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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

This article needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (July 2009)

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 often is 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^{citation needed}.

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^{citation needed}. 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).^{citation needed} It is also used as a humectant in some cigarettes.⁵

Sorbital 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 sorbitol naturally.

This article may contain original research. Please improve it by verifying the claims made and adding references. Statements consisting only of original research may be removed. More details may be available on the talk page. (June 2009)

Too much sorbitol trapped in eye and nerve cells can damage these cells, leading to retinopathy and neuropathy. Substances that prevent or slow the action of aldose reductase are being studied as a way to prevent or delay these complications of diabetes. Aldose reductase is the first enzyme in the sorbitol pathway. This pathway is responsible for the conversion of glucose to sorbitol, and of galactose to galactitol. Under conditions of hyperglycemia, sorbitol accumulation occurs. Aldose reductase inhibitors prevent the accumulation of intracellular sorbitol..⁶ Sensitivity to the substance may result in severe pain among individuals who are intolerant of it and exhibit adverse symptoms from sorbitol.

Diabetic retinopathy and neuropathy may be related to excess sorbitol in the cells of the eyes and nerves. The source of this sorbitol in diabetics is excess glucose, which goes through the sorbitol-aldose reductase pathway.⁷

In some human enzyme deficiencies such as galactosemia, sorbitol excess arises and can cause damage to the body. In diabetes mellitus, enzyme deficiency in the lens of the eye may cause sorbitol accumulation and cataracts^{citation needed}.

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.^{citation needed} 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^{citation needed}

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

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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article http://en.wikipedia.org/wiki/Sorbitol. Additionally, in some cases elements from this article might be licensed under a different license. Please refer to the original article to check the license status http://en.wikipedia.org/wiki/Sorbitol.

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