6-Hydroxycoumarin
Based on 1 Customer Validation
6-Hydroxycoumarin is a plant-derived secondary metabolite of the coumarin class, possessing insecticidal, antitumor, and other biological activities. 6-Hydroxycoumarin targets the midgut tissue of the red imported fire ant (Solenopsis invicta), inhibits CYP450, induces elevated activities of GST, CarE, and SOD, disrupts mitochondrial ultrastructure, triggers apoptosis, and also impairs insect neuromuscular behavior. 6-Hydroxycoumarin exhibits photoallergic properties and serves as an intermediate for the synthesis of isoxazolyl and triazolyl derivatives. 6-Hydroxycoumarin is applicable to research related to red imported fire ant control.
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- Pureza : 99.32%
- No. CAS: 6093-68-1
- Fòrmula: C9H6O3
- Peso molecular:162.14
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Almacenamiento:
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
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Actividad biológica
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Chemical Information
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Solvente y solubilidad
- Protocolo
- Pureza y Documentación
- Referencias
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Help & FAQs
Actividad biológica
Descripciòn
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HL-60 | IC50 |
35 μM
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Cytotoxic activity against human HL-60 leukemia cells measured by MTT assay.
Cytotoxic activity against human HL-60 leukemia cells measured by MTT assay.
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25088398 |
| COLO 205 | IC50 |
38.70 μM
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Cytotoxic activity against human Colo-205 colon cancer cells measured by MTT assay.
Cytotoxic activity against human Colo-205 colon cancer cells measured by MTT assay.
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25088398 |
| HCT-116 | IC50 |
46.2 μM
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Cytotoxic activity against human HCT-116 colon cancer cells measured by MTT assay.
Cytotoxic activity against human HCT-116 colon cancer cells measured by MTT assay.
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25088398 |
In Vitro
6-hydroxycoumarin (72 h) induces midgut epithelial damage and cell apoptosis in red imported fire ants in a dose-dependent manner; the extent of damage progresses from cell shedding at 55 mg/L to extensive epithelial detachment at 110 mg/L[1].
6-hydroxycoumarin induces severe mitochondrial ultrastructural damage in the midgut epithelial cells of red imported fire ants, including cristae disintegration and matrix swelling, which is consistent with impaired bioenergetics and apoptosis[1].
6-Hydroxycoumarin (compound 1) exhibits cytotoxic activity against human HL-60, Colo-205, and HCT-116 cancer cell lines, with the highest potency against HL-60 leukemia cells (IC50 = 35 μM)[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
In Vivo
6-Hydroxycoumarin (31.25-500 mg/L; 5-7 days) induces a progressive, dose-dependent breakdown of aggregation, gripping, climbing, and walking behaviors in Solenopsis invicta workers, with complete loss of motor and social behaviors at higher concentrations[1].
6-hydroxycoumarin induces extensive metabolic reprogramming in red imported fire ant workers and significantly inhibits CYP450-mediated xenobiotic detoxification pathways and glutathione metabolic pathways; it also induces bifunctional, isoform-specific transcriptional changes in CYP450 genes; it inhibits cytochrome P450 activity but induces concentration-dependent increases in GST, CarE, and SOD activities[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Solenopsis invicta Buren (major workers; 5-7 mm body length; field-collected)[1]
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Dosage:55 mg/L (1× LC50, T1)
110 mg/L (2× LC50, T2) -
Administration:oral (in 15% honey water); daily solution refreshment; 72 h
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Result:Decreased CYP450 enzyme activity and increased GST, CarE, and SOD activities at 55 mg/L (T1).
Significantly increased GST, CarE, and SOD activities and suppressed CYP450 activity relative to controls at 110 mg/L (T2).
Significantly upregulated CYP6AS165, CYP369A2, CYP301A1, CYP4BW10, and CYP9P26 expression at 110 mg/L (T2).
Significantly suppressed CYP336A45 and CYP4CY5v1 expression at 55 mg/L (T1).
Identified 1085 differentially abundant metabolites (327 up-regulated, 758 down-regulated) after 72 h exposure to LC50 concentration, with enrichment in amino acid metabolism, lipid metabolism, xenobiotic biodegradation, and cofactor/vitamin metabolism pathways.
Down-regulated 8 out of 11 CYP450-related metabolites and suppressed all 7 xenobiotics metabolism-by-CYP450 metabolites within CYP450-mediated detoxification pathways.
Induced initial midgut epithelial damage including cellular detachment and tissue disorganization at 55 mg/L (T1).
Caused extensive epithelial sloughing into the intestinal lumen and pronounced tissue gaps at 110 mg/L (T2).
Induced concentration-dependent apoptosis with increasing nuclear fragmentation and apoptotic bodies at higher doses in TUNEL assays.
Caused severe mitochondrial ultrastructural damage in midgut enterocytes, including matrix swelling, cristae fragmentation, partial cristolysis, and focal membrane rupture in TEM analysis.
Chemical Information
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No. CAS 6093-68-1
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Appearance Solid
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Peso molecular 162.14
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Fòrmula C9H6O3
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Color Light yellow to light brown
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SMILES
O=C1C=CC2=CC(O)=CC=C2O1
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Solvente y solubilidad
In Vitro:
DMSO : ≥ 100 mg/mL (616.75 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 5 mg/mL (30.84 mM); Clear solution
This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 5 mg/mL (30.84 mM); Clear solution
This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocolo
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
Pureza y Documentación
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Ficha de datos (285 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Luo R, et al. 6-Hydroxycoumarin from Artemisia lavandulaefolia Induces Multimodal Toxicity in Solenopsis invicta via behavioral inhibition and mitochondrial disruption. Ecotoxicology and environmental safety. 2026 Jun 15;318:120209. [Content Brief]
[3]. Shakeel-u-Rehman, et al. Synthesis and biological evaluation of novel isoxazoles and triazoles linked 6-hydroxycoumarin as potent cytotoxic agents. Bioorganic & medicinal chemistry letters. 2014 Sep 01;24(17):4243-6. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 6.1675 mL | 30.8375 mL | 61.6751 mL | 154.1877 mL |
| 5 mM | 1.2335 mL | 6.1675 mL | 12.3350 mL | 30.8375 mL | |
| 10 mM | 0.6168 mL | 3.0838 mL | 6.1675 mL | 15.4188 mL | |
| 15 mM | 0.4112 mL | 2.0558 mL | 4.1117 mL | 10.2792 mL | |
| 20 mM | 0.3084 mL | 1.5419 mL | 3.0838 mL | 7.7094 mL | |
| 25 mM | 0.2467 mL | 1.2335 mL | 2.4670 mL | 6.1675 mL | |
| 30 mM | 0.2056 mL | 1.0279 mL | 2.0558 mL | 5.1396 mL | |
| 40 mM | 0.1542 mL | 0.7709 mL | 1.5419 mL | 3.8547 mL | |
| 50 mM | 0.1234 mL | 0.6168 mL | 1.2335 mL | 3.0838 mL | |
| 60 mM | 0.1028 mL | 0.5140 mL | 1.0279 mL | 2.5698 mL | |
| 80 mM | 0.0771 mL | 0.3855 mL | 0.7709 mL | 1.9273 mL | |
| 100 mM | 0.0617 mL | 0.3084 mL | 0.6168 mL | 1.5419 mL |
6-Hydroxycoumarin Related Classifications
HY-N6656 Related Classifications
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