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Taurine

From Wikipedia, the free encyclopedia
Aminosulfonic acid
This article is about the chemical compound. For the bovine sub-species, seeTaurine cattle.

Taurine
Skeleton diagram of taurine molecule
Ball-and-stick model of taurine molecule
Names
Preferred IUPAC name
2-Aminoethanesulfonic acid
Other names
Tauric acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.003.168Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6) checkY
    Key: XOAAWQZATWQOTB-UHFFFAOYSA-N checkY
  • InChI=1/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
    Key: XOAAWQZATWQOTB-UHFFFAOYAA
  • O=S(=O)(O)CCN
Properties
C2H7NO3S
Molar mass125.14 g/mol
Appearancecolorless or white solid
Density1.734 g/cm3 (at −173.15 °C)
Melting point305.11 °C (581.20 °F; 578.26 K) Decomposes into simple molecules
Acidity (pKa)<0, 9.06
Related compounds
Related compounds
Sulfamic acid
Aminomethanesulfonic acid
Homotaurine
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Taurine (/ˈtɔːrn/ ;[1] IUPAC:2-aminoethanesulfonic acid[2]) is anaturally occurring organic compound with thechemical formulaC2H7NO3S, and is anon-proteinogenicamino sulfonic acid widely distributed in mammalian tissues and organs.[2][3] Structurally, by containing asulfonic acid group instead of acarboxylic acid group, it is not involved in protein synthesis but is still usually referred to as an amino acid.[2][4][5][6] As non-proteinogenic amino sulfonic acid, it is not encoded by thegenetic code and is distinguished from the protein-buildingα-amino acids.[7]

Taurine is a major constituent ofbile and can be found in thelarge intestine, and is named afterLatintaurus, meaningbull orox, as it was first isolated from ox bile in 1827 by German scientistsFriedrich Tiedemann andLeopold Gmelin.

Although taurine is abundant in human organs, it is not anessential human dietary nutrient and is not included among nutrients with arecommended intake level.[8] Among the diverse pathways by which natural taurine can be biosynthesized, its human pathways (primarily in the human liver) are fromcysteine and/ormethionine.[9][10]

Taurine is commonly sold as adietary supplement, but there is no good clinical evidence that taurine supplements provide any benefit to human health.[11] Taurine is used as afood additive to meet essential dietary intake levels for cats,[12] and supplemental dietary support for dogs and poultry.[13]

Discovery and name

[edit]

Taurine was first isolated from ox bile in 1827 by German scientistsFriedrich Tiedemann andLeopold Gmelin.[14][15] Another German scientist Von H. Demarcay first used its common chemical name Taurine in 1838, derived from theLatintaurus (cognate toAncient Greek ταῦρος,taûros) meaningbull orox.[16][17][15] It was subsequently identified in human bile in 1846 byEdmund Ronalds.[18][better source needed]

In nature

[edit]

Taurine is widely distributed in nature, particularly in animal tissues.[3][better source needed] Moreover, it is abundant in nature, including in animal organs,[19][better source needed] and further, as substrates in the biosynthesis ofbile salts.[9] Taurine concentrations in human cells may derive from at least three processes:

  • biosynthesis from the sulfur amino acids (e.g., cysteine);
  • active uptake by a possible taurine transporter;[medical citation needed] and
  • the extent of its release from cells by a "volume-sensitive leak pathway".[9]

It is not anessential human dietary nutrient, resulting in the absence of taurine from compounds having aReference Daily Intake.[8] Its role in human physiology is unknown.

Taurine is a major constituent ofbile, and can be found in thelarge intestine.[citation needed] Its concentrations inland plants are low or undetectable, but up to a substantial wet weight has been found inalgae.[20][21]

Chemical and biochemical features

[edit]

Taurine exists as azwitterionH3N+CH2CH2SO3, as verified byX-ray crystallography.[22] The sulfonic acid has a lowpKa[23] ensuring that it is fullyionized to thesulfonate at thepHs found in the intestinal tract.

Biosynthesis

[edit]

Among the diverse pathways by which natural taurine can be biosynthesized, its pathways in the human liver are fromcysteine and/ormethionine.[9][10] With regard to the route fromcysteine: mammalian taurine synthesis occurs in theliver via thecysteine sulfinic acid pathway. In this pathway,cysteine is first oxidized to its sulfinic acid, catalyzed by the enzymecysteine dioxygenase. Cysteine sulfinic acid, in turn, isdecarboxylated bysulfinoalanine decarboxylase to formhypotaurine. Hypotaurine is enzymatically oxidized to yield taurine byhypotaurine dehydrogenase.[24]

Taurine is also produced by thetranssulfuration pathway, which convertshomocysteine intocystathionine. The cystathionine is then converted tohypotaurine by the sequential action of three enzymes:cystathionine gamma-lyase,cysteine dioxygenase, and cysteine sulfinic acid decarboxylase. Hypotaurine is then oxidized to taurine as described above.[25]

