Sorbitol

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Sorbitol

IUPAC name[hide] (2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol Other names[hide] D-glucitol; D-Sorbitol; Sorbogem; Sorbo Identifiers CAS number 50-70-4 PubChem 5780 ChemSpider 96680 UNII 506T60A25R DrugBank DB01638 MeSH Sorbitol ChEBI CHEBI:17317 ChEMBL CHEMBL1682 A06AD18,A06AG07 B05CX02 ATC code V04CC01 Jmol-3D images Image 1 SMILES [show] InChI [show] Properties Molecular formula C6H14O6 Molar mass 182.17 g mol1 Density 1.489 g/cm Melting point 95 C, 368 K, 203 F Boiling point 296 C, 569 K, 565 F Hazards

NFPA 704

1 2 0
100C 150C

Flash point Autoignition temperature

(verify) (what is: / ?) 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, which the human body metabolizes 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-6phosphate dehydrogenase, and converted to fructose by succinate dehydrogenase and sorbitol dehydrogenase.[1] Succinate dehydrogenase is an enzyme complex that participates in the citric acid cycle.[1]

Contents
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1 Uses 1.1 Sweetener 1.2 Laxative 1.3 Medical applications 1.4 Health care, food, and cosmetic uses 1.5 Miscellaneous uses 2 Medical importance 3 Adverse medical effects 4 Overdose effects 5 Compendial status 6 References
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7 External links

[edit] Uses
[edit] Sweetener

Sorbitol is a sugar substitute. It may be listed under the inactive ingredients listed for some foods and products. Its INS number and E number is 420. 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 sugarfree chewing gum.[citation needed] It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.[2]

[edit] Laxative
Sorbitol can be used as a non-stimulant laxative via an oral suspension or enema. As with other sugar alcohols, gastrointestinal distress may result when food products that contain sorbitol are consumed. Sorbitol exerts its laxative effect by drawing water into the large intestine, thereby stimulating bowel movements.[3] Sorbitol has been determined safe for use by the elderly, although it is not recommended without consultation with a clinician.[4] Sorbitol is found in some dried fruits and may contribute to the laxative effects of prunes.[5]

[edit] 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.[6] Sorbitol, combined with kayexalate, helps the body rid itself of excess potassium ions in a hyperkalaemic state.[7] The kayexalate exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. The FDA has discouraged this combination when in 2010 it issued a warning of increased risk for GI necrosis.[8]

[edit] 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. It is also used frequently in "sugar free" chewing gum. 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 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.

[edit] Miscellaneous uses

A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel.[10] Sorbitol is identified as a potential key chemical intermediate[11] 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.

[edit] Medical importance

Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway[12] 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.[13]

[edit] Adverse medical effects

Sorbitol also may aggravate irritable bowel syndrome,[14] and similar gastrointestinal conditions, resulting in severe abdominal pain for those affected, even from small amounts ingested. It has been noted that the sorbitol added to SPS (Sodium Polystyrene Sulfonate, used in the treatment of hyperkalemia) can cause complications in the GI tract, including bleeding, perforated colonic ulcers, ischemic colitis and colonic necrosis, particularly in patients with uremia. The authors of the paper in question cite a study on rats (both non-uremic and uremic) in which all uremic rats died on a sorbitol enema regimen, whilst uremic rats on non-sorbitol regimens - even with SPS included - showed no signs of colonic damage. In humans, it is suggested that the risk factors for sorbitol-induced damage include "... immunosuppression, hypovolemia, postoperative setting, hypotension after hemodialysis, and peripheral vascular disease." They conclude that SPS-sorbitol should be used with caution, and that "Physicians need to be aware of SPS-sorbitol GI side effects while managing hyperkalemia." [15]

[edit] Overdose effects

Ingesting large amounts of sorbitol can lead to abdominal pain, flatulence, and mild to severe diarrhea.[16] 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 eight months, in a woman

originally weighing 52 kilograms (110 lb); another patient required hospitalization after habitually consuming 30 grams (1 oz) per day.[17]

[edit] Compendial status

Food Chemicals Codex[18] European Pharmacopoeia[19] 6.1[20] British Pharmacopoeia 2009[21] Japanese Pharmacopoeia 15[citation needed]

[edit] References
^ a b c Teo, G; Suzuki, Y; Uratsu, SL; Lampinen, B; Ormonde, N; Hu, WK; Dejong, TM; Dandekar, AM (2006). "Silencing leaf sorbitol synthesis alters longdistance partitioning and apple fruit quality". Proceedings of the National Academy of Sciences of the United States of America 103 (49): 188427. doi:10.1073/pnas.0605873103. PMC 1693749. PMID 17132742. 2. ^ Lehninger, Principles of Biochemistry, Nelson and Cox, Fourth Edition 3. ^ ACS :: Cancer Drug Guide: sorbitol 4. ^ Lederle, FA (1995). "Epidemiology of constipation in elderly patients. Drug utilisation and cost-containment strategies". Drugs & aging 6 (6): 4659. PMID 7663066. 5. ^ Stacewicz-Sapuntzakis, M; Bowen, PE; Hussain, EA; Damayanti-Wood, BI; Farnsworth, NR (2001). "Chemical composition and potential health effects of prunes: a functional food?". Critical reviews in food science and nutrition 41 (4): 25186. doi:10.1080/20014091091814. PMID 11401245. 6. ^ 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): 51220. PMC 270845. PMID 6355145. "The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive" 7. ^ 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): 2479. doi:10.1038/sj.jp.7211677. PMID 17377608. 8. ^ http://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm186845.htm 9. ^ Gallaher Group Plc - Ingredients 10. ^ Richard Nakka's Experimental Rocketry Web Site 11. ^ Production of Liquid Hydrocarbons from Biomass Jrgen O. Metzger Angewandte Chemie International Edition Volume 45, Issue 5 , Pages 696 - 698 2005 link to the publisher 12. ^ Nishikawa, T; Edelstein, D; Du, XL; Yamagishi, S; Matsumura, T; Kaneda, Y; Yorek, MA; Beebe, D et al. (2000). "Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage". Nature 404 (6779): 78790. doi:10.1038/35008121. PMID 10783895. 1.

13. 14.

^ Sorbitol: a hazard for diabetics? Nutrition Health Review ^ Irritable Bowel Syndrome: Causes and Treatment - What can aggravate my symptoms? 15. ^ http://www.practicalgastro.com/pdf/November10/ErfaniArticle.pdf 16. ^ Islam, MS; Sakaguchi, E (2006). "Sorbitol-based osmotic diarrhea: possible causes and mechanism of prevention investigated in rats". World journal of gastroenterology : WJG 12 (47): 763541. PMID 17171792. 17. ^ Kathleen Doheny (2008-01-10). "Sweetener Side Effects: Case Histories". WebMD Medical News. Retrieved 2008-01-10. 18. ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Retrieved 6 July 2009. 19. ^ Sigma Aldrich. "D-Sorbitol". Retrieved 6 July 2009.Unknown parameter | unused_data= ignored (help) 20. ^ European Pharmacopoeia. "Index, Ph Eur". Retrieved 6 July 2009. 21. ^ British Pharmacopoeia (2009). "Index, BP 2009". Retrieved 6 July 2009.