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2,6-Dimethoxy-1,4-benzoquinone

CAS# 530-55-2

2,6-Dimethoxy-1,4-benzoquinone

Catalog No. BCN5698----Order now to get a substantial discount!

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Quality Control of 2,6-Dimethoxy-1,4-benzoquinone

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Chemical structure

2,6-Dimethoxy-1,4-benzoquinone

3D structure

Chemical Properties of 2,6-Dimethoxy-1,4-benzoquinone

Cas No. 530-55-2 SDF Download SDF
PubChem ID 68262 Appearance Yellow powder
Formula C8H8O4 M.Wt 168.2
Type of Compound Quinones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2,6-dimethoxycyclohexa-2,5-diene-1,4-dione
SMILES COC1=CC(=O)C=C(C1=O)OC
Standard InChIKey OLBNOBQOQZRLMP-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 2,6-Dimethoxy-1,4-benzoquinone

The barks of Liriodendron tulipifera

Biological Activity of 2,6-Dimethoxy-1,4-benzoquinone

Description2,6-Dimethoxy-1,4-benzoquinone exhibits strong antibacterial activities against S. pyogenes, S. mitis, and S. mutans with MIC values of 7.8, 7.8, and 15.6 ug/mL, and MBC values of 7.8, 7.8, and 31.2  ug/mL, respectively. 2,6-Dimethoxy-1,4-benzoquinone can produce genotoxic effects in patients taking dimethophrine.
TargetsAntifection
In vitro

Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds from Ficus foveolata.[Pubmed: 24611777]

Pharm Biol. 2014 Sep;52(9):1104-9.

Medicinal plants involved in traditional Thai longevity formulations are potential sources of antimicrobial compounds. To evaluate the antimicrobial activities of some extracts from medicinal plants used in traditional Thai longevity formulations against some oral pathogens, including Streptococcus pyogenes, Streptococcus mitis, Streptococcus mutans, and Candida albicans. An extract that possessed the strongest antimicrobial activity was fractionated to isolate and identify the active compounds.
METHODS AND RESULTS:
Methanol and ethyl acetate extracts of 25 medicinal plants used as Thai longevity formulations were evaluated for their antimicrobial activity using disc diffusion (5 mg/disc) and broth microdilution (1.2-2500 µg/mL) methods. The ethyl acetate extract of Ficus foveolata Wall. (Moraceae) stems that exhibited the strongest antibacterial activity was fractionated to isolate the active compounds by an antibacterial assay-guided isolation process. The ethyl acetate extract of F. foveolata showed the strongest antibacterial activity with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 19.5-39.0 and 39.0-156.2 µg/mL, respectively. On the basis of an antibacterial assay-guided isolation, seven antibacterial compounds, including 2,6-Dimethoxy-1,4-benzoquinone (1), syringaldehyde (2), sinapaldehyde (3), coniferaldehyde (4), 3β-hydroxystigmast-5-en-7-one (5), umbelliferone (6), and scopoletin (7), were purified.
CONCLUSIONS:
Among these isolated compounds, 2,6-Dimethoxy-1,4-benzoquinone (1) exhibited the strongest antibacterial activities against S. pyogenes, S. mitis, and S. mutans with MIC values of 7.8, 7.8, and 15.6 µg/mL, and MBC values of 7.8, 7.8, and 31.2 µg/mL, respectively. In addition, this is the first report of these antibacterial compounds in the stems of F. foveolata.

Formation of 2,6-dimethoxy-1,4-benzoquinone, a highly genotoxic compound, from the reaction of sodium nitrite with the sympathomimetic drug dimethophrine in acidic aqueous solution.[Pubmed: 3208895]

Farmaco Sci. 1988 Jun;43(6):523-38.

Because of the genotoxic effects shown by Dimethophrine (DMP) nitrosation mixtures, the interaction between DMP hydrochloride and sodium nitrite in acidic aqueous solution at 37 degrees was investigated in a wide range of reagent concentrations and molar ratios, reaction times and pH values.
METHODS AND RESULTS:
Actually, depending on the operating conditions, it was possible to detect variable amounts of 2,6-Dimethoxy-1,4-benzoquinone (DMBQ), a highly genotoxic compound, but no N-nitrosoderivative. The highest conversion of DMP into DMBQ was obtained when concentrated acidic solutions of DMP and NaNO2 (molar ratio 1:1.9) reacted at pH 3.0-4.0 (50-60% after 1 hour, depending on the pH conditions). When DMP hydrochloride and NaNO2 (molar ratio 1:0.95) were allowed to react at pH 3.5 in a more diluted solution, to mimic gastric conditions, the conversion of DMP into DMBQ after 20 min was about 3%. The breakdown of DMP can be prevented by adding suitable amounts of ascorbic acid to the reagents.

In vivo

Cytotoxic, DNA-damaging and mutagenic properties of 2,6-dimethoxy-1,4-benzoquinone, formed by dimethophrine-nitrite interaction.[Pubmed: 3252018]

J Pharmacol Exp Ther. 1988 Mar;244(3):1011-5.

