2-Hydroxy-4-methoxybenzaldehyde

2-Hydroxy-4-methoxybenzaldehyde is a phenol found in P. sepium that has diverse biological activities.^1,2,3 It is active against Gram-positive (MICs = 100-200 µg/ml) and Gram-negative bacteria (MICs = 125-200 µg/ml), as well as the fungus C. albicans (MIC = 150 µg/ml).¹ 2-Hydroxy-4-methoxybenzaldehyde scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in a cell-free assay (IC₅₀ = 9.04 mg/ml) and acts as a metal chelator, inhibiting ferrozine-Fe²⁺ complex formation with an IC₅₀ value of 2.31 mg/ml. It reduces production of the virulence factor staphyloxanthin in clinical isolates of methicillin-resistant S. aureus (MRSA) when used at a concentration of 200 µg/ml and decreases the expression of the MRSA virulence regulatory genes saeS, geh, crtM, and sigB.² 2-Hydroxy-4-methoxybenzaldehyde, when used in combination with the antibiotics amikacin (Item No. 15405), gentamicin, cefotaxime (Item No. 16040), vancomycin (Item No. 15327), or tetracycline (Item No. 14328), increases MRSA antibiotic sensitivity. It is also an intermediate in the synthesis of Schiff base-metal complexes with antiproliferative activity.³

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1. Wang, J., Liu, H., Zhao, J., et al. Antimicrobial and antioxidant activites of the root bark essential oil of Periploca sepium and its main component 2-hydroxy-4-methoxybenzaldehyde. Molecules 15(8), 5807-5817 (2010).

2. Kannappan, A., Srinivasan, R., Nivetha, A., et al. Anti-virulence potential of 2-hydroxy-4-methoxybenzaldehyde against methicillin-resistant Staphylococcus aureus and its clinical isolates. Appl. Microbiol. Biotechnol. 103(16), 6747-6758 (2019).

3. Tyagi, P., Tyagi, M., Agrawal, S., et al. Synthesis, characterization of 1,2,4-triazole Schiff base derived 3d-metal complexes: Induces cytotoxicity in HepG2, MCF-7 cell line, BSA binding fluorescence and DFT study. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 171, 246-257 (2017).