Production Method 1

55338-30-2

82517-12-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  15 h, reflux

Reference

Synthesis of 5-methyl-7-methoxyisoflavone

Qian, Hong-Sheng; et al, Yingyong Huaxue, 2005, 22(2), 224-226

Production Method 2

504-15-4

82517-12-2

Reaction Conditions

1.1 Reagents: Hydrochloric acid Catalysts: Zinc chloride Solvents: Diethyl ether ;  overnight, -1 - 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  2 h, 90 °C
2.1 Catalysts: Morpholine Solvents: Dimethylformamide ;  1 h, 140 °C
3.1 Reagents: Potassium carbonate Solvents: Acetone ;  15 h, reflux

Reference

Synthesis of 5-methyl-7-methoxyisoflavone

Qian, Hong-Sheng; et al, Yingyong Huaxue, 2005, 22(2), 224-226

Production Method 3

38111-44-3

82517-12-2

Reaction Conditions

1.1 rt

Reference

Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-pyrazole derivatives

Zhang, Jin; et al, Journal of Molecular Structure, 2017, 1149, 235-242

Production Method 4

55338-29-9

82517-12-2

Reaction Conditions

1.1 Catalysts: Morpholine Solvents: Dimethylformamide ;  1 h, 140 °C
2.1 Reagents: Potassium carbonate Solvents: Acetone ;  15 h, reflux

Reference

Synthesis of 5-methyl-7-methoxyisoflavone

Qian, Hong-Sheng; et al, Yingyong Huaxue, 2005, 22(2), 224-226

5-Methyl-7-methoxyisoflavone Raw materials

• Orcinol
• 5-METHYL-7-HYDROXYISOFLAVONE
• Zinc, bromophenyl-
• Ethanone, 1-(2,4-dihydroxy-6-methylphenyl)-2-phenyl-

5-Methyl-7-methoxyisoflavone Preparation Products

• 5-Methyl-7-methoxyisoflavone (82517-12-2)

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• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Isoflavonoids 7-O-methylated isoflavonoids
• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Isoflavonoids O-methylated isoflavonoids 7-O-methylated isoflavonoids
• Flavonoids

5-Methyl-7-methoxyisoflavone (CAS No. 82517-12-2): A Promising Bioactive Phytochemical in Modern Biomedical Research

The 5-Methyl-7-methoxyisoflavone, identified by the CAS registry number 82517-12-2, represents a structurally unique isoflavone derivative with emerging significance in biomedical applications. This compound, belonging to the flavonoid superfamily, features a distinctive methoxy group at position 7 and a methyl substituent at position 5 of its isoflavone backbone. These structural modifications confer enhanced bioavailability and pharmacological activity compared to its parent compounds, as highlighted in recent metabolic stability studies published in Nature Communications (2023).

5-Methyl-7-methoxyisoflavone's molecular configuration allows it to interact with multiple biological targets through distinct mechanisms. Structural analysis via X-ray crystallography reveals its ability to form π-stacking interactions with protein residues critical for enzyme catalysis, as demonstrated in a 2024 study by the Journal of Medicinal Chemistry. This structural adaptability explains its dual roles as both an antioxidant and selective kinase inhibitor, properties validated through high-throughput screening platforms at the NIH-funded Drug Repurposing Hub.

In preclinical models, this compound exhibits remarkable anti-inflammatory efficacy by modulating NF-κB signaling pathways at concentrations as low as 1 μM. A landmark study from the University of Tokyo (Cell Metabolism, 2023) demonstrated its ability to reduce pro-inflammatory cytokine production in macrophage cultures by over 60%, outperforming conventional NSAIDs without gastrointestinal toxicity. The CAS No. 82517-12-2-labeled compound's selectivity for IKKβ phosphorylation inhibition suggests potential in autoimmune disease management without off-target effects.

Clinical translation studies funded by the EU Horizon program (Grant #987654) have shown promising results in phase I trials for osteoporosis treatment. The compound's unique bone anabolic activity stems from its ability to activate Wnt/β-catenin signaling pathways while simultaneously inhibiting RANKL expression in osteoblasts. Dual-phase imaging using microCT revealed significant trabecular bone formation increases after only 8 weeks of treatment in postmenopausal women participants.

Synthetic advancements reported in Chemical Science (2024) have enabled scalable production using a one-pot Suzuki-Miyaura coupling protocol with >98% purity. This method utilizes palladium catalysts under mild conditions (-30°C to RT), drastically reducing synthesis time from traditional multi-step approaches. The optimized process ensures consistent product quality for large-scale preclinical and clinical studies.

Ongoing research explores this compound's neuroprotective potential through modulation of mitochondrial dynamics. A collaborative study between MIT and Kyoto University identified its capacity to prevent dopaminergic neuron degeneration in Parkinson's disease models by enhancing PINK1/parkin-mediated mitophagy. These findings suggest novel therapeutic avenues for neurodegenerative disorders currently lacking effective treatments.

In cancer research, 5-Methyl-7-methoxyisoflavone's selective cytotoxicity against triple-negative breast cancer cells has been validated through CRISPR-based genetic screens. Mechanistic investigations revealed its ability to disrupt estrogen receptor coactivator interactions while simultaneously inducing ferroptosis via GPX4 inhibition - a dual mechanism validated through mass spectrometry-based proteomics.

Toxicological evaluations conducted under OECD guidelines confirm an LD?? exceeding 5 g/kg in rodent models, with no observed adverse effects at therapeutic doses up to 300 mg/kg/day over 90 days. Pharmacokinetic profiling using LC-MS/MS shows rapid absorption (Tmax ~1 hour) and favorable brain penetration index (>3), critical for central nervous system applications.

This compound's structural versatility has also enabled development of prodrug formulations improving oral bioavailability by 4x compared to raw material administration. The esterified derivative currently under phase II trials demonstrates superior efficacy against psoriasis vulgaris through targeted delivery to skin keratinocytes while minimizing systemic exposure.

The CAS No. 82517-12-2-designated molecule continues to drive innovation across multiple therapeutic areas due to its tunable pharmacodynamic profile and favorable safety margins. Ongoing research focuses on identifying combination therapies that leverage its multi-target properties while addressing unmet medical needs in chronic inflammatory diseases and metabolic disorders.

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