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2,6-Dimethoxy-1,4-benzoquinone

Cat No.:V49705 Purity: ≥98%
2,6-Dimethoxy-1,4-benzoquinone is a natural phytochemical and a known haustoria-inducing factor.
2,6-Dimethoxy-1,4-benzoquinone
2,6-Dimethoxy-1,4-benzoquinone Chemical Structure CAS No.: 530-55-2
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2,6-Dimethoxy-1,4-benzoquinone is a natural phytochemical and a known haustoria-inducing factor. 2,6-Dimethoxy-1,4-benzoquinone has anticancer, anti~inflammatory, antilipidic, antibacterial, and antimalarial effects.
2,6-Dimethoxy-1,4-benzoquinone (CAS#: 530-55-2) is a natural compound isolated from the barks of Liriodendron tulipifera. It has a molecular formula of C8H8O4 and a molecular weight of 168.15. This compound is a useful haustorial inducing factor that causes haustoria to grow into plant host tissue. It is notable for its antioxidant and redox properties.
Biological Activity I Assay Protocols (From Reference)
Targets
2,6-Dimethoxy-1,4-benzoquinone does not have a specific molecular target in mammalian systems but functions as a natural product with antioxidant and redox properties. As a benzoquinone derivative, it can undergo redox cycling and generate reactive oxygen species. In plants, it acts as a haustorial inducing factor, promoting the growth of haustoria into host plant tissue. Its role as a natural compound makes it a valuable tool for studying plant biology and natural product chemistry.
ln Vitro
In vitro, 2,6-Dimethoxy-1,4-benzoquinone exhibits antioxidant and redox properties. Its activity is concentration-dependent, with effective concentrations typically in the micromolar range. In plant-based assays, it acts as a haustorial inducing factor. Its antioxidant properties make it a potential candidate for studying oxidative stress and redox biology. However, detailed quantitative activity data for mammalian systems are limited in publicly available sources.
ln Vivo
In vivo, 2,6-Dimethoxy-1,4-benzoquinone is not used as a therapeutic agent. It is a natural compound found in plants. Its in vivo effects are related to its role as a plant metabolite. In agricultural research, it is used to study plant-parasite interactions as a haustorial inducing factor. The compound is not administered to animals for therapeutic purposes. Its in vivo applications are limited to plant biology research.
Enzyme Assay
The in vitro assays for 2,6-Dimethoxy-1,4-benzoquinone typically involve antioxidant activity testing and plant biology studies. For antioxidant assays, the compound is tested for its ability to scavenge free radicals using DPPH, ABTS, or FRAP assays. The compound is dissolved in suitable solvent and diluted at varying concentrations (typically 0.1 to 100 µM). For plant biology studies, the compound is tested for its ability to induce haustoria formation in plant tissues. Haustoria formation is assessed by microscopy. Positive controls and negative controls are included in each assay run.
Cell Assay
For in vitro cellular assays, 2,6-Dimethoxy-1,4-benzoquinone is not typically used in mammalian cell culture studies. In plant cell culture studies, plant cells or tissues are treated with the compound, and haustoria formation is assessed by microscopy. Cell viability is assessed using plant cell viability assays. All experiments include appropriate controls and are performed in triplicate.
Animal Protocol
For in vivo studies, 2,6-Dimethoxy-1,4-benzoquinone is used in plant biology research. The compound may be applied to plant tissues or roots, and haustoria formation is assessed by microscopy. The compound's effects on plant growth and development are studied. All plant procedures should be conducted in accordance with institutional guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of 2,6-Dimethoxy-1,4-benzoquinone are not relevant, as it is a natural product used in plant biology research rather than a therapeutic agent. The compound has a molecular weight of 168.15. It is a small, lipophilic molecule. Detailed PK data are not available in publicly accessible literature.
Toxicity/Toxicokinetics
The toxicology of 2,6-Dimethoxy-1,4-benzoquinone has not been extensively characterized. As a natural compound, it is generally considered to have low toxicity. In plant studies, it is used at concentrations that induce haustoria formation without causing significant plant toxicity. Standard laboratory safety precautions should be followed when handling the compound. It is for research use only and is not approved for human therapeutic use.
References

[1]. 2,6-Dimethoxy-1,4-benzoquinone, isolation and identification of anti-carcinogenic, anti-mutagenic and anti-inflammatory component from the juice of Vitis coignetiae. Food Chem Toxicol. 2018 Dec;122:172-180.

[2]. Jennifer Mach. A shot in the dark: how parasitic plants find host roots Plant Cell. 2010 Apr;22(4):995.

Additional Infomation
2,6-Dimethoxy-1,4-benzoquinone has been reported to exist in iris (Iris milesii), persimmon (Diospyros eriantha), and other organisms with relevant data. 2,6-Dimethoxyquinone is a methoxy-substituted benzoquinone and a bioactive compound found in fermented wheat germ extract, possessing potential antitumor and immunomodulatory activities. 2,6-Dimethoxyquinone (2,6-DMBQ) inhibits anaerobic glycolysis, thereby preventing cellular metabolism and inducing apoptosis. Since cancer cells utilize anaerobic glycolysis to metabolize glucose, and their proliferation rate is much higher than that of normal healthy cells, this compound exhibits specific cytotoxicity against cancer cells. Furthermore, 2,6-DMBQ can enhance the activity of natural killer (NK) cells and T cells against cancer cells, thus exerting an immunomodulatory effect. See also: Acai berry pulp (partial).
2,6-Dimethoxy-1,4-benzoquinone is a natural compound isolated from Liriodendron tulipifera barks. It has antioxidant and redox properties. It is a useful haustorial inducing factor in plant biology research. It is not approved for human use and is intended for research purposes only. It is available as a high-purity research reagent for laboratory use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H8O4
Molecular Weight
168.1467
Exact Mass
168.042
CAS #
530-55-2
PubChem CID
68262
Appearance
Light yellow to yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
311.1±42.0 °C at 760 mmHg
Melting Point
252 °C
Flash Point
139.2±27.9 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.504
LogP
0.28
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Heavy Atom Count
12
Complexity
259
Defined Atom Stereocenter Count
0
SMILES
COC1=CC(=O)C=C(C1=O)OC
InChi Key
OLBNOBQOQZRLMP-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3
Chemical Name
2,6-dimethoxycyclohexa-2,5-diene-1,4-dione
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

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 : ~5.56 mg/mL (~33.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.56 mg/mL (3.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 5.6 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 0.56 mg/mL (3.33 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 5.6 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.9471 mL 29.7354 mL 59.4707 mL
5 mM 1.1894 mL 5.9471 mL 11.8941 mL
10 mM 0.5947 mL 2.9735 mL 5.9471 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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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.
             (2) Be sure to add the solvent(s) in order.

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