7,8-Dihydroxyflavone (7,8-DHF)

Синонимы: 7,8-DHF, 7,8-Dihydroxy-2-phenyl-4H-chromen-4-one, 7,8-дигидроксифлавон, 7,8-Dihydroxy-2-phenylchromen-4-one, 4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-

7,8-Dihydroxyflavone is a synthetic flavone bearing two adjacent hydroxyl groups at the 7 and 8 positions of the A-ring, a substitution pattern that distinguishes it from the more common 5,7-dihydroxyflavones. This ortho-dihydroxy motif is not merely structural decoration: it underpins the molecule’s redox behavior, metal-chelating tendency, and its unusually high affinity for the tropomyosin-related kinase B (TrkB) receptor. In solution, the compound appears as a pale yellow chromophore with absorption maxima near 340 nm, and its planar aromatic system allows efficient π–π stacking with aromatic residues in the TrkB ligand-binding pocket.

First described in the chemical literature in the 1950s, 7,8-DHF remained a footnote in flavonoid chemistry until 2010, when a high-throughput screen identified it as a small-molecule TrkB agonist capable of mimicking brain-derived neurotrophic factor (BDNF). Since then, it has become a standard research tool in neurobiology and is produced under cGMP-compatible conditions for preclinical and clinical supply. Commercial material is typically offered as off-white to pale yellow crystals with ≥98% purity by HPLC, and it is handled as a light-sensitive solid that should be protected from prolonged exposure to strong light.

Because it is a discrete small molecule rather than a botanical extract, 7,8-DHF offers consistent potency and defined pharmacokinetics—advantages that matter when designing dose-response studies or formulating stable finished products. It is used in research on neurotrophic signaling, synaptic plasticity, and mitochondrial function, and it also serves as a reference standard for analytical method development. The compound is not naturally abundant in common dietary sources, so synthetic routes are the practical route to multi-gram and kilogram quantities.

Chemical Structure & Properties

The flavone core consists of two aromatic rings (A and B) connected through a pyran-4-one ring, with hydroxyl groups at C-7 and C-8. The 7-OH is weakly acidic (pKa ≈ 7.5), while the 8-OH participates in intramolecular hydrogen bonding with the carbonyl oxygen, influencing both the molecule’s UV spectrum and its solubility profile. 7,8-DHF is a neutral, lipophilic solid at room temperature (logP ≈ 2.8) and is practically insoluble in water, a limitation that formulation scientists often address through co-solvents, cyclodextrin complexation, or nano-suspension. It is stable as a solid under cool, dry, dark conditions but can undergo oxidative degradation in alkaline aqueous media, particularly when exposed to air and light.

Механизм действия

• TrkB agonism: Binds the extracellular domain of TrkB, promoting receptor dimerization and autophosphorylation in the absence of BDNF.
• Downstream neurotrophic signaling: Activates the PLCγ–Ca2+ and PI3K–Akt cascades, supporting neuronal survival and synaptic remodeling.
• Mitochondrial protection: Reduces reactive oxygen species and preserves mitochondrial membrane potential in neuronal and non-neuronal cell models.
• Anti-apoptotic effects: Upregulates Bcl-2 and downregulates Bax in stress-induced cell models, although these findings are largely preclinical.
• Modulation of neurotransmitter systems: May influence dopaminergic and glutamatergic transmission indirectly through TrkB-dependent plasticity.

Quality Specifications

Supply & Documentation

• Capacity: Pilot-scale batches up to 25 kg per lot; annual capacity of 200 kg with campaign scheduling.
• Срок выполнения заказа: 3–5 рабочих дней (товары, имеющиеся в наличии)
• Documentation: COA, MSDS, TDS, and stability data available on request; ICH Q3C residual solvent statement included.
• Packaging: 1 kg, 5 kg, and 25 kg fiber drums with double LDPE liners; samples in amber glass vials.

Запрос Цитировать

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