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Fructose

D-Fructose
Skeletal Structure of Cyclic D-Fructose.svg
D-Fructofuranose
D-Fructose.svg
D-Fructose (open-chain form)
β-D-Fructose structure
Haworth projection of β-D-Fructofuranose
Fructose 3D ball-and-stick model.png
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
57-48-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28645 YesY
ChEMBL ChEMBL604608 YesY
ChemSpider 388775 YesY
ECHA InfoCard 100.000.303
EC Number 200-333-3
KEGG C02336 YesY
PubChem 5984
UNII 6YSS42VSEV YesY
Properties
C6H12O6
Molar mass 180.16 g·mol−1
Density 1.694 g/cm3
Melting point 103 °C (217 °F; 376 K)
-102.60·10−6 cm3/mol
Pharmacology
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 YesYN ?)
Infobox references
Fructose, dry powdered
Nutritional value per 100 g (3.5 oz)
Energy 368 kcal (1,540 kJ)
100 g
0 g
0 g
Minerals
Calcium
(0%)
0 mg
Iron
(1%)
0.1 mg
Phosphorus
(0%)
0 mg
Potassium
(0%)
0 mg
Sodium
(1%)
12 mg

Percentages are roughly approximated using US recommendations for adults.
Source: USDA Nutrient Database

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."


Table 1. Sugar content of selected common plant foods (g/100g)
Food Item Total
Carbohydrate
including
"dietary fiber"
Total
Sugars
Free
Fructose
Free
Glucose
Sucrose Fructose/
Glucose
Ratio
Sucrose
as a % of
Total Sugars
Fruits              
Apple 13.8 10.4 5.9 2.4 2.1 2.0 19.9
Apricot 11.1 9.2 0.9 2.4 5.9 0.7 63.5
Banana 22.8 12.2 4.9 5.0 2.4 1.0 20.0
Fig, dried 63.9 47.9 22.9 24.8 0.9 0.93 0.15
Grapes 18.1 15.5 8.1 7.2 0.2 1.1 1
Navel orange 12.5 8.5 2.25 2.0 4.3 1.1 50.4
Peach 9.5 8.4 1.5 2.0 4.8 0.9 56.7
Pear 15.5 9.8 6.2 2.8 0.8 2.1 8.0
Pineapple 13.1 9.9 2.1 1.7 6.0 1.1 60.8
Plum 11.4 9.9 3.1 5.1 1.6 0.66 16.2
Vegetables              
Beet, Red 9.6 6.8 0.1 0.1 6.5 1.0 96.2
Carrot 9.6 4.7 0.6 0.6 3.6 1.0 77
Red Pepper, Sweet 6.0 4.2 2.3 1.9 0.0 1.2 0.0
Onion, Sweet 7.6 5.0 2.0 2.3 0.7 0.9 14.3
Sweet Potato 20.1 4.2 0.7 1.0 2.5 0.9 60.3
Yam 27.9 0.5 tr tr tr na tr
Sugar Cane 13 – 18 0.2 – 1.0 0.2 – 1.0 11 – 16 1.0 high
Sugar Beet 17 – 18 0.1 – 0.5 0.1 – 0.5 16 – 17 1.0 high
Grains              
Corn, Sweet 19.0 6.2 1.9 3.4 0.9 0.61 15.0
Sugar Fructose Glucose Sucrose
(Fructose+Glucose)
Other
sugars
Granulated sugar 0 0 100 0
Caramel 1 1 97 1
HFCS-42 42 53 0 5
HFCS-55 55 41 0 4
HFCS-90 90 5 0 5
Honey 50 44 1 5
Maple syrup 1 4 95 0
Molasses 23 21 53 3
Tapioca Syrup 55 45 0 0
Corn syrup 0 35 0 0

^A The carbohydrate figure is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".
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Wikipedia

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