Sorbitol

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Sorbitol
D-sorbitol.svg
Sorbitol-3D-balls.png
Names
IUPAC name
D-Glucitol [1]
Systematic IUPAC name
(2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
Other names
D-Sorbitol; Sorbogem; Sorbo
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.056 OOjs UI icon edit-ltr-progressive.svg
E number E420 (thickeners, ...)
KEGG
MeSH Sorbitol
PubChem CID
UNII
  • InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1 X mark.svgN[ pubchem ]
    Key: FBPFZTCFMRRESA-JGWLITMVSA-N X mark.svgN[ pubchem ]
  • InChI=1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
    Key: FBPFZTCFMRRESA-JGWLITMVSA
  • OC([C@H](O)[C@@H](O)[C@H](O)CO)CO
Properties
C6H14O6
Molar mass 182.17 g/mol
AppearanceWhite crystalline powder
Density 1.49 g/cm3 [2]
Melting point 94–96 °C (201–205 °F; 367–369 K) [2]
2350 g/L [2]
log P -4.67 [3]
-107.80·10−6 cm3/mol
Pharmacology
A06AD18 ( WHO ) A06AG07 ( WHO ) B05CX02 ( WHO ) V04CC01 ( WHO )
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point >100 °C (212 °F; 373 K) [2]
420 °C (788 °F; 693 K) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Sorbitol ( /ˈsɔː(r)bɪtɒl/ ), less commonly known as glucitol ( /ˈɡluːsɪtɒl/ ), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. [4] It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2. [5] While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.

As an over-the-counter drug, sorbitol is used as a laxative to treat constipation. [6]

Synthesis

Sorbitol may be synthesised via a glucose reduction reaction [7] in which the converted aldehyde group is converted into a hydroxyl group. The reaction requires NADH and is catalyzed by aldose reductase. Glucose reduction is the first step of the polyol pathway of glucose metabolism, and is implicated in multiple diabetic complications.

The mechanism involves a tyrosine residue in the active site of aldehyde reductase. The hydrogen atom on NADH is transferred to the electrophilic aldehyde carbon atom; electrons on the aldehyde carbon-oxygen double bond are transferred to the oxygen that abstracts the proton on tyrosine side chain to form the hydroxyl group. The role of aldehyde reductase tyrosine phenol group is to serve as a general acid to provide proton to the reduced aldehyde oxygen on glucose.

Glucose reduction to sorbitol.svg

Glucose reduction is not the major glucose metabolism pathway in a normal human body, where the glucose level is in the normal range. However, in diabetic patients whose blood glucose level is high, up to 1/3 of their glucose could go through the glucose reduction pathway. This will consume NADH and eventually leads to cell damage.

Uses

Sweetener

Sorbitol is a sugar substitute, and when used in food it has the INS number and E number 420. Sorbitol is about 60% as sweet as sucrose (table sugar). [8]

Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy. It is partly absorbed from the small intestine and metabolized in the body, and partly fermented in the large intestine. The fermentation produces short-chain fatty acids, acetic acid, propionic acid, and butyric acid, which are mostly absorbed and provide energy, but also carbon dioxide, methane, and hydrogen which do not provide energy. Even though the heat of combustion of sorbitol is higher than that of glucose (having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4 kilocalories per gram, versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates. [9] It is often used in diet foods (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum. [10] Most bacteria cannot use sorbitol for energy, but it can be slowly fermented in the mouth by Streptococcus mutans , a bacterium that causes tooth decay. In contrast, many other sugar alcohols such as isomalt and xylitol are considered non-acidogenic. [11] [12]

It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus . [4] [13]

Medical applications

Laxative

As is the case with other sugar alcohols, foods containing sorbitol can cause gastrointestinal distress. Sorbitol can be used as a laxative when taken orally or as an enema. [6] Sorbitol works as a laxative by drawing water into the large intestine, stimulating bowel movements. [6] [14] Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician. [6] [15]