A pathway for taurine biosynthesis fromserine andsulfate is reported inmicroalgae,[21] developingchickenembryos,[26] and chickliver.[27] Serine dehydratase converts serine to2-aminoacrylate, which is converted tocysteic acid by3-phosphoadenylyl sulfate:2-aminoacrylateC-sulfotransferase. Cysteic acid is converted to taurine by cysteinesulfinic aciddecarboxylase.

reaction diagram
Oxidative degradation of cysteine to taurine

Chemical synthesis

[edit]

Synthetic taurine is obtained by theammonolysis ofisethionic acid (2-hydroxyethanesulfonic acid), which in turn is obtained from the reaction ofethylene oxide with aqueoussodium bisulfite. A direct approach involves the reaction ofaziridine withsulfurous acid.[28]

In 1993, about5000–6000 tonnes of taurine were produced for commercial purposes: 50% for pet food and 50% in pharmaceutical applications.[29]

In the laboratory, taurine can be produced byalkylation of ammonia with bromoethanesulfonate salts.[30][needs update?]

In food

[edit]

Taurine occurs naturally in fish and meat.[11][31][15] The mean daily intake from omnivore diets was determined to be around58 mg (range9–372 mg),[32] and to be low or negligible from avegan diet.[11] Typical taurine consumption in theAmerican diet is about123–178 mg per day.[11]

Taurine is partially destroyed by heat in processes such as baking and boiling. This is a concern for cat food, as cats have a dietary requirement for taurine and can easily become deficient. Eitherraw feeding or supplementing taurine can satisfy this requirement.[33][34]

Bothlysine and taurine can mask the metallic flavor ofpotassium chloride, a salt substitute.[35]

Breast milk

[edit]

Taurine is present inbreast milk, and has been added to manyinfant formulas as a measure of prudence since the early 1980s. However, this practice has never been rigorously studied, and as such it has yet to be proven to be necessary, or even beneficial.[36]

Energy drinks and dietary supplements

[edit]

Taurine is an ingredient in someenergy drinks in amounts of1–3 grams per serving.[11][37]

Research

[edit]

Taurine is not regarded as anessential human dietary nutrient and has not been assigned recommended intake levels.[8] High-quality clinical studies to determine possible effects of taurine in the body or following dietary supplementation are absent from the literature.[11] Preliminary human studies on the possible effects of taurine supplementation have been inadequate due to low subject numbers, inconsistent designs, and variable doses.[11]

Safety and toxicity

[edit]

According to theEuropean Food Safety Authority, taurine is "considered to be a skin and eye irritant and skin sensitiser, and to be hazardous if inhaled"; it may be safe to consume up to 6 grams of taurine per day.[13] Other sources indicate that taurine is safe for supplemental intake in normal healthy adults at up to 3 grams per day.[11][38]

A 2008 review found no documented reports of negative or positive health effects associated with the amount of taurine used in energy drinks, concluding, "The amounts ofguarana, taurine, andginseng found in popular energy drinks are far below the amounts expected to deliver either therapeutic benefits or adverse events".[39]

Animal dietary requirement

[edit]

Cats

[edit]

Cats lack the enzymesulfinoalanine decarboxylase to produce taurine and must therefore acquire it from their diet.[12] A taurine deficiency in cats can lead to retinal degeneration and eventually blindness ‒ a condition known ascentral retinal degeneration[40][41] as well as hair loss and tooth decay. Other effects of a diet lacking in this essential amino acid are dilatedcardiomyopathy,[42] and reproductive failure in female cats.[12][43]

Decreased plasma taurine concentration has been demonstrated to be associated withfeline dilated cardiomyopathy. Unlike CRD, the condition is reversible with supplementation.[44]

Taurine is now a requirement of theAssociation of American Feed Control Officials (AAFCO) and any dry or wet food product labeled approved by the AAFCO should have a minimum of 0.1% taurine in dry food and 0.2% in wet food.[45] Studies suggest the amino acid should be supplied at10 mg/kg of bodyweight per day for domestic cats.[46]

Other mammals

[edit]

A number of other mammals also have a requirement for taurine. While the majority of dogs can synthesize taurine, case reports have described a singularAmerican cocker spaniel, 19Newfoundland dogs, and a family ofgolden retrievers suffering from taurine deficiency treatable with supplementation.Foxes onfur farms also appear to require dietary taurine. Therhesus,cebus andcynomolgus monkeys each require taurine at least in infancy. Thegiant anteater also requires taurine.[47]

Birds

[edit]

Taurine appears to be essential for the development ofpasserine birds. Many passerines seek out taurine-richspiders to feed their young, particularly just after hatching. Researchers compared the behaviours and development of birds fed a taurine-supplemented diet to a control diet and found the juveniles fed taurine-rich diets as neonates were much larger risk takers and more adept at spatial learning tasks. Under natural conditions, eachblue tit nestling receive1 mg of taurine per day from parents.[48]

Taurine can be synthesized by chickens. Supplementation has no effect on chickens raised under adequate lab conditions, but seems to help with growth under stresses such as heat and dense housing.[49]

Fish

[edit]

