Fructose

Source: Wikipedia, the free encyclopedia.
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[3]
Systematic IUPAC name
(3S,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one
Other names
Fruit sugar,[1] levulose,[2] d-fructofuranose, d-fructose, d-arabino-hexulose
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.303 Edit this at Wikidata
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 checkY
    Key: RFSUNEUAIZKAJO-ARQDHWQXSA-N checkY
  • 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
Std enthalpy of
combustion
(ΔcH⦵298)
 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)[5]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Fructose (

blood sugar
, is the only monosaccharide present in circulating blood.

Fructose was discovered by French chemist

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.[10]

Excessive consumption of sugars, including fructose, (especially from sugar-sweetened beverages) may contribute to

dyslipidaemia, insulin resistance, and increased visceral adiposity".[11][12] 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."[13]

Etymology

The word "fructose" was coined in 1857 from the Latin for fructus (fruit) and the generic chemical suffix for sugars, -ose.[8][14] It is also called fruit sugar and levulose or laevulose, due to its ability to rotate plane polarised light in a laevorotary fashion (anti-clockwise/to the left) when a beam is shone through it in solution. Likewise, dextrose (an isomer of glucose) is given its name due to its ability to rotate plane polarised light in a dextrorotary fashion (clockwise/to the right).[14]

Chemical properties

hemiketal
) isomers of fructose
d- and l-isomers of fructose (open-chain form)

Fructose is a 6-carbon polyhydroxyketone.

tautomers β-d-fructopyranose, β-d-fructofuranose, α-d-fructofuranose, α-d-fructopyranose and keto-d-fructose (the non-cyclic form).[16]

The distribution of d-fructose tautomers in solution is related to several variables, such as solvent and temperature.[17] d-Fructopyranose and d-fructofuranose distributions in water have been identified multiple times as roughly 70% fructopyranose and 22% fructofuranose.[18]

Reactions

Fructose and fermentation

Fructose may be anaerobically

fermented beverages, such as champagne
.

Fructose and Maillard reaction

Fructose undergoes the

mutagenic compounds.[21]

Dehydration

Fructose readily dehydrates to give hydroxymethylfurfural ("HMF", C
6H
6O
3), which can be processed into liquid dimethylfuran (C
6H
8O). This process, in the future, may become part of a low-cost, carbon-neutral system to produce replacements for petrol and diesel from plants.[22]

Physical and functional properties

Sweetness of fructose

See also: Sweetness § Examples of sweet substances

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

anomeric distribution but a decrease in the absolute sweetness of sucrose at higher temperatures.[25]

Figure 2: Relative sweetness of sugars and sweeteners

The sweetness of fructose is perceived earlier than that of sucrose or glucose, and the taste sensation reaches a peak (higher than that of sucrose), and diminishes more quickly than that of sucrose. Fructose can also enhance other flavors in the system.[23][25]

Fructose exhibits a sweetness synergy effect when used in combination with other sweeteners. The relative sweetness of fructose blended with sucrose, aspartame, or saccharin is perceived to be greater than the sweetness calculated from individual components.[28][25]

Fructose solubility and crystallization

Fructose has higher water solubility than other sugars, as well as other sugar alcohols. Fructose is, therefore, difficult to crystallize from an aqueous solution.[23] Sugar mixes containing fructose, such as candies, are softer than those containing other sugars because of the greater solubility of fructose.[29]

Fructose hygroscopicity and humectancy

Fructose is quicker to absorb moisture and slower to release it to the environment than sucrose, glucose, or other nutritive sweeteners.

relative humidity (RH). Therefore, fructose can contribute a more palatable texture, and longer shelf life to the food products in which it is used.[23]

Freezing point

Fructose has a greater effect on freezing point depression than disaccharides or oligosaccharides, which may protect the integrity of cell walls of fruit by reducing ice crystal formation. However, this characteristic may be undesirable in soft-serve or hard-frozen dairy desserts.[23]

Fructose and starch functionality in food systems

Fructose increases starch viscosity more rapidly and achieves a higher final viscosity than sucrose because fructose lowers the temperature required during gelatinizing of starch, causing a greater final viscosity.[30]

