3-Methoxycatechol
Based on 1 Customer Validation
3-Methoxycatechol is a catechol derivative with endothelium-dependent vasodilatory and antihypertensive activities. 3-Methoxycatechol activates GPR35, triggering dynamic mass redistribution and β-arrestin translocation. 3-Methoxycatechol inhibits tau self-interaction and scavenges free radicals such as DPPH. 3-Methoxycatechol combined with NaNO2 enhances forestomach proliferative lesions and papilloma formation, reduces glandular stomach lesions, and promotes esophageal lesion development. 3-Methoxycatechol can be used for research related to hypertension and papilloma.
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- Pureza : 99.98%
- No. CAS: 934-00-9
- Fòrmula: C7H8O3
- Peso molecular:140.14
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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 |
|---|---|---|---|---|
| MCF7 | GI50 |
27.55 μM
Compound: 3c
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Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 48 hrs by SRB assay
Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 48 hrs by SRB assay
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[PMID: 28041801] |
| TK-10 | GI50 |
51.63 μM
Compound: 3c
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Cytotoxicity against human TK10 cells assessed as cell growth inhibition after 48 hrs by SRB assay
Cytotoxicity against human TK10 cells assessed as cell growth inhibition after 48 hrs by SRB assay
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[PMID: 28041801] |
| UACC-62 | GI50 |
23.64 μM
Compound: 3c
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Cytotoxicity against human UACC62 cells assessed as cell growth inhibition after 48 hrs by SRB assay
Cytotoxicity against human UACC62 cells assessed as cell growth inhibition after 48 hrs by SRB assay
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[PMID: 28041801] |
In Vitro
3-Methoxycatechol (100 nM-100 μM) effectively relaxes resistance mesenteric arteries in male Wistar rats, with an EC50 of 12.5 μM[1].
3-Methoxycatechol (10 nM-100 μM) does not induce vasodilation of porcine coronary artery rings[1].
3-Methoxycatechol (100 nM-100 μM) exerts a vasodilatory effect in male Wistar rat aortic rings that is mildly endothelium-dependent[1].
3-Methoxycatechol enhances cGMP- and cAMP-mediated vasodilation in aortic rings of male Wistar rats, but does not act directly on sGC or PKG[1].
3-Methoxycatechol-induced vasodilation of aortic rings in male Wistar rats involves KV channels, especially KV7 channels, whereas BKCa, KATP, and KIR channels are not involved[1].
3-Methoxycatechol does not inhibit L-type Ca2+ channels in aortic rings of male Wistar rats, but its vasodilatory effect is attenuated when SERCA is inhibited[1].
3-Methoxycatechol exhibits potent DPPH radical scavenging activity, with an EC50 of 0.16 mol AH/mol DPPH and an AE of 48 x 103 mol DPPH/(mol AH x t)[5].
3-Methoxycatechol (10 µM; 2-24 h) significantly disrupts microtubule stability in HuH-7 cells[2].
3-Methoxycatechol molecular docking results support its mechanism of action through activation of KV7.4 channels[3].
3-Methoxycatechol (1 h) acts as a GPR35 agonist in native HT-29 cells, eliciting dose-dependent DMR with an EC50 of 147 μM and a maximum DMR signal of 219 pm[4].
3-methoxycatechol-induced DMR in HT-29 cells is biphasically inhibited by mL-145 (HY-107536)[4].
3-Methoxycatechol (5 h) is active in the Tango β-arrestin translocation assay in U2OS-GPR35-bla cells, with an EC50 of 80.7 μM and an efficacy of 41% of the maximal response to zaprinast[4].
3-Methoxycatechol (1 mM) exhibits a low oxidation potential of 0.200 V vs. Ag/AgCl at pH 7.02, confirming its high electron-donating capacity and antioxidant effect[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:A-10 rat embryonic thoracic aorta smooth muscle cell line
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Concentration:1, 10, and 100 μM
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Incubation Time:24 h
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Result:Did not significantly affect cell viability of A-10 cells, with no significant toxic effects observed.
In Vivo
3-methoxycatechol (3-methoxycatechol; mixed into feed; daily; approximately 24 weeks) combined with 0.3% NaNO2 most significantly reduces GST-P-positive liver foci and inhibits the development of glandular stomach lesions, while strongly stimulating forestomach hyperplasia[7].
