Sorbitol

Sorbitol
IUPAC name (2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
Other names D-glucitol D-Sorbitol
Identifiers
CAS number	50-70-4 Y
PubChem	82170
MeSH	Sorbitol
SMILES O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)CO
Properties
Molecular formula	C6H14O6
Molar mass	182.17 g mol−1
Density	1.489 g/cm³
Melting point	95 °C
Boiling point	296 °C
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sorbitol, also known as glucitol, is a sugar alcohol that the human body metabolises slowly. It is obtained by reduction of glucose, changing the aldehyde group to an additional hydroxyl group.

Uses

Sweetener

Sorbitol is a sugar substitute. It may be listed under the inactive ingredients listed for some foods and products. Sorbitol is referred to as a nutritive sweetener because it provides dietary energy: 2.6 kilocalories (11 kilojoules) per gram versus the average 4 kilocalories (17 kilojoules) for carbohydrates. It is often used in diet foods (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum.

It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.^[1]

Laxative

Sorbitol can be used as a non-stimulant laxative via an oral suspension or enema. It works by drawing water into the large intestine, thereby stimulating bowel movements.^[2] Sorbitol has been determined safe for use by the elderly, although it is not recommended without consultation with a clinician.^[3]

Medical applications

Sorbitol is used in bacterial culture media to distinguish Escherichia coli 0154:H7 from most other strains of E. coli .

Sorbitol, combined with kayexalate, helps the body rid itself of excess potassium ions in a hyperkalaemic state.^[4] The kayexalate exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it.

Health care, food, and cosmetic uses

Sorbitol often is used in modern cosmetics as a humectant and thickener. Sorbitol often is used in mouthwash and toothpaste. Some transparent gels can be made only with sorbitol, as it has a refractive index sufficiently high for transparent formulations.

Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a highly refined fish paste most commonly produced from Alaska (or walleye) pollock (Theragra chalcogramma). It is also used as a humectant in some cigarettes.^[5]

Sorbitol sometimes is used as a sweetener and humectant in cookies and other foods that are not identified as "dietary" items.

Medical importance

Even in the absence of dietary sorbitol, cells produce some sorbitol naturally. Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway^[6] 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 can damage these cells, leading to retinopathy, cataracts and peripheral neuropathy, respectively. Aldose reductase inhibitors, which are substances that prevent or slow the action of aldose reductase, are currently being investigated as a way to prevent or delay these complications, which frequently occur in the setting of long-term hyperglycemia that accompanies poorly-controlled diabetes. It is thought that these agents may help to prevent the accumulation of intracellular sorbitol that leads to cellular damage in diabetics.^[7]

Adverse medical effects

Sorbitol also may aggravate irritable bowel syndrome,^[8] and similar gastrointestinal conditions, resulting in severe abdominal pain for those affected, even from small amounts ingested.

Overdose effects

Ingesting large amounts of sorbitol can lead to abdominal pain, gas, and mild to severe diarrhea. Sorbitol ingestion of 20 grams (0.7 oz) per day as sugar-free gum has led to severe diarrhea leading to unintended weight loss of 11 kilograms (24 lb) in a woman originally weighing 52 kilograms (110 lb); another patient required hospitalization after habitually consuming 30 grams (1 oz) per day.^[9]

Compendial status

• Food Chemical Codex ^[10]
• European Pharmacopoeia ^[11] 6.1 ^[12]
• British Pharmacopoeia 2009 ^[13]
• Japanese Pharmacopoeia 15

Miscellaneous uses

A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel.^[14]

Sorbitol is identified as a potential key chemical intermediate^[15] from biomass resources. Complete reduction of sorbitol opens the way to alkanes such as hexane, which can be used as a biofuel. Sorbitol itself provides much of the hydrogen required for the transformation.

19 C₆H₁₄O₆ → 13 C₆H₁₄ + 36 CO₂ + 42 H₂O

The above chemical reaction is exothermic; 1.5 mole of sorbitol generates approximately 1 mole of hexane. When hydrogen is co-fed, no carbon dioxide is produced.

See also

• Mannitol
• Mouthwash
• Xylitol

External links

• NIH Diabetes dictionary — see entry on sorbitol

Notes and references