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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

(S)-(+)-Mandelic Acid (CAS No. 17199-29-0): An Overview of Its Properties, Applications, and Recent Research

(S)-(+)-Mandelic Acid (CAS No. 17199-29-0) is a chiral compound that has garnered significant attention in the fields of organic chemistry, pharmaceuticals, and biochemistry due to its unique properties and diverse applications. This article provides a comprehensive overview of (S)-(+)-Mandelic Acid, including its chemical structure, physical and chemical properties, synthesis methods, biological activities, and recent research developments.

Chemical Structure and Properties

(S)-(+)-Mandelic Acid is a chiral derivative of mandelic acid, characterized by its molecular formula C₈H₈O₃. The compound features a benzene ring with a carboxylic acid group and a hydroxymethyl group attached to it. The (S) configuration imparts optical activity to the molecule, making it an important chiral building block in organic synthesis. (S)-(+)-Mandelic Acid is a white crystalline solid that is soluble in water and many organic solvents. It has a melting point of approximately 116-118°C and a boiling point of 260°C at 760 mmHg.

Synthesis Methods

The synthesis of (S)-(+)-Mandelic Acid can be achieved through various routes, each with its own advantages and limitations. One common method involves the asymmetric reduction of benzaldehyde followed by oxidation to form the carboxylic acid. Another approach involves the enantioselective hydrolysis of mandelonitrile using enzymes such as nitrilase or mandelonitrile lyase. These methods have been optimized to achieve high yields and enantiomeric excess (ee) values, making them suitable for large-scale production.

Biological Activities and Applications

(S)-(+)-Mandelic Acid has been extensively studied for its biological activities and potential therapeutic applications. One of its notable uses is in the treatment of urinary tract infections (UTIs). The compound has been shown to inhibit the growth of certain bacteria, including Escherichia coli, by interfering with their metabolic pathways. Additionally, (S)-(+)-Mandelic Acid has demonstrated antiviral properties against herpes simplex virus (HSV) and other enveloped viruses. Its mechanism of action involves blocking viral entry into host cells or inhibiting viral replication.

Beyond its antimicrobial properties, (S)-(+)-Mandelic Acid has been explored for its potential in cancer therapy. Research has indicated that the compound can induce apoptosis in cancer cells by modulating key signaling pathways such as p53 and Bcl-2. Furthermore, it has shown promise as a chiral auxiliary in the synthesis of complex molecules with therapeutic potential.

Recent Research Developments

The ongoing research on (S)-(+)-Mandelic Acid continues to uncover new applications and mechanisms of action. A recent study published in the Journal of Medicinal Chemistry explored the use of (S)-(+)-Mandelic Acid as a lead compound for developing novel antifungal agents. The researchers synthesized a series of mandelic acid derivatives and evaluated their antifungal activity against Candida albicans. The results showed that certain derivatives exhibited potent antifungal activity with low cytotoxicity towards mammalian cells.

In another study, scientists investigated the role of (S)-(+)-Mandelic Acid in modulating immune responses. The compound was found to enhance the production of cytokines such as interferon-gamma (IFN-γ) and tumor necrosis factor-alpha (TNF-α) in immune cells, suggesting its potential as an immunomodulatory agent. This property could be leveraged in developing therapies for autoimmune diseases and chronic inflammatory conditions.

Safety Considerations and Future Prospects

The safety profile of (S)-(+)-Mandelic Acid is generally favorable, with low toxicity observed in preclinical studies. However, as with any chemical compound, proper handling and storage precautions should be followed to ensure safety. Further research is needed to fully understand the long-term effects and potential side effects of prolonged use.

The future prospects for (S)-(+)-Mandelic Acid are promising, driven by its diverse biological activities and potential applications in medicine and biotechnology. Ongoing studies are focused on optimizing its pharmacological properties through structural modifications and exploring new therapeutic targets. As research progresses, it is likely that new uses for this versatile compound will be discovered, further expanding its impact on human health.

• 18584-20-8(4-Methylmandelic Acid)
• 18937-33-2(Magnesium, bis(a-hydroxybenzeneacetato)-, (T-4)-(9CI))
• 19944-53-7(Benzeneacetic acid, a-hydroxy-, calcium salt (2:1), (aS)-)
• 10408-52-3(2-(4-ethylphenyl)-2-hydroxyacetic acid)
• 90-64-2(Mandelic acid)
• 611-71-2(D-(-)-Mandelic acid)
• 31284-89-6((R)-4-Methylmandelic Acid)
• 611-72-3(Mandelic acid)
• 114-21-6(Mandelic Acid Sodium Salt)
• 134-95-2(Benzeneacetic acid, a-hydroxy-, calcium salt (2:1))