Record Information
Version1.0
Creation date2015-10-09 22:27:19 UTC
Update date2017-01-19 02:36:10 UTC
FoodComEx IDPC000016
FoodDB RecordFDB003191
Chemical Information
NameTaurine
DescriptionEssential nutrient obtained from diet and by in vivo synthysis from methionine and cysteine. Present in meats, fish, legumes, human milk, molluscs and other foods. Dietary supplement, e.g. in Red Bull drink. Taurine is a sulfur amino acid like methionine, cystine, cysteine and homocysteine. It is a lesser-known amino acid because it is not incorporated into the structural building blocks of protein. Yet taurine is an essential amino acid in pre-term and newborn infants of humans and many other species. Adults can synthesize their own taurine, yet are probably dependent in part on dietary taurine. Taurine is abundant in the brain, heart, breast, gallbladder and kidney and has important roles in health and disease in these organs. Taurine has many diverse biological functions serving as a neurotransmitter in the brain, a stabilizer of cell membranes and a facilitator in the transport of ions such as sodium, potassium, calcium and magnesium. Taurine is highly concentrated in animal and fish protein, which are good sources of dietary taurine. It can be synthesized by the body from cysteine when vitamin B6 is present. Deficiency of taurine occurs in premature infants and neonates fed formula milk, and in various disease states. Inborn errors of taurine metabolism have been described. OMIM 168605, an unusual neuropsychiatric disorder inherited in an autosomal dominant fashion through 3 generations of a family. Symptoms began late in the fifth decade in 6 affected persons and death occurred after 4 to 6 years. The earliest and most prominent symptom was mental depression not responsive to antidepressant drugs or electroconvulsive therapy. Sleep disturbances, exhaustion and marked weight loss were features. Parkinsonism developed later, and respiratory failure occurred terminally. OMIM 145350 describes congestive cardiomyopathy and markedly elevated urinary taurine levels (about 5 times normal). Other family members had late or holosystolic mitral valve prolapse and elevated urinary taurine values (about 2.5 times normal). In 2 with mitral valve prolapse, congestive cardiomyopathy eventually developed while the amounts of urinary taurine doubled. Taurine, after GABA, is the second most important inhibitory neurotransmitter in the brain. Its inhibitory effect is one source of taurine's anticonvulsant and antianxiety properties. It also lowers glutamic acid in the brain, and preliminary clinical trials suggest taurine may be useful in some forms of epilepsy. Taurine in the brain is usually associated with zinc or manganese. The amino acids alanine and glutamic acid, as well as pantothenic acid, inhibit taurine metabolism while vitamins A and B6, zinc and manganese help build taurine. Cysteine and B6 are the nutrients most directly involved in taurine synthesis. Taurine levels have been found to decrease significantly in many depressed patients. One reason that the findings are not entirely clear is because taurine is often elevated in the blood of epileptics who need it. It is often difficult to distinguish compensatory changes in human biochemistry from true metabolic or deficiency disease. Low levels of taurine are found in retinitis pigmentosa. Taurine deficiency in experimental animals produces degeneration of light-sensitive cells. Therapeutic applications of taurine to eye disease are likely to be forthcoming. Taurine has many important metabolic roles. Supplements can stimulate prolactin and insulin release. The parathyroid gland makes a peptide hormone called glutataurine (glutamic acid-taurine), which further demonstrates taurine's role in endocrinology. Taurine increases bilirubin and cholesterol excretion in bile, critical to normal gallbladder function. It seems to inhibit the effect of morphine and potentiates the effects of opiate antagonists. Low plasma taurine levels have been found in a variety of conditions, i.e., depression, hypertension, hypothyroidism, gout, institutionalized patients, infertility, obesity, kidney failure and others. (http://www.dcnutrition.com/AminoAcids/); Taurine is an essential dietary requirement for feline health, since cats cannot synthesize the compound. The absence of taurine causes a cat's retina to slowly degenerate, causing eye problems and (eventually) irreversible blindness ? a condition known as central retinal degeneration (CRD), as well as hair loss and tooth decay. It was discovered in 1987 that taurine deficiency can also cause feline dilated cardiomyopathy. Unlike CRD, the condition is reversible with supplementation. 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.; Taurine, or 2-aminoethanesulfonic acid, is an organic acid. It is also a major constituent of bile and can be found in the lower intestine and in small amounts in the tissues of many animals, including humans. Taurine is a derivative of the sulfur-containing (sulfhydryl) amino acid, cysteine. Taurine is one of the few known naturally occurring sulfonic acids.
CAS Number107-35-7
Structure
Thumb
Synonyms
SynonymSource
β-aminoethylsulfonic acidbiospider
1-Aminoethane-2-sulfonatebiospider
1-Aminoethane-2-sulfonic acidbiospider
2-Aminoethanesulfonatebiospider
2-Aminoethanesulfonic acidChEBI
2-AminoethanesulphonateGenerator
2-Aminoethanesulphonic acidGenerator
2-aminoethyl sulfonatebiospider
2-Aminoethyl sulfonic acidGenerator
2-Aminoethyl sulphonateGenerator
2-Aminoethyl sulphonic acidGenerator
2-Aminoethylsulfonatebiospider
2-Aminoethylsulfonic acidbiospider
2-Sulfoethylaminebiospider
Aminoethanesulfonic acidbiospider
Aminoethylsulfonatebiospider
Aminoethylsulfonic aciddb_source
Aminoethylsulfonic acid (jan)biospider
AminoethylsulphonateGenerator
Aminoethylsulphonic acidGenerator
Aminoetylsulphonic acidbiospider
B-aminoethylsulfonatebiospider
B-aminoethylsulfonic acidbiospider
b-AminoethylsulphonateGenerator
b-Aminoethylsulphonic acidGenerator
Beta-aminoethylsulfonatebiospider
Beta-aminoethylsulfonic acidbiospider
beta-AminoethylsulphonateGenerator
beta-Aminoethylsulphonic acidGenerator
Ethanesulfonic acid, 2-amino-biospider
Ethanesulfonic acid, 2-amino- (9CI)biospider
Ethylaminesulfonic aciddb_source
Ethylaminesulphonic acidbiospider
FEMA 3813db_source
L-taurinebiospider
O-duebiospider
TAUbiospider
Taufonbiospider
Taukardbiospider
Tauphonbiospider
Taurinebiospider
Taurine (8CI)biospider
Taurine (JP15/USP/INN)biospider
Taurine (TN)biospider
Taurine [inn]biospider
Taurine, 8CI, INNdb_source
β-aminoethylsulfonateGenerator
β-aminoethylsulfonic acidGenerator
β-aminoethylsulphonateGenerator
β-aminoethylsulphonic acidGenerator
Chemical FormulaC2H7NO3S
IUPAC name2-aminoethane-1-sulfonic acid
InChI IdentifierInChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
InChI KeyXOAAWQZATWQOTB-UHFFFAOYSA-N
Isomeric SMILESNCCS(O)(=O)=O
Average Molecular Weight125.147
Monoisotopic Molecular Weight125.014663785
Chemical Taxonomy
Description belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water Solubility80.7 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 328° (320-325° dec.)DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 6 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci I815
AKSci J90118
Glentham GP1188
MetaSci HMDB0000251
Sigma-Aldrich HMDB0000251
Toronto Research Chemicals T007850