Sorbitol is commonly used orally as a one-time dose of 30–150 millilitres (1.1–5.3 imp fl oz; 1.0–5.1 US fl oz) 70% solution. [6] It may also be used as a one-time rectal enema. [6]

Other medical applications

Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli , because it is usually unable to ferment sorbitol, unlike 93% of known E. coli strains. [16]

A treatment for hyperkalaemia (elevated blood potassium) uses sorbitol and the ion-exchange resin sodium polystyrene sulfonate (tradename Kayexalate). [17] The resin exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. In 2010, the U.S. FDA issued a warning of increased risk for gastrointestinal necrosis with this combination. [18]

Sorbitol is also used in the manufacture of softgel capsules to store single doses of liquid medicines. [19]

Health care, food, and cosmetic uses

Sorbitol often is used in modern cosmetics as a humectant and thickener. [20] It is also used in mouthwash and toothpaste. Some transparent gels can be made only with sorbitol, because of its high refractive index.

Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a processed fish paste. [21] It is also used as a humectant in some cigarettes. [22]

Beyond its use as a sugar substitute in reduced-sugar foods, sorbitol is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves. [23] In baking, it is also valuable because it acts as a plasticizer, and slows down the staling process. [23]

Miscellaneous uses

A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel. It has similar performance to sucrose-based rocket candy, but is easier to cast, less hygroscopic and does not caramelize. [24]

Sorbitol is identified as a potential key chemical intermediate [25] for production of fuels from biomass resources. Carbohydrate fractions in biomass such as cellulose undergo sequential hydrolysis and hydrogenation in the presence of metal catalysts to produce sorbitol. [26] Complete reduction of sorbitol opens the way to alkanes, such as hexane, which can be used as a biofuel. Hydrogen required for this reaction can be produced by aqueous phase catalytic reforming of sorbitol. [27]

19 C6H14O6 → 13 C6H14 + 36 CO2 + 42 H2O

The above chemical reaction is exothermic, and 1.5 moles of sorbitol generate approximately 1 mole of hexane. When hydrogen is co-fed, no carbon dioxide is produced.

Sorbitol based polyols are used in the production of polyurethane foam for the construction industry.

It is also added after electroporation of yeasts in transformation protocols, allowing the cells to recover by raising the osmolarity of the medium.

Medical importance

Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway [28] 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, is a frequent result of long-term hyperglycemia that accompanies poorly controlled diabetes. This can damage these cells, leading to retinopathy, cataracts and peripheral neuropathy, respectively.

Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health. [29]

Potential adverse effects

Sorbitol may cause allergic reactions in some people. [6] Common side effects from use as a laxative are stomach cramps, vomiting, diarrhea or rectal bleeding. [6]

Compendial status

See also

Related Research Articles

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

Aldose reductase inhibitors are a class of drugs being studied as a way to prevent eye and nerve damage in people with diabetes.

<span class="mw-page-title-main">Alcohol dehydrogenase</span> Group of dehydrogenase enzymes

Alcohol dehydrogenases (ADH) (EC 1.1.1.1) are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to NADH. In humans and many other animals, they serve to break down alcohols that are otherwise toxic, and they also participate in the generation of useful aldehyde, ketone, or alcohol groups during the biosynthesis of various metabolites. In yeast, plants, and many bacteria, some alcohol dehydrogenases catalyze the opposite reaction as part of fermentation to ensure a constant supply of NAD+.

<span class="mw-page-title-main">Xylitol</span> Synthetic sweetener

Xylitol is a chemical compound with the formula C
5H
12O
5, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on] 'wood', with the suffix -itol used to denote it being a sugar alcohol.

<span class="mw-page-title-main">Sugar alcohol</span> Organic compounds

Sugar alcohols are organic compounds, typically derived from sugars, containing one hydroxyl group (−OH) attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by hydrogenating sugars. Since they contain multiple (−OH) groups, they are classified as polyols.

