5-O-Demethylnobiletin

Names

[ Name ]:
5-O-Demethylnobiletin

[Synonym ]:
4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-
2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one
5-hydroxy-6,7,8,3',4'-pentamethoxyflavone
Demethylnobiletin
5-O-Demethylnobiletin
5-hydroxy-3',4',6,7,8-pentamethoxyflavone
5-Demethylnobiletin
5-desmethylnobeletin
5-desmethylnobiletin

Biological Activity

[Description]:

5-O-Demethylnobiletin (5-Demethylnobiletin), a polymethoxyflavone isolated from Sideritis tragoriganum, is a direct inhibition of 5-LOX (IC50=0.1 μM), without affecting the expression of COX-2. 5-O-Demethylnobiletin (5-Demethylnobiletin) has anti-inflammatory activity, inhibits leukotriene B (4)(LTB4) formation in rat neutrophils and elastase release in human neutrophils with an IC50 of 0.35 μM[1].5-O-Demethylnobiletin (5-demethylnobiletin) promotes neuritogenesis through the activation of MAPK/ERK-, PKC-, and PKA-dependent signaling pathways[2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Leukotriene Receptor

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

Research Areas >> Neurological Disease

[Target]

IC50: 0.1 μM (Lox 5); 0.35 μM (LTB4) (5-O-Demethylnobiletin)[1]

[References]

[1]. Bas E, et al. Anti-inflammatory activity of 5-O-demethylnobiletin, a polymethoxyflavone isolated from Sideritis tragoriganum. Planta Med. 2006 Feb;72(2):136-42.

[2]. Chiu SP, et al. Neurotrophic action of 5-hydroxylated polymethoxyflavones: 5-demethylnobiletin and gardenin A stimulate neuritogenesis in PC12 cells. J Agric Food Chem. 2013 Oct 2;61(39):9453-63.

Chemical & Physical Properties

[ Density]:
1.304±0.06 g/cm3

[ Boiling Point ]:
601.4±55.0 °C at 760 mmHg

[ Melting Point ]:
145-146 ºC

[ Molecular Formula ]:
C₂₀H₂₀O₈

[ Molecular Weight ]:
388.368

[ Flash Point ]:
213.9±25.0 °C

[ Exact Mass ]:
388.115814

[ PSA ]:
96.59000

[ LogP ]:
2.10

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.583

[ Storage condition ]:
2-8C

[ Water Solubility ]:
Practically insoluble (0.058 g/L) (25 ºC)

Safety Information

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Related Compounds

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