Chemical Structure and Key Features

7-Hydroxy-2-methyl-3-phenyl-chromen-4-one belongs to the isoflavone subclass of flavonoids, characterized by a phenyl ring attached at the 3-position of the chromen-4-one core rather than the 2-position found in classical flavones. This positional difference distinguishes isoflavone analogs from flavones and has significant implications for biological receptor interactions, particularly with estrogen receptors.

The molecule contains three notable substituents: a hydroxyl group at the 7-position of the benzopyranone ring (conferring phenolic character and potential hydrogen-bonding capacity), a methyl group at the 2-position (modulating lipophilicity and steric profile), and a phenyl ring at the 3-position (the hallmark isoflavone substitution pattern). Together, these features produce a planar, aromatic scaffold with moderate polarity, relevant for membrane permeability and protein-binding studies.

Research Applications

As a synthetic isoflavone scaffold, 7-Hydroxy-2-methyl-3-phenyl-chromen-4-one is employed in medicinal chemistry and chemical biology programs focused on the flavonoid class. Researchers utilize this compound as a reference standard or synthetic building block in structure–activity relationship (SAR) studies designed to understand how modifications to the chromenone core influence bioactivity.

The 7-hydroxy substitution pattern is a common feature of naturally occurring isoflavones such as daidzein and genistein, which have been extensively studied for their phytoestrogenic, antioxidant, and enzyme-modulatory properties. Analogs with defined substitutions at the 2- and 3-positions allow researchers to dissect the contribution of individual substituents to binding affinity and selectivity, making this compound a useful tool in target-based screening campaigns and comparative biochemical assays.

Additionally, chromone and chromenone derivatives are investigated as scaffolds for kinase inhibitors, protein–protein interaction modulators, and fluorescent probes, broadening the potential scope of this compound beyond classical phytoestrogenic research.

Handling, Solubility, and Storage Recommendations

As a phenolic chromenone, 7-Hydroxy-2-methyl-3-phenyl-chromen-4-one is expected to exhibit limited aqueous solubility typical of hydrophobic flavonoid scaffolds. For in vitro biochemical assays, researchers commonly prepare stock solutions in dimethyl sulfoxide (DMSO) and dilute into aqueous buffer immediately before use, keeping the final DMSO concentration below 0.1–0.5% to avoid solvent-related artifacts. Verify solubility empirically under your specific experimental conditions.

The compound should be stored in a cool, dry environment, protected from light and moisture, to prevent photodegradation and hydrolysis of the lactone carbonyl. Inert atmosphere storage (argon or nitrogen) is advisable for long-term stability, particularly for solutions. Always consult the product-specific Safety Data Sheet (SDS) provided by Aladdin Scientific before handling.

Ordering Information

7-Hydroxy-2-methyl-3-phenyl-chromen-4-one is available from Aladdin Scientific under SKU H338724. This product is cross-referenced to Santa Cruz Biotechnology catalog number sc-278609, facilitating straightforward identification for researchers transitioning between suppliers or verifying compound identity.

For quantity requirements, custom packaging inquiries, or bulk pricing, please contact the Aladdin Scientific sales team. Certificates of Analysis (CoA) and Safety Data Sheets (SDS) are available upon request or via the Aladdin Scientific product page.