<span class="mw-page-title-main">Erythritol</span> Chemical compound

Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L-erythrose and one of the two reduced forms of erythrulose. It is used as a food additive and sugar substitute. It is synthesized from corn using enzymes and fermentation. Its formula is C
4H
10O
4, or HO(CH2)(CHOH)2(CH2)OH.

<span class="mw-page-title-main">Fructose malabsorption</span> Medical condition

Fructose malabsorption, formerly named dietary fructose intolerance (DFI), is a digestive disorder in which absorption of fructose is impaired by deficient fructose carriers in the small intestine's enterocytes. This results in an increased concentration of fructose. Intolerance to fructose was first identified and reported in 1956.

A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture in the food. Humectants are sometimes used as a component of antistatic coatings for plastics.

<span class="mw-page-title-main">Reducing sugar</span> Sugars that contain free OH group at the anomeric carbon atom

A reducing sugar is any sugar that is capable of acting as a reducing agent. In an alkaline solution, a reducing sugar forms some aldehyde or ketone, which allows it to act as a reducing agent, for example in Benedict's reagent. In such a reaction, the sugar becomes a carboxylic acid.

<span class="mw-page-title-main">Mannitol</span> Chemical compound

Mannitol is a type of sugar alcohol used as a sweetener and medication. It is used as a low calorie sweetener as it is poorly absorbed by the intestines. As a medication, it is used to decrease pressure in the eyes, as in glaucoma, and to lower increased intracranial pressure. Medically, it is given by injection or inhalation. Effects typically begin within 15 minutes and last up to 8 hours.

<span class="mw-page-title-main">Maltitol</span> Sugar alcohol used as a sweetener

Maltitol is a sugar alcohol used as a sugar substitute and laxative. It has 75–90% of the sweetness of sucrose and nearly identical properties, except for browning. It is used to replace table sugar because it is half as calorific, does not promote tooth decay, and has a somewhat lesser effect on blood glucose. In chemical terms, maltitol is known as 4-O-α-glucopyranosyl-D-sorbitol. It is used in commercial products under trade names such as Lesys, Maltisweet and SweetPearl.

The polyol pathway is a two-step process that converts glucose to fructose. In this pathway glucose is reduced to sorbitol, which is subsequently oxidized to fructose. It is also called the sorbitol-aldose reductase pathway.

Microbial metabolism is the means by which a microbe obtains the energy and nutrients it needs to live and reproduce. Microbes use many different types of metabolic strategies and species can often be differentiated from each other based on metabolic characteristics. The specific metabolic properties of a microbe are the major factors in determining that microbe's ecological niche, and often allow for that microbe to be useful in industrial processes or responsible for biogeochemical cycles.

<span class="mw-page-title-main">Aldose reductase</span> Enzyme

In enzymology, aldose reductase is an enzyme in humans encoded by the gene AKR1B1. It is an cytosolic NADPH-dependent oxidoreductase that catalyzes the reduction of a variety of aldehydes and carbonyls, including monosaccharides, and primarily known for catalyzing the reduction of glucose to sorbitol, the first step in polyol pathway of glucose metabolism.

<span class="mw-page-title-main">Sorbitol dehydrogenase</span> Enzyme

Sorbitol dehydrogenase is a cytosolic enzyme. In humans this protein is encoded by the SORD gene.

Hydrogenated starch hydrolysates (HSHs), also known as polyglycitol syrup, are mixtures of several sugar alcohols. Hydrogenated starch hydrolysates were developed by the Swedish company Lyckeby Starch in the 1960s. The HSH family of polyols is an approved food ingredient in Canada, Japan, and Australia. HSH sweeteners provide 40 to 90% sweetness relative to table sugar.

<span class="mw-page-title-main">Ranirestat</span> Chemical compound

Ranirestat is an aldose reductase inhibitor being developed for the treatment of diabetic neuropathy by Dainippon Sumitomo Pharma and PharmaKyorin. It has been granted orphan drug status. The drug is to be used orally.

