Sorbitol

Names
Other names| D-glucitol; D-Sorbitol; Sorbogem; Sorbo

IUPAC name

* (2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol

Chemical and physical data
Formula| C6H14O6
Molar mass| 182.17 g/mol g·mol−1
3D model (JSmol)|

* Interactive image

Density| 1.49 g/cm3[1] g/cm3
Solubility in water| 2350 g/L[1] mg/mL (20 °C)

SMILES

* OC([C@H](O)[C@@H](O)[C@H](O)CO)CO

InChI

* 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]

Sorbitol (/ˈsɔːrbɪtɒl/), 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.[3] 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.[4] While similar, the two sugar alcohols have very different sources in nature, melting points, and uses. It has a pKa of 13.14 +/- .2[5]

## Contents

* 1 Synthesis
* 2 Uses
* 2.1 Sweetener
* 2.2 Medical applications
* 2.2.1 Laxative
* 2.2.2 Other medical applications
* 2.3 Health care, food, and cosmetic uses
* 2.4 Miscellaneous uses
* 3 Medical importance
* 4 Adverse medical effects
* 5 Overdose effects
* 6 Compendial status
* 7 Society and culture
* 7.1 Cost
* 8 See also
* 9 References
* 10 External links

## Synthesis[edit | edit source]

Sorbitol may be synthesised via a glucose reduction reaction[6] 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 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.
Sorbitol also may be synthesized through a catalytic hydrogenation of d-glucose to form d-sorbitol.[7][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[edit | edit source]

### Sweetener[edit | edit source]

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 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.[9] 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.[10][11]

It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.[12]

### Medical applications[edit | edit source]

#### Laxative[edit | edit source]

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. Sorbitol works as a laxative by drawing water into the large intestine, stimulating bowel movements.[13] Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a doctor.[14] Sorbitol is found in some dried fruits and may contribute to the laxative effects of prunes.[15] Sorbitol was first discovered in the fresh juice of mountain ash (Sorbus aucuparia) berries in 1872.[16] It is also found in the fruits of apples, plums, pears, cherries, dates, peaches and apricots.

#### Other medical applications[edit | edit source]

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 hyperkalaemia (elevated blood potassium) uses sorbitol and the ion-exchange resin sodium polystyrene sulfonate (tradename Kayexalate).[18] 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.[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[edit | edit source]

Sorbitol often is used in modern cosmetics as a humectant and 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[edit | edit source]

A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel.[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[edit | edit source]

Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway[29] 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. 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.[30]

Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.[31]

## Adverse medical effects[edit | edit source]

People with untreated celiac disease often present sorbitol malabsorption, as a result of the small bowel damage. Sorbitol malabsorption is an important cause for persisting symptoms in patients already on a gluten-free diet. The sorbitol hydrogen breath test has been suggested as a tool to detect celiac disease because of a strict correlation between cut-off value and intestinal lesions. Nevertheless, although it may be indicated for research purposes, it is not yet recommended as a diagnostic tool in clinical practice.[32]

It has been noted that the sorbitol added to sodium polystyrene sulfonate (SPS, used in the treatment of hyperkalemia) can cause complications in the gastrointestinal tract, including bleeding, perforated colonic ulcers, ischemic colitis and colonic necrosis, particularly in patients with uremia. Risk factors for sorbitol-induced damage include immunosuppression, hypovolemia, postoperative setting, hypotension after hemodialysis, and peripheral vascular disease. SPS-sorbitol should therefore be used carefully in the management of hyperkalemia.[33]

## Overdose effects[edit | edit source]

Ingesting large amounts of sorbitol can lead to abdominal pain, flatulence, and mild to severe diarrhea. Habitual sorbitol consumption of over 20 grams (0.7 oz) per day as sugar-free gum has led to severe diarrhea, causing unintended weight loss or even requiring hospitalization.[34] In early studies, a dose of 25g of sorbitol, eaten through the day, produced a laxative effect in only 5% of individuals.[35] As a result of the large molecular weight of sorbitol, when large amounts of sorbitol are ingested, only a small amount of sorbitol is absorbed in the small intestine, and most of the sorbitol enters the colon, with consequent gastrointestinal effects.[31]

## Compendial status[edit | edit source]

* Food Chemicals Codex[36]
* European Pharmacopoeia[37] 6.1[38]
* British Pharmacopoeia 2009[39]
* Japanese Pharmacopoeia 17 [40]

## Society and culture[edit | edit source]

### Cost[edit | edit source]

The price in the use for medicinal purposes is $49 (USD) for 16000 ml(s) irrigation solution 3.3% [41]

