| Identification | Back Directory | [Name]
Oroxylin | [CAS]
480-11-5 | [Synonyms]
Oroxylin
OLOXYLINA
oxoxylin A
Oroxylia A
6-Methoxybaicalein
Baicalein 6-methyl ether
5,7-Dihydroxy-6-methoxyflavone
5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-methoxy-2-phenyl- | [Molecular Formula]
C16H12O5 | [MDL Number]
MFCD02259441 | [MOL File]
480-11-5.mol | [Molecular Weight]
284.26 |
| Chemical Properties | Back Directory | [Melting point ]
195-197℃ | [Boiling point ]
346.76°C (rough estimate) | [density ]
1.420 | [refractive index ]
1.6200 (estimate) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:4): 0.20 mg/ml | [form ]
powder | [pka]
6.48±0.40(Predicted) | [color ]
Yellow | [Major Application]
food and beverages | [InChI]
InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3 | [InChIKey]
LKOJGSWUMISDOF-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=CC=C2)OC2=CC(O)=C(OC)C(O)=C2C(=O)C=1 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow needle-shaped crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, mainly derived from Scutellaria baicalensis and Melaleuca alternifolia. | [Uses]
food and beverages | [Definition]
ChEBI: 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. | [Biological Activity]
Oroxylin A is a flavonoid isolated from Scutellaria baicalensiswhich is one of the most important medicinal herbs in traditional Korean/Chinese/Japanese medicine. The amelioration of Abeta(25-35) peptide-induced memory impairment by oroxylin A is believed to be mediated via the GABAergic neurotransmitter system after a single administrationor by reductions in Abeta(25-35) peptide-induced astrocyte and microglia activationsiNOS expressionlipid peroxidationand increased cholinergic neurotransmission after subchronic administration. | [Synthesis]
The general procedure for the synthesis of 5,7-dihydroxy-6-methoxy-2-phenyl-4H-benzopyran-4-one from 5,6,7-trimethoxy-2-phenyl-4H-benzopyran-4-one was as follows: 5,6,7-trimethoxy-2-phenyl-4H-benzopyran-4-one (0.20 g, 0.64 mmol) was dissolved in a mixture of 47% hydrobromic acid (5 mL) and glacial acetic acid (10 mL) in a mixed solution and the reaction was refluxed for 2 hours. Upon completion of the reaction, the reaction solution was quenched by carefully pouring it into crushed ice (200 g). The resulting yellow precipitate was collected by filtration and recrystallized from ethanol to afford 5,7-dihydroxy-6-methoxy-2-phenyl-4H-benzopyran-4-one (160 mg, 88% yield) with a melting point of 203-204 °C. The product structure was determined by 1H-NMR. The structure of the product was confirmed by 1H-NMR (DMSO-d6), IR, UV and MS analysis: 1H-NMR (DMSO-d6) δ: 3.91 (3H, s), 6.94 (1H, s), 6.98 (1H, s), 7.59 (3H, m), 8.10 (2H, d, J = 6.3 Hz), 8.77 (1H, s), 12.49 (1H, s); IR (KBr) cm-1: 3435, 1667; UV λmax (EtOH) nm (log ε): 322 (4.12), 278 (4.35), 216 (4.42); MS m/z: 285 (MH+). | [References]
[1] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 3, p. 339 - 340
[2] Patent: US2004/242907, 2004, A1. Location in patent: Page 3
[3] Chemistry and Biodiversity, 2015, vol. 12, # 2, p. 259 - 272
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 7, p. 2534 - 2535 |
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