Structure Determination of Sucrose by Acetylation and Acid Hydrolysis

• Published in: Journal of the Korean Wood Science and Technology Vol. 42; no. 2; pp. 183 - 192
• Main Authors: Min, Hee-Jeong, Lee, Tae-Seong, Bae, Young-Soo
• Format: Journal Article
• Language: English
• Published: 한국목재공학회 25.03.2014
• Subjects: 임학
• ISSN: 1017-0715; 2233-7180
• DOI: 10.5658/WOOD.2014.42.2.183

For the structure determination of D-(+)-sucrose, which consists of α-D-(+)-glucose and β-D-(+)-fructose, it was acetylatedwith acetic anhydride and triethyl amine, pyridine, zinc chloride, and sodium acetate as catalysts. The acetylatedD-(+)-sucrose was acid-hydrolyzed using sulfuric acid and sodium chloride in methanolic solution. The structures of thereaction products were determined by1H-NMR and13C-NMR spectra. The yield of the acetylation indicated the highvalue 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-β-D-(+)-glucose and it suggests that the acetylatedD-(+)-sucrose was rearranged through the formation of oxonium ion by mutarotation in the 2,3,4,6-tetra-O-acetyl-α-D-(+)-glucose moiety and through the ring opening in the 1',3',4',6'-tetra-O-acetyl-β-D-(+)-fructose moiety. KCI Citation Count: 0