Sorbitol - Wikipedia
Sorbitol - Wikipedia
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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, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes.[4] 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.[5] While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.
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As an over-the-counter drug, sorbitol is used as a laxative to treat constipation.[6]
Synthesis
[edit]Sorbitol may be synthesised via a glucose reduction reaction[7] in which the converted aldehyde group is converted into a hydroxyl group. The reaction requires NADH and is catalyzed by aldose reductase. Glucose reduction is the first step of the polyol pathway of glucose metabolism, and is implicated in multiple diabetic complications.
- C6H12O6 + NADH + H+ → C6H14O6 + NAD+
The mechanism involves a tyrosine residue in the active site of aldehyde reductase. The hydrogen atom on NADH is transferred to the electrophilic aldehyde carbon atom; electrons on the aldehyde carbon-oxygen double bond are transferred to the oxygen that abstracts the proton on tyrosine side chain to form the hydroxyl group. The role of aldehyde reductase tyrosine phenol group is to serve as a general acid to provide proton to the reduced aldehyde oxygen on glucose.
Glucose reduction is not the major glucose metabolism pathway in a normal human body, where the glucose level is in the normal range. However, in diabetic patients whose blood glucose level is high, up to 1/3 of their glucose could go through the glucose reduction pathway. This will consume NADH and eventually leads to cell damage.
Uses
[edit]Sweetener
[edit]Sorbitol is a sugar substitute, and when used in food it has the INS number and E number 420. Sorbitol is about 60% as sweet as sucrose (table sugar).[8]
Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy. It is partly absorbed from the small intestine and metabolized in the body, and partly fermented in the large intestine. The fermentation produces short-chain fatty acids, acetic acid, propionic acid, and butyric acid, which are mostly absorbed and provide energy, but also carbon dioxide, methane, and hydrogen which do not provide energy. Even though the heat of combustion of sorbitol is higher than that of glucose (having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4 kilocalories per gram, versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates.[9] It is often used in diet foods (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum.[10] Most bacteria cannot use sorbitol for energy, but it can be slowly fermented in the mouth by Streptococcus mutans, a bacterium that causes tooth decay. In contrast, many other sugar alcohols such as isomalt and xylitol are considered non-acidogenic.[11][12]
It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.[4][13]
Medical applications
[edit]Laxative
[edit]As is the case with other sugar alcohols, foods containing sorbitol can cause gastrointestinal distress. Sorbitol can be used as a laxative when taken orally or as an enema.[6] Sorbitol works as a laxative by drawing water into the large intestine, stimulating bowel movements.[6][14] Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.[6][15]
Sorbitol is commonly used orally as a one-time dose of 30–150 millilitres (1.1–5.3 imp fl oz; 1.0–5.1 US fl oz) 70% solution.[6] It may also be used as a one-time rectal enema.[6]
Other medical applications
[edit]Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli, because it is usually unable to ferment sorbitol, unlike 93% of known E. coli strains.[16]
A treatment for hyperkalaemia (elevated blood potassium) uses sorbitol and the ion-exchange resin sodium polystyrene sulfonate (tradename Kayexalate).[17] The resin exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. In , the U.S. FDA issued a warning of increased risk for gastrointestinal necrosis with this combination.[18]
Sorbitol is also used in the manufacture of softgel capsules to store single doses of liquid medicines.[19]
Health care, food, and cosmetic uses
[edit]Sorbitol often is used in modern cosmetics as a humectant and thickener.[20] It is also used in mouthwash and toothpaste. Some transparent gels can be made only with sorbitol, because of its high refractive index.
Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a processed fish paste.[21] It is also used as a humectant in some cigarettes.[22]
Beyond its use as a sugar substitute in reduced-sugar foods, sorbitol is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves.[23] In baking, it is also valuable because it acts as a plasticizer, and slows down the staling process.[23]
Miscellaneous uses
[edit]A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel. It has similar performance to sucrose-based rocket candy, but is easier to cast, less hygroscopic and does not caramelize.[24]
Sorbitol is identified as a potential key chemical intermediate[25] 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.[26] 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 catalytic reforming of sorbitol.[27]
- 19 C6H14O6 → 13 C6H14 + 36 CO2 + 42 H2O
The above chemical reaction is exothermic, and 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.
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Medical importance
[edit]Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway[28] 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, is a frequent result of long-term hyperglycemia that accompanies poorly controlled diabetes. This can damage these cells, leading to retinopathy, cataracts and peripheral neuropathy, respectively.
Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.[29]
Potential adverse effects
[edit]Sorbitol may cause allergic reactions in some people.[6] Common side effects from use as a laxative are stomach cramps, vomiting, diarrhea or rectal bleeding.[6]
Compendial status
[edit]- Food Chemicals Codex[30]
- European Pharmacopoeia[31] 6.1[32]
- British Pharmacopoeia [33]
- Japanese Pharmacopoeia 17 [34]
See also
[edit]- Sorbitan
- Isosorbide
References
[edit]Sorbitol: Side Effects, Uses, Dosage, Interactions, Warnings - RxList
What Is Sorbitol and How Does It Work?
Sorbitol is used to relieve occasional constipation and irregularity. Sorbitol generally produces bowel movement in 1/4 to 1 hour when used rectally.
- Sorbitol is also used as a pharmaceutical aide (sweetener).
- For other uses of sorbitol, ask your doctor.
What Are Dosages of Sorbitol?
Dosages of Sorbitol:Adult and Pediatric Dosage Forms and Strengths
Irrigation solution
- 3 g/100mL (3%)
Oral solution
- 70%
Dosage Considerations – Should be Given as Follows:
Constipation
- Adult, Oral: 30-150 mL (70% solution) once
- Adult, Rectal enema: 120 mL of 25-30% solution once
- Children under 2 years: Safety and efficacy not established
- Children 2-11 years:
- Oral: 2 mL/kg (as 70% solution) once
- Rectal enema: 30-60 mL as 25-30% solution
- Children 12 years and older:
- Oral: 30-150 mL (70% solution) once
- Rectal enema: 120 mL of 25-30% solution once
Sodium Polystyrene Sulfonate Adjunct
- Adult: 15 mL of 70% solution or 10-20 mL/2 hours orally until diarrhea occurs
- Children under 12 years: Safety and efficacy not established
- Children 12 years and older: 15 mL of 70% solution or 10-20 mL/2 hours orally until diarrhea occurs
Transurethral Surgical Procedures
- 3-3.3% as surgical procedure irrigation
What Are Side Effects Associated with Using Sorbitol?
Common side effects of sorbitol include:
- Abdominal discomfort
- Dehydration
- Diarrhea
- Dry mouth
- Excessive bowel activity
- Fluid and electrolyte losses
- High blood sugar (hyperglycemia)
- Lactic acidosis
- Nausea
- Swelling (edema)
- Vomiting
This document does not contain all possible side effects and others may occur. Check with your physician for additional information about side effects.
What Other Drugs Interact with Sorbitol?
If your doctor has directed you to use this medication, your doctor or pharmacist may already be aware of any possible drug interactions and may be monitoring you for them. Do not start, stop, or change the dosage of any medicine before checking with your doctor, health care provider, or pharmacist first.
- Sorbitol has no known severe interactions with other drugs.
- Serious Interactions of sorbitol include:
- sodium polystyrene sulfonate
- Moderate Interactions of sorbitol include:
- deflazacort
- dichlorphenamide
- Sorbitol has no known mild interactions with other drugs.
This information does not contain all possible interactions or adverse effects. Therefore, before using this product, tell your doctor or pharmacist of all the products you use. Keep a list of all your medications with you, and share this information with your doctor and pharmacist. Check with your health care professional or doctor for additional medical advice, or if you have health questions, concerns or for more information about this medicine.
What Are Warnings and Precautions for Sorbitol?
Warnings
- This medication contains sorbitol. Do not take sorbitol if you are allergic to sorbitol or any ingredients contained in this drug.
- Keep out of reach of children. In case of overdose, get medical help or contact a Poison Control Center immediately.
Contraindications
- Anuria, acute abdominal pain, nausea, vomiting, or other symptoms of appendicitis or undiagnosed abdominal pain
Effects of Drug Abuse
- No information available
Short-Term Effects
- See "What Are Side Effects Associated with Using Sorbitol?"
Long-Term Effects
- See "What Are Side Effects Associated with Using Sorbitol?"
Cautions
- Patients with severe cardiopulmonary or renal impairment.
- Dehydration, electrolyte abnormalities.
- Patients are unable to metabolize sorbitol.
Pregnancy and Lactation
For more sorbitol powderinformation, please contact us. We will provide professional answers.
- Use sorbitol with caution during pregnancy if the benefits outweigh the risks. Animal studies show risk and human studies are not available or neither animal nor human studies were done.
- Use caution with the use of sorbitol if breastfeeding. Consult your doctor.
https://reference.medscape.com/drug/sorbitol-
DailyMed. Sorbitol.
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=16cc9d47---ab84-f22cfe2e