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E4660

Sigma-Aldrich

Eupatorin

≥97% (HPLC)

Synonym(s):

3′,5-Dihydroxy-4′,6,7-trimethoxyflavone, 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one, 6-Methoxyluteolin 4′,7-dimethyl ether, NSC 106402

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About This Item

Empirical Formula (Hill Notation):
C18H16O7
CAS Number:
855-96-9
Molecular Weight:
344.32
MDL number:
MFCD00016929
UNSPSC Code:
12352200
PubChem Substance ID:
329799061
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >10 mg/mL

storage temp.

room temp

SMILES string

COc1ccc(cc1O)C2=CC(=O)c3c(O)c(OC)c(OC)cc3O2

InChI

1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

InChI key

KLAOKWJLUQKWIF-UHFFFAOYSA-N

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Application

Eupatorin has been used as reference standard for characterization of Artemisia extracts using mass spectrometry (MS).

Biochem/physiol Actions

Eupatorin acts as an antiproliferative in cells expressing the CYP1A- family. It induces G2/M block follow by apoptosis in cells expressing the CYP1A- family. It also functions as an anti-inflammatory.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Hymecromone European Pharmacopoeia (EP) Reference Standard

Y0000011

Hymecromone

Iva Dolečková et al.
Fitoterapia, 83(6), 1000-1007 (2012-06-16)
Flavone eupatorin is one of the constituents of Orthosiphon stamineus, a medicinal herb used in folk medicine in South East Asia for treatment of various disorders. In our study, we investigated the antiproliferative properties of a chloroform extract of the
Nursyamirah Abd Razak et al.
Integrative cancer therapies, 19, 1534735420935625-1534735420935625 (2020-08-25)
Eupatorin is a polymethoxy flavone extracted from Orthosiphon stamineus and was reported to exhibit cytotoxic effects on several cancer cell lines. However, its effect as an anti-breast cancer agent in vivo has yet to be determined. This study aims to
Mirka Laavola et al.
Planta medica, 78(8), 779-786 (2012-04-21)
Cytokines and other inflammatory mediators, such as prostaglandin E₂ (PGE₂) and nitric oxide (NO) produced by cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS), respectively, activate and drive inflammation and therefore serve as targets for anti-inflammatory drug development. Orthosiphon stamineus
I M Lyckander et al.
Prostaglandins, leukotrienes, and essential fatty acids, 54(4), 239-246 (1996-04-01)
15-Lipoxygenase from soybeans is inactivated by bubbling air through enzyme solutions. This inactivation is prevented by flavonoids from the East Asian medicinal plant Orthosiphon spicatus, previously found to be inhibitors of the enzyme. 5,7,4'-Trimethylapigenin, eupatorin and 5,7,3',4'-tetramethylluteolin show the strongest
Anna-Leena Salmela et al.
Experimental cell research, 318(5), 578-592 (2012-01-10)
The spindle assembly checkpoint (SAC) is a conserved mechanism that ensures the fidelity of chromosome distribution in mitosis by preventing anaphase onset until the correct bipolar microtubule-kinetochore attachments are formed. Errors in SAC function may contribute to tumorigenesis by inducing
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