| Catalog No | Package | Original Price | Price | Inventory | Quantity | Operating |
|---|---|---|---|---|---|---|
| BP0722-20mg | 20mg | $20.00 | Sign in |
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Synonym name: 7-Methoxycoumarin; Umbelliferone methyl ether; Ayapanin
Catalogue No.: BP0722
Cas No.: 531-59-9
Formula: C10H8O3
Mol Weight: 176.171
Botanical Source: Present in Herniaria spp., Eupatorium ayapana, Matricaria chamomilla var. recutita, Ruta pinnata, Prunus mahaleb (mahaleb cherry) and other plants
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HPLC of Herniarin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
7-Methoxycoumarin(CAS No.: 531-59-9) is a naturally occurring coumarin-type compound widely distributed in various flowering plants. As an important member of the coumarin family, 7-methoxycoumarin, due to its unique chemical structure and bioactivity, has attracted widespread attention in the field of natural product pharmacology in recent years. Numerous studies have shown that 7-methoxycoumarins not only have significant anticancer activity, especially in inducing apoptosis in breast cancer cells (MCF-7), but also exhibit multiple biological activities such as anti-inflammatory and antidermatophyte fungi. These pharmacological properties make it a potential candidate for malignant tumor research such as bladder and breast cancer. In addition, the role of 7-methoxycoumarins in regulating inflammation-related signaling pathways further expands its application prospects as natural medicines.
This review aims to systematically summarize the chemical structure and physicochemical properties of 7-methoxycoumarin, plant origin and extraction methods, pharmacological activity and mechanism of action. Combined with druggability evaluation and pharmacokinetic characteristics, it deeply explores its clinical application potential and future development directions, providing a theoretical foundation and reference for research in related fields.
The chemical structure of 7-methoxycoumarins is based on the coumarin-based framework, with a molecular formula of C10H8O3 and a molecular weight of 176.1710. Its structural feature is the introduction of a methoxy (-OCH3) substituent at position 7 of the coumarin's core, a structural modification that gives it unique bioactivity and physicochemical properties. The compound has a LogP value of 1.9653, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in vivo. The polarized surface area (TPSA) was 39.44 Ų, indicating that its molecules have good membrane permeability, especially high penetration of the blood-brain barrier, which aligns with its potential applications in the central nervous system.
Water solubility was 0.2367 mg/mL, indicating low solubility in water, suggesting that solubility enhancement strategies should be considered in drug formulation development. The hERG channel inhibition test results were negative, indicating a low risk of cardiotoxicity and good safety. The Ames mutagenicity test result was 1.5, which is within the low mutagenic risk range, indicating weak genotoxicity and meeting safety requirements for drug development.
7-Methoxycoumarins are widely found in several plant families and genera such as the Apiaceae, Fabaceae, and Asteraceae families, and are especially abundant in certain flowering plants such as Rutaceae. Common natural sources include celery, fennel, certain medicinal plants such as hop (Humulus lupulus), and related species.
Traditional methods for extracting 7-methoxycoumarins mainly rely on organic solvent extraction, with commonly used solvents including ethanol, methanol, and ethyl acetate. Typical extraction processes include plant material grinding, solvent immersion, ultrasound-assisted extraction, or reflux heat extraction, followed by liquid-liquid partitioning, column chromatography, and other separation and purification techniques to obtain high-purity 7-methoxycoumarin. In recent years, the application of supercritical CO2 extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, while also offering greater environmental advantages.
During purification, silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC) are widely used to ensure the structural integrity and purity of compounds. Structural identification relies on modern analytical techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR).
7-Methoxycoumarins have demonstrated significant anticancer potential in multiple in vitro cell experiments. In particular, in the breast cancer cell line MCF-7, 7-methoxycoumarins can induce apoptosis, leading to a significant decrease in cell viability. Its anticancer mechanism involves cell cycle arrest, loss of mitochondrial membrane potential, elevated reactive oxygen species (ROS) levels, and regulation of apoptosis-related protein expression. Research shows that 7-methoxycoumarins promote programmed cell death by activating apoptotic enzymes such as Caspase-3 and Caspase-9.
