7,8-Dihydroxyflavone
[CAS# 38183-03-8]

Identification

• Classification: Biochemical >> Plant extracts
• Name: 7,8-Dihydroxyflavone
• Synonyms: 7,8-Dihydroxy-2-phenyl-4H-chromen-4-one
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• CAS Registry Number: 38183-03-8
• EC Number: 253-812-4
• SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O

Properties

• Solubility: 100 mM (DMSO), 100mM (2eq. NaOH)
• Density: 1.443±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 250-251 ºC^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Cushman, Mark; Tetrahedron Letters 1990, V31(45), P6497-500.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

7,8-Dihydroxyflavone (7,8-DHF) is a naturally occurring flavonoid whose chemical structure is characterized by two hydroxyl groups at positions 7 and 8 on the flavonoid backbone. Its molecular formula is C15H10O4. The compound has attracted much attention for its neuroprotective properties and potential therapeutic applications, especially in the treatment of neurological diseases.

The discovery of 7,8-DHF can be traced back to the study of flavonoids, a class of plant metabolites known for their antioxidant properties. Researchers discovered 7,8-DHF while studying plant compounds with potential health benefits. 7,8-DHF differs from other flavonoids in its ability to mimic the activity of brain-derived neurotrophic factor (BDNF), a protein that is essential for the survival, development, and function of neurons.

BDNF works by binding to the TrkB receptor, initiating a signaling pathway that promotes neuronal growth and plasticity. In the early 2000s, scientists discovered that 7,8-DHF can selectively activate TrkB receptors, making it a promising candidate for neuroprotective therapy. This discovery opened new avenues for research into treatments for neurodegenerative diseases such as Alzheimer's, Parkinson's, and Huntington's diseases.

One of the main applications of 7,8-DHF is in the field of neuroprotection. Preclinical studies have shown that 7,8-DHF can cross the blood-brain barrier and exert protective effects on neurons. It has been shown to improve cognitive function, reduce neuroinflammation, and promote the survival of dopaminergic neurons in Parkinson's disease models. In addition, 7,8-DHF has shown the potential to mitigate the effects of traumatic brain injury and stroke by reducing neuronal death and promoting recovery.

In Alzheimer's disease models, 7,8-DHF has been found to reduce amyloid beta plaques and tau pathology, two hallmarks of the disease. By enhancing synaptic plasticity and cognitive function, 7,8-DHF holds promise for developing therapies that not only slow the progression of neurodegenerative diseases but also improve patients’ quality of life.

In addition to its neuroprotective effects, 7,8-DHF has been explored for its potential to treat mood disorders such as depression and anxiety. The compound’s ability to activate TrkB receptors and enhance BDNF signaling suggests it could help alleviate depressive symptoms, which are often associated with reduced BDNF levels. Animal studies have shown that 7,8-DHF can produce antidepressant-like effects, supporting its potential use in mental health treatments.

In addition to its therapeutic applications, 7,8-DHF is also valuable in research settings. Scientists use it as a tool to study the BDNF-TrkB signaling pathway and its role in a variety of physiological and pathological processes. This research helps better understand the mechanisms underlying neurodegenerative diseases and identify new targets for therapeutic intervention.

The safety and efficacy of 7,8-DHF are key considerations in its development as a therapeutic agent. While preclinical studies have shown promising results, clinical trials are necessary to determine its safety and effectiveness in humans. Researchers are also studying the pharmacokinetics of 7,8-DHF to optimize its bioavailability and therapeutic potential.

References

Shaolong Du, Yixi Xie and Xiaoqing Chen. Influence of glucose on the human serum albumin�flavone interaction and their antioxidant activity, Mol. Biosyst., 2013, 9, 55.