Taurine

This article is about the chemical compound. For the bovine sub-species, see Taurine cattle.

Taurine
Names
Preferred IUPAC name
2-Aminoethanesulfonic acid
Other names
Tauric acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.168 Edit 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 mass 125.14 g/mol
Appearance colorless or white solid
Density 1.734 g/cm3 (at −173.15 °C)
Melting point 305.11 °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 their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Taurine (/ˈtɔːriːn/), or 2-aminoethanesulfonic acid, is a non-proteinogenic naturally occurring amino sulfonic acid that is widely distributed in animal tissues.[1] It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight.

Taurine is named after Latin taurus (cognate to Ancient Greek ταῦρος, taûros) meaning bull or ox, as it was first isolated from ox bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin.[2] It was discovered in human bile in 1846 by Edmund Ronalds.[3]

Although taurine is abundant in human organs with diverse putative roles, it is not an essential human dietary nutrient and is not included among nutrients with a recommended intake level.[4] Taurine is synthesized naturally in human liver from methionine and cysteine.[5]

Taurine is commonly sold as a dietary supplement, but there is no good clinical evidence that taurine supplements provide any benefit to human health.[6] Taurine is used as a food additive for cats (who require it as an essential nutrient), dogs, and poultry.[7]

Taurine concentrations in land plants are low or undetectable, but up to 1000 nmol/g wet weight have been found in algae.[8][9]

Chemical and biochemical features

Taurine exists as a zwitterion H3N+CH2CH2SO−3, as verified by X-ray crystallography.[10] The sulfonic acid has a low pKa[11] ensuring that it is fully ionized to the sulfonate at the pHs found in the intestinal tract.

Synthesis

Synthetic taurine is obtained by the ammonolysis of isethionic acid (2-hydroxyethanesulfonic acid), which in turn is obtained from the reaction of ethylene oxide with aqueous sodium bisulfite. A direct approach involves the reaction of aziridine with sulfurous acid.[12]

In 1993, about 5000–6000 tonnes of taurine were produced for commercial purposes: 50% for pet food and 50% in pharmaceutical applications.[13] As of 2010, China alone has more than 40 manufacturers of taurine. Most of these enterprises employ the ethanolamine method to produce a total annual production of about 3000 tonnes.[14]

In the laboratory, taurine can be produced by alkylation of ammonia with bromoethanesulfonate salts.[15]

Biosynthesis

Taurine is naturally derived from cysteine. Mammalian taurine synthesis occurs in the liver via the cysteine sulfinic acid pathway. In this pathway, cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine dioxygenase. Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine. Hypotaurine is enzymatically oxidized to yield taurine by hypotaurine dehydrogenase.[16]

Taurine is also produced by the transsulfuration pathway, which converts homocysteine into cystathionine. The cystathionine is then converted to hypotaurine 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.[17]

A pathway for taurine biosynthesis from serine and sulfate is reported in microalgae,[9] developing chicken embryos,[18] and chick liver.[19] Serine dehydratase converts serine to 2-aminoacrylate, which is converted to cysteic acid by 3′-phosphoadenylyl sulfate:2-aminoacrylate C-sulfotransferase. Cysteic acid is converted to taurine by cysteine sulfinic acid decarboxylase.

Oxidative degradation of cysteine to taurine

In food

Taurine occurs naturally in fish and meat.[6][20][21] The mean daily intake from omnivore diets was determined to be around 58 mg (range 9–372 mg),[22] and to be low or negligible from a vegan diet.[6] Typical taurine consumption in the American diet is about 123–178 mg per day.[6]

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. Either raw feeding or addition of extra taurine can satisfy this requirement.[23][24]

Lysine and taurine can both mask the metallic flavor of potassium chloride, a salt substitute.[25]

Breast milk

Prematurely born infants are believed to lack the enzymes needed to convert cystathionine to cysteine, and may, therefore, become deficient in taurine. Taurine is present in breast milk, and has been added to many infant 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.[26]

Energy drinks and dietary supplements

Taurine is an ingredient in some energy drinks in amounts of 1–3 g per serving.[6][27][28][29] A 1999 assessment of European consumption of energy drinks found that taurine intake was 40–400 mg per day.[22][clarification needed]

