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Home > Encyclopedia > 3,5,6,7,8,3′,4′-Heptamethoxyflavone

3,5,6,7,8,3′,4′-Heptamethoxyflavone

3,5,6,7,8,3′,4′-Heptamethoxyflavone structure

3,5,6,7,8,3′,4′-Heptamethoxyflavone 

structure
  • CAS No:

    1178-24-1

  • Formula:

    C22H24O9

  • Chemical Name:

    3,5,6,7,8,3′,4′-Heptamethoxyflavone

  • Synonyms:

    4H-1-Benzopyran-4-one,2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-;Flavone,3,3′,4′,5,6,7,8-heptamethoxy-;2-(3,4-Dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-4H-1-benzopyran-4-one;3,5,6,7,8,3′,4′-Heptamethoxyflavone;3,3′,4′,5,6,7,8-Heptamethoxyflavone;3′,4′,3,5,6,7,8-Heptamethoxyflavone;NSC 618928;3-Methoxynobiletin;3,5,6,7,8,3′,4′-Heptamethphoxyflavone;2-(3,4-Dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one

  • Categories:

    Biochemical Engineering  >  Plant Extracts

Description

3,5,6,7,8,3',4'-heptamethoxyflavone, a flavonoid in C. unshiu peels, exhibits anti-tumor-initiating effect and Anti-neuroinflammatory activity[1][2][3]. 3,5,6,7,8,3',4'-heptamethoxyflavone inhibits collagenase activity and increased type I procollagen content in HDFn cells[1]. 3,5,6,7,8,3',4'-heptamethoxyflavone induces brain-derived neurotrophic factor (BDNF) expression via cAMP/ERK/CREB signaling and reduces phosphodiesterase activity in C6 cells[4].


Solid


3-Methoxynobiletin is a member of flavonoids and an ether.

3,5,6,7,8,3′,4′-Heptamethoxyflavone Basic Attributes

432.43

432.42

288R4CAV1V

618928

DTXSID70151912

2914509090

Characteristics

90.9

3.2

Solid

1.31±0.1 g/cm3(Predicted)

129-131 °C

618.7±55.0 °C(Predicted)

268.0±31.5 °C

1.576

35.1 mg/L @ 25 °C (est)

Drug Information

3,3',4',5,6,7,8-heptamethoxyflavone

3,5,6,7,8,3′,4′-Heptamethoxyflavone Use and Manufacturing

Methods of Manufacturing

Said compounds are, further more preferably, the following compounds: Compound 504:...5, 7, 3', 4'-tetra methoxyl-flavone;5, 7, 3', 4', 5'-penta methoxyl-flavanone;3, 5, 7, 8, 3', 4', 5', 6'-octa methoxyl-flavone;3, 5, 6, 7, 8, 3', 4', 5'-octa methoxyl-flavone;3, 5, 6, 7, 8, 3', 4'-hepta methoxyl-flavone;3, 5, 6, 7, 3', 4', 5'-hepta methoxyl-flavone;3, 5, 7, 8, 3', 4', 5'-hepta methoxyl-flavone;5, 6, 7, 8, 3', 4'-hexa methoxyl-flavone;...General procedure: 3, 5, 6, 7, 8, 4?-Hexamethoxyflavone (5): Me2SO4 (0.2 mL, 1 equiv.)was added dropwise to a stirred solution of 6, 8-dimethoxydiosmetin(100 mg) in acetone (20 mL) and K2CO3 (144 mg) at room temperaturefor 2 h. The mixture was filtered, and the filtrate was evaporated toafford a crude solid which was crystallised from petroleum ether/ethylacetate (3 : 1) to afford yellow crystals: 84 mg; 81%;General procedure: A flask was charged with a flavone (5 mmol) and Lawesson's reagent (2.5 mmol) under nitrogen atmosphere, after 5 min, 35 mL of dry methylbenzene was added by syringe and the mixture was stirred while being brought to reflux. The mixture was heated to 110' for 6h and then cooled to room temperature. The methylbenzene is removed and concentrated in vacuo. The residue was purified by column chromatography methods to obtain target products.

Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

Computed Properties

Molecular Weight:432.4
XLogP3:3.2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:8
Exact Mass:432.14203234
Monoisotopic Mass:432.14203234
Topological Polar Surface Area:90.9
Heavy Atom Count:31
Complexity:651
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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