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Chemical Senses 22: 53-65,
© 1997

research-article

Tastes, Structure and Solution Properties of D-Glucono-1,5-lactone

Sneha A. Parke, Gordon G. Birch, Douglas B. MacDougall and David A. Stevens1

Department of Food Science and Technology, University of Reading Whiteknights, PO Box 226, Reading RG6 6AP, UK 1On leave from Frances L. Hiatt School of Psychology, Clark University 950 Main St, Worcester, MA 01610, USA

Correspondence to be sent: Professor G. G. Birch, Department of Food Science and Technology, University of Reading, Whiteknights, PO Box 226, Reading, RG6 6AP, UK

D-glucono-1,5-lactone differs from D-glucopyranose only in that it has a C=O group instead of CHOH group at carbon atom number one. The molecule therefore possesses an intact 3,4{alpha}-glycol group and is sweet. However, it autohydrolyses in water solution at room temperature, forming D-gluconic acid and D-glucono-1,4-lactone. As the solution pH falls it becomes sweet-sour and eventually almost completely sour as the generated hydronium ions dominate both the solution properties and the taste perceptions elicited. It is shown that the ratio of generated hydronium ions to unchanged lactone accords with anticipated taste quality during the first 28 min of autohydrolysis. Changes in both apparent specific volume and apparent isentropic compressibility illustrate increasing solute-solvent interaction and increasing disturbance of water structure during the course of autohydrolysis. These changes are consistent with the concurrent sweet to sour change, but do not explain the weak bitterness which also accompanies them. Chem. Senses 22: 53–65, 1997.


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S. A. Parke, G. G. Birch, and R. Dijk
Some Taste Molecules and their Solution Properties
Chem Senses, August 1, 1999; 24(3): 271 - 279.
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