Product name: 5,7,3',4',5'-Pentamethoxyflavone
Synonym name:
Catalogue No.: BP4208
Cas No.: 53350-26-8
Formula: C₂₀H₂₀O₇
Mol Weight: 372.373
Botanical Source:
Type of Compound: Flavonoids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams
Inquire for bulk scale.

For Reference Standard and R&D, Not for Human Use Directly.

HPLC of 5,7,3',4',5'-Pentamethoxyflavone

HNMR of 5,7,3',4',5'-Pentamethoxyflavone

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

5,7,3',4',5'-Pentamethoxyflavone, as a polymethoxy-flavonoid natural product, has attracted widespread attention in the field of natural product pharmacology in recent years. Flavonoids, due to their diverse biological activities and good safety, show great potential in the prevention and treatment of various diseases such as antioxidant, anti-inflammatory, and anti-tumor properties. 5,7,3',4',5'-pentamethoxyflavones have become a research hotspot due to their unique molecular structure and superior pharmacological properties, especially showing significant activity in the antioxidant field. This article will systematically review the chemical structure, origin, pharmacological activity, mechanism of action, and druggability evaluation of this compound, aiming to provide a theoretical basis and reference for its clinical development and related basic research.

Chemical structure and physicochemical properties

5,7,3',4',5'-pentamethoxyflavone is a polymethoxy derivative among flavonoid compounds, with a molecular formula of C21H22O7 and a molecular weight of 372.3730. Its structural feature is that methoxy groups are replaced by methoxy groups at positions 5 and 7, as well as at 3', 4', and 5' in the basic flavonoid backbone, forming five methoxy groups that impart strong lipid solubility and stability. The compound has a LogP value of 2.8527, indicating moderate lipophilicity, which facilitates cell membrane penetration and distribution in vivo.

Its topological pole surface area (TPSA) is 76.36 Ų, indicating that the molecule has certain polar groups, which facilitate binding to biological macromolecule targets. Low water solubility (0.0043 mg/mL) suggests limited solubility in the aqueous phase, which may affect bioavailability. However, high lipid solubility helps penetrate the blood-brain barrier, and experimental data support its high penetration ability. Additionally, this compound did not exhibit hERG channel inhibitory activity, suggesting a low risk of cardiotoxicity; The Ames test result was 0.6, indicating a low genotoxicity risk and good safety.

Plant Origins and Extraction Methods

5,7,3',4',5'-pentamethoxyflavones are mainly found in various plants, especially in certain traditional Chinese medicinal materials and flavonoid enrichment plants with medicinal value, such as Rutaceae and Lamiaceae. Specific plant species include, but are not limited to, certain citrus and mint species. Although their content is not as high as common flavonoids, their unique methoxy-substituting structure gives them special biological activity.

The extraction method mostly uses organic solvent extraction combined with chromatography separation technology. Typically, ethanol or methanol is first used for extraction, followed by liquid-liquid partitioning, silica gel column chromatography, or high-performance liquid chromatography (HPLC) purification to obtain high-purity 5,7,3',4',5'-pentamethoxyflavones. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, reduced solvent usage and extraction time, and aligned with the concept of green extraction.

Pharmacological activity research

Antioxidant activity

5,7,3',4',5'-pentamethoxyflavones exhibited significant antioxidant activity. In vitro experiments have shown that this compound can effectively scavenge free radicals, inhibit lipid peroxidation, and protect cells from oxidative stress damage. Its antioxidant mechanism mainly works by activating endogenous antioxidant enzyme systems, including superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and hemoglobin oxygenase 1 (HMOX1), thereby enhancing cellular antioxidant defenses.

Anti-inflammatory and anti-tumor potential

Although the anti-inflammatory and antitumor effects of 5,7,3',4',5'-pentamethoxyflavones are still in the preliminary research stage, existing studies have shown that by regulating matrix metalloproteinase (MMP1, MMP3) expression, they inhibit the release of inflammatory mediators and tumor cell invasion and metastasis, demonstrating potential anti-inflammatory and antitumor activities.

