Product name: 5,7-Dimethoxyflavone
Synonym name: Dimethylchrysin
Catalogue No.: BP4263
Cas No.: 21392-57-4
Formula: C₁₇H₁₄O₄
Mol Weight: 282.295
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-Dimethoxyflavone

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

Introduction/Overview

5,7-Dimethoxyflavone (CAS number: 21392-57-4) is a typical dimethoxyflavonoid compound, which is a methylated derivative of 5,7-dihydroxyflavone and widely present in various plants. As an important flavonoid member in natural products, Baiyin dimethyl ether has attracted widespread attention in the field of pharmacology research in recent years due to its unique chemical structure and diverse biological activities. Especially in the field of tumor treatment, especially in the prevention and treatment of prostate cancer, Baiyin dimethyl ether has shown significant potential, involving the regulation of multiple signaling pathways and key molecular targets.

This review aims to systematically summarize the chemical structure and physicochemical properties, plant sources and extraction methods, pharmacological activity and mechanism of action, pharmacological evaluation and pharmacokinetic characteristics of Baiyin dimethyl ether. The focus is on exploring its molecular targets and mechanism of action in the treatment of prostate cancer, and finally looking forward to its clinical application prospects and future research directions, providing reference and inspiration for researchers in related fields.

Chemical structure and physicochemical properties

The molecular formula of Baiyin dimethyl ether is C17H14O4, with a molecular weight of 282.2950. Its chemical structure is based on the flavonoid skeleton, specifically, the two hydroxyl groups at positions 5,7 are replaced by methyl to form a dimethoxy structure, and its chemical name is 5,7-dimethoxyflavone. The structure contains a typical flavonoid C6-C3-C6 skeleton, with good planarity and conjugated system, which provides the possibility for its binding with various biomolecules.

In terms of physical and chemical properties, the LogP value of Baiyin dimethyl ether is 3.0945, indicating that it has moderate lipid solubility and is conducive to cell membrane penetration. The topological polar surface area (TPSA) is 48.67 Å ², indicating good membrane permeability. The water solubility is relatively low (0.0021 mg/mL), which to some extent limits its oral bioavailability, but the fat solubility is good, which is beneficial for its distribution in the body, especially for its strong ability to cross the blood-brain barrier (high blood-brain barrier permeability). In addition, the hERG channel inhibition experiment results were negative, indicating a low risk of cardiac toxicity. The Ames mutagenicity test score is 0.6, indicating a low risk of genetic toxicity and a good safety basis.

Plant sources and extraction methods

Baiyin dimethyl ether is widely present in various plants, especially in the roots, stems, leaves, and flowers of certain leguminous, labiaceae, and Asteraceae plants. Its natural sources are abundant, and the content varies depending on the plant species, harvesting period, and growth environment. Common plants containing berberine dimethyl ether include Scutellaria spp. and Populus spp.

The extraction method mainly adopts organic solvent extraction combined with chromatographic separation technology. The general steps include:

1. Sample Pretreatment Dry and crush plant materials, and screen for suitable particle sizes.
2. Solvent extraction Commonly used polar organic solvents such as methanol, ethanol, or ethyl acetate are subjected to multiple reflux or ultrasonic extractions to fully dissolve flavonoids.
3. Crude extract concentration Remove the solvent by vacuum concentration to obtain a concentrated extract.
4. Separation and purification Using methods such as silica gel column chromatography and reverse phase high performance liquid chromatography (RP-HPLC), combined with UV detection and mass spectrometry confirmation, the separation and purification of lignin dimethyl ether were achieved.
5. Structural Identification Confirm purity and structure through techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR).

In recent years, green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction have also been applied to the extraction of lignin dimethyl ether, improving extraction efficiency and purity, reducing the use of organic solvents, and complying with the concept of green chemistry.

Pharmacological activity research

Baiyangsu dimethyl ether, as a natural flavonoid compound, exhibits various pharmacological activities, including anti-tumor, antioxidant, anti-inflammatory, neuroprotective, and endocrine regulation.

Antitumor activity

Prostate cancer is a key area of research in the field of poplar extract dimethyl ether. In vitro cell experiments have shown that berberine dimethyl ether can significantly inhibit the proliferation of prostate cancer cell lines (such as LNCaP, PC-3, DU145), induce cell cycle arrest and apoptosis. Its anti-tumor effect is closely related to regulating multiple signaling pathways, including inhibiting the activity of STAT3 signaling pathway, regulating the expression of BCL2 family proteins, and promoting the endogenous apoptosis pathway mediated by CASP9. In addition, berberine dimethyl ether can reverse the multidrug resistance of tumor cells and enhance the sensitivity of chemotherapy drugs.

Antioxidant and anti-inflammatory effects

Baiyin dimethyl ether has significant antioxidant activity, which can scavenge free radicals and alleviate oxidative stress damage. It activates the NFE2L2 (Nrf2) signaling pathway, induces the expression of antioxidant enzymes, and enhances the antioxidant defense ability of cells. In the inflammatory model, berberine dimethyl ether inhibits the secretion of pro-inflammatory factors such as TNF - α and IL-6, reduces inflammatory response, and demonstrates good anti-inflammatory potential.

Neuroprotective effect

Due to its excellent blood-brain barrier penetration, Baiyin dimethyl ether has also shown potential in the field of neuroprotection. Related studies have shown that this compound can alleviate oxidative damage and inflammatory response of nerve cells, promote nerve cell survival, and may have a protective effect on neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.

Other pharmacological activities

Baiyin dimethyl ether also exhibits the ability to regulate endocrine function, which may affect the development of hormone dependent diseases by modulating the activity of estrogen receptor (ESR2) and androgen receptor (AR). In addition, its regulatory effect on drug metabolizing enzyme CYP19A1 suggests its potential application value in hormone metabolism and the treatment of related diseases.