3-methoxycatechol (2%; mixed into feed; daily; until week 28) induces forestomach hyperplasia and glandular stomach adenomas in rats without initiation, but does not promote forestomach carcinogenesis[7].
3-methoxycatechol (2%; mixed into feed; daily; until week 28), in combination with NaNO2, strongly stimulates forestomach hyperplasia and papilloma development in non-initiated rats, while significantly reducing the incidence of glandular stomach lesions[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Spontaneously hypertensive rats (SHR) (male and female, 20 weeks of age, males 280 g, females 180 g)[1]
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Dosage:0.001-1 mg/kg (males); 0.001-10 mg/kg (females)
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Administration:i.v.
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Result:Decreased diastolic blood pressure significantly from 0.1 mg/kg in males.
Decreased systolic blood pressure significantly from 1 mg/kg in males.
Decreased diastolic and systolic blood pressure from 1 mg/kg in females.
Did not significantly change heart rate in both sexes.
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Animal Model:F344 (male, 6 weeks old, multiorgan carcinogenesis model)[7]
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Dosage:2%
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Administration:p.o. (dietary admixture); daily; approximately 24 weeks
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Result:Significantly enhanced the induction of forestomach papillomas (13 of 14 rats, 93%) and weakly enhanced that of carcinomas (3 of 14 rats, 21% SCC; 4 of 14 rats, 29% CIS or SCC).
Induced glandular stomach submucosal hyperplasia in 12 of 14 rats (86%) and adenomas in 9 of 14 rats (64%).
Resulted in liver GST-P-positive foci numbered 3.16 per cm2 with an area of 0.20 mm2/cm2, and hyperplastic nodules in 1 of 14 rats (7%).
Significantly enhanced the induction of esophageal papillomas (5 of 14 rats, 36%).
Induced tongue hyperplasia in 2 of 14 rats (14%), papillomas in 4 of 14 rats (29%), and carcinoma in 1 of 14 rats (7%).
Induced thyroid follicular cell hyperplasia in 4 of 14 rats (29%), follicular cell adenoma in 1 of 14 rats (7%), and follicular cell carcinoma in 4 of 14 rats (29%).
Induced lung adenomas in 11 of 14 rats (79%).
Induced kidney nephroblastomas in 2 of 14 rats (14%).
Induced urinary bladder papillary or nodular hyperplasia in 2 of 14 rats (14%), papillomas in 1 of 14 rats (7%), and carcinoma in 0 rats.
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Animal Model:F344 (male, 6 weeks old, non-initiated)[7]
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Dosage:2%
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Administration:p.o. (dietary admixture); daily; until week 28
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Result:Induced forestomach mild hyperplasia in 7 of 10 rats (70%), moderate hyperplasia in 2 of 10 rats (20%), and no severe or marked hyperplasia.
Induced glandular stomach submucosal hyperplasia in 9 of 10 rats (90%) and adenomas in 7 of 10 rats (70%).
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Animal Model:F344 (male, 6 weeks old, multiorgan carcinogenesis model)[7]
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Dosage:2% (this compound); 0.3% (NaNO2)
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Administration:p.o. (dietary admixture for this compound; drinking water for NaNO2); daily; approximately 24 weeks
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Result:Resulted in forestomach papillomas in 12 of 14 rats (86%), carcinoma in situ in 3 of 14 rats (25%), squamous cell carcinoma in 2 of 14 rats (14%), and CIS or SCC in 4 of 14 rats (29%).
Reduced glandular stomach submucosal hyperplasia to 2 of 14 rats (14%) and adenomas to 2 of 14 rats (14%), with no adenocarcinomas.
Resulted in liver GST-P-positive foci numbered 1.52 per cm2 with an area of 0.12 mm2/cm2, with no hyperplastic nodules or hepatocellular carcinomas observed.
Induced esophageal papillomas in 7 of 14 rats (50%).
Induced tongue hyperplasia in 5 of 14 rats (36%), papillomas in 3 of 14 rats (21%), and no carcinoma.
