1-(2-Hydroxy-3-sulfopropyl)-pyridinium betane
[CAS# 3918-73-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Hydroxypyridine
• Name: 1-(2-Hydroxy-3-sulfopropyl)-pyridinium betane
• Synonyms: Pyridinium hydroxy propyl sulphobetaine; PPS-OH
• Molecular Formula: C₈H₁₁NO₄S
• Molecular Weight: 217.24
• CAS Registry Number: 3918-73-8
• EC Number: 223-485-2
• SMILES: C1=CC=[N+](C=C1)CC(CS(=O)(=O)[O-])O

Properties

• Density: 1.30
• Boiling point: 111 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

1-(2-Hydroxy-3-sulfopropyl)-pyridinium betaine is a zwitterionic compound featuring a pyridinium ring substituted with a hydroxy-sulfopropyl group. The discovery of this compound emerged from research into surfactants and ionic liquids, particularly those exhibiting unique solubility and surface-active properties. The incorporation of a sulfonate group into the pyridinium structure enhances its ability to interact with various materials and biomolecules, making it useful in a range of applications.

The synthesis of 1-(2-hydroxy-3-sulfopropyl)-pyridinium betaine involves the reaction of pyridine derivatives with sulfopropyl halides, followed by a quaternization process to yield the final zwitterionic structure. This synthetic pathway allows for the efficient introduction of functional groups that impart desirable properties to the compound, including increased hydrophilicity and improved solubility in aqueous solutions.

One of the primary applications of this betaine is in the formulation of surfactants and detergents. Its zwitterionic nature provides excellent surface-active properties, enabling the compound to lower surface tension and enhance the wetting and emulsifying capabilities of cleaning products. This makes 1-(2-hydroxy-3-sulfopropyl)-pyridinium betaine particularly useful in personal care formulations, such as shampoos and body washes, where it can effectively remove dirt and oil while being gentle on the skin.

In addition to its role in personal care products, this compound is utilized in the pharmaceutical industry. Its unique properties enable it to act as a solubilizing agent for poorly soluble drugs, enhancing their bioavailability. The hydrophilic sulfonate group facilitates interactions with biological membranes, aiding in the absorption of drugs in the gastrointestinal tract. This application is particularly important for developing formulations that require improved drug delivery systems.

Moreover, 1-(2-hydroxy-3-sulfopropyl)-pyridinium betaine has been explored in biochemical research as a stabilizing agent for proteins and enzymes. Its zwitterionic nature helps to maintain the structural integrity of biomolecules in various conditions, providing a suitable environment for biochemical assays and studies. This stabilizing effect is beneficial in enzyme assays, protein crystallization, and other applications where maintaining protein structure and function is critical.

Overall, the discovery and development of 1-(2-hydroxy-3-sulfopropyl)-pyridinium betaine illustrate the significance of functionalized zwitterionic compounds in enhancing the performance of everyday products and improving drug formulations.

References

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