Fructose

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D-Fructose

IUPAC name[hide]
Fructose
Other names[hide]
fruit sugar,[1] levulose,[2] D-fructofuranose, D-fructose, D-
arabino-hexulose
Identifiers
CAS number 57-48-7 Y
PubChem 11769129
ChemSpider 388775 Y

UNII 6YSS42VSEV Y

EC-number 200-333-3
KEGG C02336 Y

ChEMBL CHEMBL604608 Y

Jmol-3D images Image 1

SMILES
[show]
• O[C@H]1[C@H](O)[C@H](O[C@]1(O)CO)CO
InChI
[show]
• 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

InChI=1/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
Key: RFSUNEUAIZKAJO-ARQDHWQXBD
 Properties
Molecular formula C6H12O6
Molar mass 180.16 g/mol
Melting point 103 °C

Y(what is this?) (verify)

Except where noted otherwise, data are given for materials in
their standard state (at 25 °C, 100 kPa)
Infobox references
Fructose, or fruit sugar, is a simple monosaccharide found in many foods. It is one of the three
important dietary monosaccharides along with glucose and galactose. The organic fructose
molecule was first discovered by Augustin-Pierre Dubrunfaut in 1847.[3] Fructose is a white solid
that dissolves in water – it is the most water-soluble of all the sugars.[4] Honey, tree fruits,
berries, melons, and some root vegetables contain significant amounts of molecular fructose,
usually in combination with glucose, stored in the form of sucrose. About 240,000 tonnes of
crystalline fructose are produced annually.[5]
Fructose is a component of sucrose. Sucrose is a disaccharide derived from the condensation of
glucose and fructose. Fructose is derived from the digestion of table sugar (sucrose).
Crystalline fructose and high-fructose corn syrup are often confused as the same product.
Crystalline fructose, which is often produced from a fructose-enriched corn syrup, is indeed the
monosaccharide. High-fructose corn syrup, however, refers to a family of mixtures of varying
amounts of fructose and glucose.

Contents
[hide]
• 1 Chemical properties
○ 1.1 Reactions
 1.1.1 Fructose and fermentation
 1.1.2 Fructose and Maillard reaction
 1.1.3 Dehydration
• 2 Physical and functional properties
○ 2.1 Relative sweetness
 2.1.1 Sweetness synergy
 2.1.2 Fructose solubility and crystallization
 2.1.3 Fructose hygroscopicity and humectancy
 2.1.4 Freezing point
 2.1.5 Fructose and starch functionality in food systems
• 3 Food sources
○ 3.1 Carbohydrate content of commercial sweeteners (percent)
• 4 Fructose digestion and absorption in humans
 ○ 4.1 Capacity and rate of absorption
○ 4.2 Malabsorption
• 5 Fructose metabolism
○ 5.1 Fructolysis
○ 5.2 Metabolism of fructose to DHAP and glyceraldehyde
○ 5.3 Synthesis of glycogen from DHAP and glyceraldehyde 3 phosphate
○ 5.4 Synthesis of triglyceride from DHAP and glyceraldehyde 3 phosphate
• 6 Health effects
○ 6.1 Digestive problems
○ 6.2 Metabolic syndrome
○ 6.3 Compared to sucrose
○ 6.4 Liver disease
○ 6.5 Gout
○ 6.6 Glycemic index
• 7 See also
• 8 External links
• 9 References

