Thiotaurine
[CAS# 2937-54-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonic acid / sulfinic acid
• Name: Thiotaurine
• Synonyms: 2-hydroxysulfonothioylethanamine
• Molecular Formula: C₂H₇NO₂S₂
• Molecular Weight: 141.21
• CAS Registry Number: 2937-54-4
• EC Number: 220-918-7
• SMILES: C(CS(=O)(=S)O)N

Properties

• Solubility: 1e+006 mg/L (25 °C water)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.622, Calc.^*
• Melting point: 63.35 °C
• Boiling Point: 324.6±44.0 °C (760 mmHg), Calc.^*, 269.13 °C
• Flash Point: 150.1±28.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Discovered in the early 20th century, thiotaurine is a derivative of taurine, an amino acid found in large quantities in animal tissues. Thiotaurine was originally identified as a compound found in mammalian bile, particularly the liver. Its chemical structure consists of taurine bound to sulfur, which gives it enhanced antioxidant and antimicrobial properties compared to its parent compound. The sulfur portion of thiotaurine enables it to form stable complexes with heavy metals, effectively ridding the body of harmful pollutants. One notable application of thiotaurine is in skin care products. Due to its powerful antioxidant and anti-inflammatory properties, thiotaurine is widely used in cosmetic and skin care formulations to protect the skin from oxidative stress, UV radiation, and environmental pollutants. It helps keep the skin healthy by reducing inflammation, preventing collagen degradation, and promoting wound healing. Additionally, the antimicrobial activity of thiotaurine makes it effective against acne-causing bacteria, making it a valuable ingredient in acne treatment products. Research has shown that thiotaurine is able to prevent liver damage caused by alcohol consumption and certain medications by reducing oxidative stress and inflammation in liver cells. Additionally, the antioxidant properties of thiotaurine may have cardioprotective effects, reducing the risk of cardiovascular events such as heart attack and stroke. Additionally, studies suggest that thiotaurine may play a role in neuroprotection, potentially delaying the onset or progression of neurodegenerative diseases such as Alzheimer's and Parkinson's diseases. In the food industry, thiotaurine is used as a preservative and antioxidant to extend the shelf life of perishable products. Its ability to inhibit the growth of spoilage microorganisms and prevent lipid oxidation makes it a valuable additive in food and beverage products, especially those that are susceptible to microbial contamination and rancidity.

References

2019. Thiotaurine: From Chemical and Biological Properties to Role in H2S Signaling, _Advances in experimental medicine and biology_, 1155
DOI: https://doi.org/10.1007/978-981-13-8023-5_66

2015, Thiotaurine Protects Mouse Cerebellar Granule Neurons from Potassium Deprivation-Induced Apoptosis by Inhibiting the Activation of Caspase-3, _Advances in experimental medicine and biology_, 803
DOI: https://doi.org/10.1007/978-3-319-15126-7_41

2013, Comparative Evaluation of Taurine and Thiotaurine as Protectants Against Diabetes-Induced Nephropathy in a Rat Model, _Advances in experimental medicine and biology_, 775
DOI: https://doi.org/10.1007/978-1-4614-6130-2_29