In conditions similar to those occurring in the stomach, the sympathomimetic drug dimethophrine was found to react with nitrite yielding 2,6-Dimethoxy-1,4-benzoquinone (DMBQ).
METHODS AND RESULTS:
The in vitro and in vivo studies carried out to evaluate the capability of 2,6-Dimethoxy-1,4-benzoquinoneto produce cytotoxic and genotoxic effects provided the following results. A dose-related reduction of V79 cells plating efficiency was observed for 2,6-Dimethoxy-1,4-benzoquinone concentrations ranging from 10 to 80 microM; a similar reduction in the fraction of viable cells excluding trypan blue occurred after exposure to 4-fold higher concentrations. A dose-dependent amount of DNA fragmentation was revealed by the alkaline elution technique either in V79 cells exposed to 2,6-Dimethoxy-1,4-benzoquinone concentrations ranging from 10 to 80 microM or in kidney, gastric mucosa and brain of rats treated with single p.o. doses ranging from 33 to 300 mg/kg. Both in vitro and in vivo DNA lesions were largely repaired within 24 hr, but their promutagenic character was demonstrated by the induction of 6-thioguanine-resistance in V79 cells. Primary cultures of rat hepatocytes displayed a greater resistance to the cytotoxic and DNA-damaging activities of 2,6-Dimethoxy-1,4-benzoquinone, and did not exhibit a clear evidence of DNA repair synthesis. Similarly, DNA fragmentation was practically undetectable in the rat liver. Therefore, 2,6-Dimethoxy-1,4-benzoquinone should be considered as a direct-acting genotoxic chemical which is metabolized to less, or nonreactive, species.
CONCLUSIONS:
These findings suggest that 2,6-Dimethoxy-1,4-benzoquinone could produce genotoxic effects in patients taking dimethophrine.

2,6-Dimethoxy-1,4-benzoquinone Dilution Calculator

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2,6-Dimethoxy-1,4-benzoquinone Molarity Calculator

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Preparing Stock Solutions of 2,6-Dimethoxy-1,4-benzoquinone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.9453 mL 29.7265 mL 59.453 mL 118.9061 mL 148.6326 mL
5 mM 1.1891 mL 5.9453 mL 11.8906 mL 23.7812 mL 29.7265 mL
10 mM 0.5945 mL 2.9727 mL 5.9453 mL 11.8906 mL 14.8633 mL
50 mM 0.1189 mL 0.5945 mL 1.1891 mL 2.3781 mL 2.9727 mL
100 mM 0.0595 mL 0.2973 mL 0.5945 mL 1.1891 mL 1.4863 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 2,6-Dimethoxy-1,4-benzoquinone

Cytotoxic, DNA-damaging and mutagenic properties of 2,6-dimethoxy-1,4-benzoquinone, formed by dimethophrine-nitrite interaction.[Pubmed:3252018]

J Pharmacol Exp Ther. 1988 Mar;244(3):1011-5.

In conditions similar to those occurring in the stomach, the sympathomimetic drug dimethophrine was found to react with nitrite yielding 2,6-Dimethoxy-1,4-benzoquinone (DMBQ). The in vitro and in vivo studies carried out to evaluate the capability of DMBQ to produce cytotoxic and genotoxic effects provided the following results. A dose-related reduction of V79 cells plating efficiency was observed for DMBQ concentrations ranging from 10 to 80 microM; a similar reduction in the fraction of viable cells excluding trypan blue occurred after exposure to 4-fold higher concentrations. A dose-dependent amount of DNA fragmentation was revealed by the alkaline elution technique either in V79 cells exposed to DMBQ concentrations ranging from 10 to 80 microM or in kidney, gastric mucosa and brain of rats treated with single p.o. doses ranging from 33 to 300 mg/kg. Both in vitro and in vivo DNA lesions were largely repaired within 24 hr, but their promutagenic character was demonstrated by the induction of 6-thioguanine-resistance in V79 cells. Primary cultures of rat hepatocytes displayed a greater resistance to the cytotoxic and DNA-damaging activities of DMBQ, and did not exhibit a clear evidence of DNA repair synthesis. Similarly, DNA fragmentation was practically undetectable in the rat liver. Therefore, DMBQ should be considered as a direct-acting genotoxic chemical which is metabolized to less, or nonreactive, species. These findings suggest that DMBQ could produce genotoxic effects in patients taking dimethophrine.

Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds from Ficus foveolata.[Pubmed:24611777]

Pharm Biol. 2014 Sep;52(9):1104-9.

CONTEXT: Medicinal plants involved in traditional Thai longevity formulations are potential sources of antimicrobial compounds. OBJECTIVE: To evaluate the antimicrobial activities of some extracts from medicinal plants used in traditional Thai longevity formulations against some oral pathogens, including Streptococcus pyogenes, Streptococcus mitis, Streptococcus mutans, and Candida albicans. An extract that possessed the strongest antimicrobial activity was fractionated to isolate and identify the active compounds. MATERIALS AND METHODS: Methanol and ethyl acetate extracts of 25 medicinal plants used as Thai longevity formulations were evaluated for their antimicrobial activity using disc diffusion (5 mg/disc) and broth microdilution (1.2-2500 microg/mL) methods. The ethyl acetate extract of Ficus foveolata Wall. (Moraceae) stems that exhibited the strongest antibacterial activity was fractionated to isolate the active compounds by an antibacterial assay-guided isolation process. RESULTS AND DISCUSSION: The ethyl acetate extract of F. foveolata showed the strongest antibacterial activity with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 19.5-39.0 and 39.0-156.2 microg/mL, respectively. On the basis of an antibacterial assay-guided isolation, seven antibacterial compounds, including 2,6-Dimethoxy-1,4-benzoquinone (1), syringaldehyde (2), sinapaldehyde (3), coniferaldehyde (4), 3beta-hydroxystigmast-5-en-7-one (5), umbelliferone (6), and scopoletin (7), were purified. Among these isolated compounds, 2,6-Dimethoxy-1,4-benzoquinone (1) exhibited the strongest antibacterial activities against S. pyogenes, S. mitis, and S. mutans with MIC values of 7.8, 7.8, and 15.6 microg/mL, and MBC values of 7.8, 7.8, and 31.2 microg/mL, respectively. In addition, this is the first report of these antibacterial compounds in the stems of F. foveolata.

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