Sorbitol

Chembox new
ImageFile = Sorbitol.png ImageSize = 200px
IUPACName = (2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
OtherNames =
Section1 = Chembox Identifiers
CASNo = 50-70-4
PubChem = 82170
SMILES = OCC(O)C(O)C(O)C(O)CO
MeSHName = Sorbitol
Section2 = Chembox Properties
Formula = carbon₆hydrogen₁₄oxygen₆
MolarMass = 182.17 g/mol
Appearance =
Density = 1.489 g/cm³
MeltingPt = 95 °C
BoilingPt = 296 °C
Section3 = Chembox Hazards
Solubility =
MainHazards =
FlashPt =
Autoignition =

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".

Uses

weetener

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 [Lehninger "Principles of Biochemistry", Nelson and Cox, Fourth Edition] . 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 kilojoules).

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. [ [http://www.cancer.org/docroot/CDG/content/CDG_sorbitol.asp ACS :: Cancer Drug Guide: sorbitol ] ] Sorbitol has been determined safe to use in the elderly although it is by no means recommended. [Lederle FA: Epidemiology of constipation in elderly patients. Drug utilization and cost-containment strategies. Drugs and Ageing 6:465-469, 1995.]

Miscellanea

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. [ [http://www.gallaher-group.com/products/table3_display.asp?brand_name=Benson+%26+Hedges+Gold&brand_family=Benson+%26+Hedges&product_type=CIGARETTE&country=UNITED+KINGDOM Gallaher Group Plc - Ingredients ] ]

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"). Fact|date=October 2007

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.Fact|date=June 2007

Sorbitol when combined with potassium nitrate has found some success as an amateur solid rocket fuel. [ [http://members.aol.com/riccnakk/sorb.html Richard Nakka's Experimental Rocketry Web Site] ]

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 ["Production of Liquid Hydrocarbons from Biomass " Jürgen O. Metzger Angewandte Chemie International Edition Volume 45, Issue 5 , Pages 696 - 698 2005 [http://dx.doi.org/10.1002/anie.200502895 Abstract] ] 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.

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 a 114 lb woman; another patient required hospitalization after habitually consuming 30g/d.cite web |url=http://www.webmd.com/diet/news/20080110/sweetener-side-effects-case-histories |title=Sweetener Side Effects: Case Histories |date=2008-01-10
author=Kathleen Doheny|publisher=WebMD Medical News
accessdate=2008-01-10 |format= |work=] Sorbitol can also aggravate irritable bowel syndrome and fructose malabsorption. [cite news |first=Jenny |last=Hope |authorlink= |coauthors= |title=Sweetener in chewing gum can damage your health|url=http://www.dailymail.co.uk/pages/live/articles/health/healthmain.html?in_article_id=507483&in_page_id=1774&ICO=HEALTH&ICL=TOPART |work= |publisher=Daily Mail |date=11th January 2008 |accessdate=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.]

Even in the absence of dietary sorbitol, cells produce sorbitol naturally. When too much sorbitol is produced inside cells, it can cause damage. [ [http://findarticles.com/p/articles/mi_m0876/is_n67/ai_14676055 Sorbitol: a hazard for diabetics? Nutrition Health Review] ] 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 [ [http://www.ncbi.nlm.nih.gov/pubmed/10783895 Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage.] ] .Fact|date=October 2007

afety

Sorbitol’s safety is supported by numerous studies reported in the scientific literature. In developing the current U.S. food and drug regulation which affirms sorbitol as GRAS, the safety data were carefully evaluated by qualified scientists of the Select Committee on GRAS Substances selected by the Life Sciences Office of the Federation of American Societies for Experimental Biology (FASEB). In the opinion of the Select Committee, there was no evidence demonstrating a hazard where sorbitol was used at current levels or at levels that might be expected in the future. The U.S. Food and Drug Administration’s regulation for sorbitol requires the following label statement for foods whose reasonably foreseeable consumption may result in the daily ingestion of 50 grams of sorbitol: “Excess consumption may have a laxative effect.”

The Joint Food and Agriculture Organization/World Health Organization Expert Committee on Food Additives (JECFA) has reviewed the safety data and concluded that sorbitol is safe. JECFA has established an acceptable daily intake (ADI) for sorbitol of “not specified,” meaning no limits are placed on its use. An ADI “not specified” is the safest category in which JECFA can place a food ingredient. JECFA’s decisions are often adopted by many small countries which do not have their own agencies to review food additive safety.

The Scientific Committee for Food of the European Union (EU) published a comprehensive assessment of sweeteners in 1985, concluding that sorbitol is acceptable for use, also without setting a limit on its use.

See also

* Mannitol
* Xylitol

External links

* [http://diabetes.niddk.nih.gov/dm/pubs/dictionary/P-T.htm#S NIH Diabetes dictionary] — see entry on sorbitol

References