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Digitalose

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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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: MPQBLCRFUYGBHE-JRTVQGFMBY
SMILES
  • O=C(O)(OC)(O)(O)C
Properties
Chemical formula C7H14O5
Molar mass 178.184 g·mol
Melting point 106 °C (223 °F; 379 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. The chemical structure was first elucidated in 1943 by the German chemist Otto Schmidt. Chemically, it is a methyl ether of D-fucose.

See also

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.
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