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SML1689

Sigma-Aldrich

Eupatilin

≥98% (HPLC)

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

biological source

(Isolated from Artemisia sp.)

Quality Level

100

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

SMILES string

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

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

InChI key

DRRWBCNQOKKKOL-UHFFFAOYSA-N

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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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 attenuates the inflammatory response induced by intracerebral hemorrhage through the TLR4/MyD88 pathway
Fei X, et al.
International Immunopharmacology, 76, 105837-105837 (2019)
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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