| Identification | More | [Name]
D-Sorbitol | [CAS]
50-70-4 | [Synonyms]
D-GALACTITOL
D-GLUCITOL
D-GLUITOL
D-SORBIT
D(-)-SORBITOL
D-SORBITOL
FEMA 3029
GLUCITOL
KARION
PARTECK(R) SI 150 SORBITOL
PARTECK(R) SI 200 SORBITOL
PARTECK(R) SI 400 SORBITOL
PARTECK SI 150
PARTECK SI 400
PARTECK SI 400 LEX
PARTECK SI 450
P-SORBITOL
SI 150 SORBITOL
SI 400 LEX SORBITOL, LOW ENDOTOXIN
SI 450 SORBITOL | [EINECS(EC#)]
200-061-5 | [Molecular Formula]
C6H14O6 | [MDL Number]
MFCD00004708 | [Molecular Weight]
182.17 | [MOL File]
50-70-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White or almost white, crystalline powder. | [Melting point ]
98-100 °C (lit.) | [alpha ]
4 º (per eur. pharm.) | [Boiling point ]
bp760 105° | [density ]
1.28 g/mL at 25 °C
| [vapor density ]
<1 (vs air)
| [vapor pressure ]
<0.1 mm Hg ( 25 °C)
| [FEMA ]
3029 | [refractive index ]
n20/D 1.46
| [Fp ]
>100°C | [storage temp. ]
Store at RT. | [solubility ]
H2O: 1 M at 20 °C, clear, colorless
| [form ]
liquid
| [pka]
pKa (17.5°): 13.6 | [color ]
White | [Specific Gravity]
1.28 | [Odor]
Odorless | [PH]
5.0-7.0 (25℃, 1M in H2O) | [PH Range]
5 - 7 at 182 g/l at 25 °C | [Stability:]
Stable. Avoid strong oxidizing agents. Protect from moisture. | [Odor Type]
caramellic | [optical activity]
[α]20/D 1.5±0.3°, c = 10% in H2O | [Water Solubility ]
SOLUBLE | [Sensitive ]
Hygroscopic | [λmax]
λ: 260 nm Amax: 0.04
λ: 280 nm Amax: 0.045 | [Merck ]
14,8725 | [BRN ]
1721899 | [Dielectric constant]
33.5（27℃） | [InChIKey]
FBPFZTCFMRRESA-JGWLITMVSA-N | [LogP]
-4.67 | [Uses]
Sorbitol is a humectant that is a polyol (polyhydric alcohol) produced by hydrogenation of glucose with good solubility in water and poor solubility in oil. It is approximately 60% as sweet as sugar, and has a caloric value of 2.6 kcal/g. It is highly hygroscopic and has a pleasant, sweet taste. It maintains moistness in shredded coconut, pet foods, and candy. In sugarless frozen desserts, it depresses the freezing point, adds solids, and contributes some sweetness. It is used in low-calorie beverages to provide body and taste. It is used in dietary foods such as sugarless candy, chewing gum, and ice cream. It is also used as a crystallization modifier in soft sugar-based confections. | [CAS DataBase Reference]
50-70-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Sorbitol(50-70-4) | [EPA Substance Registry System]
50-70-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S8:Keep container dry .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2 | [RTECS ]
LZ4290000 | [F ]
3 | [Autoignition Temperature]
420 °C | [TSCA ]
Yes | [HS Code ]
29054491 | [Safety Profile]
Mildly toxic by ingestion. Human systemic effects by ingestion: hypermotility and diarrhea. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. | [Hazardous Substances Data]
50-70-4(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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. |
| Questions And Answer | Back Directory | [Product Features]
Sorbitol is a non-volatile polyhydric sugar alcohol. It is chemically stable and not easily to be oxidized by air. It is easily soluble in water, hot ethanol, methanol, isopropanol, butanol alcohol, cyclohexanol, phenol, acetone, acetic acid and dimethyl formamide. It is widely distributed in nature plant fruit. It is not easy to be fermented by various kinds of microorganism and have a excellent heat resistance without decomposing even at high temperature (200 °C). It is initially separated from the mountain strawberry by the Boussingault (French) et al. The pH value of the saturated aqueous solution is 6 to 7. It is isomer of mannitol, Taylor alcohol, and galactose alcohol. It has a refreshing sweet taste with sweetness being 65% of sucrose. It has excellent moisture absorption capability with a low calorific value and has very wide range of effects on the food, cosmetic, pharmaceutical field. When applied in food, it can prevent the food drying, aging, and can extend the shelf life of products as well as effectively prevent the precipitation of sugars and salts contained in the foods and thus maintain the strength balance of sweetness, sour, bitter and enhance food flavor. It can be synthesize from the hydrogenation of glucose under heating and high pressure with the existence of nickel catalyst.
| [Uses]
1. Daily chemical industry
Sorbitol can be used as an excipient, moisturizing agents, and antifreeze agents in toothpaste, with the added amount being up to 25 to 30%. This can help maintain the lubrication, color, and good taste for the paste. In cosmetics field, it is used as an anti-drying agent (substitute glycerol) which can enhance the stretch and lubricity of emulsifier, and thus is suitable for long-term storage; Sorbitan esters and sorbitan fatty acid ester as well as its ethylene oxide adducts having a advantage of a small skin irritation which is thus widely used in the cosmetics industry.