* Sorbitol costs (US)

* Sorbitol prescriptions (US)

## See also[edit | edit source]

* Sorbitan
* Isosorbide

## References[edit | edit source]

1. ↑ 1.0 1.1 1.2 1.3 1.4 Record  in the GESTIS Substance Database of the Institute for Occupational Safety and Health
2. ↑ "Sorbitol_msds". Archived from the original on 2021-08-29. Retrieved 2018-05-24.
3. ↑ 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.
4. ↑ Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261.
5. ↑ SciFinderWeb
6. ↑ "Reduction of Glucose". butane.chem.uiuc.edu. Archived from the original on 2017-09-25. Retrieved 2017-10-03.
7. ↑ SRINIVASAN, K.; GUNDEKARI, S. India Patent WO2017/60922. April 13, 2017.
8. ↑ Sugar substitute
9. ↑ Campbell; Farrell (2011). Biochemistry (Seventh ed.). Brooks/Cole. ISBN 978-1-111-42564-7.
10. ↑ 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.
11. ↑ Nicolas, Guillaume G.; Lavoie, Marc C. (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.
12. ↑ Nelson; Cox (2005). Lehninger Principles of Biochemistry (Fourth ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.
13. ↑ "sorbitol". Cancer Drug Guide. American Cancer Society. Archived from the original on 2007-06-30.
14. ↑ 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.
15. ↑ 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): 251–86. doi:10.1080/20014091091814. PMID 11401245. S2CID 31159565.
16. ↑ Panda, H. (2011). The Complete Book on Sugarcane Processing and By-Products of Molasses (with Analysis of Sugar, Syrup and Molasses). ASIA PACIFIC BUSINESS PRESS Inc. p. 416\. ISBN 978-8178331447. Archived from the original on 2021-08-29. Retrieved 2020-11-04.
17. ↑ 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"
18. ↑ 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.
19. ↑ "Kayexalate (sodium polystyrene sulfonate) powder". fda.gov. Archived from the original on 4 May 2015. Retrieved 12 July 2015.
20. ↑ "Home – Catalent". catalent.com. Archived from the original on 7 January 2011. Retrieved 12 July 2015.
21. ↑ "Sorbitol 70%". bttcogroup.in. Archived from the original on 10 July 2020. Retrieved 12 July 2015.
22. ↑ Medina, J.R.; Garrote, R.L. (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.
23. ↑ "Gallaher Group". gallaher-group.com. Archived from the original on 27 December 2008. Retrieved 12 July 2015.
24. ↑ 24.0 24.1 Chemical and functional properties of food saccharides. Tomasik, Piotr. Boca Raton: CRC Press. 2004. ISBN 9780203495728. OCLC 317752036.`{{cite book}}`: CS1 maint: others (link)
25. ↑ "Richard Nakka's Experimental Rocketry Web Site". nakka-rocketry.net. Archived from the original on 16 May 2015. Retrieved 12 July 2015.
26. ↑ Metzger, Jürgen O. (2006). "Production of Liquid Hydrocarbons from Biomass". Angewandte Chemie International Edition. 45 (5): 696–698. doi:10.1002/anie.200502895. PMID 16374789.
27. ↑ Shrotri, Abhijit; 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.
28. ↑ Tanksale, Akshat; 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. doi:10.1016/j.rser.2009.08.010.
29. ↑ 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.
30. ↑ "Sorbitol: a hazard for diabetics?". Archived from the original on 2012-07-10.
31. ↑ 31.0 31.1 Islam, M. S.; 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.
32. ↑ Montalto M, Gallo A, Ojetti V, Gasbarrini A (2013). "Fructose, trehalose and sorbitol malabsorption" (PDF). Eur Rev Med Pharmacol Sci (Review). 17 (Suppl 2): 26–9. PMID 24443064. Archived (PDF) from the original on 2016-04-12. Retrieved 2016-03-28.
33. ↑ Mohamad Erfani, Yougandhar Akula, Touraj Zolfaghari, Hilary I. Hertan (2010). "Sodium Polystyrene Sulfonate (SPS): Sorbitol-induced Colonic Necrosis" (PDF). Practical Gastroenterology (Case report). Archived from the original (PDF) on May 8, 2013.`{{cite web}}`: CS1 maint: uses authors parameter (link)
34. ↑ Kathleen Doheny (2008-01-10). "Sweetener Side Effects: Case Histories". WebMD Medical News. Archived from the original on 2008-01-13. Retrieved 2008-01-10.
35. ↑ Peters, Ronald; Lock, R. H. (1958-09-13). "Laxative Effect of Sorbitol". British Medical Journal. 2 (5097): 677–678. doi:10.1136/bmj.2.5097.677. ISSN 0007-1447. PMC 2026423. PMID 13572866.
36. ↑ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Archived from the original on 5 July 2010. Retrieved 6 July 2009.
37. ↑ Sigma Aldrich. "D-Sorbitol". Archived from the original on 11 January 2022. Retrieved 6 July 2009.
38. ↑ European Pharmacopoeia. "Index, Ph Eur" (PDF). Archived from the original (PDF) on 20 July 2011. Retrieved 6 July 2009.
39. ↑ British Pharmacopoeia (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 6 July 2009.
40. ↑ National Institute of Health Sciences (2016). "The Japanese Pharmacopoeia, Seventeenth Edition" (PDF). Archived (PDF) from the original on 4 March 2018. Retrieved 17 August 2018.
41. ↑ "Sorbitol Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 3 March 2021. Retrieved 8 April 2021.

