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5-Geranoxy-7-methoxycoumarin

Cat No.:V52493 Purity: ≥98%
5-Geranoxy-7-methoxycoumarin is a coumarin with anticancer, antifungal, and anti-bacterial effect.
5-Geranoxy-7-methoxycoumarin
5-Geranoxy-7-methoxycoumarin Chemical Structure CAS No.: 7380-39-4
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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10mg
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500mg
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Product Description
5-Geranoxy-7-methoxycoumarin is a coumarin with anticancer, antifungal, and anti-bacterial effect. 5-Geranoxy-7-methoxycoumarin causes apoptosis.
5-Geranoxy-7-methoxycoumarin (CAS 7380-39-4) is a naturally occurring coumarin derivative found in various plants. It belongs to the class of oxygenated coumarins and has been studied for its potential biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. This compound is characterized by a geranyloxy group at position 5 and a methoxy group at position 7 on the coumarin core.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary targets of 5-Geranoxy-7-methoxycoumarin include inflammatory pathways, microbial pathogens, and cancer cell lines. It has been shown to exhibit anti-inflammatory activity by modulating cytokine production and inhibiting inflammatory mediators. The compound also demonstrates antimicrobial activity against various bacterial and fungal strains. Its anticancer potential is attributed to its ability to induce apoptosis and inhibit cell proliferation in cancer cells.
ln Vitro
In SW480 cells, 5-geranoxy-7-methoxycoumarin (12.5-200 µM; 24-72 hours) significantly inhibits cell proliferation in a time-dependent fashion[1]. 5-Geranoxy-7-methoxycoumarin (50 µM; 48 hours) inhibits the p38 MAPK signaling pathway in SW480 cells, which leads to DNA fragmentation and apoptosis[1]. After 48 hours of incubation, the percentage of cells in the sub G1/G0 phase rises from 5.3% (in control cells) to 18% when 5-geranoxy-7-methoxycoumarin (50 µM) is added[1].
In vitro, 5-Geranoxy-7-methoxycoumarin has been reported to possess anti-inflammatory, antimicrobial, and anticancer activities. Studies have shown that it can inhibit the production of pro-inflammatory cytokines and reduce the activation of NF-κB signaling. The compound also exhibits inhibitory effects against the growth of several Gram-positive and Gram-negative bacteria, as well as fungi. In cancer cell lines, it induces cell cycle arrest and apoptosis.
ln Vivo
In vivo activity of 5-Geranoxy-7-methoxycoumarin has not been extensively characterized. As a natural coumarin derivative, it has potential therapeutic applications in the treatment of inflammatory diseases, infections, and cancer. However, detailed in vivo pharmacokinetic and pharmacodynamic studies are lacking. The compound is primarily studied for its in vitro biological activities.
Enzyme Assay
In vitro enzyme/receptor binding assays for 5-Geranoxy-7-methoxycoumarin are not well established, as it is a natural product with multiple activities. Standard assays include anti-inflammatory activity using LPS-stimulated macrophages and measuring cytokine levels. Antimicrobial activity is assessed by broth microdilution to determine MIC values. Anticancer activity is evaluated by MTT assays on cancer cell lines. The compound is typically tested in a concentration range of 1-100 µM.
Cell Assay
Cell Proliferation Assay [1]
Cell Types: SW480
Tested Concentrations: 0-20 μM
Incubation Duration: 24, 48 and 72 hrs (hours)
Experimental Results: Inhibited cell growth by 67% at 72 hrs (hours).
Apoptosis Analysis[1]
Cell Types: SW480 cells
Tested Concentrations: 50 μM
Incubation Duration: 48 hrs (hours)
Experimental Results: Induced cell apoptosis.
Cell Cycle Analysis[1]
Cell Types: SW480 cells
Tested Concentrations: 50 μM
Incubation Duration: 48 hrs (hours)
Experimental Results: Inhibited cell cycle progression in vitro.
In vitro cellular assays for 5-Geranoxy-7-methoxycoumarin involve testing its effects on immune cells, microbial cultures, and cancer cells. For anti-inflammatory studies, macrophages are stimulated with LPS and treated with the compound; cytokine levels are measured by ELISA. For antimicrobial studies, bacterial and fungal cultures are treated with serial dilutions, and growth inhibition is monitored. For anticancer studies, cancer cell lines are treated, and cell viability and apoptosis are assessed.
Animal Protocol
In vivo animal studies for 5-Geranoxy-7-methoxycoumarin are limited. For anti-inflammatory efficacy, animal models of inflammation (e.g., carrageenan-induced paw edema) could be used. For antimicrobial efficacy, infection models could be applied. For anticancer efficacy, tumor xenograft models could be employed. Animals would be treated with the compound via oral or intraperitoneal administration, and relevant endpoints would be measured.
ADME/Pharmacokinetics
5-Geranoxy-7-methoxycoumarin has a molecular formula of C20H24O4 and a molecular weight of 328.40. It appears as a solid with a purity of ≥98%. It is soluble in organic solvents such as DMSO, ethanol, and methanol. The compound should be stored in a dry, dark place at -20°C. Stability information in solution is limited, and it is recommended to prepare fresh stock solutions. It is intended for research use only and is not for human consumption.
Toxicity/Toxicokinetics
The toxicity profile of 5-Geranoxy-7-methoxycoumarin has not been extensively characterized. As a natural coumarin, it is generally considered to have low to moderate toxicity. Standard toxicity studies would include acute oral toxicity, dermal irritation, and repeated-dose toxicity in animal models. The compound is intended for research use only and is not approved for clinical use.
References

