Sorbitol | |
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(2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
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Other names
D-glucitol
D-Sorbitol |
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Identifiers | |
CAS number | 50-70-4 |
PubChem | 107428 |
ChemSpider | 96680 |
UNII | 506T60A25R |
MeSH | Sorbitol |
ChEMBL | CHEMBL1682 |
O=C([C@H](O)[C@@H](O)[C@H](O)CO)CO
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InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m1/s1
Key: BJHIKXHVCXFQLS-PYWDMBMJSA-N InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m1/s1 Key: BJHIKXHVCXFQLS-PYWDMBMJBD |
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Properties | |
Molecular formula | C6H14O6 |
Molar mass | 182.17 g mol−1 |
Density | 1.489 g/cm³ |
Melting point |
95 °C |
Boiling point |
296 °C |
(what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Sorbitol, also known as glucitol, is a sugar alcohol that the human body metabolises slowly. It can be obtained by reduction of glucose, changing the aldehyde group to a hydroxyl group. Sorbitol is found in apples, pears, peaches, and prunes.[1] It is synthesized by sorbitol-6-phosphate dehydrogenase and sorbitol dehydrogenase, and converted to fructose by succinate dehydrogenase.[2] Succinate dehydrogenase is an enzyme complex that participates in the citric acid cycle.[3]
Contents |
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.[4]
Laxative
Sorbitol can be used as a non-stimulant laxative via an oral suspension or enema, and like other sugar alcohols with the exception of erythritol, may cause inadvertent GI distress when consuming food products with Sorbitol in excess. It works by drawing water into the large intestine, thereby stimulating bowel movements.[5] Sorbitol has been determined safe for use by the elderly, although it is not recommended without consultation with a clinician.[6]
Medical applications
Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli, as it is usually incapable of fermenting sorbitol, but 93% of known E. coli strains are capable of doing so. [7]
Sorbitol, combined with kayexalate, helps the body rid itself of excess potassium ions in a hyperkalaemic state.[8] 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.[9]
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[10] 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.[11]
In 2007, the Center for Disease Control estimated that around 186,300 people younger than 20 years old had diabetes. Another 23.5 million people 20 years or older were also estimated to have diabetes. Diabetes can lead to disease, blindness, and kidney failure.[12]
Adverse medical effects
Sorbitol also may aggravate irritable bowel syndrome,[13] 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 one day, in a woman originally weighing 52 kilograms (110 lb); another patient required hospitalization after habitually consuming 30 grams (1 oz) per day.[14]
Compendial status
- Food Chemical Codex [15]
- European Pharmacopoeia [16] 6.1 [17]
- British Pharmacopoeia 2009 [18]
- Japanese Pharmacopoeia 15[citation needed]
Miscellaneous uses
A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel.[19]
Sorbitol is identified as a potential key chemical intermediate[20] 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 moles of sorbitol generate approximately 1 mole of hexane. When hydrogen is co-fed, no carbon dioxide is produced.
See also
External links
- NIH Diabetes dictionary — see entry on sorbitol
Notes and references
- ^ [Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality. Proc Natl Acad Sci]
- ^ [Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality. Proc Natl Acad Sci]
- ^ [Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality. Proc Natl Acad Sci]
- ^ Lehninger Principles of Biochemistry, Nelson and Cox, Fourth Edition
- ^ ACS :: Cancer Drug Guide: sorbitol
- ^ Lederle FA: Epidemiology of constipation in elderly patients. Drug utilization and cost-containment strategies. Drugs and Ageing 6:465-469, 1995.
- ^ Wells JG, Davis BR, Wachsmuth IK, et al. (September 1983). "Laboratory investigation of hemorrhagic colitis outbreaks associated with a rare Escherichia coli serotype". Journal of clinical microbiology 18 (3): 512–20. PMID 6355145. PMC 270845. http://jcm.asm.org/cgi/pmidlookup?view=long&pmid=6355145. "The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive".
- ^ Rugolotto S, Gruber M, Solano PD, Chini L, Gobbo S, Pecori S (April 2007). "Necrotizing enterocolitis in a 850 gram infant receiving sorbitol-free sodium polystyrene sulfonate (Kayexalate): clinical and histopathologic findings". J Perinatol 27 (4): 247–9. doi:10.1038/sj.jp.7211677. PMID 17377608.
- ^ Gallaher Group Plc - Ingredients
- ^ Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage.
- ^ Sorbitol: a hazard for diabetics? Nutrition Health Review
- ^ Diabetes
- ^ Irritable Bowel Syndrome: Causes and Treatment - What can aggravate my symptoms?
- ^ Kathleen Doheny (2008-01-10). "Sweetener Side Effects: Case Histories". WebMD Medical News. http://www.webmd.com/diet/news/20080110/sweetener-side-effects-case-histories. Retrieved 2008-01-10.
- ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport04.html. Retrieved 6 July 2009.
- ^ Sigma Aldrich. "D-Sorbitol". http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=97336. Retrieved 6 July 2009.
- ^ European Pharmacopoeia. "Index, Ph Eur". https://www.edqm.eu/store/images/majbdd/200709201618250.6_1%20IndexE.pdf. Retrieved 6 July 2009.
- ^ British Pharmacopoeia (2009). "Index, BP 2009". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 6 July 2009.
- ^ Richard Nakka's Experimental Rocketry Web Site
- ^ Production of Liquid Hydrocarbons from Biomass Jürgen O. Metzger Angewandte Chemie International Edition Volume 45, Issue 5 , Pages 696 - 698 2005 link to the publisher
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