Although some artificial sweeteners are not suitable for home baking, many traditional recipes use fructose.[31]

Food sources

Crystalline fructose

Natural sources of fructose include fruits, vegetables (including sugar cane), and honey.

agave nectar, honey, molasses, maple syrup, fruit and fruit juices, as these have the highest percentages of fructose (including fructose in sucrose) per serving compared to other common foods and ingredients. Fructose exists in foods either as a free monosaccharide or bound to glucose as sucrose, a disaccharide
. Fructose, glucose, and sucrose may all be present in food; however, different foods will have varying levels of each of these three sugars.

The sugar contents of common fruits and vegetables are presented in Table 1. In general, in foods that contain free fructose, the ratio of fructose to glucose is approximately 1:1; that is, foods with fructose usually contain about an equal amount of free glucose. A value that is above 1 indicates a higher proportion of fructose to glucose and below 1 a lower proportion. Some fruits have larger proportions of fructose to glucose compared to others. For example, apples and pears contain more than twice as much free fructose as glucose, while for apricots the proportion is less than half as much fructose as glucose.

Apple and pear juices are of particular interest to

osmolarity in the small intestine, which draws water into the gastrointestinal tract, resulting in osmotic diarrhea. This phenomenon is discussed in greater detail in the Health Effects
section.

Table 1 also shows the amount of sucrose found in common fruits and vegetables. Sugarcane and sugar beet have a high concentration of sucrose, and are used for commercial preparation of pure sucrose. Extracted cane or beet juice is clarified, removing impurities; and concentrated by removing excess water. The end product is 99.9%-pure sucrose. Sucrose-containing sugars include common white sugar and powdered sugar, as well as brown sugar.[34]

Sugar content of selected common plant foods (g/100g)[35]
[Some of these ratios don't agree]
Food Item Total
carbohydrateA
including
"dietary fiber" 		Total
sugars 		Free
fructose 		Free
glucose 		Sucrose Fructose/
glucose
ratio 		Sucrose
as a % of
total sugars 		Free fructose
as a % of
total sugars
Fruits
Apple 13.8 10.4 5.9 2.4 2.1 2.0? 19.9 57
Apricot 11.1 9.2 0.9 2.4 5.9 0.7? 63.5 10
Banana 22.8 12.2 4.9 5.0 2.4 1.0 20.0 40
Fig, dried 63.9 47.9 22.9 24.8 0.9? 0.93 1.9 47.8
Grapes 18.1 15.5 8.1 7.2 0.2 1.1 1 52
Navel orange
 12.5 8.5 2.25 2.0 4.3 1.1 50.4 26
Peach 9.5 8.4 1.5 2.0 4.8 0.9? 56.7 18
Pear 15.5 9.8 6.2 2.8 0.8 2.1? 8.0 63
Pineapple 13.1 9.9 2.1 1.7 6.0 1.1 60.8 21
Plum 11.4 9.9 3.1 5.1 1.6 0.66 16.2 31
Vegetables
Beet
, Red		 9.6 6.8 0.1 0.1 6.5 1.0 96.2 1.5
Carrot 9.6 4.7 0.6 0.6 3.6 1.0 77 13
Red Pepper, Sweet 6.0 4.2 2.3 1.9 0.0 1.2 0.0 55
Onion, Sweet 7.6 5.0 2.0 2.3 0.7 0.9 14.3 40
Sweet Potato
 20.1 4.2 0.7 1.0 2.5 0.9 60.3 17
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 1.5-5.6
Sugar Beet
 17–18 0.1 – 0.5 0.1 – 0.5 16–17 1.0 high 0.59-2.8
Grains
Maize, Sweet 19.0 6.2 1.9 3.4 0.9 0.61 15.0 31
^A The carbohydrate figure is calculated in FoodData Central and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".

All data with a unit of g (gram) are based on 100 g of a food item. The fructose/glucose ratio is calculated by dividing the sum of free fructose plus half sucrose by the sum of free glucose plus half sucrose.

