Fructose metabolism

D-Fructose

D-Fructofuranose D-Fructose (open-chain form)
Haworth projection of β-D-Fructofuranose
Ball-and-stick model of D-fructose
Names
IUPAC name (3R,4S)-1,3,4,5,6-Pentahydroxy-2-hexanone
Other names Fruit sugar, levulose,D-fructofuranose, D-fructose, D-arabino-hexulose
Identifiers
CAS Number	57-48-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28645 Y
ChEMBL	ChEMBL604608 Y
ChemSpider	388775 Y
ECHA InfoCard	100.000.303
EC Number	200-333-3
KEGG	C02336 Y
PubChem	5984
UNII	6YSS42VSEV Y
InChI InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1 Y Key: RFSUNEUAIZKAJO-ARQDHWQXSA-N Y
SMILES O[C@H]1[C@H](O)[C@H](O[C@]1(O)CO)CO
Properties
Chemical formula	C6H12O6
Molar mass	180.16 g·mol−1
Density	1.694 g/cm3
Melting point	103 °C (217 °F; 376 K)
Magnetic susceptibility (χ)	-102.60·10−6 cm3/mol
Pharmacology
ATC code	V06DC02 (WHO)
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	15000 mg/kg (intravenous, rabbit)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Fructose, or fruit sugar, is a simple ketonic 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. The name "fructose" was coined in 1857 by the English chemist William Miller. Pure, dry fructose is a very sweet, white, odorless, crystalline solid and is the most water-soluble of all the sugars. 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 corn. 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.

There is research indicating that excessive fructose consumption is a cause of insulin resistance, obesity, elevated LDL cholesterol and triglycerides, leading to metabolic syndrome,type 2 diabetes and cardiovascular disease. However, the European Food Safety Authority stated that fructose may be preferred over sucrose and glucose in sugar-sweetened foods and beverages because of its lower effect on postprandial blood sugar levels, but also noted that "high intakes of fructose may lead to metabolic complications such as dyslipidaemia, insulin resistance and increased visceral adiposity". Further, the UK's Scientific Advisory Committee on Nutrition in 2015 disputed the claims of fructose causing metabolic disorders, stating that "there is insufficient evidence to demonstrate that fructose intake ... leads to adverse health outcomes independent of any effects related to its presence as a component of total and free sugars."