Mechanism of action and molecular targets

The pharmacological effects of Baiyin dimethyl ether are mainly achieved by regulating various key molecular targets, especially in the treatment of prostate cancer. The following is the main mechanism of action and target analysis:

1. Anti apoptosis and cell cycle regulation

• BCL2 Baiyin dimethyl ether downregulates the expression of anti apoptotic protein BCL2 and promotes cell apoptosis.
• CASP9 Activate the key protease CASP9 in the endogenous apoptotic pathway and induce programmed cell death.
• MAPK1 By regulating the MAPK signaling pathway, it affects the balance between cell proliferation and apoptosis.

2. Regulation of signal transduction pathways

• STAT3 Inhibit the phosphorylation and activity of STAT3, block its function of promoting tumor cell growth and immune escape.
• PTPN1 Regulating protein tyrosine phosphatase 1 (PTPN1), affecting cell signaling and metabolic regulation.

3. Hormone receptor regulation

• ESR2 (estrogen receptor beta)and AR (androgen receptor)Baiyin dimethyl ether affects hormone dependent tumor growth by regulating the expression and activity of these two hormone receptors.
• CYP19A1 (aromatase)Regulating aromatase activity, affecting estrogen biosynthesis, and indirectly regulating hormone levels.

4. Multi drug resistance related targets

• ABCB1（P-gp）Inhibiting the function of multidrug resistance protein ABCB1, promoting the accumulation of chemotherapy drugs in tumor cells, and enhancing drug efficacy.
• NFE2L2（Nrf2）Activate the Nrf2 signaling pathway, enhance cellular antioxidant capacity, and alleviate oxidative stress damage to cells.

In summary, Baiyangsu dimethyl ether exerts its anti-tumor and other pharmacological activities through multi-target and multi pathway synergistic effects, demonstrating its multifunctionality as a natural product and potential clinical application value.

Evaluation of drug properties and pharmacokinetics

Drug formation is a crucial step in the conversion of natural products into clinical drugs. The pharmacological parameters of Baiyangsu dimethyl ether indicate that it has certain potential for drug development.

Physical and chemical properties of drugs

• Molecular weight (282.2950)Complies with Lipinski's rules and is beneficial for oral absorption.
• LogP（3.0945）Moderate, indicating good lipid solubility and facilitating cell membrane penetration.
• TPSA（48.67 Ų）Low, indicating good membrane permeability.
• Water solubility (0.0021 mg/mL)Low, may limit oral bioavailability, and needs to be improved through formulation optimization.

safety evaluation

• HERG inhibition negative Reduced the risk of cardiac toxicity.
• Ames test 0.6 This indicates a low risk of genetic toxicity.

Pharmacokinetic characteristics

At present, there are relatively few systematic pharmacokinetic studies on Baiyuansu dimethyl ether. However, based on its physicochemical properties and studies similar to flavonoids, it can be inferred that it:

• Has good oral absorption potential, but may have limited bioavailability due to low water solubility.
• Due to its high lipophilicity and wide distribution, especially its ability to penetrate the blood-brain barrier, it is suitable for the treatment and development of neurological diseases.
• The metabolic pathway may involve the liver CYP450 enzyme system, and further research is needed on its metabolic stability, as well as the activity and toxicity of its metabolites.
• Excretion mainly occurs through the renal and biliary pathways, and specific kinetic parameters need to be validated through in vivo experiments.

Future research should focus on conducting systematic pharmacokinetic and toxicological evaluations to lay the foundation for clinical applications.

Clinical application prospects and prospects

Baiyangsu dimethyl ether has good clinical translation prospects due to its multi-target and multi mechanism pharmacological activity, especially its potential in the treatment of prostate cancer. Its advantages include:

• Targeting multiple key pathogenic molecules BCL2, STAT3, AR, etc. can overcome the resistance problem of single target drugs.
• Low toxicity and good safety Provide assurance for long-term treatment.
• Good blood-brain barrier permeability This has expanded its potential applications in neurological diseases.
• Antioxidant and anti-inflammatory effects Can help improve the tumor microenvironment and chronic inflammation related diseases.

However, clinical applications still face several challenges:

• Poor water solubility and low bioavailability It needs to be improved through drug formulation technologies such as nanocarriers, liposomes, and solid dispersions.
• Insufficient systematic pharmacokinetic and toxicological data It is urgent to conduct animal models and preclinical studies.
• The mechanism of action needs further clarification Especially its multi-target synergistic effect in complex tumor microenvironments.

Suggestions for future research directions include:

• Develop efficient green extraction and purification processes to ensure the quality and yield of raw materials.
• Systematically conduct pharmacokinetic, toxicological, and pharmacodynamic studies to improve drug safety and efficacy evaluation.
• Utilizing modern molecular biology and omics techniques to deeply analyze its mechanism of action and target network.
• Explore combination therapy strategies to enhance anti-tumor efficacy and overcome drug resistance.
• Develop new drug carriers and delivery systems to enhance bioavailability and targeting.

Conclusion

Baiyangsu dimethyl ether, as a natural dimethoxyflavonoid with unique structure and rich biological activity, has shown extensive pharmacological potential, especially in the prevention and treatment of tumor diseases such as prostate cancer, demonstrating significant multi-target regulatory ability. Its good pharmacological parameters and safety provide strong support for clinical translation. In the future, through in-depth pharmacological mechanism research, pharmacokinetic evaluation, and formulation technology optimization, Baiyangsu dimethyl ether is expected to become an important candidate molecule for natural product drug development, promoting the application of natural flavonoid drugs in the treatment of tumors and related diseases.