Sorbose
Appearance
(Redirected from Sorbinose)
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Names | |||
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IUPAC name
L-xylo-Hex-2-ulose
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Systematic IUPAC name
(3S,4R,5S)-1,3,4,5,6-Pentahydroxyhexan-2-one | |||
Other names
Sorbinose
L-xylo-Hexulose | |||
Identifiers | |||
3D model (JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.001.611 | ||
PubChem CID
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UNII | |||
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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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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.
Synthesis
[edit]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
[edit]- ^ a b Merck Index, 12th Edition, 8874
- ^ 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.