Research

Taurine is not regarded as an essential human dietary nutrient and has not been assigned recommended intake levels.[4] High-quality clinical studies to determine possible effects of taurine in the body or following dietary supplementation are absent from the literature.[6] Preliminary human studies on the possible effects of taurine supplementation have been inadequate due to low subject numbers, inconsistent designs, and variable doses.[6] Preliminary studies have suggested that supplementing with taurine may increase exercise capacity[30][31][32] and affects lipid profiles in individuals with diabetes.[33][34]

Safety and toxicity

According to the European Food Safety Authority (EFSA), 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.[7] Other sources indicate that taurine is safe for supplemental intake in normal healthy adults at up to 3 grams per day.[6][35]

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 of guarana, taurine, and ginseng found in popular energy drinks are far below the amounts expected to deliver either therapeutic benefits or adverse events".[36]

Animal dietary requirement

Cats

Cats lack the enzymatic machinery (sulfinoalanine decarboxylase) to produce taurine and must therefore acquire it from their diet.[37] A taurine deficiency in cats can lead to retinal degeneration and eventually blindness – a condition known as central retinal degeneration[38][39] as well as hair loss and tooth decay. Other effects of a diet lacking in this essential amino acid are dilated cardiomyopathy and reproductive failure in female cats.[40]

Decreased plasma taurine concentration has been demonstrated to be associated with feline dilated cardiomyopathy. Unlike CRD, the condition is reversible with supplementation.[41]

Taurine is now a requirement of the Association 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.[42] Studies suggest the amino acid should be supplied at 10 mg per kilogram of bodyweight per day for domestic cats.[43]

Other mammals

A number of other mammals also have a requirement for taurine. While the majority of dogs can synthesize taurine, case reports have described a singular American cocker spaniel, 19 Newfoundland dogs, and a family of golden retrievers suffering from taurine deficiency treatable with supplementation. Foxes on fur farms also appear to require dietary taurine. The rhesus, cebus and cynomolgus monkeys each require taurine at least in infancy. The giant anteater also requires taurine.[44]

Birds

Taurine appears to be essential for the development of passerine birds. Many passerines seek out taurine-rich spiders 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, each blue tit nestling receive 1 mg of taurine per day from parents.[45]

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.[46]

Fish

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.[47]

The need of taurine in fish is conditional, differing by species and growth stage. The Olive flounder, for example, has lower capacity to synthesize taurine compared to the rainbow trout. Juvenile fish are less efficient at taurine biosyntheis due to reduced cysteine sulfinate decarboxylase levels.[48]

Derivatives

See also: Derivative (chemistry)

See also

References

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2020 studio album by PentagonUniverse: The HistoryType C and digital coverStudio album by PentagonReleasedSeptember 23, 2020Recorded2017–2020GenreJ-popLanguageJapaneseLabelCubeU-CubePentagon chronology Universe: The Black Hall(2020) Universe: The History(2020) We:th(2020) Pentagon Japanese chronology Shine(2018) Universe: The History(2020) Do or Not(2021) Alternative coverType A Type B Singles from Universe: The History Dr. Bebe (Japanese Ver.)Released: September 14, 2020 Universe: ...

 

 

Evagrius Scholasticus

6th-century Syrian scholar and intellectual Evagrius ScholasticusBorn536Epiphania, Byzantine EmpireDied594OccupationScholar and intellectualNotable worksEcclesiastical History Evagrius Scholasticus (Greek: Εὐάγριος Σχολαστικός) was a Syrian scholar and intellectual living in the 6th century AD, and an aide to the patriarch Gregory of Antioch.[1] His surviving work, Ecclesiastical History (Ἐκκλησιαστικὴ Ἱστορία), comprises a six-volume collect...

Dracula's Dog

1977 American horror film Dracula's DogTheatrical release posterDirected byAlbert BandWritten byFrank Ray PerilliBased onHounds of Draculaby Ken JohnsonProduced byPhilip CollinsStarring José Ferrer Michael Pataki Arlene Martel CinematographyBruce LoganEdited byHarry KeramidasMusic byAndrew BellingProductioncompanyVic ProductionsDistributed byCrown International Pictures (US)EMI Films (UK)Release dates May 8, 1977 (1977-05-08) (UK) March 29, 1978 (1978-03-29)...

