1-Allyloxy-2-hydroxy-propyl-starch : synthesis and characterization

A.M.L. Huijbrechts, J. Huang, H.A. Schols, B. van Lagen, G.M. Visser, C.G. Boeriu, E.J.R. Sudhölter

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24 Citations (Scopus)


New reactive unsaturated starch derivatives, 1-allyloxy-2-hydroxy-propyl-starches (AHP-starches), were synthesized by the reaction of waxy maize starch (WMS) and amylose-enriched maize starch (AEMS) with allyl glycidyl ether in a heterogeneous alkaline suspension containing NaOH and Na2SO4. The degree of substitution (DS) was determined by H-1 NMR spectroscopy, and a DS of 0.20 +/- 0.01 was found for both AHP-WMS and AHP-AEMS, respectively. The AHP derivatives of WMS and AEMS were further characterized with H-1 and C-13 NMR. It was shown that the AHP substitution was located on the C-6 hydroxyl group of the glucose residues in the starch. The substitution pattern of the AHP groups along the polymer chain was randomly clustered, as determined by enzymatic digestion using pullulanase, a-amylase, and amyloglucosidase, followed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analysis of the digestion products. With X-ray diffraction and scanning electron microscopy, no changes in the granular morphology and crystallinity between the unmodified starches and AHP-starches were detected. (c) 2007 Wiley Periodicals, Inc.
Original languageEnglish
Pages (from-to)2734-2744
JournalJournal of Polymer Science. Part A, Polymer Chemistry
Issue number13
Publication statusPublished - 2007


  • sweet-potato starches
  • acetyl substitution
  • amylopectin populations
  • amylose
  • cellulose
  • granules
  • acetate
  • pattern
  • waxy


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