Fruttosio

Proprietà e caratteristiche del fruttosio

Il fruttosio è un glucide con formula bruta C6H12O6.

E' noto anche con il nome di levulosio in quanto è levogiro (ovvero una
sua soluzione acquosa ruota il piano della luce polarizzata verso sinistra).

E' uno zucchero naturale che si trova in molti frutti e nel miele; è presente anche nel
saccarosio nel quale è legato al glucosio mediante un legame glicosidico.

Ha massa molare di 180,16 g/mol, densità pari a 1,65 g/cm3 (in c.s.) e punto di

fusione di 102°C. Alla temperatura di 20°C ha una solubilità in acqua pari a 3760 g/L.

Si presenta come un solido bianco o incolore.

Lo si ritrova inoltre:

 nel processo di fermentazione alcolica, in cui viene trasformato in etanolo e CO2;

 nel processo di glicolisi, nel quale i suoi esteri fosforici costituiscono intermedi di
importanza fondamentale.

Struttura chimica del fruttosio

Il fruttosio esiste prevalentemente in forma ciclica, come la maggior parte degli

altri monosaccaridi.

Questa struttura costituisce un emichetale che si forma coinvolgendo l'ossidrile

dell'atomo di carbonio 5.

Tuttavia, siccome il carbonile chetonico nel fruttosio è in posizione C-2, l'anello che si
forma contiene solo cinque atomi.

Oltre alla struttura fruttofuranosica sopracitata, la struttura chimica di chetoesoso a

catena aperta del fruttosio è in equilibrio con un'altra forma ciclica a sei atomi (forma
piranosica).

E' inoltre importante notare che la chiusura dell'anello del fruttosio converte

il carbonio chetonico in un carbonio asimmetrico.

Sia per la struttura piranosica che per la struttura furanosica, si possono quindi avere (in
soluzione acquosa) due emichetali in equilibrio con il chetone libero; essi sono designati
con le lettere α e ß:

Potere dolcificante del glucosio

Il fruttosio presenta potere dolcificante nettamente superiore al saccarosio,

caratteristica che, unita alla più lenta utilizzazione da parte dell’organismo, lo rende
idoneo come succedaneo dello zucchero comune nelle diete ipocaloriche.
 Produzione industriale del glucosio

Il glucosio può essere prodotto industrialmente sia dal polisaccaride inulina (che lo

contiene in grande quantità) sia dal saccarosio per trattamento enzimatico.

Usi del glucosio

Il tre principali impieghi del glucosio sono:

 come dolcificante dietetico;

 come conservante;

 come additivo alimentare.

TRADUZIONE IN INGLESE
Fructose
Properties and characteristics of fructose

Fructose is a glucide with the brute formula C6H12O6.

It is also known by the name of levulose as it is levogiro (i.e. an aqueous solution of it rotates the
plane of polarized light to the left).
It is a natural sugar found in many fruits and honey; it is also present in sucrose in which it is linked
to glucose through a glycosidic bond.
It has a molar mass of 180.16 g / mol, density equal to 1.65 g / cm3 (in c.s.) and a melting point of
102 ° C. At a temperature of 20 ° C it has a solubility in water equal to 3760 g / L
It looks like a white or colorless solid.
It is also found:
• in the alcoholic fermentation process, in which it is transformed into ethanol and CO2;
• in the glycolysis process, in which its phosphoric esters were intermediates of fundamental
importance.

Chemical structure of fructose

Fructose exists predominantly in cyclic form, like most other monosaccharides.

This structure constitutes an emicetal which is formed by involving the hydroxyl of the carbon
atom 5.
However, since the ketone carbonyl in fructose is in position C-2, the ring that is formed contains
only five atoms.
In addition to the aforementioned fructofuranosic structure, the chemical structure of open chain
ketohexose of fructose is in balance with another cyclic six-atom form (pyranosic form).
It is also important to note that closing the fructose ring converts the ketone carbon into an
asymmetric carbon.
Both for the pyranosic structure and for the furanosic structure, it is therefore possible to have (in
aqueous solution) two hemichetals in equilibrium with the free ketone; they are designated with
the letters α and ß:
Sweetening power of glucose
Fructose has a sweetening power clearly superior to sucrose, a feature that, combined with the
slower use by the body, makes it suitable as a substitute for common sugar in low-calorie diets.
Industrial production of glucose
Glucose can be industrially produced both from the polysaccharide inulin (which contains it in
large quantities) and from sucrose by enzymatic treatment.
Use of glucose
The three main uses of glucose are:
• as a dietary sweetener;
• as a preservative;
• as a food additive.

• When your digestive system doesn't absorb fructose properly, it can cause abdominal pain,
diarrhea and gas.

 Fructose has several roles in the body.