 

 

Adi Da

Adi Da Samraj2010Lahir(1939-11-03)3 November 1939New YorkMeninggal27 November 2008(2008-11-27) (umur 69)Naitauba, Lau Islands, FijiNama lainFranklin Albert JonesPekerjaanGuru spiritual, penulis, artisDikenal atasPemrakasa AdidamAnakShawnee Free Jones Adi Da Samraj adalah seorang guru, penulis, dan Seniman spiritual Amerika yang. Adi Da adalah pendiri gerakan keagamaan baru yang dikenal sebagai Adidam. Terlahir dengan nama Franklin Albert Jones (3 November 1939 - 27 November 2008), d...

 

 

Alexei Fjodorowitsch Trjoschnikow

Alexei Fjodorowitsch Trjoschnikow Alexei Fjodorowitsch Trjoschnikow (russisch Алексей Фёдорович Трёшников, wiss. Transliteration Aleksej Fëdorovič Trëšnikov; * 1. Apriljul. / 14. April 1914greg. in Pawlowka, Gouvernement Simbirsk; † 18. November 1991 in Sankt Petersburg) war ein sowjetischer Polarforscher, Geograph und Ozeanologe. Inhaltsverzeichnis 1 Studium und erste Expeditionen 2 Zweiter Weltkrieg und Untersuchungen der Arktis 3 Sowjetische An...

Henry Thiele Restaurant

Defunct restaurant in Portland, Oregon, U.S. Henry Thiele RestaurantRestaurant informationEstablishedApril 14, 1932 (1932-04-14)Closed1990sFood typeGerman[1][2]Street address2315 Northwest Westover RoadCityPortland, OregonCountryUnited StatesCoordinates45°31′25″N 122°41′56″W / 45.52370°N 122.69883°W / 45.52370; -122.69883Seating capacity150 Henry Thiele Restaurant, or Henry Thiele's, was a restaurant located at 2315 Northwest ...

 

 

Automotive industry in South Africa

South Africa is traditionally the leader in Africa of the automotive industry and now produces more than half a million automobiles annually of all types. While domestic development of trucks and military vehicles exists, cars built under license of foreign brands are the mainstay. Current situation South Africa Export Treemap by Product (2012) from Harvard Atlas of Economic Complexity The modern automotive industry in South Africa was launched in 1995 and has since provided a large number of...

 

 

Legio XX Valeria Victrix

Roman legion Legion XX redirects here. For the album, see Legion: XX. Map of the Roman empire in AD 125, under emperor Hadrian, showing the Legio XX Valeria Victrix, stationed at Deva Victrix (Chester, England), in the province of Britannia. They were stationed there from AD 88 until at least the late 3rd century. Moulded antefix roof tile showing the badge and standard of Legion XX, from Holt, Clwyd, Wales Legio XX Valeria Victrix, in English Twentieth Victorious Valeria Legion, wa...

Timeline of Bursa

This is a dynamic list and may never be able to satisfy particular standards for completeness. You can help by adding missing items with reliable sources. Part of a series on the History of Turkey PrehistoryPrehistory of Anatolia Palaeolithic Anatolia c. 500,000– 10,000 BC Mesolithic Anatolia c. 11,000– 9,000 BC Neolithic Anatolia c. 8,000– 5,500 BC Bronze AgeTroy 3000–700 BCHattians 2500–2000 BCAkkadian Empire 2400–2150 BCLuwians 2300–1400 BCAssyria 1950–1750 B...

 

 

Cucurbita ficifolia

Plant species cultivated for edible shoots, leaves, flowers, fruit, and seeds Cidra redirects here. Not to be confused with Cidra, Puerto Rico or cider. Cucurbita ficifolia Scientific classification Kingdom: Plantae Clade: Tracheophytes Clade: Angiosperms Clade: Eudicots Clade: Rosids Order: Cucurbitales Family: Cucurbitaceae Genus: Cucurbita Species: C. ficifolia Binomial name Cucurbita ficifoliaBouché Synonyms[1] Cucurbita melanosperma A.Braun ex Gasp. Cucurbita mexicana Damma...

 

 

Strategi Solo vs Squad di Free Fire: Cara Menang Mudah!