United States Pharmacopeia (USP) Reference Standard
Synonym: D-Glucitol, D-Sorbitol
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CAS Number 50-70-4
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Empirical Formula (Hill Notation) C6H14O6
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Molecular Weight 182.17
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Beilstein Registry
Number 1721899
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MDL number MFCD00004708
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PubChem Substance ID 329751137
Properties
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Related Categories
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vapor density
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<1 (vs air)
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vapor pressure
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<0.1 mmHg ( 25 °C)
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InChI Key
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FBPFZTCFMRRESA-JGWLITMVSA-N
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form
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neat
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mp
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98-100 °C(lit.)
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format
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neat
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Sorbitol, less commonly known as glucitol,
is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained
by reduction of glucose, changing the aldehyde group to a hydroxyl group.
Detailed description
Most
sorbitol is made from corn syrup, but it is also found in apples, pears,
peaches, and prunes.[2] It is converted
to fructose by sorbitol-6-phosphate
2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ
only in the orientation of the hydroxyl group on carbon
2.[3] While similar,
the two sugar alcohols have very different sources in nature, melting points,
and uses.
Uses
Sweetener
Sorbitol is a sugar
substitute. It may be listed under the inactive ingredients
listed for some foods and products. Its INS number and E
number is 420. Sorbitol has approximately 60% the sweetness of sucrose
(table sugar).[4]
Sorbitol is referred to as a nutritive sweetener
because it provides dietary energy: 2.6 kilocalories (11 kilojoules) per gram versus the average 4
kilocalories (17 kilojoules) for carbohydrates. It is often used in diet
foods (including diet drinks and ice cream), mints, cough
syrups, and sugar-free chewing
gum.[5]
It also occurs naturally in many stone fruits and berries from
trees of the genus Sorbus.[6]
Laxative
Sorbitol can be used as a laxative via an oral
suspension or enema. As with other sugar
alcohols, gastrointestinal distress may result when food
products that contain sorbitol are consumed. Sorbitol exerts its laxative
effect by drawing water into the large
intestine, thereby stimulating bowel
movements.[7] Sorbitol has been
determined safe for use by the elderly, although it is not recommended without
consultation with a clinician.[8] Sorbitol is found in
some dried fruits and may contribute to the laxative effects of prunes.[9]Sorbitol was discovered initially in the fresh juice of mountain
ash (Sorbus
aucuparia) berries in 1872.[10] It is found in the
fruits of apples, plums, pears, cherries, dates, peaches, and apricots.
Medical applications
Sorbitol is used in bacterial culture media to
distinguish the pathogenic Escherichia coli O157:H7 from most other
strains of E.
coli, as it is usually incapable of fermenting sorbitol,
but 93% of known E. coli strains are capable of doing so.[11]
A treatment using sorbitol and ion-exchange resin sodium polystyrene sulfonate (tradename
Kayexalate), helps remove excess potassium ions when in a hyperkalaemic state.[12] The resin exchanges
sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate
it. In 2010 the U.S. FDA issued a warning of
increased risk for GI necrosis with this combination.[13]
Health care, food, and cosmetic uses
Sorbitol often is used in modern cosmetics as a humectant and thickener.[15] Sorbitol often is
used in mouthwash and toothpaste. Some transparent gels can be made only
with sorbitol, as it has a refractive
index sufficiently high for transparent formulations.
Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a processed fish
paste.[16] It is also used as a
humectant in some cigarettes.[17]
Sorbitol sometimes is used as a sweetener and
humectant in cookies and other foods that are not identified as
"dietary" items.
Miscellaneous uses
A mixture of sorbitol and potassium
nitrate has found some success as an amateur solid rocket
fuel.[18]
Sorbitol is identified as a potential key chemical
intermediate[19] for production of fuels from biomass resources. Carbohydrate fractions in biomass
such as cellulose undergo sequential hydrolysis and hydrogenation in the presence of
metal catalysts to produce sorbitol.[20] Complete reduction
of sorbitol opens the way to alkanes, such as hexane, which can be used as a biofuel. Hydrogen required
for this reaction can be produced by aqueous phase reforming of sorbitol.[21]
19
C6H14O6 →
13 C6H14 +
36 CO2 + 42 H2O
The above chemical
reaction is exothermic; 1.5 moles of sorbitol generate
approximately 1 mole of hexane. When hydrogen is co-fed, no carbon
dioxide is produced.
Sorbitol based polyols are used in the production of polyurethane foam for the
construction industry.
It is also added after electroporation of yeasts in transformation protocols,
allowing the cells to recover by raising the osmolarity of the medium.
Medical importance
Aldose reductase is the first enzyme
in the sorbitol-aldose reductase pathway[22] responsible for the
reduction of glucose to sorbitol, as well as the reduction of galactose to galactitol. Too much sorbitol
trapped in retinal cells, the cells of the lens, and the Schwann
cells that myelinate peripheral nerves can damage these
cells, leading to retinopathy, cataracts and peripheral neuropathy, respectively. Aldose reductase inhibitors, which are
substances that prevent or slow the action of aldose reductase, are currently
being investigated as a way to prevent or delay these complications, which
frequently occur in the setting of long-term hyperglycemia that accompanies
poorly controlled diabetes. It is thought that these agents may help to prevent the
accumulation of intracellular sorbitol that leads to cellular damage in
diabetics.
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