Sorbitol Chemical Properties

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)

refractive index 

n20/D 1.46

FEMA 

3029 | D-SORBITOL

Flash point:

>100°C

storage temp. 

room temp

solubility 

Very soluble in water, slightly soluble in ethanol

form 

liquid

pka

pKa (17.5°): 13.6

color 

White

Specific Gravity

1.28

Odor

Odorless

PH Range

5 - 7 at 182 g/l at 25 °C

PH

5.0-7.0 (25℃, 1M in H2O)

optical activity

[α]20/D 1.5±0.3°, c = 10% in H2O

Odor Type

caramellic

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℃）

Stability:

Stable. Avoid strong oxidizing agents. Protect from moisture.

InChIKey

FBPFZTCFMRRESA-JGWLITMVSA-N

LogP

-4.67

CAS DataBase Reference

50-70-4(CAS DataBase Reference)

NIST Chemistry Reference

Sorbitol(50-70-4)

EPA Substance Registry System

Sorbitol (50-70-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

8-36-26-24/25

WGK Germany 

2

RTECS 

LZ4290000

F 

3

Autoignition Temperature

420 °C

TSCA 

Yes

HS Code 

29054491

Hazardous Substances Data

50-70-4(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 15900 mg/kg

MSDS

• Language:English Provider:D-Sorbitol
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Sorbitol Usage And Synthesis

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%.

Chemical Properties

d-Sorbitol has a sweet taste. In comparison to sucrose, the relative sweetness of sorbitol is approximately 50%. Sorbitol can exist in any of several crystalline forms with melting points ranging from 89 to 101°C. For a detailed description of this compound, refer to Burdock (1997).

Chemical Properties

White or almost white, crystalline powder.

Chemical Properties

Sorbitol is D-glucitol. It is a hexahydric alcohol related to mannose and is isomeric with mannitol.
Sorbitol occurs as an odorless, white or almost colorless, crystalline, hygroscopic powder. Four crystalline polymorphs and one amorphous form of sorbitol have been identified that have slightly different physical properties, e.g. melting point. Sorbitol is available in a wide range of grades and polymorphic forms, such as granules, flakes, or pellets that tend to cake less than the powdered form and have more desirable compression characteristics. Sorbitol has a pleasant, cooling, sweet taste and has approximately 50–60% of the sweetness of sucrose.

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.

Uses

D-Sorbitol is a sugar alcohol that is naturally found in Toyon berries. D-Sorbitol is used to increase stability of silver nanoparticles and is also used as a sugar substitute.

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.

Uses

In manufacture of sorbose, ascorbic acid, propylene glycol, synthetic plasticizers and resins; as humectant (moisture conditioner) on printing rolls, in leather, tobacco. In writing inks to insure a smooth flow and to prevent crusting on the point of the pen. In antifreeze mixtures with glycerol or glycols. In candy manufacture of to increase shelf life by retarding the solidification of sugar; as humectant and softener in shredded coconut and peanut butter; as texturizer in foods; as sequestrant in soft drinks and wines. Used to reduce the undesirable aftertaste of saccharin in foodstuffs; as sugar substitute for diabetics. Pharmaceutic aid (flavor; tablet excipient); to increase absorption of vitamins and other nutrients in pharmaceutical preparations: Chem. Eng. News 36, 59 (Feb. 24, 1958).

Definition

ChEBI: The D-enantiomer of glucitol (also known as D-sorbitol).

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.

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.

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.

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

General Description

Odorless colorless solid. Sinks and mixes with water.

Air & Water Reactions

Water soluble.

Reactivity Profile

D-Sorbitol 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.

Health Hazard

Hot liquid will burn skin.

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 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.

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.

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