Oroxylin A
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Oroxylin A
structure -
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CAS No:
480-11-5
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Formula:
C16H12O5
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Chemical Name:
Oroxylin A
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Synonyms:
4H-1-Benzopyran-4-one,5,7-dihydroxy-6-methoxy-2-phenyl-;Flavone,5,7-dihydroxy-6-methoxy-;Oroxylin;5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one;Oroxylin A;6-Methoxybaicalein;5,7-Dihydroxy-6-methoxyflavone;Baicalein 6-methyl ether
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CAS No:
Description
Oroxylin A is a natural active flavonoid with strong anticancer effects.IC50 value:Target:In vitro: Oroxylin A suppressed the MDM2-mediated degradation of p53 via downregulating MDM2 transcription in wt-p53 cancer cells [1]. Oroxylin A remarkably reduced the generation of lactate and glucose uptake under hypoxia in HepG2 cells, inhibited HIF-1α expression and its stability [2]. Oroxylin A promotes superoxide dismutase (SOD2) gene expression through SIRT3-regulated DNA-binding activity of
Oroxylin A is a dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-6. It has a role as an antineoplastic agent and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a monomethoxyflavone and a dihydroxyflavone. It is a conjugate acid of an oroxylin A(1-).
Characteristics
76
2.1
1.4±0.1 g/cm3
231-232 °C
540.9°C at 760 mmHg
207.4±23.6 °C
1.669
2-8°C
2.6E-12mmHg at 25°C
Safety Information
22
Xn
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory.
Drug Information
Oroxylin A has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(5-hydroxy-6-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid.
5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one
Oroxylin A Use and Manufacturing
A solution of flavone 2 (0.20 g, 0.64 mmol) in 47percent HBr (5 ml) and glacial acetic acid (10 ml) was refluxed for 2 h, and then carefully poured onto crushed ice (200 g). The resulting yellow precipitate was filtered and collected. Recrystallization from ethanol afforded 160 mg (88percent) of oroxylin A: mp 203-204 C. 1H-NMR (DMSO-d6) ?: 3.91 (3 H, s), 6.94 (1 H, s), 6.98 (1 H, s), 7.59 (3 H, m), 8.10 (2 H, d, J=6.3 Hz), 8.77 (1 H, s), 12.49 (1 H, s). IR (KBr) cm-1: 3435, 1667. UV 'max (EtOH) nm (log ?): 322 (4.12), 278 (4.35), 216 (4.42). MS m/z: 285 (MH+).First of all, Adding baicalin (223 mg, 0.5 mmole) to the reaction flask, Dimethyl sulfate (1.26 g, 10 mmole) and potassium carbonate (345 mg, 2.5 mmole), Stir at room temperature for 24 hours, The 6-hydroxyl group of the baicalin is subjected to a methylation reaction.Next, 10 ml of a HCl-EtOH (1:9) mixed solution (second reaction liquid) was added to complete the methylation reaction described above.In the first reaction solution, the reaction of the layer of paper A is completed by further reacting at 80 ° C for 10 to 12 hours. After the reaction is completed, the temperature is returned to room temperature.Add water and extract with ethyl acetate, and finally concentrate the organic layer.Rapid product chromatography on silica gelAfter purification by the method, the Melaleuca A is obtained. Total yield: 56percent (80 mg).First, baicalin (223 mg, 0.5 mmole) was added to the reaction flask.Dimethyl sulfate (1.26 g, 10 mmole) and potassium carbonate (345 mg, 2.5 mmloe), Stir at room temperature for 24 hours, The 6-hydroxyl group of the baicalin is subjected to a methylation reaction.Then add 10ml of HCl-EtOH (1:9)a mixed solution (second reaction liquid) in the first reaction liquid in which the methylation reaction is completed as described above, React at 80 ° C for 10 to 12 hours, To complete the synthesis of oroxylin A. After the reaction is completed, the temperature is returned to room temperature.Add water and extract with ethyl acetate.Finally, the organic layer is concentrated, After the crude product is purified by silica gel rapid column chromatography, To obtain the oroxylin A. Total yield: 56percent (80 mg).
Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Computed Properties
Molecular Weight:284.26
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:284.06847348
Monoisotopic Mass:284.06847348
Topological Polar Surface Area:76
Heavy Atom Count:21
Complexity:426
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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