Taurine

• IUPAC: 2- aminoethanesulfonic acid
• 2- Sulfoethylamin
• β - aminoethanesulfonic

Monoclinic, colorless and odorless prisms

Fixed

1.709 g · cm -3

328 ° C ( decomposition above 300 ° C)

• PKS1 = 1.5
• PKa2 = 8.74

• Soluble in water ( 63 g · l-1 at 20 ° C)
• Insoluble in ethanol and diethyl ether

Attention

> 5000 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Taurine ( INN) or 2- aminoethanesulphonic acid is an organic acid having a sulfonic acid group and contains an amino group. Aminosulfonic acid as it can not form peptides. Taurine is a degradation product of the amino acids cysteine ​​and methionine, but any amino acid, since it contains no carboxyl group.

History

Taurine was first isolated in 1827 by chemists Leopold Gmelin and Friedrich Tiedemann from the bile of ox (Bos taurus) and initially called bile - asparagine. It is located in the bile as taurocholic ago, a Cholsäureamid from which it can be released by acid hydrolysis. The term " taurine " comes from the Latin for bull bile, Fel tauri, or from the Greek word tauros for " bull" and is first mentioned in 1838 in the literature. This common name has probably owe the emergence of numerous legends about its effect taurine.

Chemical and physical properties

Taurine is a colorless crystalline substance that decomposes above 300 ° C and melts at 328 ° C. It is soluble in water up to about 100 g / l. The good water solubility and high melting point agree - similar to amino acids - the formation of the zwitterion ( H3N - C2H4 - SO3 ).

Taurine is produced industrially by addition of sulfite to aziridine.

Biological Properties

The adult human body can make taurine from the amino acid cysteine ​​itself. This cysteine ​​is oxidized to NAD and oxygen consumption in a number of intermediate steps to taurine. A second formation mechanism results in the degradation of coenzyme A by decarboxylation of cysteamine. A supply of food is not necessary in adults.

It is believed that the taurine content is within the body of a healthy human of 70 kg body weight, between 30 and 70 g, of which about 75% are present in the muscle cells, particularly in the remainder of the brain, heart and blood. A healthy person has thus 0.43 to 1 g of taurine per 1 kg of body weight in the body. Breast milk contains a concentration of between 25 to 50 milligrams of taurine per liter.

Dogs can make taurine itself. Cats make only small quantities, so they have to take taurine as a nutrient from their diet.

Biological effect

One of the few clearly defined functions in the metabolism of taurine include the formation of Gallensäurenkonjugaten, the influence of the signal transmission and potential role in the development of the central nervous system and the heart function. Taurine stimulates the influx and the membrane binding of calcium. In addition, it assists the movement of sodium and potassium through the cell membrane. The resulting supported stabilization of the membrane potential has an increase in the contraction and an antiarrhythmic effect on the heart. Taurine is a potent antioxidant and can protect tissues from oxidative damage. A low intramuscular taurine is characteristic of chronic renal failure. Taurine deficiency in the human body leads to an impaired immune system.

In addition, in animal studies an anti-inflammatory effect of taurine was found. A Taurinverarmung tissue pools, especially lung tissue, resulting in inflammation. Researchers at the School of Pharmacy, University of London found that taurine may reduce alcohol-induced liver damage. In a study of endurance athletes no performance-enhancing effect could be detected. In some cases a placebo effect is assumed.

In animal studies in rats taurine lowered blood pressure and resulted in the concomitant use of salt to a life-threatening hypernatremia. It also accelerated by influencing the level of insulin metabolism; that explains the enhancing effect of taurine in energy drinks, where it is next to caffeine and sugar one of the main ingredients. A can (250 ml) of known energy drinks Red Bull contains eg 1000 mg ( = 1 g) taurine. There is evidence that taurine should be supplied in renal failure and pneumonia. Others seem to show that taurine should be avoided in renal failure.