Sorbitol

Source: Wikipedia, the free encyclopedia.
Sorbitol
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 Edit this at Wikidata
E number E420 (thickeners, ...)
KEGG
MeSH Sorbitol
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 ☒N[pubchem]
    Key: FBPFZTCFMRRESA-JGWLITMVSA-N ☒N[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
Appearance White 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 four-colored diamondHealth 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).
☒N verify (what is checkY☒N ?)

Sorbitol (

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

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.

Mechanism of glucose aldehyde reduction into sorbitol

Glucose reduction is not the major

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.

Sorbitol also may be synthesized through a catalytic hydrogenation of d-glucose to form d-sorbitol.[8][not specific enough to verify] This reaction has a 100% yield of d-sorbitol when d-glucose is reacted with hydrogen in water at 120 degrees Celsius, under 150001.5 Torr, for 1 hour.[citation needed]

Uses

Sweetener

Sorbitol is a

INS number and E number 420. Sorbitol is about 60% as sweet as sucrose (table sugar).[9]

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

cough syrups, and sugar-free chewing gum.[11] 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.[12][13]

It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.[4][14]

Medical applications

Laxative

As is the case with other

bowel movements.[6][15] Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.[6][16]

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.[17]

A treatment for

FDA issued a warning of increased risk for gastrointestinal necrosis with this combination.[19]

Sorbitol is also used in the manufacture of softgel capsules to store single doses of liquid medicines.[20]

Health care, food, and cosmetic uses

Sorbitol often is used in modern

thickener.[21] 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.[22] It is also used as a humectant in some cigarettes.[23]

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.[24] In baking, it is also valuable because it acts as a plasticizer, and slows down the staling process.[24]

Miscellaneous uses

A mixture of sorbitol and

rocket fuel. It has similar performance to sucrose-based rocket candy, but is easier to cast, less hygroscopic and does not caramelize.[25]

Sorbitol is identified as a potential key chemical intermediate[26] 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.[27] 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.[28]

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

neuropathy
, respectively.

Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.[30]

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

References

  1. ^ publications.iupac.org/pac/1996/pdf/6810x1919.pdf
  2. ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ "Sorbitol_msds".
  4. ^
    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. ^ a b c d e f g h "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. ^ SRINIVASAN, K.; GUNDEKARI, S. India Patent WO2017/60922. April 13, 2017.
  9. ^ Sugar substitute
  10. doi:10.1351/pac200274071253
    .
  11. ISBN 978-1-111-42564-7
    .
  12. PMID 11699985
    .
  13. PMID 21217792
    .
  14. ISBN 0-7167-4339-6
    .
  15. ^ "sorbitol". Cancer Drug Guide. American Cancer Society. Archived from the original on 2007-06-30.
  16. S2CID 43386314
    .
  17. PMID 6355145
    . The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive
  18. PMID 17377608
    .
  19. ^ "Kayexalate (sodium polystyrene sulfonate) powder". fda.gov. Retrieved 12 July 2015.
  20. ^ "Home – Catalent". catalent.com. Retrieved 12 July 2015.
  21. ^ "Sorbitol 70%". bttcogroup.in. Archived from the original on 10 July 2020. Retrieved 12 July 2015.
  22. ISSN 0104-6632
    .
  23. ^ "Gallaher Group". gallaher-group.com. Archived from the original on 27 December 2008. Retrieved 12 July 2015.
  24. ^
    OCLC 317752036.{{cite book}}: CS1 maint: others (link
    )
  25. ^ Nakka R. "KNSB Propellant". nakka-rocketry.net. Retrieved 12 July 2015.
  26. PMID 16374789
    .
  27. doi:10.1039/C2CY20119D
    .
  28. doi:10.1016/j.rser.2009.08.010
    .
  29. S2CID 4426750
    .
  30. PMID 17171792
    .
  31. ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Archived from the original on 5 July 2010. Retrieved 6 July 2009.
  32. Sigma Aldrich. "D-Sorbitol"
    . Retrieved 15 February 2022.
  33. ^ European Pharmacopoeia. "Index, Ph Eur" (PDF). Archived from the original (PDF) on 20 July 2011. Retrieved 6 July 2009.
  34. ^ British Pharmacopoeia (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 6 July 2009.
  35. ^ 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.

External links

  • Media related to Sorbitol at Wikimedia Commons
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