107-35-7 Usage
Description
Taurine, also known as 2-aminoethanesulfonic acid, is a sulfur-containing amino acid found in animal tissues. It is a major constituent of bile and plays a crucial role in various biological processes such as conjugation of bile acids, antioxidation, osmoregulation, membrane stabilization, and modulation of calcium signaling. Taurine is a conditionally essential amino acid for the human body and is important for the development of the fetal and infant nervous system. It is an odorless, slightly sour, white crystalline powder or white powder that is stable to heat and exists in both bound and free forms in different tissues.
Uses
Used in Medicine:
Taurine is used as a vitamin B1 and enzyme cofactor, playing a vital role in various metabolic processes.
Used in Food Additives:
Taurine is used as a food additive due to its various physiological functions, including its role as a neurotransmitter in the brain, regulation of cardiovascular function, and development and function of skeletal muscle, the retina, and the central nervous system.
Used in Energy Drinks:
Taurine is used in energy drinks due to its highly important physiological role, providing energy and supporting overall health.
Used in Cosmetics:
Taurine is used in cosmetics to maintain skin hydration, benefiting from its osmoregulation properties.
Used in Contact Lens Solutions:
Taurine is used in contact lens solutions to maintain eye health and support the function of the retina.
Used in Biochemical Research:
Taurine can be used as a biochemical reagent, wetting agent, and pH buffer, supporting various research applications.
Used in Fluorescent Brighteners and Organic Synthesis:
Taurine can be used in the production of fluorescent brighteners and organic synthesis, highlighting its versatility in different industries.
Occurrence:
Taurine is found in various natural sources such as beef, black beans, chicken, chickpeas, clams, cod, fish, lamb, milk, octopus, oysters, pistachios, pork, scallops, shrimp, and more.
History
As the conditionally essential amino acid of the human body, it is a kind of β- sulphamic acid. In mammalian tissues, it is a metabolite of methionine and cystine. It was first isolated from ox bile in 1827, hence the name taurine. It commonly exists in the form of free amino acids in various tissues of animals, but not goes into proteins without combination. Taurine is rarely found in plants. Early on, people had considered it a bile acid binding agent of taurocholic combined with cholic acid. However, recent studies have shown that taurine has many important biological functions apart from the above mentioned forming taurocholic acid and participating in the digestion and absorption of lipids.It is important nutrients for normal development and function of cranial nerve to play the role in adjusting a variety of nerve cells of the central nervous system; taurine in retina accounts for 40% to 50% of total free amino acid, which is necessary for maintaining the structure and function of photoreceptor cells; affecting the myocardial contracts dint, regulating calcium metabolism, controlling arrhythmia, lowering blood pressure, etc; maintaining cellular antioxidant activity to protect the tissues from damaging free radicals; decreasing platelet aggregation and so on.
As the metabolites containing sulphur amino acids, mammals have different abilities to synthesize taurine: The synthetic ability of rats and dogs is stronger, the synthetic ability of human and primate is lower, while that of kits and human infants is very low. Taurine in the infant mainly comes from the diet, so it is recommended to supplement the taurine in the baby's diet. Foods with a higher content of taurine include conch, clam, mussel, oyster, squid and other shellfish food, which chould be up to 500 ~ 900mg/100g in the table part; the content in fish is comparably different; the content in poultry and offal is also rich; the content in human milk is higher than cow milk; taurine is not found in eggs and vegetable food.
Medicinal effect
Liver-strengthening cholagogue function: The combination of taurine and cholic acid can increase biliary permeability and is related to bile backflow; this product can also reduce cholesterol levels in the liver and reduce the formation of cholesterol calculus.
Anti-inflammatory and antipyretic effects: It can lower the body temperature by effects on the central 5-HT system or catecholamine system.
Hypotensive effect: After injecting this product, it shows the effects including reducing blood pressure, slowing down heart rate, regulating vascular tension and so on.
Cardiac and anti-arrhythmia action: This product can regulate the combination of Ca++ in cardiac myocytes and can reverse the adverse effects of Ca++ on the myocardium.