2. The food industry
Adding sorbitol into foods can prevent the drying of food and make food stay fresh and soft. Application in bread cake has a significant effect.
The sweetness of sorbitol is lower than that of sucrose, and can’t be exploited by any bacteria. It is an important raw material for production of sugar-free candy and a variety of anti-caries food. Since the metabolism of the product does not cause increase of blood sugar, it can also be applied as a sweetener agent and nutrient agent for the food of patients with diabetes.
Sorbitol does not contain an aldehyde group and is not easily oxidized. It will not have Maillard reaction with amino acids upon heating. It also has certain physiological activity. It can prevent the denaturation of the carotenoids and edible fats and protein; adding this product to the concentrated milk can extend the shelf life; it can also be used to improve the color, flavor and taste of small intestine and has significant stabilizing effect and long-term storage effect on fish pate. Similar effect can also be observed in the jam.
3. the pharmaceutical industry
Sorbitol can be used as raw material in vitamin C; also can be used as feed syrup, injection fluids, and raw material of medicine tablet; as a drug dispersion agent and fillers, cryoprotectants, anti-crystallizing agent, medicine stabilizers, wetting agents, capsules plasticized agents, sweetening agents, and ointment matrix.
4. the chemical industry
Sorbitol abietin is often used as the raw material for common architectural coatings, also used as plasticizers and lubricants for application in polyvinyl chloride resin and other polymers.
It can from complex with iron, copper, and aluminum ion in alkaline solution to be applied to the washing and bleaching in textile industry.
Using sorbitol and propylene oxide as a starting material can produce rigid polyurethane foam as well as have some flame retardant properties.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
| [Toxicity]
LD50 orally in Rabbit: 15900 mg/kg | [Limited use]
FAO/WHO: raisins, 5g/kg; Edible ices and ice drink: 50g/kg (alone or the amount of its combination with glycerol).
FDA, §184.1835 (2000): 99% hard candy; gum 75%, candy 98%; jams, jellies, 30%; frozen dairy dessert 17%; bakery products 30%; other food 2%.
FEMA (mg/kg): 1300 Soft drinks; cold drink 70,000; candy 21000; bakery 50000; pudding category 8000; sugar-coat 500; top Decorating 280,000.
GB 2760-2000: with the "02319, maltitol."
| [Chemical Properties]
It is white and odorless crystalline powder with sweet taste and being hygroscopic. It can be dissolved in water (235g/100g water, 25 °C), glycerin, and propylene glycol; and is slightly soluble in methanol, ethanol, acetic acid, and phenol and acetamide solution but almost insoluble in most other organic solvents.
| [Production method]
1. Pour the prepared 53% aqueous solution of glucose into the autoclave, adding the nickel catalyst of 0.1% the weight of glucose; after replacement of the air, add hydrogen at about 3.5MPa, 150 °C, and pH8.2-8.4; control the endpoint with residual sugar content being lower than 0.5%. After precipitation for 5 min, put the resulting solution of sorbitol through ion exchange resin to obtain the refined product. Material fixed consumption amount: hydrochloric acid 19kg/t, caustic 36kg/ t, solid base 6kg/t, aluminum-nickel alloy powder 3kg/t, orally administrated glucose 518kg/t, activated carbon 4kg/t.
2. It is obtained from the hydrogenation of glucose with the nickel catalyst at high temperature and high pressure after which the product is further refined through the ion exchange resin, concentrated,crystallized, and, separated to obtain the final product.
3. Domestic production of sorbitol mostly applied continuously or intermittently hydrogenation of refined glucose obtained from starch saccharification:
C6H12O6 + H2 [Ni] → C6H14O6
Pour the prepared 53% aqueous solution of glucose into the autoclave, adding the nickel catalyst of 0.1% the weight of glucose; after replacement of the air, add hydrogen at about 3.5MPa, 150 °C, and pH8.2-8.4; control the endpoint with residual sugar content being lower than 0.5%. After precipitation for 5 min, put the resulting solution of sorbitol through ion exchange resin to obtain the refined product. The above-mentioned process is simple without the necessity of isolation before obtaining qualified products as well as without "three wastes" pollution. However, for the starch, the yield is only 50%, and thus has a higher cost. Introduction of new technology by direct hydrogenation on starch saccharification liquid can obtain a yield up to 85%.
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