[edit] Chemical properties

Figure 1: Relationship between the acyclic and the cyclic (hemiketal) isomers of fructose.
D- and L-isomers of fructose (open-chain form)
Fructose is a 6-carbon polyhydroxyketone. It is an isomer of glucose, i.e. both have the same
molecular formula (C6H12O6) but they differ structurally. Crystalline fructose adopts a cyclic six-
membered structure owing to the stability of its hemiketal and internal hydrogen-bonding. This
form is formally called D-fructopyranose. In solution, fructose exists as an equilibrium mixture
of 70% fructopyranose and about 22% fructofuranose, as well as small amounts of three other
forms, including the acylic structure.[6]
[edit] Reactions
[edit] Fructose and fermentation
Fructose may be anaerobically fermented by yeast or bacteria.[7] Yeast enzymes convert sugar
(glucose, or fructose) to ethanol and carbon dioxide. The carbon dioxide released during
fermentation will remain dissolved in water where it will reach equilibrium with carbonic acid
unless the fermentation chamber is left open to the air. The dissolved carbon dioxide and
carbonic acid produce the carbonation in bottle fermented beverages.[8]
[edit] Fructose and Maillard reaction
Fructose undergoes the Maillard reaction, non-enzymatic browning, with amino acids. Because
fructose exists to a greater extent in the open-chain form than does glucose, the initial stages of
the Maillard reaction occurs more rapidly than with glucose. Therefore, fructose potentially may
contribute to changes in food palatability, as well as other nutritional effects, such as excessive
browning, volume and tenderness reduction during cake preparation, and formation of mutagenic
compounds.[9]
[edit] Dehydration
Fructose readily dehydrates to give hydroxymethylfurfural ("HMF"). This process may in the
future be part of a low-cost, carbon-neutral system to produce replacements for petrol and diesel
from plantations.[10]
[edit] Physical and functional properties
[edit] Relative sweetness
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.
Fructose is generally regarded as being 1.73 times as sweet as sucrose.[11][12] However, it is the 5-
ring form of fructose that is sweeter; the 6-ring form tastes about the same as usual table sugar.
Warming fructose leads to formation of the 6-ring form.[13]

Figure 2: Relative sweetness of sugars and sweeteners.

The sweetness of fructose is perceived earlier than that of sucrose or dextrose, and the taste
sensation reaches a peak (higher than sucrose) and diminishes more quickly than sucrose.
Fructose can also enhance other flavors in the system.[11]
[edit] Sweetness synergy
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.[14]
[edit] Fructose solubility and crystallization
Fructose has higher solubility than other sugars as well as other sugar alcohols. Fructose is
therefore difficult to crystallize from an aqueous solution.[11] Sugar mixes containing fructose,
such as candies, are softer than those containing other sugars because of the greater solubility of
fructose.[15]
[edit] Fructose hygroscopicity and humectancy
Fructose is quicker to absorb moisture and slower to release it to the environment than sucrose,
dextrose, or other nutritive sweeteners.[14] Fructose is an excellent humectant and retains moisture
for a long period of time even at low relative humidity (RH). Therefore, fructose can contribute
to improved quality, better texture, and longer shelf life to the food products in which it is used.
[11]

[edit] 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.[11]
[edit] 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.[16]
[edit] Food sources
Natural sources of fructose include fruits, vegetables (including sugar cane), and honey.[17]
Fructose is often further concentrated from these sources. The highest dietary sources of
fructose, besides pure crystalline fructose, are foods containing table sugar (sucrose), high-
fructose corn syrup, agave nectar, honey, molasses, maple syrup, 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
a 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 pediatricians because the high concentrations of
free fructose in these juices can cause diarrhea in children. The cells (enterocytes) that line
children's small intestines have less affinity for fructose absorption than for glucose and sucrose.
[18]
Unabsorbed fructose creates higher 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. Sugar cane
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 table white granulated sugar and powdered sugar, as well as brown sugar.[19]

Table 1. Sugar content of selected common plant foods (g/100g)

Fructose/ Sucrose
Total Total Free Free
Food Item Sucrose Glucose as a % of
Carbohydrate Sugars Fructose Glucose
Ratio 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 0.07 0.93 0.001

