Sorbitol

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Sorbitol
IUPAC name (2R,3S,4S,5S)-Hexane-1,2,3,4,5,6-hexol
Identifiers
CAS number [50-70-4]
PubChem 82170
MeSH Sorbitol
SMILES OCC(O)C(O)C(O)C(O)CO
Properties
Molecular formula C6H14O6
Molar mass 182.17 g/mol
Density 1.489 g/cm³
Melting point

95 °C
Boiling point

296 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

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

Contents

[edit] Uses

[edit] Sweetener

Sorbitol is used in "sugar-free" mints and various cough syrups and is usually listed under the inactive ingredients.

Sorbitol is a sugar substitute often used in diet foods (including diet drinks and ice cream) and sugar-free chewing gum. It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus[1]. Sorbitol is also referred to as a nutritive sweetener because it provides dietary energy: 2.6 kilocalories (11 kilojoules) per gram versus the average 4 kilocalories (17 kJ) of sugar and starch, while retaining 60% of the sweetness.[citation needed] As a food additive it has an E number E420, categorized as a sweetener, emulsifier and humectant.

[edit] Laxative

Sorbitol can be used as a non-stimulant laxative as either an oral suspension or suppository. The drug works by drawing water into the large intestine, thereby stimulating bowel movements.[2] Sorbitol has been determined safe to use in the elderly although it is by no means recommended. [3]

[edit] Miscellaneous

Sorbitol is often used in modern cosmetics as a humectant and thickener. Some transparent gels can only be made with sorbitol as it has a refractive index sufficiently high for transparent formulations. It is also used as a humectant in some cigarettes.[4]

Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a highly refined, uncooked fish paste most commonly produced from Alaska (or walleye) pollock (Theragra chalcogramma).[citation needed]

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

Sorbitol when combined with potassium nitrate has found some success as an amateur solid rocket fuel.[5]

Sorbitol is often used in Mouthwash, as it said that when mixed with other certain ingredients it can help fight plaque.

Sorbitol is identified as a potential key chemical intermediate [6] 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 C6O6H14 → 13 C6H14 + 36 CO2 + 42 H2O

The above chemical reaction is exothermic and 1.5 mole of sorbitol generates 1 mole of hexane. When hydrogen is co-fed, no carbon dioxide production takes place.

[edit] Overdose effects

Ingesting large amounts of sorbitol can lead to some abdominal pain, gas, and mild to severe diarrhea. Sorbitol ingestion of 20 grams/day (g/d) as sugar-free gum has led to severe diarrhea leading to unintended weight loss of 24 lbs in an 114 lb woman; another patient required hospitalization after habitually consuming 30g/d.[7] Sorbitol can also aggravate irritable bowel syndrome and fructose malabsorption. [8]

Even in the absence of dietary sorbitol, cells also produce sorbitol naturally. When too much sorbitol is produced inside cells, it can cause damage.[9] 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 polyol pathway [10].[citation needed]

[edit] See also

[edit] External links

[edit] References

  1. ^ Lehninger Principles of Biochemistry, Nelson and Cox, Fourth Edition
  2. ^ ACS :: Cancer Drug Guide: sorbitol
  3. ^ Lederle FA: Epidemiology of constipation in elderly patients. Drug utilization and cost-containment strategies. Drugs and Ageing 6:465-469, 1995.
  4. ^ Gallaher Group Plc - Ingredients
  5. ^ Richard Nakka's Experimental Rocketry Web Site
  6. ^ Production of Liquid Hydrocarbons from Biomass Jürgen O. Metzger Angewandte Chemie International Edition Volume 45, Issue 5 , Pages 696 - 698 2005 Abstract
  7. ^ Kathleen Doheny (2008-01-10). Sweetener Side Effects: Case Histories. WebMD Medical News. Retrieved on 2008-01-10.
  8. ^ Hope, Jenny. "Sweetener in chewing gum can damage your health", Daily Mail, 11th January 2008. Retrieved on 2008-01-11.  "A sweetener used in sugar-free chewing gum, some toothpastes and thousands of other products could be a severe health risk, doctors warned." Reports The British Medical Journal.
  9. ^ Sorbitol: a hazard for diabetics? Nutrition Health Review
  10. ^ Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage.