| Identification | Back Directory | [Name]
eupatilin | [CAS]
22368-21-4 | [Synonyms]
eupatilin
NSC 122413
Eupatilin, BR
Eupatilin 22368-21-4
5,7-Dihydroxy-3',4',6-trimethoxyflavone
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy-
Eupatilin
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one (EUPATILIN) | [EINECS(EC#)]
618-347-7 | [Molecular Formula]
C18H16O7 | [MDL Number]
MFCD13194819 | [MOL File]
22368-21-4.mol | [Molecular Weight]
344.31 |
| Chemical Properties | Back Directory | [Melting point ]
236-238 °C | [Boiling point ]
583.6±50.0 °C(Predicted) | [density ]
1.387±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Store in freezer, under -20°C | [solubility ]
Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
6.47±0.40(Predicted) | [color ]
Pale Beige | [biological source]
(Isolated from Artemisia sp.) | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-14(12)23-2)13-7-10(19)16-15(25-13)8-11(20)18(24-3)17(16)21/h4-8,20-21H,1-3H3 | [InChIKey]
DRRWBCNQOKKKOL-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=C(OC)C(OC)=C2)OC2=CC(O)=C(OC)C(O)=C2C(=O)C=1 |
| Hazard Information | Back Directory | [Uses]
Eupatilin maintains anticoagulant and antiplatelet activity isolated from the Artemisia princeps Pampanini flower. | [Definition]
ChEBI: A trimethoxyflavone with flavone substituted by hydroxy groups at C-5 and C-7 and methoxy groups at C-6, C-3' and C-4' respectively. Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer a
d antineoplastic activities. | [Biological Activity]
Eupatilin is a flavone with anti-oxidativeanti-inflammatoryand anti-cancer properties.''Eupatilin is an important constituent in the leaves of Artemisia argyi and also an active component of DA-9601. It exhibits anti-apoptotic effects. Eupatilin provides protection against tumor necrosis factor α (TNF-α)-mediated inflammation in human umbilical vein endothelial cells. It is used in the treatment of gastritis and peptic ulcers. Eupatilin safeguards gastric epithelial cells from oxidative damage and smooth muscle cells from indomethacin-induced cell damage. Eupatilin lowers bile acid-stimulated hepatocyte apoptosis. | [Synthesis]
The general procedure for the synthesis of 2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-benzopyran-4-one from 5,7-dihydroxy-3',4',6-trimethoxyflavone was as follows: 7-hydroxy-3',4',5,6-tetramethoxyflavone (4.44 g, 12.4 mmol) was suspended in 88 mL of acetonitrile. Aluminum trichloride (8.27 g, 5 eq.) was added to the suspension at room temperature and the reaction mixture was subsequently heated to reflux for 1.5 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. To the residue, 10% aqueous hydrochloric acid and chloroform were added and the mixed solution was heated to reflux until it became clear. After the solution was cooled to room temperature, the organic layer was separated, washed sequentially with water and brine, and then dried with anhydrous magnesium sulfate. The solvent of the organic layer was removed by evaporation under reduced pressure to obtain the crude product. The crude product was recrystallized in methanol to give 3.18 g of the target compound in 74% yield. The structure of the product was confirmed by NMR (CDCl3): δ 13.05 (s, 1H), 7.50 (dd, J = 8.6, 2.2 Hz, 1H), 7.31 (d, J = 2.1 Hz, 1H), 6.96 (d, J = 8.5 Hz, 1H), 6.59 (s, 1H), 6.56 (s, 1H), 6.48 (br s, 1H). 4.03 (s, 3H), 3.96 (s, 3H), 3.95 (s, 1H). | [in vivo]
Eupatilin (1.5% or 3.0%) restores PPARα mRNA expression, and improves atopic dermatitis (AD)-like symptoms in oxazolone-induced Balb/c mice. Eupatilin causes significant decrease in serum IgE, IL-4 levels, oxazolone-induced TNFα, IFNγ, IL-1β, TSLP, IL-33 and IL-25 mRNA expression in oxazolone-induced mice. Eupatilin also increases filaggrin and loricrin mRNA expression in oxazolone-induced mice[1]. | [IC 50]
PPARα | [storage]
+4°C | [References]
[1] Patent: US6025387, 2000, A
[2] Patent: KR101871166, 2018, B1. Location in patent: Paragraph 0137-0139
[3] Patent: US2017/239211, 2017, A1. Location in patent: Paragraph 1/15 |
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