General Description
Odorless colorless solid. Sinks and mixes with water.
Reactivity Profile
SORBITOL(50-70-4) is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Air & Water Reactions
Water soluble.
Health Hazard
Hot liquid will burn skin.
Originator
Sorbitol,Memphis Co.
Occurrence
Sorbitol is one of the most widely found sugar alcohols in nature with relatively high concentrations occurring in apples, pears, plums, peaches and apricots. Also reported found in several varieties of berries, seaweed and algae.
Definition
A hexahydric alcohol
that occurs in rose hips and rowan berries.
It can be synthesized by the reduction of
glucose. Sorbitol is used to make vitamin C
(ascorbic acid) and surfactants. It is also
used in medicines and as a sweetener (particularly in foods for diabetics). It is an isomer of mannitol.
Definition
A polyhydric alcohol, CH2OH(CHOH)4CH2OH, derived from glucose; it is isomeric with mannitol. It is found in rose hips and rowan berries and is manufactured by the catalytic reduction of glucose with hydrogen. Sorbitol is used as a sweetener (in diabetic foods) and in the manufacture of vitamin C and various cosmetics, foodstuffs, and medicines.
Definition
ChEBI: The D-enantiomer of glucitol (also known as D-sorbitol).
Preparation
Sorbitol is manufactured by hydrogenation of glucose with hydrogen and active nickel catalyst. It is commercially available as 70% syrup or as a pure white powder.
Production Methods
Sorbitol occurs naturally in the ripe berries of many trees and
plants. It was first isolated in 1872 from the berries of the Mountain
Ash (Sorbus americana).
Industrially, sorbitol is prepared by high-pressure hydrogenation
with a copper–chromium or nickel catalyst, or by electrolytic
reduction of glucose and corn syrup. If cane or beet sugars are used
as a source, the disaccharide is hydrolyzed to dextrose and fructose
prior to hydrogenation.
Manufacturing Process
20 ml of a suspension of CTAB-permeabilized cells of Zymomonas mobilis
were mixed with 80 ml of a 4% carrageenan solution and the mixture was
poured into shallow dishes and allowed to rigidify. The rigidified immobilizate
was then divided into 3x3x3 mm cubes, exposed to a solution of 0.3 M KCl
overnight and then divided into batches and exposed to one of the following
treatments:
(A) Cubes stabilized with potassium ions were used without further treatment
for production of sorbitol/gluconic acid.
(B) Cubes were incubated with a 1.0% solution of polyethyleneimine at room
temperature for 30 min and then treated with glutaraldehyde at 4°C for 30
min.
Comparison of two rigidification methods:
A volume of 450 ml of cubes treated by the method described in (A) were
reacted in a 1.5 liter fluidized bed fermenter with a substrate solution
comprised of 100 g/L glucose, 100 g/L fructose and a protein concentration of
6.1 g/L, at a D of 0.053 h-1, and titrated with 3 N KOH. After 48 hours, 68.8%
of the substrate was converted with a resulting production of 3.65 g
sorbitol/L*h and 0.6 g sorbitol/g protein*h. After approximately 50 days, the
productivity of the fermenter was reduced by about one half.
Cubes treated as described (B) using glutaraldehyde at a concentration of
0.5%, were reacted in a 1.6 liter fermenter with a substrate solution
comprised of 100 g/L glucose, 100 g/L fructose and a protein concentration of
8.6 g/L, at a D of 0.055 h-1, and titrated with 3 N KOH. After 48 hours, 90.0%
of the substrate was converted with a resulting production of 4.95 g
sorbitol/L*h and 0 58 g sorbitol/g protein*h. After 75 days, the productivity of
the fermenter was reduced by only 3.5%.
Brand name
Sorbo (ICI Americas).
Therapeutic Function
Cholecystokinetic, Diuretic, Pharmaceutic aid
Pharmaceutical Applications
Sorbitol is widely used as an excipient in pharmaceutical formulations.
It is also used extensively in cosmetics and food products.
Sorbitol is used as a diluent in tablet formulations prepared by
either wet granulation or direct compression. It is particularly
useful in chewable tablets owing to its pleasant, sweet taste and
cooling sensation. In capsule formulations it is used as a plasticizer
for gelatin. Sorbitol has been used as a plasticizer in film
formulations.