[1]. 5-Geranyloxy-7-methoxycoumarin inhibits colon cancer (SW480) cells growth by inducing apoptosis. Planta Med. 2013 Mar;79(3-4):219-26.

[2]. Synergism of coumarins from the Chinese drug Zanthoxylum nitidum with antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA). Phytomedicine.

Additional Infomation
5-Germanoxy-7-methoxycoumarin is a terpene lactone.
5-Geranoxy-7-methoxycoumarin (CAS 7380-39-4) is a naturally occurring coumarin derivative found in various plants. It has a molecular formula of C20H24O4 and a molecular weight of 328.40. The compound has been studied for its anti-inflammatory, antimicrobial, and anticancer activities. It exhibits inhibition of pro-inflammatory cytokines, antimicrobial effects against various pathogens, and antiproliferative effects on cancer cells. It is intended for research use only and is not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24O4
Molecular Weight
328.40
Exact Mass
328.167
CAS #
7380-39-4
PubChem CID
6441377
Appearance
White to off-white solid
Density
1.092g/cm3
Boiling Point
487.1ºC at 760 mmHg
Melting Point
86-88ºC
Flash Point
213.2ºC
Index of Refraction
1.542
Source
Originated from plants: Rutaceae Citrus limon (L.) Burm. F.
LogP
4.873
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Heavy Atom Count
24
Complexity
514
Defined Atom Stereocenter Count
0
SMILES
CC(=CCCC(=CCOC1=CC(=CC2=C1C=CC(=O)O2)OC)C)C
InChi Key
WXUOSNJWDJOHGW-XNTDXEJSSA-N
InChi Code
InChI=1S/C20H24O4/c1-14(2)6-5-7-15(3)10-11-23-18-12-16(22-4)13-19-17(18)8-9-20(21)24-19/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+
Chemical Name
5-[(2E)-3,7-dimethylocta-2,6-dienoxy]-7-methoxychromen-2-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~14.3 mg/mL (~43.5 mM; with ultrasonication and warming by heating to 60°C)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.43 mg/mL (4.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (14.3 mg/mL) to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0451 mL 15.2253 mL 30.4507 mL
5 mM 0.6090 mL 3.0451 mL 6.0901 mL
10 mM 0.3045 mL 1.5225 mL 3.0451 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration: mg/mL;

Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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