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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

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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Yan Pan et al.
Journal of ethnopharmacology, 133(2), 881-887 (2010-11-26)
Andrographis paniculata (AP), Centella asiatica (CA) and Orthosiphon stamineus (OS) are three popular herbs traditionally used worldwide. AP is known for the treatment of infections and diabetes and CA is good for wound healing and healthy skin while OS is
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
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
Bioactive Phenolics of the Genus Artemisia (Asteraceae): HPLC-DAD-ESI-TQ-MS/MS Profile of the Siberian Species and Their Inhibitory Potential Against
Olennikov DN, et al.
Frontiers in Pharmacology, 9 (2018)
Mun Fei Yam et al.
Journal of acupuncture and meridian studies, 5(4), 176-182 (2012-08-18)
Orthosiphon stamineus extracts contain three flavonoids (3'-hydroxy-5,6,7,4'-tetramethoxyflavone, sinensetin, and eupatorin) as bioactive substances. Previous reported high performance liquid chromatography- ultraviolet (HPLC-UV) methods for the determination of these flavonoids have several disadvantages, including unsatisfactory separation times and not being well validated
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