4457. Gluconolactone

Nomenclature

CAS number: 90-80-2
d-Gluconic acid δ-lactone; glucono delta lactone; delta gluconolactone; Fujiglucon (Fujisawa).
C6H10O6; mol wt 178.14.
C 40.45%, H 5.66%, O 53.89%.

Description and references

Prepn by oxidation of glucose with bromine water: Isbell, Pigman, J. Res. Natl. Bur. Stand. 10, 337 (1933); by oxidation of glucose in Acetobacter suboxydans: King, Cheldelin, Biochem. J. 68, 31P (1958). Structure: J. Stanék et al., The Monosaccharides (Academic Press, New York, 1963) p 271.

Chemical structure

Properties

Crystals, dec 153°. Sweet taste (different from gluconic acid). [α]D20 +61.7° (c = 1). Soly in water 59 g/100 ml; in alc about 1 g/100 g. Insol in ether. Hydrolyzed to gluconic acid by water. A freshly prepd 1% aq soln has a pH of 3.6 changing to pH 2.5 within 2 hrs.

Use

Component of many cleaning cmpds because of the sequestering ability of the gluconate radical which remains active in alk solns; in the dairy industry to prevent milkstone; in breweries to prevent beerstone; as latent acid catalyst for acid colloid resins, particularly in textile printing; as a coagulant for tofu.