Digitalose

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.

Digitalose

Names
IUPAC name 6-Deoxy-3-O-methyl-D-galactose
Other names D-Digitalose; 6-Deoxy-3-O-methylgalactose; 3-Methyl-D-fucose
Identifiers
CAS Number	4481-08-7
3D model (JSmol)	Interactive image
ChemSpider	167312
PubChem CID	192798
InChI InChI=1S/C7H14O5/c1-4(9)6(11)7(12-2)5(10)3-8/h3-7,9-11H,1-2H3/t4-,5+,6+,7-/m1/s1 Key: MPQBLCRFUYGBHE-JRTVQGFMSA-N InChI=1/C7H14O5/c1-4(9)6(11)7(12-2)5(10)3-8/h3-7,9-11H,1-2H3/t4-,5+,6+,7-/m1/s1 Key: MPQBLCRFUYGBHE-JRTVQGFMBY
SMILES O=C[C@H](O)[C@@H](OC)[C@@H](O)[C@H](O)C
Properties
Chemical formula	C7H14O5
Molar mass	178.184 g·mol^−1
Melting point	106 °C (223 °F; 379 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• Sarmentose, a related deoxy sugar

References

1. Digitalose, Merck Index, 12th Edition, 3202
2. Kiliani (1892). "Ueber Digitalonsäure". Chem. Ber. 25 (1): 2116–2118. doi:10.1002/cber.189202501328.
3. Otto Th. Schmidt; Walter Mayer; Alfred Distelmaier (1943). "Digitalose". Naturwissenschaften. 31 (21–22): 247–248. Bibcode:1943NW.....31..247S. doi:10.1007/bf01482327.