<span class="mw-page-title-main">AKR1B1</span> Protein-coding gene in the species Homo sapiens

Aldo-keto reductase family 1, member B1 (AKR1B1) is an gene in humans that encodes the enzyme aldose reductase. It is a reduced nicotinamide-adenine dinucleotide phosphate (NADPH)-dependent enzyme catalyzing the reduction of various aldehydes and ketones to the corresponding alcohol. The involvement of AKR1B1 in oxidative stress diseases, cell signal transduction, and cell proliferation process endows AKR1B1 with potential as a therapeutic target.

<span class="mw-page-title-main">Sorbinil</span> Chemical compound

Sorbinil (INN) is an aldose reductase inhibitor being investigated for treatment of diabetic complications including neuropathy and retinopathy. Aldose reductase is an enzyme present in lens and brain that removes excess glucose by converting it to sorbitol. Sorbitol accumulation can lead to the development of cataracts in the lens and neuropathy in peripheral nerves. Sorbinil has been shown to inhibit aldose reductase in human brain and placenta and calf and rat lens. Sorbinil reduced sorbitol accumulation in rat lens and sciatic nerve of diabetic rats orally administered 0.25 mg/kg sorbinil.

Pseudohypoxia refers to a condition that mimics hypoxia, by having sufficient oxygen yet impaired mitochondrial respiration due to a deficiency of necessary co-enzymes, such as NAD+ and TPP. The increased cytosolic ratio of free NADH/NAD+ in cells (more NADH than NAD+) can be caused by diabetic hyperglycemia and by excessive alcohol consumption. Low levels of TPP results from thiamine deficiency.