Induced thyroid follicular cell hyperplasia in 0 of 14 rats, follicular cell adenoma in 0 of 14 rats, and follicular cell carcinoma in 1 of 14 rats (7%).
Induced lung adenomas in 4 of 14 rats (29%).
Induced kidney renal cell adenoma in 2 of 14 rats (14%) and nephroblastoma in 1 of 14 rats (7%).
Induced urinary bladder papillary or nodular hyperplasia in 3 of 14 rats (21%), papillomas in 1 of 14 rats (7%), and no carcinoma.
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Animal Model:F344 (male, 6 weeks old, non-initiated)[7]
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Dosage:2% (this compound); 0.3% (NaNO2)
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Administration:p.o. (dietary admixture for this compound; drinking water for NaNO2); daily; until week 28
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Result:Induced forestomach mild hyperplasia in 10 of 10 rats (100%), moderate hyperplasia in 10 of 10 rats (100%), severe hyperplasia in 10 of 10 rats (100%), and marked hyperplasia in 5 of 10 rats (50%).
Induced forestomach papillomas in 5 of 10 rats (50%).
Reduced glandular stomach submucosal hyperplasia to 1 of 10 rats (10%) and adenomas to 2 of 10 rats (20%), with no adenocarcinomas.
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Animal Model:F344 (male, 10 weeks of age)[8]
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Dosage:2% (this compound); 0.3% NaNO2 (drinking water)
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Administration:p.o.; free feeding; 24 weeks
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Result:Induced forestomach papillomas in 5 rats and severe forestomach hyperplasia in 100% of rats when combined with NaNO2.
Induced glandular stomach submucosal hyperplasia in 9 rats and adenomas in 7 rats when administered alone.
Reduced body weights compared to controls.
Chemical Information
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No. CAS 934-00-9
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Appearance <42.8°C Solid,>42.8°C Liquid
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Peso molecular 140.14
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Fòrmula C7H8O3
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Color Colorless to off-white
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SMILES
COC1=CC=CC(=C1O)O
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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 : 200 mg/mL (1427.14 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
H2O : 100 mg/mL (713.57 mM; Need ultrasonic)
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.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
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.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
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 (35.68 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 (35.68 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.
Working solution concentration: 0.22 mg/mL
This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
Pureza y Documentación
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Ficha de datos (309 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[6]. Tao Y, et al. Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone. Journal of bacteriology. 2004 Jul;186(14):4705-13. [Content Brief]
[7]. Hirose M, et al. Effects of sodium nitrite and catechol, 3-methoxycatechol, or butylated hydroxyanisole in combination in a rat multiorgan carcinogenesis model. Cancer research. 1993 Jan 01;53(1):32-7. [Content Brief]
[8]. Ito N, et al. Carcinogenicity and modification of carcinogenic response by plant phenols[J]. 1992.
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 |
|---|---|---|---|---|---|
| H2O / DMSO | 1 mM | 7.1357 mL | 35.6786 mL | 71.3572 mL | 178.3930 mL |
| 5 mM | 1.4271 mL | 7.1357 mL | 14.2714 mL | 35.6786 mL | |
| 10 mM | 0.7136 mL | 3.5679 mL | 7.1357 mL | 17.8393 mL | |
| 15 mM | 0.4757 mL | 2.3786 mL | 4.7571 mL | 11.8929 mL | |
| 20 mM | 0.3568 mL | 1.7839 mL | 3.5679 mL | 8.9197 mL | |
| 25 mM | 0.2854 mL | 1.4271 mL | 2.8543 mL | 7.1357 mL | |
| 30 mM | 0.2379 mL | 1.1893 mL | 2.3786 mL | 5.9464 mL | |
| 40 mM | 0.1784 mL | 0.8920 mL | 1.7839 mL | 4.4598 mL | |
| 50 mM | 0.1427 mL | 0.7136 mL | 1.4271 mL | 3.5679 mL | |
| 60 mM | 0.1189 mL | 0.5946 mL | 1.1893 mL | 2.9732 mL | |
| 80 mM | 0.0892 mL | 0.4460 mL | 0.8920 mL | 2.2299 mL | |
| 100 mM | 0.0714 mL | 0.3568 mL | 0.7136 mL | 1.7839 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
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