Overview
9-Hydroxy-α-lapachone is a derivative of α-lapachone, a naturally occurring naphthoquinone isolated from the lapacho tree (Tabebuia spp.). It is widely investigated for its bioactive properties, particularly in oncology and microbiology research. The compound’s ability to generate reactive oxygen species (ROS) under specific conditions makes it a candidate for targeted cancer therapies and antimicrobial agents. Industrially, its redox activity is leveraged in catalytic processes. Due to its photosensitivity, handling requires controlled environments. Research-grade 9-hydroxy-α-lapachone is typically supplied in crystalline form, with purity critical for experimental reproducibility.
Physical and Chemical Properties
As a quinone derivative, 9-hydroxy-α-lapachone exhibits distinct electrochemical behavior, undergoing reversible reduction-oxidation cycles. Its yellow-orange color is characteristic of conjugated quinoid systems. The compound’s melting point (180-185°C) and solubility profile (soluble in DMSO, ethanol) make it suitable for laboratory use. Key challenges include its instability in aqueous solutions and sensitivity to light, necessitating storage under inert conditions. Spectroscopic methods (UV-Vis, NMR) are commonly employed for characterization. The molecular weight (256.25 g/mol) and formula (C15H12O4) align with its structural class, featuring a hydroxyl group at the 9-position of the naphthoquinone core.
Main Applications
In pharmaceutical research, 9-hydroxy-α-lapachone is studied for its potential to induce apoptosis in cancer cells via ROS generation and NAD(P)H:quinone oxidoreductase 1 (NQO1)-dependent pathways. Preclinical trials explore its synergy with chemotherapy agents. Beyond oncology, its antimicrobial properties are tested against drug-resistant bacteria and fungi. Industrial applications include its use as a redox mediator in electrochemical systems and organic synthesis. The compound’s niche applications demand high-purity grades, often customized for specific research needs.
Safety and Storage
Due to its pro-oxidant nature, 9-hydroxy-α-lapachone requires careful handling to avoid unintended oxidative stress. Lab personnel should use nitrile gloves, safety goggles, and fume hoods. Skin contact may cause irritation; rinse immediately with water. Storage recommendations include amber glass vials under nitrogen or argon, at temperatures below 25°C. Long-term stability is enhanced by desiccants to prevent moisture absorption. Dispose of waste according to hazardous chemical protocols, as it may react with incompatible substances.
B2B Procurement Guide
When sourcing 9-hydroxy-α-lapachone, prioritize suppliers with analytical certificates (e.g., HPLC purity ≥95%) and batch-specific COAs. Custom synthesis options are available for bulk orders, but lead times may vary. Key procurement considerations include stability data (accelerated degradation studies), solvent compatibility, and packaging (sealed ampoules vs. bulk powder). Prices fluctuate based on purity and scale; negotiate contracts for recurring orders. Verify regulatory compliance (REACH, OSHA) if importing internationally.