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Sorbose

Names

IUPAC name

L-xylo-Hex-2-ulose

Systematic IUPAC name

(3S,4R,5S)-1,3,4,5,6-Pentahydroxyhexan-2-one

Other names

Sorbinose
L-xylo-Hexulose

Identifiers

CAS Number

87-79-6^Y

3D model (JSmol)

Interactive image

ChemSpider

6638^N

ECHA InfoCard

100.001.611

PubChem CID

6904

UNII

NV2001607Y^Y

InChI

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

SMILES

C([C@@H]([C@H]([C@@H](C(=O)CO)O)O)O)O

Properties^[1]

Chemical formula

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)

Solubility in water

Highly Soluble

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

Infobox references

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

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

^ ^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.

Types of carbohydrates

General

Geometry

Monosaccharides

Dioses	Aldodiose Glycolaldehyde
Trioses	Aldotriose Glyceraldehyde Ketotriose Dihydroxyacetone
Tetroses	Aldotetroses Erythrose Threose Ketotetrose Erythrulose
Pentoses	Aldopentoses Arabinose Lyxose Ribose Xylose Ketopentoses Ribulose Xylulose Deoxy sugars Deoxyribose
Hexoses	Aldohexoses Allose Altrose Galactose Glucose Gulose Idose Mannose Talose Ketohexoses Fructose Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose
Heptoses	Ketoheptoses Mannoheptulose Sedoheptulose
Above 7	Octoses Nonoses Neuraminic acid

Multiple

Disaccharides	Cellobiose Isomaltose Isomaltulose Lactose Lactulose Maltose Sucrose Trehalose Turanose
Trisaccharides	Maltotriose Melezitose Raffinose
Tetrasaccharides	Stachyose
Other oligosaccharides	Acarbose Fructooligosaccharide (FOS) Galactooligosaccharide (GOS) Isomaltooligosaccharide (IMO) Maltodextrin
Polysaccharides	Beta-glucan Oat beta-glucan Lentinan Sizofiran Zymosan Cellulose Chitin Chitosan Dextrin / Dextran Fructose / Fructan Inulin Galactose / Galactan Glucose / Glucan Glycogen Hemicellulose Levan beta 2→6 Lignin Mannan Pectin Starch Amylopectin Amylose Xanthan gum

Category

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