In addition, 7-methoxycoumarins have also shown activity in inhibiting proliferation and promoting apoptosis in bladder cancer cells, suggesting its potential application value in the treatment of urinary system tumors. Its anticancer activity may also be related to inhibiting tumor cell migration and invasion, thereby reducing the risk of metastasis.
Research on 7-methoxycoumarin's anti-inflammatory effects has also made progress. It can significantly inhibit the expression and release of various inflammatory mediators, including IL-6, TNF-α, NOS2, PTGS2 (COX-2), and others. By modulating the NF-κB signaling pathway and STAT3 transcription factor activity, 7-methoxycoumarins suppress inflammatory responses and reduce tissue damage.
Additionally, 7-methoxycoumarins regulate TRPV1 and TRPA1 plasma channels, which play important roles in inflammatory pain transmission, indicating their potential in managing inflammatory pain.
7-Methoxycoumarins exhibits good inhibitory effects against dermatophytes, indicating its potential as an antifungal drug development. Its antibacterial mechanism may involve cell membrane destruction and metabolic inhibition, and the specific targets require further research.
The multi-target mechanism of 7-methoxycoumarin, which forms the basis for its multiple pharmacological activities, is the basis of its multiple pharmacological activities. Its main targets include:
The synergistic regulation of these targets enables 7-methoxycoumarins to exhibit multiple mechanisms of action in both anticancer and anti-inflammatory fields, highlighting their complexity and potential as natural drug molecules.
The druggability parameters of 7-methoxycoumarins indicate that it has good potential for drug development. A molecular weight of 176.1710 conforms to the Lipinski rule, and a LogP value of 1.9653 indicates moderate lipid solubility, which is beneficial for oral absorption and internal distribution. TPSA is 39.44 Ų, and its low polarization surface area facilitates cell membrane penetration and blood-brain barrier passage, supporting its potential applications in central nervous system diseases.
Low water solubility (0.2367 mg/mL) suggests the need for solubility improvement technologies such as nanocarriers and solid dispersions in formulation design to enhance bioavailability. Negative inhibition of the hERG channel indicates a lower risk of cardiotoxicity and better safety. The Ames trial result was 1.5, indicating a low genotoxicity risk and meeting preclinical safety evaluation criteria.
Regarding pharmacokinetics, research on metabolism and excretion in vivo is currently limited. It is speculated that 7-methoxycoumarin, metabolized via the liver, may involve the cytochrome P450 enzyme system, and the activity and toxicity of these metabolites require further evaluation. Its high blood-brain barrier permeability suggests good distribution in the central nervous system, but potential central nervous system side effects should also be considered.
Based on the diverse biological activities of 7-methoxycoumarin, including anticancer, anti-inflammation, and antibacterial effects, its clinical application prospects are broad. Especially in adjuvant therapy for breast and bladder cancers, 7-methoxycoumarins are expected to serve as natural antitumor candidates, inducing tumor cell apoptosis and inhibiting tumor progression.
Moreover, its anti-inflammatory activity offers new ideas for treating chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease. Antidermatophyte activity supports its potential application in the treatment of fungal skin infections.
Future research should focus on the following aspects:
Through multidisciplinary collaboration, 7-methoxycoumarins are expected to become an important breakthrough in natural drug development.
As a natural coumarin, 7-methoxycoumarin, with its remarkable anticancer, anti-inflammatory, and antibacterial properties, demonstrates broad pharmacological application potential. Its unique chemical structure endows it with excellent druggability and safety, providing a solid foundation for new drug development. In the future, combining modern medicinal chemistry, molecular biology, and pharmacokinetic research, further elucidating its mechanism of action and optimizing drug properties will help promote 7-methoxycoumarin's shift from laboratory research to clinical application, benefiting patients. As a key resource for drug discovery, the research progress of 7-methoxycoumarin, further demonstrates the irreplaceable value of natural products in modern pharmaceutical development.
