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| | 3',4',5,7-Tetramethoxyflavone Basic information |
| Product Name: | 3',4',5,7-Tetramethoxyflavone | | Synonyms: | 2-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one;3',4',5,7-Tetramethoxyflavone ,98%;LUTEOLIN TETRAMETHYL ETHER;5,7,3’,4’-tetramethylluteolin;Luteolinetetramethylether;LUTEOLIN TETRAMETHYLETHER(RG);Tetramethoxyluteolin;Tetramethylluteolin | | CAS: | 855-97-0 | | MF: | C19H18O6 | | MW: | 342.34 | | EINECS: | | | Product Categories: | Tetra-substituted Flavones;Herbal extracts | | Mol File: | 855-97-0.mol |  |
| | 3',4',5,7-Tetramethoxyflavone Chemical Properties |
| Melting point | 195-197°C | | Boiling point | 528.8±50.0 °C(Predicted) | | density | 1.243±0.06 g/cm3(Predicted) | | storage temp. | 4°C, protect from light | | solubility | DMSO:6.85(Max Conc. mg/mL);20.0(Max Conc. mM) | | form | Solid | | color | White to off-white | | BRN | 336320 | | LogP | 3.360 (est) | | CAS DataBase Reference | 855-97-0(CAS DataBase Reference) |
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| | 3',4',5,7-Tetramethoxyflavone Usage And Synthesis |
| Uses | 5,7,3',4'-Tetramethoxyflavone, an orally active polymethoxyflavones (PMFs) that can be isolated from M. exotica, possesses various bioactivities, including anti-fungal, anti-malarial, anti-mycobacterial, and anti-inflammatory activities. 5,7,3',4'-Tetramethoxyflavone exhibits chondroprotective activity by targeting β-catenin signaling[1]. | | Synthesis | Example 17: Synthesis of 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (14)
1. 1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-4,6-dimethoxyphenyl)propane-1,3-dione (7.40 g, 20.53 mmol, 1 eq.) was suspended in glacial acetic acid (30 mL) and heated to 100°C.
2. 20 mL of an acetic acid solution of 20% H2SO4 was added to the suspension and kept stirring at 100 °C for 10 min.
3. The reaction mixture was poured into 150 g of crushed ice and a light yellow gel-like solid precipitated.
4. The solid was collected, partially dried by filtration and dispensed between 300 mL of CHCl3 and 300 mL of distilled water.
5. The organic layer was separated and washed sequentially with 150 mL of 5% NaHCO3 solution and 150 mL of saturated brine.
6. The organic layer was dried over MgSO4, filtered and the solvent evaporated to give a light yellow solid.
7. 6.05 g (86% yield) of white needle-like crystals were obtained by recrystallization from 50 mL of acetone.
Product Characterization:
- Molecular weight: 342.34 (C19H18O6)
- 1H-NMR (CDCl3, 300 MHz) δ (ppm, J/Hz): 3.86 (s, 3H, MeO), 3.90 (s, 6H, MeOx2), 3.92 (s, 3H, MeO), 6.30 (d, 1H, J = 2.1, H-6), 6.48 (d, 1H, J = 2.1, H-8), 6.53 (s 1H, H-3), 6.88 (d, 1H, J = 8.6, H-5'), 7.24 (d, 1H, J = 2.1, H-2'), 7.42 (dd, 1H, J = 2.1, 8.6, H-6')
- 13C-NMR (CDCl3, 75 MHz) δ (ppm): 55.8 (MeO), 56.1 (MeOx2), 56.4 (MeO), 92.9 (C-6), 96.1 (C-8), 107.8 (C-3), 108.5 (C-2'), 109.1 (C-4a), 111.0 (C-5'), 119.5 (C-6') 119.5 (c-6'), 123.9 (c-1'), 149.2 (c-4'), 151.7 (c-3'), 159.8 (c-8a), 160.6 (c-5), 160.8 (c-2), 163.9 (c-7), 177.6 (c-4) | | in vivo | 5,7,3',4'-Tetramethoxyflavone (25-100 mg/kg, i.g.) exhibits chondroprotective activity in rats[1].
5,7,3',4'-Tetramethoxyflavone (5-20 mg/kg; i.v., p.o.) has the absolute bioavailability of 14.3 % in rats[3].
1.19 Pharmacokinetic Analysis in Sprague-dawley Rats Model[3]| Route | Dose (mg/kg) | AUC (min μg/mL) | AUC/Dose (min/mL) | t1/2 (h) | Tmax (h) | Cmax (ng/mL) | Bioavailability (%) | | i.v. | 5 | 161.49 ± 58.78 | 0.1154 ± 0.0420 | 62.85 ± 27.92 | / | / | 14.3 | | p.o. | 50 | 231.43 ± 71.87 | 0.0165 ± 0.0051 | 273.76 ± 90.23 | 190.34 ± 24.50 | 0.79 ± 0.30 | / |
| Animal Model: | Rat knee OA model[1] | | Dosage: | 25-100 mg/kg | | Administration: | i.g. | | Result: | Decreased the contents of IL-1b, TNF-a, and PGE2 in a dose-dependent manner.
Decreases the expression of the inflammatory cytokines in rat knee osteoarthritis (OA) synovial fluid (SF) lavages.
Inhibited chondrocytes hypertrophy and decreased the cartilage thickness.
Exhibited down regulation of b-catenin in a dose-dependent manner.
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| | IC 50 | Plasmodium | | storage | Store at -20°C | | References | [1] Wu L, et al. 5,7,3',4'-Tetramethoxyflavone exhibits chondroprotective activity by targeting β-catenin signaling in vivo and in vitro. Biochem Biophys Res Commun. 2014 Sep 26;452(3):682-8. DOI:10.1016/j.bbrc.2014.08.129
[2] Wu L, et al. 5,7,3',4'-Tetramethoxyflavone protects chondrocytes from ER stress-induced apoptosis through regulation of the IRE1α pathway. Connect Tissue Res. 2018 Mar;59(2):157-166. DOI:10.1080/03008207.2017.1321639
[3] Wei G, et al. Absolute bioavailability, pharmacokinetics and excretion of 5,7,30 ,40 -tetramethoxyflavone |
| | 3',4',5,7-Tetramethoxyflavone Preparation Products And Raw materials |
| Raw materials | 2''-Hydroxy-3,4,4'',6''-tetramethoxychalcone-->1,3-Propanedione, 1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-4,6-dimethoxyphenyl)--->3-(3,4-Dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-2-propyn-1-one-->Luteolin-->Dimethyl sulfate-->Sulfuric acid-->Acetic acid | | Preparation Products | 3,7,3',4'-Tetramethylgossypetin |
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