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Merck
CN

SML1689

Eupatilin

from (Isolated from Artemisia sp.), ≥98% (HPLC), powder, lipophilic flavonoid

Synonym(s):

2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one, 5,7-Dihydroxy-3′,4′,6-trimethoxyflavone, NSC 122413

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About This Item

Empirical Formula (Hill Notation):
C18H16O7
CAS Number:
22368-21-4
Molecular Weight:
344.32
UNSPSC Code:
12352200
PubChem Substance ID:
329826018
NACRES:
NA.77
MDL number:
MFCD13194819

Key Documents

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Product Name

Eupatilin, ≥98% (HPLC)

SMILES string

O=C1C=C(C2=CC=C(OC)C(OC)=C2)OC3=CC(O)=C(OC)C(O)=C31

InChI key

DRRWBCNQOKKKOL-UHFFFAOYSA-N

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

biological source

(Isolated from Artemisia sp.)

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

Quality Level

100

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Application

Eupatilin has been used to investigate its inhibitory effects on intracranial hemorrhage (ICH)-induced inflammation and its anti-inflammatory mechanisms in mouse BV2 cells, in vitro. It has also been used as a standard for its quantitative estimation in Artemisia extracts by microcolumn high performance liquid chromatography with diode array (HPLC-DAD) assay.

Biochem/physiol Actions

Eupatilin is a flavone with anti-oxidative, anti-inflammatory, and 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.
Flavone with anti-oxidative, anti-inflammatory, and anti-cancer properties

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000357852
0000357852
0000257612
0000227860
0000227860

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Eupatilin attenuates the inflammatory response induced by intracerebral hemorrhage through the TLR4/MyD88 pathway
Fei X, et al.
International Immunopharmacology, 76, 105837-105837 (2019)
Bioactive phenolics of the genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS profile of the Siberian species and their inhibitory potential against alpha-amylase and alpha-glucosidase
Olennikov DN, et al.
Frontiers in Pharmacology, 9, 756-756 (2018)
Eupatilin inhibits lipopolysaccharide-induced expression of inflammatory mediators in macrophages
Choi EJ, et al.
Life Sciences, 88(25-26), 1121-1126 (2011)
Yawei Wang et al.
Molecular medicine reports, 13(2), 1141-1146 (2015-12-18)
Eupatilin, one of the major flavonoids in Artemisia asiatica Nakai (Asteraceae), has been reported to possess antitumor properties. However, thus far there have been no reports regarding the effects of eupatilin on glioma. Therefore, in the current study the effects
Antonia Wiegering et al.
Molecular biology of the cell, 32(8), 675-689 (2021-02-25)
A range of severe human diseases called ciliopathies is caused by the dysfunction of primary cilia. Primary cilia are cytoplasmic protrusions consisting of the basal body (BB), the axoneme, and the transition zone (TZ). The BB is a modified mother

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