Fructose

Title: Fructose
CAS Registry Number: 57-48-7
CAS Name: D-Fructose
Additional Names: b-D-fructose; levulose; fruit sugar
Trademarks: Fructosteril; Laevoral (Laevosan); Levugen; Laevosan (Laevosan)
Molecular Formula: C6H12O6
Molecular Weight: 180.16
Percent Composition: C 40.00%, H 6.71%, O 53.28%
Literature References: Occurs in a large number of fruits, honey, and as the sole sugar in bull and human semen: Auerbach, Bodlander, Angew. Chem. 36, 602 (1923); Mann, Nature 157, 79 (1946); Pryde, ibid. 660. Prepd by adding abs alcohol to the syrup obtained from the acid hydrolysis of inulin: Bates et al., Natl. Bur. Std. Circ. C440, 399 (1942). Prepn from dextrose: Cantor, Hobbs, US 2354664 (1944 to Corn Prod. Refining). From sucrose by enzymatic conversion: Koepsell et al., US 2729587 (1956 to U.S.A.). Crystal and molecular structure: J. A. Kanters et al., Acta Crystallogr. B33, 665 (1977). Review: Barry, Honeyman, Adv. Carbohydr. Chem. 7, 53-98 (1952); M. Chen, R. L. Whistler, ibid. 34, 285-343 (1977). Occurs in both the furanose and pyranose forms. An aq soln at 20° contains about 20% of the furanose form.
Properties: Orthorhombic, bisphenoidal prisms from alc, dec 103-105°. Sweetest of the sugars. Shows mutarotation. [a]D20 -132° to -92° (c = 2). Rapid and anomalous mutarotation involves pyranose-furanose interconversion. The final value is obtained instantly in the presence of hydroxyl ions. pKa (18°): 12.06. Freely sol in water. One gram dissolves in 15 ml alc, in 14 ml methanol. Slightly sol in cold, freely in hot acetone; sol in pyridine, ethylamine, methylamine.
pKa: pKa (18°): 12.06
Optical Rotation: [a]D20 -132° to -92° (c = 2)
Derivative Type: Ferric Form
CAS Registry Number: 12286-76-9
Manufacturers' Codes: CB-302
Trademarks: Ferritose (Calbiochem)
Literature References: Prepn: Stitt et al., Proc. Soc. Exp. Biol. Med. 110, 70 (1962); Saltman, Charley, US 3074927 and US 3275514 (1966).
Use: To prevent sandiness in ice cream.
Therap-Cat: Fluid and nutrient replenisher, and ferric form as hematinic.
Therap-Cat-Vet: For bovine ketosis.
Fructose-1,6-diphosphate Fructose-6-phosphate Fucosamine Fucosterol Fucoxanthin

D-Fructose
D-Fructofuranose D-Fructose.svg
Skeletal Structure of D-Fructose.svg
Identifiers
CAS number 57-48-7 YesY
PubChem 11769129
ChemSpider 388775 YesY
UNII 6YSS42VSEV YesY
EC-number 200-333-3
KEGG C02336 YesY
ChEBI CHEBI:28645 YesY
ChEMBL CHEMBL604608 YesY
ATC code V06DC02
Jmol-3D images Image 1
Properties
Molecular formula C6H12O6
Molar mass 180.16 g mol−1
Density 1.694 g/cm3
Melting point 103 °C; 217 °F; 376 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Fructose, or fruit sugar, is a simple monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed directly into the bloodstream during digestion. Fructose was discovered by French chemist Augustin-Pierre Dubrunfaut in 1847.[3][4] The name "fructose" was coined in 1857 by the English chemist William Miller.[5] Pure, dry fructose is a very sweet, white, odorless, crystalline solid and is the most water-soluble of all the sugars.[6] From plant sources, fructose is found in honey, tree and vine fruits, flowers, berries, and most root vegetables.

Commercially, fructose is frequently derived from sugar cane, sugar beets, and maize. Crystalline fructose is the monosaccharide, dried, ground, and of high purity. High-fructose corn syrup (HFCS) is a mixture of glucose and fructose as monosaccharides. Sucrose is a compound with one molecule of glucose covalently linked to one molecule of fructose. All forms of fructose, including fruits and juices, are commonly added to foods and drinks for palatability and taste enhancement, and for browning of some foods, such as baked goods.

About 240,000 tonnes of crystalline fructose are produced annually.[7]