References

  1. ↑ publications.iupac.org/pac/1996/pdf/6810x1919.pdf
  2. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ↑ "Sorbitol_msds".
  4. 1 2 Teo G, Suzuki Y, Uratsu SL, Lampinen B, Ormonde N, Hu WK, Dejong TM, Dandekar AM (2006). "Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality". Proceedings of the National Academy of Sciences of the United States of America. 103 (49): 18842–7. Bibcode:2006PNAS..10318842T. doi: 10.1073/pnas.0605873103 . PMC   1693749 . PMID   17132742.
  5. ↑ Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261.
  6. 1 2 3 4 5 6 7 8 "Sorbitol". Drugs.com. 23 November 2021. Retrieved 8 July 2022.
  7. ↑ "Reduction of Glucose". butane.chem.uiuc.edu. Archived from the original on 2017-09-25. Retrieved 2017-10-03.
  8. ↑ Sugar substitute
  9. ↑ Tsuneyuki Oku and Sadako Nakamura (2002). "Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy" (PDF). Pure Appl. Chem. 74 (7): 1253–1261. doi:10.1351/pac200274071253.
  10. ↑ Campbell, Farrell (2011). Biochemistry (Seventh ed.). Brooks/Cole. ISBN   978-1-111-42564-7.
  11. ↑ Hayes C (October 2001). "The effect of non-cariogenic sweeteners on the prevention of dental caries: a review of the evidence". Journal of Dental Education. 65 (10): 1106–1109. doi:10.1002/j.0022-0337.2001.65.10.tb03457.x. ISSN   0022-0337. PMID   11699985.
  12. ↑ Nicolas GG, Lavoie MC (January 2011). "[Streptococcus mutans and oral streptococci in dental plaque]". Canadian Journal of Microbiology. 57 (1): 1–20. doi:10.1139/w10-095. ISSN   1480-3275. PMID   21217792.
  13. ↑ Nelson, Cox (2005). Lehninger Principles of Biochemistry (Fourth ed.). New York: W. H. Freeman. ISBN   0-7167-4339-6.
  14. ↑ "sorbitol". Cancer Drug Guide. American Cancer Society. Archived from the original on 2007-06-30.
  15. ↑ Lederle FA (1995). "Epidemiology of constipation in elderly patients. Drug utilisation and cost-containment strategies". Drugs & Aging. 6 (6): 465–9. doi:10.2165/00002512-199506060-00006. PMID   7663066. S2CID   43386314.
  16. ↑ 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. doi:10.1128/JCM.18.3.512-520.1983. PMC   270845 . PMID   6355145. The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive
  17. ↑ 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.
  18. ↑ "Kayexalate (sodium polystyrene sulfonate) powder". fda.gov. Retrieved 12 July 2015.
  19. ↑ "Home – Catalent". catalent.com. Retrieved 12 July 2015.
  20. ↑ "Sorbitol 70%". bttcogroup.in. Archived from the original on 10 July 2020. Retrieved 12 July 2015.
  21. ↑ Medina J, Garrote R (2002). "The effect of two cryoprotectant mixtures on frozen surubí surimi". Brazilian Journal of Chemical Engineering. 19 (4): 419–424. doi: 10.1590/S0104-66322002000400010 . ISSN   0104-6632.
  22. ↑ "Gallaher Group". gallaher-group.com. Archived from the original on 27 December 2008. Retrieved 12 July 2015.
  23. 1 2 Chemical and functional properties of food saccharides. Tomasik, Piotr. Boca Raton: CRC Press. 2004. ISBN   9780203495728. OCLC   317752036.{{cite book}}: CS1 maint: others (link)
  24. ↑ Nakka R. "KNSB Propellant". nakka-rocketry.net. Retrieved 12 July 2015.
  25. ↑ Metzger JO (2006). "Production of Liquid Hydrocarbons from Biomass". Angewandte Chemie International Edition. 45 (5): 696–698. doi:10.1002/anie.200502895. PMID   16374789.
  26. ↑ Shrotri A, Tanksale, Akshat, Beltramini, Jorge Norberto, Gurav, Hanmant, Chilukuri, Satyanarayana V. (2012). "Conversion of cellulose to polyols over promoted nickel catalysts". Catalysis Science & Technology. 2 (9): 1852–1858. doi:10.1039/C2CY20119D.
  27. ↑ Tanksale A, Beltramini, Jorge Norberto, Lu, GaoQing Max (2010). "A review of catalytic hydrogen production processes from biomass". Renewable and Sustainable Energy Reviews. 14 (1): 166–182. Bibcode:2010RSERv..14..166T. doi:10.1016/j.rser.2009.08.010.
  28. ↑ 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): 787–90. Bibcode:2000Natur.404..787N. doi:10.1038/35008121. PMID   10783895. S2CID   4426750.
  29. ↑ Islam MS, Sakaguchi E (2006). "Sorbitol-based osmotic diarrhea: Possible causes and mechanism of prevention investigated in rats". World Journal of Gastroenterology. 12 (47): 7635–7641. doi: 10.3748/wjg.v12.i47.7635 . PMC   4088045 . PMID   17171792.
  30. ↑ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Archived from the original on 5 July 2010. Retrieved 6 July 2009.
  31. ↑ Sigma Aldrich. "D-Sorbitol" . Retrieved 15 February 2022.
  32. ↑ European Pharmacopoeia. "Index, Ph Eur" (PDF). Archived from the original (PDF) on 20 July 2011. Retrieved 6 July 2009.
  33. ↑ British Pharmacopoeia (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 6 July 2009.
  34. ↑ National Institute of Health Sciences (2016). "The Japanese Pharmacopoeia, Seventeenth Edition" (PDF). Archived from the original (PDF) on 4 March 2018. Retrieved 17 August 2018.
  1. ↑ Beebe JA, Frey PA (1998-10-01). "Galactose Mutarotase: Purification, Characterization, and Investigations of Two Important Histidine Residues". Biochemistry . 37 (42): 14989–14997. doi:10.1021/bi9816047. ISSN   0006-2960.
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