## External links[edit | edit source]

Identifiers:|

* ATC code:

* A06AD18 (WHO)

* CAS Number: 50-70-4 Y
* PubChem CID: 5780
* DrugBank:

* DB01638 Y

* ChemSpider:

* 5576 N

* UNII:

* 506T60A25R

* ChEBI:

* CHEBI:17924

* ChEMBL:

* ChEMBL1682 N

|

* v
* t
* e

Alcohols

By consumption|

| Alcohols found in
alcoholic drinks|

* 1-Propanol
* 2-Methyl-1-butanol
* Ethanol
* Isoamyl alcohol
* Isobutanol
* Phenethyl alcohol
* tert-Amyl alcohol
* tert-Butyl alcohol
* Tryptophol

|

Medical alcohol|

* Ethchlorvynol
* Methylpentynol
* Methanol poisoning
* Ethanol

Toxic alcohols|

* Isopropyl alcohol
* Methanol

Primary
alcohols (1°)|

| Methanol|

* 4-Methylcyclohexanemethanol
* Aminomethanol
* Cyclohexylmethanol
* Methoxymethanol
* Methylazoxymethanol
* Trifluoromethanol

|

Ethanol|

* 1-Aminoethanol
* 2,2,2-Trichloroethanol
* 2,2,2-Trifluoroethanol
* 2-(2-Ethoxyethoxy)ethanol
* 2-(2-Methoxyethoxy)ethanol
* 2-(2-Methoxyethoxy)ethanol
* 2-Butoxyethanol
* 2-Chloroethanol
* 2-Ethoxyethanol
* 2-Fluoroethanol
* 2-Mercaptoethanol
* 2-Methoxyethanol
* Aminoethylethanolamine
* Diethylethanolamine
* Dimethylethanolamine
* Ethanol
* Ethanolamine
* N,N-Diisopropylaminoethanol
* N-Methylethanolamine
* Phenoxyethanol
* Tribromoethanol

Butanol|

* 2-Methyl-1-butanol
* Isobutanol
* n-Butanol

Straight-chain
saturated
C1 — C9|

* Methanol
* Ethanol
* 1-Propanol
* 1-Butanol
* 1-Pentanol
* 1-Hexanol
* 1-Heptanol
* 1-Octanol (capryl)
* 1-Nonanol (pelargonic)

Straight-chain
saturated
C10 — C19|

* 1-Decanol (capric)
* 1-Undecanol (hendecyl)
* 1-Dodecanol (lauryl)
* 1-Tridecanol
* 1-Tetradecanol (myristyl)
* 1-Pentadecanol
* 1-Hexadecanol (cetyl / palmityl)
* 1-Heptadecanol
* 1-Octadecanol (stearyl)
* 1-Nonadecanol

Straight-chain
saturated
C20 — C29|

* 1-Icosanol (arachidyl)
* 1-Heneicosanol
* 1-Docosanol (behenyl)
* 1-Tricosanol
* 1-Tetracosanol (lignoceryl)
* 1-Pentacosanol
* 1-Hexacosanol (ceryl)
* 1-Heptacosanol
* 1-Octacosanol (cluytyl / montanyl)
* 1-Nonacosanol

Straight-chain
saturated
C30 — C39|

* 1-Triacontanol (melissyl / myricyl)
* 1-Hentriacontanol
* 1-Dotriacontanol (lacceryl)
* 1-Tritriacontanol
* 1-Tetratriacontanol (geddyl)
* 1-Pentatriacontanol
* 1-Hexatriacontanol
* 1-Heptatriacontanol
* 1-Octatriacontanol
* 1-Nonatriacontanol

