12-03202. Digitalose [Archived]

Nomenclature

CAS number: 4481-08-7
6-Deoxy-3-O-methylgalactose; 3-methyl-d-fucose.
C7H14O5; mol wt 178.18.
C 47.19%, H 7.92%, O 44.90%.

Description and references

First obtained by Kiliani, Ber. 25, 2116 (1892), by hydrolysis of Digitalinum verum, a glycoside of gitoxigenin with glucose and digitalose. By hydrolysis of a glycoside from the seeds of Strophanthus eminii Aschers & Pax., Apocynaceae: Lamb, Smith, J. Chem. Soc. 1936, 442. Configuration: Schmidt et al., Naturwissenschaften 31, 247 (1943); Ann. 555, 26 (1944). Elderfield in Advances in Carbohydrate Chemistry vol. I (New York, 1945) p 150. Prepn by isoln and hydrolysis of emicymarin from Strophanthus eminii seeds: Elderfield, ibid. 156. Synthesis: Reber, Reichstein, Helv. Chim. Acta 29, 343 (1946). Schmidt, Wernicke, Ann. 558, 70 (1947).

Chemical structure

Properties

Rosettes of needles from ethyl acetate. mp 106° when freshly prepd, mp 115° after 3 days, mp 119° after 4 mos. [α]275461 +109° (15 min c = 1.7) → [α]225461 +126° or [α]D22 +106° (17 hrs). By the Bertrand micro method, 1 mg digitalose has the same reducing power as 9.32 mg anhydr glucose. Soluble in water.

Status

This monograph has been retired and is no longer subject to revision or update.