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DESCRIPTION
D-Glucitol, commonly known as sorbitol, is a sugar alcohol (polyol) derived from glucose.
D-Glucitol is naturally found in various fruits, including apples, pears, and peaches, and is widely used as a sweetener in food and beverages, as well as in cosmetics and pharmaceuticals.
Cas Number
50-70-4
SYNONYMS
Sorbitol,Sorbit,Glucitol,D-Sorbitol,D-Glucitol, 1,2,3,4,5,6-Hexahexanol,Polyglucitol
Overview of D-Glucitol (Sorbitol)
D-Glucitol, commonly known as sorbitol, is a sugar alcohol used primarily as a sweetener in food products.
D-Glucitol is also found in a variety of other products such as pharmaceuticals, cosmetics, and oral hygiene products.
Sorbitol has a chemical formula of C6H14O6 and is derived from glucose by reduction.
Sorbitol occurs naturally in some fruits (apples, pears, peaches) and berries.
D-Glucitol is also produced synthetically from glucose via chemical or enzymatic processes.
Historical Context and Discovery
Sorbitol was first discovered in 1872 by the French chemist Louis Maquenne, who extracted it from the berries of the sorbus tree.
Sorbitol's name is derived from the genus name of the tree.
Over time, its use expanded due to its ability to provide sweetness with fewer calories than sugar, making it popular in the development of sugar-free and diabetic-friendly foods.
Chemical Structure and Properties
Sorbitol is a hexose sugar alcohol formed by the reduction of glucose.
Its structure consists of six carbon atoms, each bonded to hydroxyl groups (-OH), except for one carbon that forms part of the alcohol group.
As a sugar alcohol, sorbitol does not metabolize in the body in the same way as sugar.
It has a caloric value of around 2.6 kcal/g, compared to the 4 kcal/g of regular sugars.
Uses of D-Glucitol in Various Industries
Sorbitol is used extensively in the food industry as a low-calorie sweetener, humectant (moisture retention), and stabilizer for products such as chewing gum, candies, and baked goods.
It is also present in pharmaceuticals as a laxative and as an excipient in tablets, syrups, and oral solutions.
Cosmetics and personal care products utilize sorbitol for its moisture-retaining properties, making it useful in skin lotions, soaps, and shampoos.
Chemical Structure and Properties
Molecular Properties
Sorbitol is a white, crystalline powder at room temperature.
It is odorless and has a sweet taste that is about 60% to 70% as sweet as sucrose.
It is highly soluble in water, which makes it useful in formulations where moisture retention is important.
Boiling point: 295°C (for pure sorbitol), but it decomposes at higher temperatures.
Stereochemistry of D-Glucitol and Its Isomerism
Sorbitol exists in two stereoisomeric forms: D-sorbitol (the biologically active form) and L-sorbitol (which is not metabolized in humans).
The D-form is the naturally occurring one in biological systems.
The stereochemistry of sorbitol means that it is non-digestible in the same way as sugars, leading to its reduced caloric content.
Stability and Reactivity
Sorbitol is stable under acidic conditions and does not easily degrade at room temperature. However, it is susceptible to oxidation in the presence of strong oxidizers.
When used in high-temperature applications, it can undergo Maillard reactions, especially in the presence of reducing sugars, which can cause browning.
Biosynthesis and Metabolism
Biological Synthesis of D-Glucitol in Humans and Other Organisms
In humans, sorbitol is produced via the polyol pathway, primarily in tissues such as the liver, kidneys, and eyes.
This pathway involves the enzyme aldose reductase, which reduces glucose to sorbitol using NADPH as a cofactor.
Pathways Involved in Sorbitol Metabolism
Sorbitol is further metabolized by sorbitol dehydrogenase, which converts it to fructose.
This fructose can be used in cellular metabolism, such as entering the glycolytic pathway for energy production.
The polyol pathway is particularly significant in conditions of hyperglycemia (high blood sugar), where excess glucose is converted to sorbitol and can accumulate in tissues, leading to complications like diabetic neuropathy and cataracts.
Role of Aldose Reductase and Sorbitol Dehydrogenase in Sorbitol Metabolism
Aldose reductase catalyzes the initial reduction of glucose to sorbitol.
This enzyme is involved in the conversion of glucose to the polyol sorbitol, which can accumulate in high levels under hyperglycemic conditions.
Sorbitol dehydrogenase catalyzes the oxidation of sorbitol to fructose.
In some tissues, such as the liver, this enzyme is active and helps to prevent sorbitol accumulation.
Sorbitol Accumulation in Tissues
Sorbitol accumulation can cause osmotic stress, leading to tissue damage.
In diabetic patients, the polyol pathway is activated, and high sorbitol levels can contribute to the formation of diabetic complications such as retinopathy, neuropathy, and nephropathy.
Sorbitol's ability to retain water in tissues can lead to swelling and damage to cellular structures.
Production Methods
Commercial Production Methods
Glucose Hydrogenation: Sorbitol is most commonly produced by the hydrogenation of glucose in the presence of a catalyst (usually nickel).
This process reduces the aldehyde group of glucose to a hydroxyl group, forming sorbitol.
Fermentation: In some cases, sorbitol can be produced by the fermentation of sugars using bacteria like S. cerevisiae or other microorganisms.
This is an environmentally friendly approach that is gaining interest for producing sorbitol sustainably.
Enzymatic vs. Chemical Synthesis
Enzymatic synthesis involves using specific enzymes to catalyze the reduction of glucose to sorbitol, providing high specificity and lower energy costs compared to chemical methods.
Chemical synthesis involves the use of high temperatures and pressure in the presence of hydrogen gas to reduce glucose.
While more energy-intensive, this method is widely used in industry for its simplicity and scalability.
Efficiency, Yield, and Economic Considerations
The chemical process yields sorbitol in high purity but can result in higher energy consumption and higher costs.
Enzymatic processes, though more environmentally friendly, can have lower yields and require more precise conditions.
Overview of Industrial Production of D-Glucitol
The majority of sorbitol produced worldwide is used in the food industry, followed by applications in pharmaceuticals and cosmetics.
The demand for sorbitol continues to grow, driven by the rising popularity of sugar-free and low-calorie products.
Applications in Food Industry
Sorbitol as a Sugar Alcohol: Sweetener and Humectant
Sorbitol is widely used as a sugar substitute in sugar-free and low-calorie foods.
It provides sweetness without significantly affecting blood glucose levels.
It is also used as a humectant, helping to retain moisture in products like cakes, cookies, and candies, which improves their texture and shelf life.
Use in Sugar-Free and Low-Calorie Products
Sorbitol is used in dietary products, chewing gum, and candy as a way to reduce caloric content without compromising on sweetness.
Unlike sucrose, sorbitol does not contribute to tooth decay, making it a preferred ingredient in sugar-free gums and oral care products.
Impact on Taste, Texture, and Preservation of Food
Sorbitol provides a smooth texture and mouthfeel in candies and chocolates.
It also enhances the chewability of sugar-free gum and can prevent the crystallization of sugar in confections.
Sorbitol in the Formulation of Candies, Gums, and Baked Goods
Sorbitol is frequently included in gum and candy formulations to replace sugar and provide bulk without excessive calories.
It is also used in baked goods, where its ability to hold moisture extends the shelf life of the products.
SAFETY INFORMATION ABOUT D-GLUCITOL
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