Fructose is also found in the manufactured

breakfast cereals, bakery foods, and some soft drinks.[36]

Carbohydrate content of commercial sweeteners (percent on dry basis)

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 98 0 2

[34] for HFCS, and USDA for fruits and vegetables and the other refined sugars.[35]

Cane and beet sugars have been used as the major sweetener in food manufacturing for centuries. However, with the development of HFCS, a significant shift occurred in the type of sweetener consumption in certain countries, particularly the United States.[37] Contrary to the popular belief, however, with the increase of HFCS consumption, the total fructose intake relative to the total glucose intake has not dramatically changed. Granulated sugar is 99.9%-pure sucrose, which means that it has equal ratio of fructose to glucose. The most commonly used forms of HFCS, HFCS-42, and HFCS-55, have a roughly equal ratio of fructose to glucose, with minor differences. HFCS has simply replaced sucrose as a sweetener. Therefore, despite the changes in the sweetener consumption, the ratio of glucose to fructose intake has remained relatively constant.[38]

Figure 3: Adjusted consumption of refined sugar per capita in the US

Nutritional information

Providing 368 kcal per 100 grams of dry powder (table), fructose has 95% the caloric value of sucrose by weight.[39][40] Fructose powder is 100% carbohydrates and supplies no other nutrients in significant amount (table).

Fructose, dry powdered
Nutritional value per 100 g (3.5 oz)
Energy368 kcal (1,540 kJ)
100 g
0 g
0 g
MineralsQuantity
%DV†
Calcium
0%
0 mg
Iron
1%
0.1 mg
Phosphorus
0%
0 mg
Potassium
0%
0 mg
Sodium
1%
12 mg
Full Link to USDA Database entry
†Percentages estimated using US recommendations for adults,[41] except for potassium, which is estimated based on expert recommendation from the National Academies.[42]

Fructose digestion and absorption in humans

Figure 4: Hydrolysis of sucrose to glucose and fructose by sucrase
Figure 5: Intestinal sugar transport proteins

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

hepatic portal vein
and is directed toward the liver.

The mechanism of fructose absorption in the small intestine is not completely understood. Some evidence suggests

enterocytes, assisted by transport proteins. Fructose may be transported out of the enterocyte across the basolateral membrane by either GLUT2 or GLUT5, although the GLUT2 transporter has a greater capacity for transporting fructose, and, therefore, the majority of fructose is transported out of the enterocyte through GLUT2.[44]

Capacity and rate of absorption

The absorption capacity for fructose in monosaccharide form ranges from less than 5 g to 50 g (per individual serving) and adapts with changes in dietary fructose intake.

cotransport
of fructose. In addition, fructose transfer activity increases with dietary fructose intake. The presence of fructose in the lumen causes increased mRNA transcription of GLUT5, leading to increased transport proteins. High-fructose diets (>2.4 g/kg body wt) increase the transport proteins within three days of intake.[47]

Malabsorption

Main article: Fructose malabsorption

Several studies have measured the intestinal absorption of fructose using the

fermentation process and dissolves into the blood of the portal vein. This hydrogen is transported to the lungs, where it is exchanged across the lungs and is measurable by the hydrogen breath test. The colonic flora also produces carbon dioxide, short-chain fatty acids, organic acids, and trace gases in the presence of unabsorbed fructose.[52] The presence of gases and organic acids in the large intestine causes gastrointestinal symptoms such as bloating, diarrhea, flatulence, and gastrointestinal pain.[48] Exercise immediately after consumption can exacerbate these symptoms by decreasing transit time in the small intestine, resulting in a greater amount of fructose emptied into the large intestine.[53]

Fructose metabolism

All three dietary monosaccharides are transported into the liver by the GLUT2 transporter.[54] Fructose and galactose are phosphorylated in the liver by fructokinase (Km= 0.5 mM) and galactokinase (Km = 0.8 mM), respectively. By contrast, glucose tends to pass through the liver (Km of hepatic glucokinase = 10 mM) and can be metabolised anywhere in the body. Uptake of fructose by the liver is not regulated by insulin. However, insulin is capable of increasing the abundance and functional activity of GLUT5, fructose transporter, in skeletal muscle cells.[55]

Fructolysis

Main article: Fructolysis

The initial

phosphate group. A third enzyme, triokinase, is therefore required to phosphorylate glyceraldehyde, producing glyceraldehyde 3-phosphate. The resulting trioses are identical to those obtained in glycolysis and can enter the gluconeogenic pathway for glucose or glycogen synthesis, or be further catabolized through the lower glycolytic pathway to pyruvate
.