Straight-chain
saturated
C40 — C49|

* 1-Tetracontanol
* 1-Hentetracontanol
* 1-Dotetracontanol
* 1-Tritetracontanol
* 1-Tetratetracontanol
* 1-Pentatetracontanol
* 1-Hexatetracontanol
* 1-Heptatetracontanol
* 1-Octatetracontanol
* 1-Nonatetracontanol

* 2-Ethylhexanol
* Allyl alcohol
* Anisyl alcohol
* Benzyl alcohol
* Cinnamyl alcohol
* Crotyl alcohol
* Furfuryl alcohol
* Isoamyl alcohol
* Neopentyl alcohol
* Nicotinyl alcohol
* Perillyl alcohol
* Phenethyl alcohol
* Propargyl alcohol
* Salicyl alcohol
* Tryptophol
* Vanillyl alcohol
* Veratrole alcohol

Secondary
alcohols (2°)|

* 1-Phenylethanol
* 2-Butanol
* 2-Deoxyerythritol
* 2-Heptanol
* 3-Heptanol
* 2-Hexanol
* 3-Hexanol
* 3-Methyl-2-butanol
* 2-Nonanol
* 2-Octanol
* 2-Pentanol
* 3-Pentanol
* Cyclohexanol
* Cyclopentanol
* Cyclopropanol
* Diphenylmethanol
* Isopropanol
* Pinacolyl alcohol
* Pirkle's alcohol
* Propylene glycol methyl ether

Tertiary
alcohols (3°)|

* 2-Methyl-2-pentanol
* 2-Methylheptan-2-ol
* 2-Methylhexan-2-ol
* 3-Methyl-3-pentanol
* 3-Methyloctan-3-ol
* Diacetone alcohol
* Ethchlorvynol
* Methylpentynol
* Nonafluoro-tert-butyl alcohol
* tert-Amyl alcohol
* tert-Butyl alcohol
* Triphenylethanol
* Triphenylmethanol

Hydric alcohols|

| Monohydric alcohols|

* Methanol
* Ethanol
* Isopropanol

|

Dihydric alcohols|

* Ethylene glycol

Trihydric alcohols|

* Glycerol

Amyl alcohols|

* 2,2-Dimethylpropan-1-ol
* 2-Methylbutan-1-ol
* 2-Methylbutan-2-ol
* 3-Methylbutan-1-ol
* 3-Methylbutan-2-ol
* Pentan-1-ol
* Pentan-2-ol
* Pentan-3-ol

Aromatic alcohols|

* Benzyl alcohol
* 2,4-Dichlorobenzyl alcohol
* 3-Nitrobenzyl alcohol

Branched and
unsaturated
fatty alcohols|

* tert-Butyl alcohol
* tert-Amyl alcohol
* 3-Methyl-3-pentanol
* Palmitoleyl alcohol
* Oleyl alcohol
* Erucyl alcohol

Sugar alcohols|

| C2 — C7|

* Ethylene glycol (C2)
* Glycerol (C3)
* Erythritol (C4)
* Threitol (C4)
* Arabitol (C5)
* Ribitol (C5)
* Xylitol (C5)
* Mannitol (C6)
* Sorbitol (C6)
* Galactitol (C6)
* Iditol (C6)
* Volemitol (C7)

|

Deoxy sugar
alcohols|

* Fucitol

Cyclic sugar
alcohols|

* Inositol

Glycylglycitols|

* Maltitol
* Lactitol
* Isomalt
* Maltotriitol
* Maltotetraitol
* Polyglycitol

Terpene alcohols|

| Monoterpene
alcohol|

* Terpineol

|

Diterpene
alcohols|

* Phytol

Dialcohols|

* 1,4-Butanediol
* 1,5-Pentanediol
* 2-Methyl-2-propyl-1,3-propanediol
* Diethylpropanediol
* Ethylene glycol
* Catechol

Fluoroalcohols|

* 1,3-Difluoro-2-propanol
* 2,2,2-Trifluoroethanol
* 2-Fluoroethanol
* Nonafluoro-tert-butyl alcohol
* Trifluoromethanol

Preparations|

* Substitution of haloalkane
* Carbonyl reduction
* Ether cleavage
* Hydrolysis of epoxide
* Hydration of alkene
* Ziegler process

