Sorbose

Sorbose is a ketose belonging to the group of sugars known as monosaccharides. It has a sweetness that is equivalent to sucrose (table sugar).[1] The commercial production of vitamin C (ascorbic acid) often begins with sorbose. L-Sorbose is the configuration of the naturally occurring sugar. It can be prepared from inexpensive O-benzylglucose.

Sorbose
Names
IUPAC name
Sorbose
Systematic IUPAC name
(3S,4R,5S)-1,3,4,5,6-Pentahydroxyhexan-2-one
Other names
Sorbinose
L-xylo-Hexulose
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.611
UNII
  • InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m0/s1 ☒N
    Key: BJHIKXHVCXFQLS-OTWZMJIISA-N ☒N
  • InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m0/s1
    Key: BJHIKXHVCXFQLS-OTWZMJIIBK
  • C([C@@H]([C@H]([C@@H](C(=O)CO)O)O)O)O
Properties[1]
C6H12O6
Molar mass 180.156 g·mol−1
Appearance white solid
Density 1.65 g/cm3 (15 °C)
Melting point 165 °C (329 °F; 438 K)
Highly Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

Under conditions employed for a Meerwein-Ponndorf-Verley reduction, the tetra-O-benzyl aldose converts to tetra-O-benzylsorbose. Hydrogenolysis removes the four benzyl groups, leaving sorbose.[2]

References
  1. Merck Index, 12th Edition, 8874
  2. Frihed, Tobias Gylling; Bols, Mikael; Pedersen, Christian Marcus (2015). "Synthesis of l-Hexoses". Chemical Reviews. 115 (9): 3615–3676. doi:10.1021/acs.chemrev.5b00104. PMID 25893557.
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