Grapes 18.1 15.5 8.1 7.2 0.2 1.1 1.0

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 0.16

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 70.0

Corn, Sweet 19.0 3.2 0.5 0.5 2.1 1.0 64.0

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 1.0 100

Sugar Beet 17 - 18 0.1 – 0.5 0.1 – 0.5 16 - 17 1.0 100

Data obtained at [3].[20] 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 synthetically manufactured sweetener, high-fructose corn syrup
(HFCS). Hydrolyzed corn starch is used as the raw material for production of HFCS. Through
the enzymatic treatment, glucose molecules are converted into fructose.[19] There are three types
of HFCS, each with a different proportion of fructose: HFCS-42, HFCS-55, and HFCS-90. The
number for each HFCS corresponds to the percentage of synthesized fructose present in the
syrup. HFCS-90 has the highest concentration of fructose, and is typically used to manufacture
HFCS-55; HFCS-55 is used as sweetener in soft drinks, while HFCS-42 is used in many
processed foods and baked goods.
[edit] Carbohydrate content of commercial sweeteners (percent)
Sugar Fructose Glucose Sucrose (Fructose-Glucose) Other Sugars
Granulated Sugar 0 0 100 0
Brown Sugar 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
Corn Syrup 0 35 0 0
Data obtained from Kretchmer, N. & Hollenbeck, CB (1991). Sugars and Sweeteners, Boca
Raton, FL: CRC Press, Inc.[19] for HFCS, and USDA for fruits and vegetables and the other
refined sugars.[20]
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. As seen in Figure 3, this change happened in the 1970s. Contrary to the popular
belief, however, with the increase of HFCS consumption, the total fructose 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.[21]

Figure 3: Adjusted consumption of refined sugar per capita in the U.S.

[edit] Fructose digestion and absorption in humans
Fructose exists in foods as either a monosaccharide (free fructose) or as a unit of a disaccharide
(sucrose). Free fructose is absorbed directly by the intestine; however, when fructose is
consumed in the form of sucrose, digestion occurs entirely in the upper small intestine. 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. Fructose is
absorbed in the small intestine, then enters the hepatic portal vein and is directed toward the
liver.

Figure 4: Hydrolysis of sucrose to glucose and fructose by sucrase.

The mechanism of fructose absorption in the small intestine is not completely understood. Some
evidence suggests active transport, because fructose uptake has been shown to occur against a
concentration gradient.[22] However, the majority of research supports the claim that fructose
absorption occurs on the mucosal membrane via facilitated transport involving GLUT5 transport
proteins. Since the concentration of fructose is higher in the lumen, fructose is able to flow down
a concentration gradient into the 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.
Figure 5: Intestinal sugar transport proteins.
[edit] Capacity and rate of absorption
The absorption capacity for fructose in monosaccharide form ranges from less than 5 g to 50 g
and adapts with changes in dietary fructose intake. Studies show the greatest absorption rate
occurs when glucose and fructose are administered in equal quantities.[23] When fructose is
ingested as part of the disaccharide sucrose, absorption capacity is much higher because fructose
exists in a 1:1 ratio with glucose. It appears that the GLUT5 transfer rate may be saturated at low
levels, and absorption is increased through joint absorption with glucose.[24] One proposed
mechanism for this phenomenon is a glucose-dependent 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[vague] have been shown to increase abundance of transport proteins within 3
days of intake.[25]
[edit] Malabsorption
Main article: Fructose malabsorption
Several studies have measured the intestinal absorption of fructose using hydrogen breath test.[26]
[27][28][29]
These studies indicate that fructose is not completely absorbed in the small intestine.
When fructose is not absorbed in the small intestine, it is transported into the large intestine,
where it is fermented by the colonic flora. Hydrogen is produced during 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.[30] The presence of gases and organic acids in the large intestine
causes gastrointestinal symptoms such as bloating, diarrhea, flatulence, and gastrointestial pain
[26]
Exercise immediately after consumption can exacerbate these symptoms by decreasing transit
time in the small intestine, resulting in a greater amount of fructose being emptied into the large
intestine.[31]
[edit] Fructose metabolism
All three dietary monosaccharides are transported into the liver by the GLUT 2 transporter.[32]
Fructose and galactose are phosphorylated in the liver by fructokinase (Km= 0.5 mM) and
galactokinase (Km = 0.8 mM). 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 in skeletal muscle cells.[33]
[edit] Fructolysis
Fructolysis initially produces fructose 1,6-bisphosphate, which is split with aldolase to produce
phosphate derivatives of the trioses dihydroxyacetone (dihydroxyacetone phosphate) and
glyceraldehyde (glyceraldehyde 3-phosphate).[4] These are then metabolized either in the
gluconeogenic pathway for glycogen replenishment and/or complete metabolism in the
fructolytic pathway to pyruvate, which after conversion to acetyl-CoA enters the Krebs cycle,
and is converted to citrate and subsequently directed toward ’’de novo’’ synthesis of the free
fatty acid palmitate.[34]
[edit] 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
converted to glycerol 3-phosphate by glyceraldehyde 3-phosphate dehydrogenase. The
metabolism of fructose at this point yields intermediates in the gluconeogenic and fructolytic
pathways leading to glycogen synthesis as well as fatty acid and triglyceride synthesis.
[edit] 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.
[35]
It appears that fructose is a better substrate for glycogen synthesis than glucose and that
glycogen replenishment takes precedence over triglyceride formation.[citation needed] Once liver
glycogen is replenished, the intermediates of fructose metabolism are primarily directed toward
triglyceride synthesis.[citation needed]