Species of fish, mostly carnivorous ones, show reduced growth and survival when the fish-based feed in their food is replaced with soy meal or feather meal. Taurine has been identified as the factor responsible for this phenomenon; supplementation of taurine to plant-based fish feed reverses these effects. Future aquaculture is expected to use more of these more environmentally-friendly protein sources, so supplementation would become more important.[50]

The need of taurine in fish is conditional, differing by species and growth stage. Theolive flounder, for example, has lower capacity to synthesize taurine compared to therainbow trout. Juvenile fish are less efficient at taurine biosyntheis due to reducedcysteine sulfinate decarboxylase levels.[51]

Derivatives

[edit]
See also:Derivative (chemistry)

See also

[edit]

References

[edit]
  1. ^"Oxford Learner's Dictionaries -- Taurine".Oxford Learner's Dictionaries. Oxford University Press. Archived fromthe original on 28 June 2017. Retrieved6 July 2025.
  2. ^abc"Taurine".National Center for Biotechnology Information. Retrieved6 July 2025.
  3. ^abSchuller-Levis GB, Park E (September 2003)."Taurine: new implications for an old amino acid".FEMS Microbiology Letters.226 (2):195–202.doi:10.1016/S0378-1097(03)00611-6.PMID 14553911. Archived fromthe original on 23 November 2024.
  4. ^Lehninger AL, Nelson DL, Cox MM (2013).Lehninger Principles of Biochemistry (6th ed.). New York: W.H. Freeman. p. 730.ISBN 978-1-4292-3414-6. RetrievedJuly 7, 2025 – via Internet Archive.
  5. ^Voet D, Voet JG, Pratt CW (2013).Fundamentals of Biochemistry: Life at the Molecular Level (4th ed.). John Wiley & Sons. p. 86.ISBN 978-1-118-12918-0. RetrievedJuly 7, 2025 – via Internet Archive.
  6. ^Hendler SS (1990).The Doctors' Vitamin and Mineral Encyclopedia. Simon & Schuster. p. 208.ISBN 978-0671667849. RetrievedJuly 7, 2025 – via Internet Archive.
  7. ^Nelson DL, Cox MM (2021).Lehninger Principles of Biochemistry (8th ed.). New York: W.H. Freeman. p. 866.ISBN 978-1-319-22800-2.
  8. ^abc"Daily Value on the New Nutrition and Supplement Facts Labels". US Food and Drug Administration. 25 February 2022. Archived fromthe original on June 14, 2020. Retrieved26 August 2023.
  9. ^abcdRipps H, Shen W (12 November 2012)."Taurine: A "Very Essential" Amino Acid"(review).Molecular Vision.18:2673–2686.PMC 3501277.PMID 23170060.
  10. ^ab"Taurine". PubChem, US National Library of Medicine. 25 May 2024. Retrieved31 May 2024.
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  13. ^abEFSA Panel on Additives and Products or Substances used in Animal Feed (2012)."Scientific Opinion on the safety and efficacy of taurine as a feed additive for all animal species".EFSA Journal.10 (6): 2736.doi:10.2903/j.efsa.2012.2736.
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  18. ^Ronalds BF (2019)."Bringing Together Academic and Industrial Chemistry: Edmund Ronalds' Contribution".Substantia.3 (1):139–152. Retrieved7 April 2025.
  19. ^Lambert IH (2004). "Regulation of the Cellular Content of the Organic Osmolyte Taurine in Mammalian Cells".Neurochemical Research.29 (1):27–63.doi:10.1023/b:nere.0000010433.08577.96.PMID 14992263.
  20. ^Kataoka H, Ohnishi N (1986)."Occurrence of Taurine in Plants".Agricultural and Biological Chemistry.50 (7):1887–1888.doi:10.1271/bbb1961.50.1887.
  21. ^abMcCusker S, Buff PR, Yu Z, Fascetti AJ (2014)."Amino acid content of selected plant, algae and insect species: a search for alternative protein sources for use in pet foods".Journal of Nutritional Science.3 e39.doi:10.1017/jns.2014.33.ISSN 2048-6790.PMC 4473169.PMID 26101608.
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  33. ^Jacobson SG, Kemp CM, Borruat FX, Chaitin MH, Faulkner DJ (October 1987). "Rhodopsin topography and rod-mediated function in cats with the retinal degeneration of taurine deficiency".Experimental Eye Research.45 (4):481–490.doi:10.1016/S0014-4835(87)80059-3.PMID 3428381.
  34. ^Spitze AR, Wong DL, Rogers QR, Fascetti AJ (Aug 2003)."Taurine concentrations in animal feed ingredients; cooking influences taurine content"(PDF).Journal of Animal Physiology and Animal Nutrition.87 (7–8):251–262.doi:10.1046/j.1439-0396.2003.00434.x.PMID 12864905. RetrievedJanuary 27, 2024.
  35. ^dos Santos BA, Campagnol PC, Morgano MA, Pollonio MA (January 2014). "Monosodium glutamate, disodium inosinate, disodium guanylate, lysine and taurine improve the sensory quality of fermented cooked sausages with 50% and 75% replacement of NaCl with KCl".Meat Science.96 (1):509–513.doi:10.1016/j.meatsci.2013.08.024.PMID 24008059.
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