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Urolithin A has emerged as a landmark compound in senotherapeutic and mitochondrial medicine research, representing a critical metabolite produced via microbial transformation of dietary ellagitannins. In high-purity industrial synthesis and pharmaceutical research and development, understanding the exact chemical structure of this dibenzopyranone derivative is essential for ensuring compound stability, purity verification, and successful assay optimization. Research labs worldwide rely on precise structural coordinates to explore its molecular targets, making a comprehensive chemical profile indispensable for any reliable Urolithin A Raw Material Supplier and for efficient Urolithin A Ingredient Sourcing.
Under systematic IUPAC guidelines, Urolithin A is classified as 3,8-dihydroxy-6H-dibenzo[b,d]pyran-6-one, or 3,8-dihydroxybenzo[c]chromen-6-one. It features a standardized chemical formula of C13H8O4, with a defined molecular weight of exactly 228.20 g/mol. For researchers handling Bulk Urolithin A Powder, this moderate molecular weight matches the standard "rule-of-five" criteria for drug-likeness, indicating highly favorable theoretical drug-like absorption dynamics during in vivo studies. In a crystalline state, the compound presents itself as off-white to pale yellow microcrystalline structure. The backbone comprises a fused tricyclic ring structure composed of a benzopyranone core. The carbon layout consists of thirteen skeletal carbon atoms arranged into a planar system, establishing strong pi-electron conjugation across the entire molecule.
When conducting laboratory-level quality assurance, researchers must map Urolithin A using specific structural parameters. The molecular structure carries two critical phenolic hydroxyl groups, positioned specifically at the C-3 and C-8 coordinates, and a central lactone carbonyl group at C-6. These functional arrangements dictate its unique reactivity, rendering the compound sensitive to basic environments where deprotonation can alter the absorption spectra. In UV-visible spectrophotometry, pure Urolithin A in ethanol yields characteristic absorption peaks at approximately 305 nm and 355 nm, reflecting the electronic transitions of the conjugated system. Infrared spectroscopy further isolates Urolithin A by highlighting a sharp carbonyl stretching band near 1680 cm⁻¹ and broad, intense O-H stretching bands ranging between 3200 cm⁻¹ and 3400 cm⁻¹.
To correctly identify Urolithin A in raw material batches—especially when considering Urolithin A Wholesale purchases—laboratories must compare its structural attributes with closely related metabolites. In technical comparison to its metabolic sibling, Urolithin B (3-hydroxy-6H-dibenzo[b,d]pyran-6-one), Urolithin A differs by the addition of a single hydroxyl moiety. This tiny structural variance creates a substantial shift in physical and physiological parameters. Specifically, Urolithin A has a molecular weight of 228.20 g/mol, which is larger than the molecular weight of Urolithin B at 212.20 g/mol by exactly 16.00 units, indicating the absence of the C-8 oxygen atom in the latter. When compared to the precursor molecule Ellagic Acid (C14H6O8), which features a molecular weight of 302.19 g/mol, Urolithin A is lighter by 73.99 g/mol. In terms of hydrogen bond profiles, Ellagic Acid presents exactly 4 hydrogen bond donors and 8 hydrogen bond acceptors, whereas Urolithin A displays a highly balanced layout of 2 hydrogen bond donors (the C-3 and C-8 phenolic groups) and 4 hydrogen bond acceptors (the lactone and phenolic oxygens). This structural reduction dramatically shifts the polar surface area from 141 Ų in Ellagic Acid down to 70.0 Ų in Urolithin A, indicating that Urolithin A possesses significantly higher cell membrane permeability coefficient values. This structural contrast is the primary chemical reason why Urolithin A can effectively cross biological barriers in cellular assays where larger polymers fail.
The fully conjugated planar framework of Urolithin A provides robust thermodynamic stability under standard storage conditions. However, the lactone ring situated in the central pyranone core remains a primary point of observation for formulation scientists. Under high alkaline stress (pH greater than 9.0), the lactone bond undergoes hydrolysis, opening the pyran ring to yield a carboxylated biphenyl derivative. Consequently, technical formulations must avoid highly basic buffers to prevent structural degradation. For applications requiring enhanced solubility, specialized Water-soluble Urolithin A derivatives or formulations have been developed, allowing broader use in aqueous bioassays. For analytical validation, High-Performance Liquid Chromatography (HPLC) remains the gold standard, achieving resolution based on the highly hydrophobic aromatic core. The retention time on standard C18 reverse-phase columns is highly predictable, and is directly determined by the dual phenolic groups' interaction with mobile phase dynamics.
Leadingchem is your premier manufacturer and supplier of high-purity Urolithin A. Reach out to our team for bulk inquiries, technical support, or custom sourcing solutions.
[1] NCBI PubChem Compound Database.
[2] ScienceDirect Academic Topic Pages.
[3] Nature Medicine Research Journal.
[4] FDA Dietary Supplements Database.
[5] PubMed Central (Water-soluble polyphenol formulations).