Reactions|

* Deprotonation
* Protonation
* Alcohol oxidation
* Glycol cleavage
* Nucleophilic substitution
* Fischer–Speier esterification
* Williamson ether synthesis
* Elimination reaction
* Nucleophilic substitution of carbonyl group
* Friedel-Crafts alkylation
* Nucleophilic conjugate addition
* Transesterification

* Category

* v
* t
* e

Blood substitutes and perfusion solutions (B05)

Blood and related products (B05A)|

* Serum albumin
* Dextran
* Gelatin agents
* Hemoglobin crosfumaril
* Hemoglobin raffimer
* Hydroxyethyl starch
* Erythrocytes
* Thrombocytes
* Blood plasma
* Stem cells from umbilical cord blood

Intravenous solutions (B05B)|

* Amino acids
* Fat emulsions
* Carbohydrates
* Protein hydrolysates
* Electrolytes
* Trometamol
* Mannitol
* Carbamide

Irrigating solutions (B05C)|

* Cetylpyridinium
* Chlorhexidine
* Nitrofural
* Sulfamethizole
* Taurolidine
* Mandelic acid
* Noxytiolin
* Ethacridine lactate
* Neomycin
* Sodium chloride
* Sodium citrate
* Magnesium citrate
* Sodium bicarbonate
* Glucose
* Sorbitol
* Glycine
* Mannitol

Others (B05D, B05X)|

* Peritoneal dialysis solutions
* Potassium chloride
* Sodium bicarbonate
* Sodium chloride
* Ammonium chloride
* Magnesium sulfate
* Potassium phosphate
* Calcium chloride
* Sodium acetate
* Sodium phosphate
* Magnesium phosphate
* Magnesium chloride
* Zinc chloride
* Hydrochloric acid
* Sodium glycerophosphate
* Potassium lactate
* Cardioplegia solutions
* Potassium acetate
* Arginine
* Alanyl glutamine
* Lysine

* v
* t
* e

Consumer food safety

Adulterants, food contaminants|

* 3-MCPD
* Aldicarb
* Antibiotic use in livestock
* Cyanide
* Formaldehyde
* HGH controversies
* Lead poisoning
* Melamine
* Mercury in fish
* Sudan I

Flavorings|

* Monosodium glutamate (MSG)
* Salt
* Sugar
* High-fructose corn syrup

Intestinal parasites and parasitic disease|

* Amoebiasis
* Anisakiasis
* Cryptosporidiosis
* Cyclosporiasis
* Diphyllobothriasis
* Enterobiasis
* Fasciolopsiasis
* Fasciolosis
* Giardiasis
* Gnathostomiasis
* Paragonimiasis
* Toxoplasmosis
* Trichinosis
* Trichuriasis

Microorganisms|

* Botulism
* Campylobacter jejuni
* Clostridium perfringens
* Cronobacter
* Enterovirus
* Escherichia coli O104:H4
* Escherichia coli O157:H7
* Hepatitis A
* Hepatitis E
* Listeria
* Norovirus
* Rotavirus
* Salmonella
* Vibrio cholerae

Pesticides|

* Chlorpyrifos
* DDT
* Lindane
* Malathion
* Methamidophos

Preservatives|

* Benzoic acid
* Ethylenediaminetetraacetic acid (EDTA)
* Sodium benzoate

Sugar substitutes|

* Acesulfame potassium
* Aspartame
* Saccharin
* Sodium cyclamate
* Sorbitol
* Sucralose

Toxins, poisons, environment pollution|

* Aflatoxin
* Arsenic contamination of groundwater
* Benzene in soft drinks
* Bisphenol A
* Dieldrin
* Diethylstilbestrol
* Dioxin
* Mycotoxins
* Nonylphenol
* Shellfish poisoning

Food contamination incidents|

* Devon colic
* Swill milk scandal
* Esing Bakery incident
* 1858 Bradford sweets poisoning
* 1900 English beer poisoning
* Morinaga Milk arsenic poisoning incident
* Minamata disease
* 1971 Iraq poison grain disaster
* Toxic oil syndrome
* 1985 diethylene glycol wine scandal
* UK mad cow disease outbreak
* 1993 Jack in the Box E. coli outbreak
* 1996 Odwalla E. coli outbreak
* 2006 North American E. coli outbreaks
* ICA meat repackaging controversy
* 2008 Canada listeriosis outbreak
* 2008 Chinese milk scandal
* 2008 Irish pork crisis
* 2008 United States salmonellosis outbreak
* 2011 Germany E. coli outbreak
* 2011 United States listeriosis outbreak
* 2013 Bihar school meal poisoning
* 2013 horse meat scandal
* 2015 Mozambique beer poisoning
* 2017 Brazil weak meat scandal
* 2017–18 South African listeriosis outbreak
* 2018 Australian rockmelon listeriosis outbreak
* 2018 Australian strawberry contamination
* Food safety incidents in China
* Food safety incidents in Taiwan
* Food safety in Australia
* Foodborne illness
* outbreaks
* death toll
* United States

