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Eupatilin

CAT: 0013-GTR19163002-01Size: 200 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19163002-01Size:200 mg
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Description
Eupatilin (NSC 122413, Stillen) is a pharmacologically active flavone derived from Artemisia plants, possess anti-inflammatory, anti-oxidative and anti-cancer activities; induces cell cycle arrest in ras-transformed human mammary epithelial cells; attenuates aortic smooth muscle cell proliferation and migration by inhibiting PI3K, MKK3/6, and MKK4 activities; inhibits angiogenesis-mediated human hepatocellular metastasis by reducing MMP-2 and VEGF signaling. (In Vitro) :Eupatilin is a PPARα agonist. Eupatilin (10, 30, 100 μM) suppresses IL-4 expression and degranulation in RBL-2H3 cells. Eupatilin (50-100 μM) slightly reduces cell viability of HaCaT cells. Eupatilin (10, 30, 50, 100 μM) increases PPARα transactivation and expression in HaCaT cells. Eupatilin (10, 30, 50 μM) also suppresses TNFα-induced MMP-2/-9 expression in HaCaT cells. Furthermore, Eupatilin inhibits TNFα-induced p65 translocation, IκBα Phosphorylation, AP-1 and MAPK signaling via PPARα. Eupatilin (10-50 μM) shows no cytotoxic effects on ARPE19 cells. Eupatilin (10, 25, 50 μM) elevates cell viability from oxidative stress, and inhibits H2O2-induced ROS production in ARPE19 cells. Moreover, Eupatilin (50 μM) inbibits H2O2-induced cells apoptosis and promotes the activation of PI3K/Akt pathway in RPE cells. (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.
CAS Number
22368-21-4
Product Name Alternative
NSC 122413 | Stillen
Purity
>98% (HPLC)
Solubility
DMSO: 62 mg/mL (180.1 mM) (< 1 mg/ml refers to the product slightly soluble or insoluble)
Smiles
COC1=C (C=C (C=C1) C2=CC (=O) C3=C (C (=C (C=C3O2) O) OC) O) OC
Molecular Formula
C18H16O7
Molecular Weight
344.32
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
2- (3,4-Dimethoxyphenyl) -5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one

Chemical Information

Eupatilin

Eupatilin is a trimethoxyflavone that is 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 and antineoplastic activities. It has a role as a metabolite, an antineoplastic agent, an anti-ulcer drug, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor and an anti-inflammatory agent. It is a trimethoxyflavone and a dihydroxyflavone.

CAS Number22368-21-4
PubChem CID5273755
IUPAC Name2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one
Molecular FormulaC18H16O7
Molecular Weight344.3
XLogP2.9
Topological Polar Surface Area94.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Heavy Atom Count25
Formal Charge0
Complexity520
SMILES
COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)OC)O)OC
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
Chemical Structure
2D Structure
2D structure of Eupatilin
CAS: 22368-21-4
CID: 5273755
Formula: C18H16O7
MW: 344.3
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight344.3
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass344.08960285
Monoisotopic Mass344.08960285
Topological Polar Surface Area94.5 Ų
Heavy Atom Count25
Formal Charge0
Complexity520
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes