5346. Lactulose

Nomenclature

CAS number: 4618-18-2
4-O-β-d-Galactopyranosyl-d-fructose; 4-d-galactopyranosyl-4-d-fructofuranose; 4-O-β-d-galactosyl-d-fructose; 4-β-d-galactosido-d-fructose; Cholac (Alra); Constilac (Alra); Duphalac (Solvay); Generlac (Morton Grove); Lactuflor (Chephasaar); Laevilac (Fresenius); Normase (Molteni).
C12H22O11; mol wt 342.30.
C 42.11%, H 6.48%, O 51.41%.

Description and references

Prebiotic, synthetic disaccharide composed of galactose and fructose. Prepn: E. M. Montgomery, C. S. Hudson, J. Am. Chem. Soc. 52, 2101 (1930); Oosten, Rec. Trav. Chim. 86, 673 (1967); K. B. Hicks, F. W. Parrish, Carbohydr. Res. 82, 393 (1980). Clinical evaluation of effects on fecal bifidobacteria and selected metabolic indices: Y. Bouhnik et al., Eur. J. Clin. Nutr. 58, 462 (2004).

Chemical structure

Properties

Hexagonal clustered plates from methanol, mp 168-171°. Sweeter than lactose, but not as sweet as sucrose. Shows mutarotation; constant value after 24 hrs: [α]D22 51.5°. Soly in water (w/w) at 30°: 76.4%; at 60°: 81%; at 90°: >86%. Acid hydrolysis yields galactose and fructose.

Therapeutic Category

Laxative.

Therapeutic Category (Veterinary)

Reducer of blood ammonia levels; in treatment of hepatic encephalopathy; laxative.

Keywords

Laxative/Cathartic