Regulation, standards, watchdogs|

* Acceptable daily intake
* E number
* Food labeling regulations
* Food libel laws
* International Food Safety Network
* ISO 22000
* Nutrition facts label
* Organic certification
* The Non-GMO Project
* Quality Assurance International
* Food Standards Agency

Institutions|

* Institute for Food Safety and Health
* European Food Safety Authority
* Food and Drug Administration
* International Food Safety Network
* Spanish Agency for Food Safety and Nutrition
* Food Information and Control Agency (Spain)
* Centre for Food Safety (Hong Kong)
* Ministry of Food and Drug Safety (South Korea)

* v
* t
* e

Diagnostic agents (V04)

Digestive system|

| Diabetes|

* Glucose
* Tolbutamide

|

Fat absorption|

* Vitamin A concentrates

Bile duct patency|

* Ceruletide
* Magnesium sulfate
* Sincalide
* Sorbitol

Liver functional capacity|

* Galactose
* Sulfobromophthalein

Gastric secretion|

* Betazole
* Caffeine and sodium benzoate
* Cation exchange resins
* Histamine phosphate
* Methylthioninium chloride
* Pentagastrin

Exocrine pancreatic function|

* Bentiromide
* Pancreozymin
* cholecystokinin
* Secretin

Endocrine system|

| Pituitary function|

* cortisol
* Corticorelin
* Metyrapone
* GH
* Pralmorelin
* Sermorelin
* Somatorelin

|

Thyroid function|

* Protirelin
* Thyrotropin

Fertility disturbances|

* Gonadorelin

Tuberculosis|

* Tuberculin

Renal function|

* Alsactide
* Aminohippuric acid
* Indigo carmine
* Inulin and other polyfructosans
* Phenolsulfonphthalein

* v
* t
* e

* Metabolism: carbohydrate metabolism
* fructose and galactose enzymes

Fructose / Fructolysis|

* Hepatic fructokinase
* Aldolase B
* Triokinase

Sorbitol|

* Sorbitol dehydrogenase
* Aldose reductase

Galactose / Galactolysis|

* Galactokinase
* Galactose-1-phosphate uridylyltransferase/UDP-glucose 4-epimerase
* Aldose reductase

Lactose|

* Lactose synthase
* Lactase

Mannose|

* Mannose phosphate isomerase

* v
* t
* e

Drugs for constipation (laxatives and cathartics) (A06)

Stool softeners|

* Docusate

Stimulant laxatives|

* Bisacodyl
* Bisoxatin
* Cascara
* Castor oil
* Dantron
* Oxyphenisatine
* Phenolphthalein
* Senna glycosides
* Sodium picosulfate

Bulk-forming laxatives|

* Dietary fiber
* Ethulose
* Ispaghula
* Methylcellulose
* Polycarbophil calcium
* Sterculia
* Triticum

Lubricant laxatives|

* Liquid paraffin
* Mineral oil
* White petrolatum (petroleum jelly)

Osmotic laxatives|

* Lactitol
* Lactulose
* Laminarid
* Magnesium carbonate
* Magnesium citrate
* Magnesium hydroxide (milk of magnesia)
* Magnesium oxide
* Magnesium peroxide
* Magnesium sulfate
* Mannitol
* Pentaerythritol
* Polyethylene glycol (macrogol)
* Sodium phosphate
* Sodium sulfate
* Sodium tartrate
* Sorbitol

Enemas|

* Bisacodyl
* Dantron
* Glycerol
* Oil
* Sodium laurilsulfate
* Sodium lauryl sulfoacetate
* Sodium phosphate
* Sorbitol

Opioid antagonists|

* Naloxone (Oxycodone/naloxone)
* PAMORAs
* Alvimopan
* Axelopran
* Bevenopran
* Methylnaltrexone
* Naldemedine
* Naloxegol

Others|

* Linaclotide
* Lubiprostone
* Oxyphenisatine
* Plecanatide
* Prucalopride
* Tegaserod
* Tenapanor
* Ulimorelin

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