Hypoglycemic effect: This product directly affects the insulin receptor of the liver and muscle cell membrane and has the effect of insulin-like hypoglycemic action.
Other effects: loosening up skeletal muscle, reversing myotonia and fighting fatigue after exercise. Local application of this product can reduce the increased pressure in the eyeball caused by prostaglandin; there are still nutritional effects. Clinical use at acute hepatitis, chronic hepatitis, fatty liver, cholecystitis, etc.,as well as use in bronchitis, tonsillitis, ophthalmia and other infectious diseases. This product can be tried for cold, alcohol withdrawal symptoms, arthritis, myotonia, etc.
Preparation
Extract from the mollusk such as fish, shellfish and so on.
After reacting to form sodium 2-hydroxyethanesulfonate at 70℃with ethylene oxide and sodium hydrogen sulfite as raw materials, this product can be obtained by further aminolysis and desalination [1].
It can be obtained by reaction between ethylene imine and sulfurous acid [1].
It can be obtained with nitroethylene and sodium bisulfite as raw materials[1]. CH2＝CHNO2+NaHSO3→[1]
It can be obtained preparing by sulfonation of sodium sulfite and aminolysis in liquid ammonia with sodium sulfite as the raw material [1].
Ethanolamine is used as the raw material to react with hydrochloric acid to form chloroethylamine hydrochloride, which is reacted with sodium sulfite to produce sodium ethylamine sulfonate. This product can be obtained by desalination with dilute sulphuric acid [1].
Use aziridine as the raw material and react with sulfur dioxide and water to obtain this product [1].
Like 6, it can be obtained by using bromoethylamine hydrobromide as the raw material and reacting with sodium sulfite [1].
Use 1, 2-dichloroethane as the raw material and react with sodium sulfite to produce chloroethanesulfonic acid sodium salt. React with ammonia under heating with pressure to form sodium amino ethyl sulfonate. Then it can be prepared by hydrochloric acid-acidification desalination [1].
Like 9, we use hydroxyethanesulphonic acid as the raw material and react with ammonia under heating with pressure to obtain this product [1].
We use 2,2-dimethyl thiazoles as the raw material, hydrogen peroxide or manganese dioxide as the oxidizing agent. This product can be obtained by oxidation under pressure [1], with acetone as by-product at the same time.
It can be obtained by using 2-amino alcohol monoester as the raw material and reacting with sodium sulfite [1]. (H2NCH2CH2O)HSO3+Na2SO3→ [1]+Na2SO4
N- vinyl propanamide is used as the raw material to react with sodium bisulfite to produce sodium 2- propane amino ethyl sulfonate. Then this product can be obtained by acidification desalination and hydrolysis.
References
https://en.wikipedia.org/wiki/Taurine
https://pubchem.ncbi.nlm.nih.gov/compound/taurine#section=Top
Biosynthesis
In addition to the intake of taurine directly from the diet, the animal body can also biosynthesis in the liver. The intermediate product of methionine and cysteine metabolism, cysteine, is decarboxylated to taurine by cysteine decarboxylase (CSAD), and then oxidized to taurine. CSAD is considered to be the rate limiting enzyme of taurine biosynthesis in mammals, and compared with other mammals, the activity of human CSAD is lower, which may be due to the low taurine synthesis ability in human body. Taurine can participate in the formation of taurocholic acid and hydroxyethyl sulfonic acid after decomposition in vivo. The amount of taurine required depends on cholic acid binding capacity and muscle content.
Air & Water Reactions
Water soluble.
Reactivity Profile
Taurine is an amino acid found in combination with bile acids [Hawley].
Hazard
Toxic by ingestion.
Health Hazard
ACUTE/CHRONIC HAZARDS: Taurine evolves highly toxic fumes when heated to decomposition, and may cause irritation on contact.
Fire Hazard
Flash point data are not available for Taurine, but Taurine is probably combustible.