DIAPOSITIVA 2
Fructose, or fruit sugar, is a simple ketonic monosaccharide with the brute
formula C6H12O6 and It’s classified as an alkene due to a double bond present
in this compound.
Weight of a fructose compound: 180,16 g/mol and a melting point of 102 ° C. At
a temperature of 20 ° C it has a solubility in water equal to 3760 g / L.
The fructose is 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.
Monosaccharides are the fundamental units of carbohydrates that cannot be
further reduced to simpler compounds. They are classified based on the
functional group attached to the carbohydrate.
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.

DIAPOSITIVA 3
Fructose along with glucose and galactose are three monosaccharides that are
an important part of our diet. And as I say before, They are classified based on
the functional group attached to the carbohydrate.

DIAPOSITIVA 4/5
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.
Food rich in fructose includes many types of sweetened beverages and snacks,
fruit, especially when in concentrated form such as juices or dried, and honey
(see table below).
Chains of fructose molecules, fructo-oligosaccharides or fructans, are present in
high concentrations in some vegetables and cereal products and often lead to
symptoms in individuals with fructose intolerance.
DIAPOSITIVA 6/7
Energy Production
Body cells need energy to be able to engage in various processes. For instance,
according to Drs. Reginald Garrett and Charles Grisham in their book
"Biochemistry," a major use of energy by many cells is to maintain the so-called
"resting membrane potential," which allows cells to take in certain substances
from the fluid that surrounds them and allows cell-to-cell communication. Like
glucose, fructose is a source of energy for the cells. Cells process fructose to
extract energy through a process called aerobic respiration, which essentially
means burning of fructose in the presence of oxygen to produce ATP, the
cellular energy molecule.

DIAPOSITIVA 8
Glycogen Production
The cells can also use fructose to make an important form of storage
carbohydrate, called glycogen. According to Dr. Lauralee Sherwood in her book
"Human Physiology," the liver and muscles store glycogen, which is made up of
long chains of glucose, to provide for cellular glucose needs during emergencies
or periods of fasting. The muscles maintain glycogen for their own use, while the
liver breaks down glycogen to release glucose into the bloodstream for use by
all body cells. Partial breakdown of fructose produces the compounds
glyceraldehyde and dihydroxyacetone phosphate. Modification of
glyceraldehyde to produce glyceraldehyde-3 phosphate allows for production of
glycogen -- the glyceraldehyde-3 phosphate reacts with dihydroxyacetone
phosphate to produce a precursor in glycogen synthesis.

DIAPOSITIVA 9
Fat Storage
In addition to storing energy in the form of glycogen, the body also stores energy
in the form of triglyceride, or fat. Fat, says Dr. Gary Thibodeau in his book
"Anatomy and Physiology," is an important form of energy storage because it's
both light and energetically dense. As such, the body can store a significant
quantity of energy without a significant amount of stored weight. Chemical
reactions modify fructose to produce the precursors to fat synthesis.
DIAPOSITIVA 10
Fructose has a cyclic structure. This structure constitutes a hemiacetal which is
formed by involving the hydroxyl of the carbon atom 5.
However, since the ketone carbonyl in fructose is in position C-2, the ring that is
formed contains only five atoms.
In addition to that, the chemical structure of open chain ketohexose of fructose is
in balance with another cyclic six-atom form (pyranose form).
It is also important to note that closing the fructose ring converts the ketone
carbon into an asymmetric carbon.
Both for the pyranose and furanose structure, it is therefore possible to have (in
aqueous solution) two hemiacetals in equilibrium with the free ketone; they are
designated with the letters α and ß:

DIAPOSITIVA 11
This is a phot of the Fructose A-Monosaccharide

DIAPOSITIVA 12
And this is a photo that describe the relationship between the acyclic and the
cyclic (hemiketal) isomers of fructose

DIAPOSITIVA 13
The three main uses of glucose are:
- as a dietary sweetener;
- as a preservative;
- as a food additive.
In addition:
Crystalline fructose is used in enhancing the taste in food industries.
It is used in flavoured water, energy drinks, low-calorie products, etc.
Fruit sugar is used in the manufacturing of soft moist cookies, nutrition bars,
reduced-calorie products etc.
DIAPOSITIVA 14
When your digestive system doesn't absorb fructose properly, it can cause
abdominal pain, diarrhea and gas.
People who have fructose intolerance should limit high-fructose foods, such as
juices, apples, grapes, watermelon, asparagus, peas and zucchini.
They must use some lower fructose foods — such as bananas, blueberries,
strawberries, carrots, avocados, green beans and lettuce — may be tolerated in
limited quantities with meals.

DIAPOSITIVA 15
Fructose can be industrially produced both from the polysaccharide inulin (which
contains it in large quantities) and from sucrose by enzymatic treatment.
It is also commercially produced as invert sugar and high fructose corn syrup
(HFCS).