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Fructose (Molecule of the Month for March 2020)

Fruit sugar



Fructose 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 blood 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 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. Fructose exists in foods either as a monosaccharide (free fructose) or as a unit of a disaccharide (sucrose). Free fructose is absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. As sucrose comes into contact with the membrane of the small intestine, the enzyme sucrase catalyzes the cleavage of sucrose to yield one glucose unit and one fructose unit, which are then each absorbed.

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 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. The primary reason that fructose is used commercially in foods and beverages, besides its low cost, is its high relative sweetness. It is the sweetest of all naturally occurring carbohydrates. The relative sweetness of fructose has been reported in the range of 1.21.8 times that of sucrose.

Excessive consumption of 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 stated 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."

Formal Chemical Name (IUPAC)
(3S,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one

References

https://en.wikipedia.org/wiki/Fructose

Picture of Fructose 3D model

click on the picture of  Fructose above to interact
with the 3D model of the
Fructose structure
(this will open a new browser window)

Picture of Fructose

C6 H12 O6



Update by Karl Harrison
(Molecule of the Month for March 2020 )

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