Biological Activity
One of the most abundant free amino acids in the brain. A partial agonist at the inhibitory glycine receptor.
Biochem/physiol Actions
Non-selective endogenous agonist at glycine receptors. Conditionally essential sulfonated amino acid which modulates apoptosis in some cells; functions in many metabolic activities; a product of methionine and cysteine metabolism.
Pharmacology
Taurine is an organic osmotic regulator. It not only participates in the regulation of cell volume, but also provides the basis for the formation of bile salts. It also plays an important role in the modulation of intracellular free calcium concentration. Although taurine is a special amino acid not included in proteins, taurine is the most abundant amino acid in brain, retina and muscle tissue. Taurine is widely used, such as in the function of central nervous system, cell protection, cardiomyopathy, renal insufficiency, abnormal development of renal function and retinal nerve injury. Almost all eye tissues contain taurine. The quantitative analysis of rat eye tissue extract showed that taurine was the most abundant amino acid in retina, vitreous, lens, cornea, iris and ciliary body. Many studies have found that taurine is an active substance that regulates the normal physiological activities of the body. It has the functions of anti-inflammatory, analgesic, maintaining the osmotic pressure balance of the body, maintaining normal visual function, regulating the calcium balance of cells, reducing blood sugar, regulating nerve conduction, participating in endocrine activities, regulating lipid digestion and absorption, increasing the contractility of the heart, improving the immune capacity of the body, and enhancing the antioxidant capacity of cell membrane Protect a wide range of biological functions such as cardiomyocytes.
Safety Profile
Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Veterinary Drugs and Treatments
Taurine has proven beneficial in preventing retinal degeneration
and the prevention and treatment of taurine-deficiency dilated
cardiomyopathy in cats. Although modern commercial feline diets
have added taurine, some cats still develop taurine-deficiency associated
dilated cardiomyopathy. It may also be of benefit in taurine
(±carnitine) deficient cardiomyopathy in American Cocker
Spaniels and certain other breeds such as, Golden Retrievers,
Labrador Retrievers, Newfoundlands, Dalmations, Portuguese
Water Dogs, and English Bulldogs. Preliminary studies have shown
evidence that it may be useful as adjunctive treatment for cardiac
disease in animals even if taurine deficiency is not present. Because
of its low toxicity, some have suggested it be tried for a multitude
of conditions in humans and animals; unfortunately, little scientific
evidence exists for these uses.
Check Digit Verification of cas no
The CAS Registry Mumber 107-35-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 107-35:
(5*1)+(4*0)+(3*7)+(2*3)+(1*5)=37
37 % 10 = 7
So 107-35-7 is a valid CAS Registry Number.
InChI:InChI=1/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H-,4,5,6)
107-35-7Relevant articles and documents
Reactivity and the mechanisms of reactions of β-sultams with nucleophiles
Wood, J. Matthew,Hinchliffe, Paul S.,Laws, Andrew P.,Page, Michael I.
, p. 938 - 946 (2002)
Ethane-1,2-sultam has a pKa of 12.12±0.06 at 30 °C and its rate of alkaline hydrolysis shows a pH-dependence reflecting this so that the observed pseudo first-order rate constant at phs above the pKa are pH independent. There is no evidence of neighbouring group participation in the hydrolysis of either N-α-carboxybenzylethane-1,2-sultam or N-(hydroxyaminocarbonylmethyl)-2-benzylethane-1,2-sultam. Oxyanions, but not amines or thiols, react with N-benzoylethane-1,2-sultam in water by a nucleophilic ring opening reaction confirmed by product analysis and kinetic solvent isotope effects. A Bronsted plot for this reaction has two distinct correlations with βnuc = 0.52 and 0.65 for weak and strong bases, respectively, although a statistically corrected plot may indicate a single correlation.
-
Goldberg
, p. 4 (1943)
-
Human flavin-containing monooxygenase 1 and its long-sought hydroperoxyflavin intermediate
Catucci, Gianluca,Cheropkina, Hanna,Fenoglio, Ivana,Gilardi, Gianfranco,Marucco, Arianna,Sadeghi, Sheila J.
