Preparation and solubility of phosphorylated β-cyclodextrins

Sang Ah Lee, Seung Taik Lim

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

β-Cyclodextrin (CD) was phosphorylated with phosphoryl chloride in aqueous alkaline media at different temperatures and pH values. The phosphorylated cyclodextrin (PCD) were characterized by phosphorus contents and positions of substitution as determined by 31p-NMR spectroscopy. Reaction of CD with equivmolar POCl3 for 3 hr at pH 12 and 45°C yielded in a PCD with a phosphorus content of 5.67%. The ratio of mono-and diphosphate esters increased when the reaction temperature was raised from 25 to 60°C. The monoesterified phosphate groups were mainly located at C-6 of the anhydroglucose units when the reaction pH was 11 or 12. Reactions at pH 10, however, led to a higher degree of substitution at C-2 than at C-6. Phosphorylation enhanced the water solubility of CD. Solubility of a PCD (5.65% phosphorus) was 35% at pH 8 and 25°C. Simultaneously, solubility of the PCD in 25% ethanol in water was much greater than unsubstituted CD (22.3 vs. 2.8%). The PCD enhanced the water solubility of nonpolar compounds, such as β-carotene.

Original languageEnglish
Pages (from-to)690-694
Number of pages5
JournalCereal Chemistry
Volume75
Issue number5
Publication statusPublished - 1998 Sep 1

Fingerprint

cyclodextrins
Cyclodextrins
Solubility
solubility
Phosphorus
water solubility
phosphorus
Water
Substitution reactions
Phosphorylation
Temperature
Diphosphates
Carotenoids
carotenes
Nuclear magnetic resonance spectroscopy
nuclear magnetic resonance spectroscopy
phosphorylation
chlorides
temperature
Esters

ASJC Scopus subject areas

  • Food Science
  • Chemistry (miscellaneous)

Cite this

Preparation and solubility of phosphorylated β-cyclodextrins. / Lee, Sang Ah; Lim, Seung Taik.

In: Cereal Chemistry, Vol. 75, No. 5, 01.09.1998, p. 690-694.

Research output: Contribution to journalArticle

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AB - β-Cyclodextrin (CD) was phosphorylated with phosphoryl chloride in aqueous alkaline media at different temperatures and pH values. The phosphorylated cyclodextrin (PCD) were characterized by phosphorus contents and positions of substitution as determined by 31p-NMR spectroscopy. Reaction of CD with equivmolar POCl3 for 3 hr at pH 12 and 45°C yielded in a PCD with a phosphorus content of 5.67%. The ratio of mono-and diphosphate esters increased when the reaction temperature was raised from 25 to 60°C. The monoesterified phosphate groups were mainly located at C-6 of the anhydroglucose units when the reaction pH was 11 or 12. Reactions at pH 10, however, led to a higher degree of substitution at C-2 than at C-6. Phosphorylation enhanced the water solubility of CD. Solubility of a PCD (5.65% phosphorus) was 35% at pH 8 and 25°C. Simultaneously, solubility of the PCD in 25% ethanol in water was much greater than unsubstituted CD (22.3 vs. 2.8%). The PCD enhanced the water solubility of nonpolar compounds, such as β-carotene.

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