Neuroprotective effects

Given its excellent blood-brain barrier permeability, the application prospects of 5,7,3',4',5'-pentamethoxyflavones in neurodegenerative diseases have attracted attention. It activates the nuclear factor 2-related factor 2 (NRF2/NFE2L2) signaling pathway, inducing antioxidant enzyme expression, reducing oxidative damage to neurons, and demonstrating neuroprotective effects.

Mechanism of action and molecular targets

The main mechanisms of action of 5,7,3',4',5'-pentamethoxyflavones involve multiple signaling pathways and key molecular targets:

1. NFE2L2/NRF2 signaling pathway activates
   This compound promotes the translocation of NRF2 from the cytoplasm to the nucleus, activating transcription of its downstream antioxidant enzyme genes such as SOD1, SOD2, CAT, GPX1, and HMOX1, thereby enhancing cellular resistance to oxidative stress.

2. Matrix metalloproteinases (MMP1, MMP3) are regulated
   By inhibiting MMP expression, it reduces extracellular matrix degradation, blocks inflammatory responses and tumor cell invasion, and exerts anti-inflammatory and anti-tumor effects.

3. Tyrosinase (TYR) regulation
   The regulatory effects of 5,7,3',4',5'-pentamethoxyflavones on TYR may affect melanin synthesis, suggesting their potential applications in skin protection and whitening.

4. Free radical scavenging and enhanced antioxidant enzyme activity
   While directly scavenging free radicals, it enhances endogenous antioxidant enzyme activity and reduces oxidative damage.

In summary, this compound exerts significant biological effects through synergistic action with multiple targets and multiple pathways.

Druggability evaluation and pharmacokinetics

Druggability evaluation of 5,7,3',4',5'-pentamethoxyflavones shows good drug development potential. The molecular weight of 372.3730 conforms to the Lipinski rule, and the LogP of 2.85 is moderate, indicating good membrane permeability and oral absorption potential. The TPSA is 76.36 Ų, supporting its effective binding to biological targets.

Low water solubility is a major challenge in its druggability, which may limit its oral bioavailability. It requires improved solubility through formulation technologies such as nanocarriers and solid dispersions. Its high blood-brain barrier permeability provides advantages for treating neurological diseases.

In terms of safety, it has no hERG inhibitory effect, reducing the risk of cardiotoxicity; The Ames test result was 0.6, indicating a low genotoxicity risk and good safety.

Pharmacokinetic research is still incomplete. Preliminary in vivo metabolic kinetics data indicate that this compound is mainly metabolized in the liver via the CYP450 enzyme system, and the metabolites require further identification. Its half-life is moderate, and it has a certain degree of internal stability.

Prospects and outlooks for clinical applications

Due to their significant antioxidant and neuroprotective effects, 5,7,3',4',5'-pentamethoxyflavones have broad application prospects in the prevention and treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. Moreover, its anti-inflammatory and anti-tumor potential offers new ideas for adjunctive treatment of related diseases.

Future research should focus on:

• Optimize extraction and synthesis processes to increase yield and purity;
• In-depth analysis of its molecular mechanisms, especially its interactions with inflammatory and tumor-related signaling pathways;
• Conduct systematic pharmacokinetic and toxicological evaluations to clarify their in vivo behavior and safety;
• Developing new drug delivery systems to improve water solubility and bioavailability;
• Design preclinical and clinical trials to verify treatment efficacy and safety.

Through multidisciplinary collaboration, 5,7,3',4',5'-pentamethoxyflavones are expected to become new stars in the development of natural product drugs.

Conclusion

5,7,3',4',5'-pentamethoxyflavone, as a structurally unique polymethoxyflavonoid natural product, exhibits excellent antioxidant, anti-inflammatory, and neuroprotective activities. Its multi-target mechanism of action and excellent druggability have laid a solid foundation for its drug development. Although research into its pharmacokinetics and clinical applications is still in its early stages, with technological advances and deeper research, this compound is expected to play an important role in the field of natural product pharmacology, promoting the prevention and treatment of related diseases and the development of new drugs. Future research should strengthen mechanism analysis and clinical translation to promote its transition from the laboratory to clinical application.