, (2021)
Out of the five isoforms of human flavin-containing monooxygenase (hFMO), FMO1 and FMO3 are the most relevant to Phase I drug metabolism. They are involved in the oxygenation of xenobiotics including drugs and pesticides using NADPH and FAD as cofactors. Majority of the characterization of these enzymes has involved hFMO3, where intermediates of its catalytic cycle have been described. On the other hand, research efforts have so far failed in capturing the same key intermediate that is responsible for the monooxygenation activity of hFMO1. In this work we demonstrate spectrophotometrically the formation of a highly stable C4a-hydroperoxyflavin intermediate of hFMO1 upon reduction by NADPH and in the presence of O2. The measured half-life of this flavin intermediate revealed it to be stable and not fully re-oxidized even after 30 min at 15 °C in the absence of substrate, the highest stability ever observed for a human FMO. In addition, the uncoupling reactions of hFMO1 show that this enzyme is 2O2 with no observable superoxide as confirmed by EPR spin trapping experiments. This behaviour is different from hFMO3, that is shown to form both H2O2 and superoxide anion radical as a result of ～50% uncoupling. These data are consistent with the higher stability of the hFMO1 intermediate in comparison to hFMO3. Taken together, these data demonstrate the different behaviours of these two closely related enzymes with consequences for drug metabolism as well as possible toxicity due to reactive oxygen species.
Oxyhalogen-sulfur chemistry: Non-linear oxidation of 2-aminoethanethiolsulfuric acid (AETSA) by bromate in acidic medium
Darkwa, James,Mundoma, Claudius,Simoyi, Reuben H.
, p. 4407 - 4413 (1996)
The reaction between bromate and 2-aminoethanethiolsulfuric acid, H2NCH2CH2S-SO3H (AETSA), has been studied in high acid environments. The stoichiometry in excess AETSA is BrO3- + H2NCH2CH2S-SO3H + H2O → H2NCH2CH2SO3H + SO42- + 2H+ + Br- . In excess BrO3- the stoichiometry is: 7BrO3- + 5H2NCH2CH2S-SO3H → 5Br(H)NCH2CH2SO3H + 5SO42- + Br2 + 3H+ + H2O. The reaction displays clock reaction characteristics in which there is initial quiescence followed by a sudden and rapid formation of Br2(aq). The oxidation proceeds by successive addition of oxygen on the inner sulfur atom followed by cleavage of the S-S bond to form taurine and SO42-. The Br2(aq) and the HOBr in solution oxidize the taurine to form a mixture of monobromotaurine and dibromotaurine. Computer simulations of a proposed 13-step reaction scheme produced a reasonable fit to the experimental data.
Bioactive metabolites from the Caribbean sponge Aka coralliphagum
Grube, Achim,Assmann, Michael,Lichte, Ellen,Sasse, Florenz,Pawlik, Joseph R.,Koeck, Matthias
, p. 504 - 509 (2007)
The chemistry of the burrowing sponge Aka coralliphagum was investigated to identify chemically labile secondary metabolites. The HPLC-MS analysis of the two growth forms typica and incrustans revealed different metabolites. The previously unknown sulfated compounds siphonodictyals B1 to B3 (6-8), corallidictyals C (9) and D (10), and siphonodictyal G (11) were isolated, and their structures were elucidated by NMR and MS experiments. The compounds were tested in a DPPH assay, in antimicrobial assays against bacteria, yeasts, and fungi, and in antiproliferation assays using cultures of mouse fibroblasts. The biological activity was linked to the presence of the ortho-hydroquinone moiety.
