Thiomandelic acid

• CAT Number: I037236
• CAS Number: 4695-09-4
• Molecular Formula: C8H8O2S
• Molecular Weight: 168.21
• Purity: ≥95%
• Synonyms: 2-phenyl-2-sulfanylacetic acid
• InChI: InChI=1S/C8H8O2S/c9-8(10)7(11)6-4-2-1-3-5-6/h1-5,7,11H,(H,9,10)
• InChIKey: QYIGFZOHYGYBLX-UHFFFAOYSA-N
• SMILES: C1=CC=C(C=C1)C(C(=O)O)S

Thiomandelic acid (Cat No.: I037236) is a sulfur-containing analog of mandelic acid, featuring a thiol (-SH) group that imparts distinct chemical reactivity. It is used as a chiral building block and intermediate in organic synthesis, particularly in the preparation of β-lactamase inhibitors, pharmaceutical agents, and fine chemicals. Thiomandelic acid exhibits inhibitory activity against certain metallo-β-lactamases, making it relevant in antibiotic resistance research. Its stereochemistry can influence biological activity, and it serves as a valuable tool in medicinal chemistry, asymmetric synthesis, and enzymology studies targeting drug-resistant bacterial pathogens.

Reference

[1]. C Mollard, et al. Thiomandelic acid, a broad spectrum inhibitor of zinc beta-lactamases: kinetic and spectroscopic studies. J Biol Chem. 2001 Nov 30;276(48):45015-23.
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[2]. Christian Damblon, et al. The inhibitor thiomandelic acid binds to both metal ions in metallo-beta-lactamase and induces positive cooperativity in metal binding. J Biol Chem. 2003 Aug 1;278(31):29240-51.
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