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

[edit] Synthesis of triglyceride from DHAP and glyceraldehyde 3 phosphate
Carbons from dietary fructose are found in both the free fatty acid and glycerol moieties of
plasma triglycerides. High fructose consumption can lead to excess pyruvate production, causing
a buildup of Krebs cycle intermediates.[34] Accumulated citrate can be transported from the
mitochondria into the cytosol of hepatocytes, converted to acetyl CoA by citrate lyase and
directed toward fatty acid synthesis.[34][36] Additionally, DHAP can be converted to glycerol 3-
phosphate as previously mentioned, providing the glycerol backbone for the triglyceride
molecule.[36] Triglycerides are incorporated into 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.

[edit] Health effects
[edit] Digestive problems
Fructose absorption occurs via the GLUT-5[37] (fructose only) transporter, and the GLUT2
transporter, for which it competes with glucose and galactose. A deficiency of GLUT 5 may
result in excess fructose carried into the lower intestine.[citation needed] There, it can provide nutrients
for the existing gut flora, which produce gas. It may also cause water retention in the intestine.
These effects may lead to bloating, excessive flatulence, loose stools, and even diarrhea
depending on the amounts eaten and other factors. For some people, fructose malabsorption may
be a major health concern.
[edit] Metabolic syndrome
Excess fructose consumption has been hypothesized to be a cause of insulin resistance, obesity,
[38]
elevated LDL cholesterol and triglycerides, leading to metabolic syndrome.[39] Fructose
consumption has been shown to be correlated with obesity,[40][41] especially central obesity which
is thought to be the most dangerous kind of obesity. A study in mice showed that a high fructose
intake increases adiposity.[42]
Although all simple sugars have nearly identical chemical formulae, each has distinct chemical
properties. This can be illustrated with pure fructose. A journal article reports that, "...fructose
given alone increased the blood glucose almost as much as a similar amount of glucose (78% of
the glucose-alone area)".[43][44][45][45][46]
One study concluded that fructose "produced significantly higher fasting plasma triacylglycerol
values than did the glucose diet in men" and "...if plasma triacylglycerols are a risk factor for
cardiovascular disease, then diets high in fructose may be undesirable".[47] Bantle et al. "noted the
same effects in a study of 14 healthy volunteers who sequentially ate a high-fructose diet and one
almost devoid of the sugar."[48]
Fructose is a reducing sugar, as are all monosaccharides. The spontaneous chemical reaction of
simple sugar molecules binding to proteins, known as glycation, is thought to be a significant
cause of damage in diabetics. Fructose appears to be equivalent to glucose in this regard and so
does not seem to be a better answer for diabetes for this reason alone, save for the smaller
quantities required to achieve equivalent sweetness in some foods.[49] This may be an important
contribution to senescence and many age-related chronic diseases.[50]
[edit] Compared to sucrose
Studies that have compared high-fructose corn syrup (an ingredient in nearly all soft drinks sold
in the US) to sucrose (common table sugar) find that most measured physiological effects are
equivalent. For instance, Melanson et al. (2006), studied the effects of HFCS and sucrose
sweetened drinks on blood glucose, insulin, leptin, and ghrelin levels. They found no significant
differences in any of these parameters.[51] This is not surprising, since sucrose is a disaccharide
that digests to 50% fructose and 50% glucose, whereas the high-fructose corn syrup most
commonly used on soft drinks is 55% fructose and 45% glucose. The difference between the two
lies in the fact that HFCS contains little sucrose, the fructose and glucose being independent
moieties.
Fructose is often recommended for diabetics because it does not trigger the production of insulin
by pancreatic β cells, probably because β cells have low levels of GLUT5.[52][53][54] Fructose has a
very low glycemic index of 19 ± 2, compared with 100 for glucose and 68 ± 5 for sucrose.[55]
Fructose is also seventy-three percent sweeter than sucrose (see 2.1 Relative Sweetness) at room
temperature, so diabetics can use less of it. Studies show that fructose consumed before a meal
may even lessen the glycemic response of the meal.[56] Its sweetness changes at higher
temperatures, so its effects in recipes are not equivalent to those of sucrose (i.e., table sugar).
[citation needed]