Kermack,Slater
, p. 1065 (1927)
Trofosides A and B and other cytostatic steroid-derived compounds from the far east starfish Trofodiscus ueber
Levina,Kalinovsky,Andriyashchenko,Menzorova,Dmitrenok
, p. 334 - 340 (2007)
Three new polar steroids identified as trofoside A, 20R,24S)-24-O-(3-O- methyl-β-D-xylopyranosyl)-3β,6α,8,15β,24-pentahydroxy- 5α-cholestane, its 22(23)-dehydro derivative (trofoside B), and 15-sulfooxy-(20R,24S)-5α-cholestane-3β,6β,8,15α, 24-pentaol sodium salt, were isolated fromTrofodiscus ueber starfish extracts collected in the Sea of Ohotsk. Two known compounds, trofoside A aglycone, (20R,24S)-3β,6α,8,15β,24-pentahydroxy-5α- cholestane, and triseramide, (20R,24R,25S,22E)-24-methyl-3β6α,8, 15β-tetrahydroxy-5α-cholest-22-en-27-oic acid (2-sulfoethyl)amide sodium salt, were also found. The structures of the isolated polyoxysteroids were established from their spectra. Minimal concentrations causing degradation of unfertilized egg-cells of the sea-urchin Strongylocentrotus intermedius(C min) and terminating the cell division at the stage of the first division (C min embr.), as well as the concentrations causing 50% immobilization of sperm cells (OC50) and inhibiting their ability to fertilize egg-cells by 50% (IC50) were determined for the isolated compounds. Of three compounds highly toxic in embryos and sea-urchin sperm cells, the polyol with a sulfo group in the steroid core was the most active; two glycosides with monosaccharide chains located at C3 and C24 atoms were less toxic. Note that all the compounds with the spermiotoxic activities differently affected the embryo development. The positions of monosaccharide residues in the core considerably influence the compound activity. For example, both mono-and double chained glycosides with the monosaccharide fragment at C3 and fragments at C3 and C4 atoms are active against sea-urchin sperm cells and embryos, whereas the C24 glycosylated trofoside A does not affect embryos and displays a poor spermiotoxicity. Nauka/Interperiodica 2007.
Purification and characterization of the first archaeal glutamate decarboxylase from Pyrococcus horikoshii
Kim, Han-Woo,Kashima, Yasuhiro,Ishikawa, Kazuhiko,Yamano, Naoko
, p. 224 - 227 (2009)
Glutamate decarboxylase (GAD) from the archaeon Pyrococcus horikoshii was successfully expressed and purified, with the aim of developing a hyperthermostable GAD for industrial applications. Its biochemical properties were different from those reported for other GADs. The enzyme had broad substrate specificity, and its optimum pH and temperature were pH 8.0 and >97°C.
PROCESS SULFONATION OF AMINOETHYLENE SULFONIC ESTER TO PRODUCE TAURINE
-
Paragraph 0030-0031, (2021/06/04)
A process comprises continuously adding a first stream and a second stream to a sulfonation vessel, wherein the first stream comprises aminoethanol sulfate ester (AES) and the second stream comprises an aqueous solution of sodium sulfite (Na2SO3). The process comprises continuously mixing the AES and the aqueous solution of Na2SO3 in the sulfonation vessel, thus producing a mixture. The process comprises continuously subjecting the mixture to heat in the presence of an inert gas, thus converting the AES to the taurine via sulfonation. In an aspect, the AES has a residence time of no more than four hours in the sulfonation vessel. In an aspect the heating step is conducted at a temperature of at least 115° C and a pressure of at least 200 psi.
Taurine synthesis method (by machine translation)
-
Paragraph 0036; 0039-0041; 0044-0045; 0048-0049; 0052, (2020/07/15)
The invention provides a taurine synthesis method, and solves the problems of by-product accumulation, high temperature and high pressure in ammonia decomposition reaction, strong strong acid and strong base in acidification and the like in an addition reaction in a traditional taurine synthesis process. The method comprises the following steps: 1) carrying out cyclization reaction of sulfur solution and ethylene contact to obtain a solution of sulfur dissolved in carbon disulfide; 2) carrying out an addition reaction with ammonia or liquid ammonia contact to obtain an amino thiol; 3) carrying out an oxidation reaction in the presence of a catalyst to obtain the crude taurine. (by machine translation)