In liquid preparations sorbitol is used as a vehicle in sugar-free
formulations and as a stabilizer for drug, vitamin, and
antacid suspensions. Furthermore, sorbitol is used as an excipient in
liquid parenteral biologic formulations to provide effective protein
stabilization in the liquid state. It has also been shown to be a
suitable carrier to enhance the in vitro dissolution rate of
indometacin. In syrups it is effective in preventing crystallization
around the cap of bottles. Sorbitol is additionally used in
injectable and topical preparations, and therapeutically as an
osmotic laxative.
Sorbitol may also be used analytically as a marker for assessing
liver blood flow.
Biochem/physiol Actions
D-Sorbitol is a sugar alcohol that is commonly used as a sugar substitute. It occurs naturally and is also produced synthetically from glucose. The food industry uses D-sorbitol as an additive in the form of a sweetener, humectant, emulsifier, thickener, or dietary supplement. D-Sorbitol has also been found in cosmetics, paper, and pharmaceuticals. Naturally, D-sorbitol occurs widely in plants via photosynthesis, ranging from algae to higher order fruits of the family Rosaceae.
Safety
Sorbitol is widely used in a number of pharmaceutical products and
occurs naturally in many edible fruits and berries. It is absorbed
more slowly from the gastrointestinal tract than sucrose and is
metabolized in the liver to fructose and glucose. Its caloric value is
approximately 16.7 J/g (4 cal/g). Sorbitol is better tolerated by diabetics than sucrose and is widely used in many sugar-free liquid
vehicles. However, it is not considered to be unconditionally safe for
diabetics.
Reports of adverse reactions to sorbitol are largely due to its
action as an osmotic laxative when ingested orally,(17–19) which may
be exploited therapeutically. Ingestion of large quantities of sorbitol
(>20 g/day in adults) should therefore be avoided.
Sorbitol is not readily fermented by oral microorganisms and has
little effect on dental plaque pH; hence, it is generally considered to
be noncariogenic.
Sorbitol is generally considered to be more irritating than
mannitol.
LD50 (mouse, IV): 9.48 g/kg
LD50 (mouse, oral): 17.8 g/kg
LD50 (rat, IV): 7.1 g/kg
LD50 (rat, SC): 29.6 g/kg
storage
Sorbitol is chemically relatively inert and is compatible with most
excipients. It is stable in air in the absence of catalysts and in cold,
dilute acids and alkalis. Sorbitol does not darken or decompose at
elevated temperatures or in the presence of amines. It is
nonflammable, noncorrosive, and nonvolatile.
Although sorbitol is resistant to fermentation by many microorganisms,
a preservative should be added to sorbitol solutions.
Solutions may be stored in glass, plastic, aluminum, and stainless
steel containers. Solutions for injection may be sterilized by
autoclaving.
The bulk material is hygroscopic and should be stored in an
airtight container in a cool, dry place.
Purification Methods
Crystallise D(-)-sorbitol (as hemihydrate) several times from EtOH/water (1:1), then dry it by fusing and storing over anhydrous MgSO4. [Koch et al. J Am Chem Soc 75 953 1953, Beilstein 1 IV 2839.]
Incompatibilities
Sorbitol will form water-soluble chelates with many divalent and
trivalent metal ions in strongly acidic and alkaline conditions.
Addition of liquid polyethylene glycols to sorbitol solution, with
vigorous agitation, produces a waxy, water-soluble gel with a
melting point of 35–40℃. Sorbitol solutions also react with iron
oxide to become discolored.
Sorbitol increases the degradation rate of penicillins in neutral
and aqueous solutions.
Regulatory Status
GRAS listed. Accepted for use as a food additive in Europe.
Included in the FDA Inactive Ingredients Database (intra-articular
and IM injections; nasal; oral capsules, solutions, suspensions,
syrups and tablets; rectal, topical, and vaginal preparations).
Included in parenteral and nonparenteral medicines licensed in the
UK. Included in the Canadian List of Acceptable Non-medicinal
Ingredients.