[edit] Liver disease

"The medical profession thinks fructose is better for diabetics than sugar," says Meira Field,
Ph.D., a research chemist at United States Department of Agriculture, "but every cell in the body
can metabolize glucose. However, all fructose must be metabolized in the liver. The livers of the
rats on the high fructose diet looked like the livers of alcoholics, plugged with fat and
cirrhotic."[57] While a few other tissues (e.g., sperm cells[58] and some intestinal cells) do use
fructose directly, fructose is almost entirely metabolized in the liver.[57]
"When fructose reaches the liver," says Dr. William J. Whelan, a biochemist at the University of
Miami School of Medicine, "the liver goes bananas and stops everything else to metabolize the
fructose." Eating fructose instead of glucose results in lower circulating insulin and leptin levels,
and higher ghrelin levels after the meal.[59] Since leptin and insulin decrease appetite and ghrelin
increases appetite, some researchers suspect that eating large amounts of fructose increases the
likelihood of weight gain.[60]
Excessive fructose consumption is also believed to contribute to the development of non-
alcoholic fatty liver disease.[61]
[edit] Gout
It has been suggested in a recent British Medical Journal study that high consumption of fructose
is linked to gout. Cases of gout have risen in recent years, despite commonly being thought of as
a Victorian disease, and it is suspected that the fructose found in soft drinks (e.g., carbonated
beverages) and other sweetened drinks is the reason for this.[62][63]
In order for the liver to process fructose, it must be phosphorylated by removal of phosphates
from adenosine triphosphate (ATP). The ATP gets converted to adenosine monophosphate
(AMP), then to inositol monophosphate (IMP), and finally to uric acid,[64] the agent in gout.
[edit] Glycemic index
Fructose has the lowest glycemic index (GI = 19) of all the natural sugars and may be used in
moderation by diabetics. It is recommended that a maximum intake of 25g - 40g per day is
adopted, provided that this is counted towards the daily calorie count. In comparison, ordinary
table sugar (sucrose) has a GI of 65 and honey has a GI of 55. Fruit sugar has the advantage for
diabetics that, being nearly twice as sweet as ordinary sugar if not heat-processed, the daily
allowance can be stretched by using less for most applications. Many artificial sweeteners are not
suitable for home-baking, but, with a little adjustment, many traditional recipes can be prepared
using fructose.[65]
[edit] See also
• Tagatose
• Inverted sugar
• DMF (potential fructose-based biofuel)
• Fructose intolerance
• Fructose malabsorption
• Fructan (fructose polymer)
• Galactose
• Glucose
• Glycation
• High fructose corn syrup
• Hyperuricemia
• Seliwanoff's test
• Sucrose
• Sugars in wine
• Agave nectar
[edit] External links
 • [5] Hereditary Fructose Intolerance
• [6]
• How Fructose Impairs the Memory
• Cancer cells metabolize fructose to increase proliferation
[edit] References
1. ^ Fructose - Merriam Webster dictionary
2. ^ Levulose comes from the Latin word laevus, levo, "left side", levulose is the old word
for the most occurring isomer of fructose. D-fructose rotate plane-polarised light to the
left, hence the name.[1].
3. ^ Fruton, J.S. Molecules of Life 1972, Wiley-Interscience
4. ^ Hyvonen, L., & Koivistoinen, P (1982). "Fructose in Food Systems". In Birch, G.G. &
Parker, K.J. Nutritive Sweeteners. London & New Jersey: Applied Science Publishers.
pp. 133–144. ISBN 0-85334-997-5
5. ^ Wolfgang Wach "Fructose" in Ullmann's Encyclopedia of Industrial Chemistry 2004,
Wiley-VCH, Weinheim.doi:10.1002/14356007.a12_047.pub2
6. ^ "Institute of Organic Chemistry".
http://www.oci.unizh.ch/edu/lectures/material/AC_BII/Kap14/kap14.html.
7. ^ McWilliams, Margaret. Foods: Experimental Perspectives, 4th Edition.
ISBN 0130212822.
8. ^ Keusch, P. "Yeast and Sugar- the Chemistry must be right". http://www.chemie.uni-
regensburg.de/Organische_Chemie/Didaktik/Keusch/D-fermentation_sugar-e.htm.
9. ^ Dills, WL (1993). "Protein fructosylation: Fructose and the Maillard reaction". Journal
of Clinical Nutrition 58: 779–787.
10. ^ Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044 - 4098.
doi:10.1021/cr068360d
11. ^ a b c d e Hanover, LM; White, JS (1993). "Manufacturing, composition, and application
of fructose". Journal of Clinical Nutrition 58: 724s-732.
12. ^ Oregon State University. "Sugar Sweetness". Last accessed May 5, 2008.
http://food.oregonstate.edu/sugar/sweet.html Archived May 16, 2008 at the Wayback
Machine.
13. ^ Fructose in our diet: http://www.medbio.info/Horn/Time%201-
2/carbohydrate_metabolism.htm last visited 2008-12-28
14. ^ a b Nabors, LO (2001). American Sweeteners. pp. 374–375.
15. ^ McWilliams, Margaret (2001). Foods: Experimental Perspectives, 4th Edition. Upper
Saddle River, NJ : Prentice Hall. ISBN 0130212822.
16. ^ White, DC; Lauer GN (1990). "Predicting gelatinization temperature of
starch/sweetener system for cake formulation by differential scanning calorimetry I.
Development of a model". Cereal Foods Wold 35: 728–731.
17. ^ Park, KY; Yetley AE (1993). "Intakes and food sources of fructose in the United
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[show]v · d · eTypes of Carbohydrates

