction products were determined by $^1H$-NMR and $^{13}C$-NMR spectra. The yield of the acetylation indicated the high value in zinc chloride as 70% in zinc chloride catalyst. The acid-hydrolyzed product of the acetylated D-(+)-sucrose, 2,3,4,6,1',3',4',6'-octa-O-acetyl-D-(+)-sucrose, gave 2,3,4,6-tetra-O-acetyl-${\beta}$-D-(+)-glucose and it suggests that the acetylated D-(+)-sucrose was rearranged through the formation of oxonium ion by mutarotation in the 2,3,4,6-tetra-O-acetyl-${\alpha}$-D-(+)-glucose moiety and through the ring opening in the 1',3',4',6'-tetra-O-acetyl-${\beta}$-D-(+)-fructose moiety.

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References

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