Digitalose

Title: Digitalose
CAS Registry Number: 4481-08-7
CAS Name: 6-Deoxy-3-O-methylgalactose
Additional Names: 3-methyl-D-fucose
Molecular Formula: C7H14O5
Molecular Weight: 178.18
Percent Composition: C 47.19%, H 7.92%, O 44.90%
Literature 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).
Properties: Rosettes of needles from ethyl acetate. mp 106° when freshly prepd, mp 115° after 3 days, mp 119° after 4 mos. [a]275461 +109° (15 min c = 1.7) ® [a]225461 +126° or [a]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.
Melting point: mp 106° when freshly prepd; mp 115° after 3 days; mp 119° after 4 mos
Optical Rotation: [a]275461 +109° (15 min c = 1.7); [a]225461 +126° or [a]D22 +106° (17 hrs)
Status: This monograph has been retired and is no longer subject to revision or update.
Digitogenin Digitonin Digitoxigenin Digitoxin Digitoxose

Digitalose
Digitalose.svg
Identifiers
CAS number 4481-08-7
PubChem 192798
ChemSpider 167312
Jmol-3D images Image 1
Properties
Molecular formula C7H14O5
Molar mass 178.18 g mol−1
Melting point 106 °C; 223 °F; 379 K ([1])
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Digitalose is a deoxy sugar that is a component of various cardiac glycosides including thevetin and emicymarin. It was first reported in 1892 as being obtained by the hydrolysis of Digtalinum verum.[1][2] The chemical structure was first elucidated in 1943 by the German chemist Otto Schmidt.[3] Chemically, it is a methyl ether of D-fucose.