G
e
n
e
Aldose · Ketose · Furanose · Pyranose
r
a
l
:

G
e
o
m
Cyclohexane conformation · Anomer · Mutarotation
e
t
r
y

MDioses Aldodiose (Glycolaldehyde)

o
nTrioses Ketotriose (Dihydroxyacetone) · Aldotriose (Glyceraldehyde)
o
sTetroses Ketotetrose (Erythrulose) · Aldotetroses (Erythrose, Threose)
a
c
c Ketopentose (Ribulose, Xylulose)
hPentoses Aldopentose (Ribose, Arabinose, Xylose, Lyxose)
a Deoxy sugar (Deoxyribose)
r
i
d Ketohexose (Psicose, Fructose, Sorbose, Tagatose)
eHexoses Aldohexose (Allose, Altrose, Glucose, Mannose, Gulose, Idose, Galactose, Talose)
s
Deoxy sugar (Fucose, Fuculose, Rhamnose)
HeptosesKetoheptose (Sedoheptulose, Mannoheptulose)

>7 Octose · Nonose (Neuraminic acid)

Disaccharides Sucrose · Lactose · Maltose · Trehalose · Turanose · Cellobiose

Trisaccharides Raffinose · Melezitose · Maltotriose

MTetrasaccharidesAcarbose · Stachyose
u
lOther Fructooligosaccharide (FOS) · Galactooligosaccharides (GOS) · Mannan-
toligosaccharides oligosaccharides (MOS)
i
p Glucose/Glucan: Glycogen · Starch (Amylose, Amylopectin) · Cellulose ·
l Dextrin/Dextran · Beta-glucan (Zymosan, Lentinan, Sizofiran) · Maltodextrin
e Fructose/Fructan: Inulin · Levan beta 2→6
Polysaccharides
Mannose/Mannan
Galactose/Galactan
N-Acetylglucosamine: Chitin

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) ·
amac/i · ncbs/i · ttpy/i
Retrieved from "http://en.wikipedia.org/wiki/Fructose"
Categories: Nutrition | Sweeteners | Ketohexoses
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