Fructose

Fructose (/ˈfrʌktoʊs, -oʊz/), or fruit sugar, is a ketonic simple sugar 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 by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

d-Fructose
d-Fructofuranose
d-Fructose (open-chain form)

Haworth projection of β-d-fructofuranose
Ball-and-stick model of β-d-fructopyranose
Names
IUPAC name
D-arabino-Hex-2-ulose
Systematic IUPAC name
(3S,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one
Other names
Fruit sugar, levulose, d-fructofuranose, d-fructose, d-arabino-hexulose
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.303
EC Number
  • 200-333-3
KEGG
UNII
  • 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
  • O[C@H]1[C@H](O)[C@H](O[C@]1(O)CO)CO
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Density 1.694 g/cm3
Melting point 103 °C (217 °F; 376 K)
~4000 g/L (25 °C)
−102.60×10−6 cm3/mol
Thermochemistry
675.6 kcal/mol (2,827 kJ/mol) (Higher heating value)
Pharmacology
V06DC02 (WHO)
Hazards
Lethal dose or concentration (LD, LC):
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 verify (what is YN ?)
Infobox references

Fructose was discovered by French chemist Augustin-Pierre Dubrunfaut in 1847. The name "fructose" was coined in 1857 by the English chemist William Allen Miller. Pure, dry fructose is a 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 derived from sugar cane, sugar beets, and maize. High-fructose corn syrup 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 those found in 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. As of 2004, about 240,000 tonnes of crystalline fructose were being produced annually.

Excessive consumption of sugars, including fructose, (especially from sugar-sweetened beverages) may contribute to insulin resistance, obesity, elevated LDL cholesterol and triglycerides, leading to metabolic syndrome. The European Food Safety Authority (EFSA) stated in 2011 that fructose may be preferable over sucrose and glucose in sugar-sweetened foods and beverages because of its lower effect on postprandial blood sugar levels, while also noting the potential downside that "high intakes of fructose may lead to metabolic complications such as dyslipidaemia, insulin resistance, and increased visceral adiposity". 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, at levels consumed in the normal UK diet, leads to adverse health outcomes independent of any effects related to its presence as a component of total and free sugars."

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