Metabolism of fructose to DHAP and glyceraldehyde

The first step in the metabolism of fructose is the phosphorylation of fructose to fructose 1-phosphate by fructokinase, thus trapping fructose for metabolism in the liver. Fructose 1-phosphate then undergoes hydrolysis by aldolase B to form DHAP and glyceraldehydes; DHAP can either be isomerized to glyceraldehyde 3-phosphate by triosephosphate isomerase or undergo reduction to glycerol 3-phosphate by glycerol 3-phosphate dehydrogenase. The glyceraldehyde produced may also be converted to glyceraldehyde 3-phosphate by glyceraldehyde kinase or further converted to glycerol 3-phosphate by glycerol 3-phosphate dehydrogenase. The metabolism of fructose at this point yields intermediates in the gluconeogenic pathway leading to glycogen synthesis as well as fatty acid and triglyceride synthesis.

Synthesis of glycogen from DHAP and glyceraldehyde 3-phosphate

The resultant glyceraldehyde formed by aldolase B then undergoes phosphorylation to glyceraldehyde 3-phosphate. Increased concentrations of DHAP and glyceraldehyde 3-phosphate in the liver drive the gluconeogenic pathway toward glucose and subsequent glycogen synthesis.[56] It appears that fructose is a better substrate for glycogen synthesis than glucose and that glycogen replenishment takes precedence over triglyceride formation.[57] Once liver glycogen is replenished, the intermediates of fructose metabolism are primarily directed toward triglyceride synthesis.[58]

Figure 6: Metabolic conversion of fructose to glycogen in the liver

Synthesis of triglyceride from DHAP and glyceraldehyde 3-phosphate

Carbons from dietary fructose are found in both the

very-low-density lipoproteins
(VLDL), which are released from the liver destined toward peripheral tissues for storage in both fat and muscle cells.

Figure 7: Metabolic conversion of fructose to triglyceride in the liver

Potential health effects

In 2022, the European Food Safety Authority stated that there is research evidence that fructose and other added free sugars may be associated with increased risk of several chronic diseases:

non-alcoholic fatty liver disease, type 2 diabetes (from 15% to 50%) and hypertension. EFSA further stated that clinical research did "not support a positive relationship between the intake of dietary sugars, in isocaloric exchange with other macronutrients, and any of the chronic metabolic diseases or pregnancy-related endpoints assessed" but advised "the intake of added and free sugars should be as low as possible in the context of a nutritionally adequate diet."[12]

Cardiometabolic diseases

When fructose is consumed in excess as a sweetening agent in foods or beverages, it may be associated with increased risk of obesity, diabetes, and cardiovascular disorders that are part of metabolic syndrome.[12]

Compared with sucrose

Fructose was found to increase triglycerides in type-2 but not type-1 diabetes and moderate use of it has previously been considered acceptable as a sweetener for diabetics,[61] possibly because it does not trigger the production of insulin by pancreatic β cells.[62] For a 50 gram reference amount, fructose has a glycemic index of 23, compared with 100 for glucose and 60 for sucrose.[63] Fructose is also 73% sweeter than sucrose at room temperature, allowing diabetics to use less of it per serving. Fructose consumed before a meal may reduce the glycemic response of the meal.[64] Fructose-sweetened food and beverage products cause less of a rise in blood glucose levels than do those manufactured with either sucrose or glucose.[11]

See also

References

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External links

  • Media related to Fructose at Wikimedia Commons
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