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Scutellarein tetramethyl ether

Alias: Scutellarein tetramethyl ether; 1168-42-9; 4',5,6,7-Tetramethoxyflavone; Tetramethyl-O-scutellarin; Tetra-O-methylscutellarein; Tetramethylscutellarein; Flavone, 4',5,6,7-tetramethoxy-; 5,6,7,4'-Tetramethoxyflavone;
Cat No.:V33717 Purity: ≥98%
Scutellarein tetramethyl ether (4',5,6,7-Tetramethoxyflavone) is the bioactive component of Eupatorium odoratum extract.
Scutellarein tetramethyl ether
Scutellarein tetramethyl ether Chemical Structure CAS No.: 1168-42-9
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Scutellarein tetramethyl ether (4',5,6,7-Tetramethoxyflavone) is the bioactive component of Eupatorium odoratum extract. Scutellarein tetramethyl ether (4',5,6,7-Tetramethoxyflavone) exerts anti~inflammatory activity through the NF-κB pathway. Scutellarein tetramethyl ether (4',5,6,7-Tetramethoxyflavone) modulates bacterial resistance through efflux pump inhibition. Scutellarein tetramethyl ether (4',5,6,7-Tetramethoxyflavone) can enhance coagulation function.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural flavone; anti-inflammatory, anti-tumor, anti-oxidant, neuroprotective, anti-fungal activities
ln Vitro
Cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) are critical pro-inflammatory proteins. The level of protein and mRNA expression of these enzymes induced by lipopolysaccharide (LPS) was dramatically suppressed by treatment with SWE, scutellarein tetramethyl ether/scu, or stigmasterol compounds in a dose-dependent manner. They also reduced PGE2 and NO release. We further analyzed the NF-κB pathway and found that the scu compound suppressed IκB kinase complex alpha/beta (IKKα/β) and Inhibitory-kappa-B-alpha (IκBα), thereby suppressing COX-2 and iNOS expression. Conclusion: This is the first report of the anti-inflammatory molecular mechanism in SWE and/or its bioactive component scu, indicating alteration NF-κB pathway and further providing potential uses in the treatment of inflammatory-related diseases.[1]
The purified compound, 4', 5, 6, 7-tetramethoxyflavone, is an active ingredient isolated from Eupatorium odoratum, a Thai indigenous plant that has long been used to stop bleeding. This compound was studied in vitro for the effect on blood clotting factor activities. It was found that the compound enhanced blood coagulation, the observed APTT being shorter than that observed in the control. The result suggested that the compound accelerated clotting time through the intrinsic pathway of the coagulation which may involve the reaction of factor XII, factor XI, factor IX or factor VIII.[3]
Cell Assay
Siam weed (Chromolaena odorata (L.) King and Robinson) is a medicinal herb used for wound healing and inflammation-related diseases. Aim of the study: In this study, we evaluated the molecular mechanism by which Siam weed extract (SWE) and its bioactive components, scutellarein tetramethyl ether (scu), stigmasterol, and isosakuranetin affect anti-inflammatory activity. Materials and methods: The expression of several inflammatory proteins in RAW 264.7 (murine) macrophages was assessed by Western blot and reverse transcription-polymerase chain reaction (RT-PCR). Biochemical assays including prostaglandin E2 (PGE2) and nitric-oxide (NO) quantification were performed. Luciferase promoter activity and immunocytochemistry of Nuclear factor-κB (NF-κB) were investigated[1].
References

[1]. Effect of Siam weed extract and its bioactive component scutellarein tetramethyl ether on anti-inflammatory activity through NF-κB pathway. J Ethnopharmacol. 2013 May 20;147(2):434-41.

[2]. Flavonoids from Praxelis clematidea R.M. King and Robinson modulate bacterial drug resistance. Molecules. 2011 Jun 10;16(6):4828-35.

[3]. Effect of Eupatorium odoratum on blood coagulation. J Med Assoc Thai. 1991 May;74(5):283-7.

Additional Infomation
4',5,6,7-tetramethoxyflavone is a tetramethoxyflavone that is the tetra-O-methyl derivative of scutellarein. It has a role as an antimutagen and a plant metabolite. It is functionally related to a scutellarein.
4',5,6,7-Tetramethoxyflavone has been reported in Citrus reticulata, Marrubium peregrinum, and other organisms with data available.
See also: Tangerine peel (part of); Citrus aurantium fruit rind (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H18O6
Molecular Weight
342.34262
Exact Mass
342.11
Elemental Analysis
C, 66.66; H, 5.30; O, 28.04
CAS #
1168-42-9
PubChem CID
96118
Appearance
Off-white to light yellow solid powder
Density
1.243g/cm3
Boiling Point
525.7ºC at 760mmHg
Melting Point
142-143ºC
Flash Point
232.4ºC
Vapour Pressure
3.84E-11mmHg at 25°C
Index of Refraction
1.574
LogP
3.494
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
5
Heavy Atom Count
25
Complexity
496
Defined Atom Stereocenter Count
0
InChi Key
URSUMOWUGDXZHU-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18O6/c1-21-12-7-5-11(6-8-12)14-9-13(20)17-15(25-14)10-16(22-2)18(23-3)19(17)24-4/h5-10H,1-4H3
Chemical Name
5,6,7-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms
Scutellarein tetramethyl ether; 1168-42-9; 4',5,6,7-Tetramethoxyflavone; Tetramethyl-O-scutellarin; Tetra-O-methylscutellarein; Tetramethylscutellarein; Flavone, 4',5,6,7-tetramethoxy-; 5,6,7,4'-Tetramethoxyflavone;
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 : ~83.33 mg/mL (~243.41 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.08 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 20.8 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: ≥ 2.08 mg/mL (6.08 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 20.8 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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.08 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9211 mL 14.6054 mL 29.2107 mL
5 mM 0.5842 mL 2.9211 mL 5.8421 mL
10 mM 0.2921 mL 1.4605 mL 2.9211 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.

Calculator

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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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g/mol

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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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