4449. Glucamine

Nomenclature

CAS number: 488-43-7
1-Amino-1-deoxy-d-glucitol; 1-amino-1-deoxysorbitol; glycamine; d-glucamine.
C6H15NO5; mol wt 181.19.
C 39.77%, H 8.34%, N 7.73%, O 44.15%.

Description and references

Prepn from d-glucose: Holly et al., J. Am. Chem. Soc. 72, 5416 (1950); from N-benzylglycamine: Kagan et al., ibid. 79, 3541 (1957); by catalytic reduction of glucose in the presence of hydrazine: Lemieux, US 2830983 (1958 to Natl. Res. Council, Ottawa). Commercial prepn: Flint, Salzberg, US 2016962 (1935 to du Pont); Groggins, Stirton, Ind. Eng. Chem. 29, 1358 (1937).

Chemical structure

Properties

Crystals from methanol, mp 127°. Sharp, slightly sweet taste. [α]D15 7.95° (c = 10 in water). Very sol in water; slightly sol in alcohol. Practically insol in ether.