Taurine

Catalog	BBC107357
CAS	107-35-7
Structure
Description	Taurine is an organic acid found in animal tissues and is a major constituent of bile. Taurine has many biological roles such as conjugation of bile acids, antioxidation, osmoregulation, membrane stabilization and modulation of calcium signaling.
Synonyms	Aminoethanesulfonic acid
IUPAC Name	2-Aminoethanesulfonic acid
Molecular Weight	125.15
Molecular Formula	C2H7NO3S
Canonical SMILES	C(CS(=O)(=O)O)N
InChI	InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
InChI Key	XOAAWQZATWQOTB-UHFFFAOYSA-N
Melting Point	>300 °C(lit.)
Purity	98%
Density	1.00 g/mL at 20 °C
Solubility	Soluble in water
Appearance	Solid
Storage	2-8 °C
Active Content	95%
EC Number	203-483-8
pH	4.5-6.0 (0.5M, H₂O, 25°C)
pKa	1.5(at 25 °C)
Refractive Index	1.5130
Solubility in Water	50-100 g/L

Case Study

How Taurine Plays a Role in Inflammatory Diseases

Janusz Marcinkiewicz, et al. Amino acids, 2014, 46, 7-20.

Taurine is an abundant free amino acid in humans and plays crucial roles in bile acid conjugation, calcium homeostasis, osmoregulation, and membrane stabilization. Additionally, taurine has a potential role in inflammation and immune responses, particularly in rheumatoid arthritis.
Taurine links to inflammation and oxidative stress
· Taurine reaches high concentrations in tissues exposed to elevated levels of oxidants, suggesting its potential importance in inflammation associated with oxidative stress.
· At the site of inflammation, taurine reacts with hypochlorous acid generated by neutrophil myeloperoxidase, producing less toxic taurine chloramine (TauCl) with antimicrobial and anti-inflammatory properties.
· Taurine may contribute to the pathogenesis of inflammatory diseases through its links to inflammation, neutrophils, myeloperoxidase, and oxidative stress.
· Taurine plays an essential role in cytoprotection and maintains cellular homeostasis in the presence of acute and chronic inflammatory/oxidative stress. It protects immune cells, including leukocytes, from oxidative stress and tissue damage.
· Most established antioxidant action of taurine includes neutralizing hypochlorous acid, leading to anti-inflammatory effects.

Protective Effect of Taurine Against Oxidative Stress

Baliou, Stella, et al. Molecular medicine reports, 2021, 24(2), 1-19.

Taurine is a cytoprotective molecule implicated in processes as diverse as energy production, neuromodulation, calcium homeostasis, and osmoregulation, all of which support its antioxidant properties. This work discusses the antioxidant properties of taurine and the underlying molecular mechanisms of its action in various pathological conditions related to oxidative stress. Some examples of diseases related to oxidative stress include hypertension, muscle/nerve related diseases, cirrhosis, heart dysfunction, etc.
Molecular mechanism of taurine against oxidative stress
· A decline in respiration slows electron flux along the respiratory chain and promotes the diversion of electrons to oxygen to form superoxide. Excessive superoxide generation overwhelms cellular antioxidants, thereby causing oxidative stress. Oxidative stress in turn causes cellular damage and results in more reactive oxygen species being produced; a vicious cycle that contributes to a progressive decline in cellular function.
· Taurine reverses all the adverse effects of excessive oxidative stress through various mechanisms, including:
(1) Upregulation of UUG decoding (5-taurine methyluridine tRNA);
(2) Downregulation of H2O2 or 02- or ·OH or NO;
(3) Downregulation of pro-inflammatory mediator expression;
(4) Upregulation of fatty acid oxidation;
(5) Downregulation of activation of MAPK cascade;
(6) Upregulation of membrane stabilization.