eupatilin
- Product Name
- eupatilin
- CAS No.
- 22368-21-4
- Chemical Name
- eupatilin
- Synonyms
- Isozepin;eupatilin;NSC 122413;Eupatilin-RM;Eupatilin, BR;Eupatilin 22368-21-4;Eupatilin, 10 mM in DMSO;5,7-Dihydroxy-3',4',6-trimethoxyflavone;2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one;2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
- CBNumber
- CB51326292
- Molecular Formula
- C18H16O7
- Formula Weight
- 344.32
- MOL File
- 22368-21-4.mol
eupatilin Property
- Melting point:
- 236-238 °C
- Boiling point:
- 583.6±50.0 °C(Predicted)
- Density
- 1.387±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- solubility
- Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- pka
- 6.47±0.40(Predicted)
- color
- Pale Beige
- biological source
- (Isolated from Artemisia sp.)
- Stability:
- Hygroscopic
- 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
- SMILES
- C1(C2=CC=C(OC)C(OC)=C2)OC2=CC(O)=C(OC)C(O)=C2C(=O)C=1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- SML1689
- Product name
- Eupatilin
- Purity
- ≥98% (HPLC)
- Packaging
- 5 mg
- Price
- $111
- Updated
- 2025/07/31
- Product number
- SML1689
- Product name
- Eupatilin
- Purity
- ≥98% (HPLC)
- Packaging
- 25 mg
- Price
- $422.41
- Updated
- 2025/07/31
- Product number
- PHL80337
- Product name
- Eupatilin
- Purity
- phyproof? Reference Substance
- Packaging
- 10MG
- Price
- $717
- Updated
- 2025/07/31
- Product number
- E1409
- Product name
- Eupatilin
- Packaging
- 10MG
- Price
- $59
- Updated
- 2025/07/31
- Product number
- E1409
- Product name
- Eupatilin
- Packaging
- 50MG
- Price
- $177
- Updated
- 2025/07/31
eupatilin Chemical Properties,Usage,Production
Chemical Properties
Soluble in DMSO, hot methanol, chloroform methanol mixed solvent, insoluble in petroleum ether and other solvents. Derived from the dried leaves of Artemisia argyi Levl. et Vant.
Uses
Eupatilin maintains anticoagulant and antiplatelet activity isolated from the Artemisia princeps Pampanini flower.
Definition
ChEBI: A trimethoxyflavone with 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 a d antineoplastic activities.
Biological Activity
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.
Synthesis
40983-99-1
22368-21-4
The general procedure for the synthesis of 2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-benzopyran-4-one from 5,7-dihydroxy-3',4',6-trimethoxyflavone was as follows: 7-hydroxy-3',4',5,6-tetramethoxyflavone (4.44 g, 12.4 mmol) was suspended in 88 mL of acetonitrile. Aluminum trichloride (8.27 g, 5 eq.) was added to the suspension at room temperature and the reaction mixture was subsequently heated to reflux for 1.5 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. To the residue, 10% aqueous hydrochloric acid and chloroform were added and the mixed solution was heated to reflux until it became clear. After the solution was cooled to room temperature, the organic layer was separated, washed sequentially with water and brine, and then dried with anhydrous magnesium sulfate. The solvent of the organic layer was removed by evaporation under reduced pressure to obtain the crude product. The crude product was recrystallized in methanol to give 3.18 g of the target compound in 74% yield. The structure of the product was confirmed by NMR (CDCl3): δ 13.05 (s, 1H), 7.50 (dd, J = 8.6, 2.2 Hz, 1H), 7.31 (d, J = 2.1 Hz, 1H), 6.96 (d, J = 8.5 Hz, 1H), 6.59 (s, 1H), 6.56 (s, 1H), 6.48 (br s, 1H). 4.03 (s, 3H), 3.96 (s, 3H), 3.95 (s, 1H).
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[1].
IC 50
PPARα
storage
+4°C
References
[1] Patent: US6025387, 2000, A
[2] Patent: KR101871166, 2018, B1. Location in patent: Paragraph 0137-0139
[3] Patent: US2017/239211, 2017, A1. Location in patent: Paragraph 1/15
eupatilin Preparation Products And Raw materials
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View Lastest Price from eupatilin manufacturers
- Product
- Eupatilin 22368-21-4
- Price
- US $200.00-85.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-04-23
- Product
- Eupatilin 22368-21-4
- Price
- US $400.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 10kg
- Release date
- 2020-06-13
- Product
- Eupatilin 22368-21-4
- Price
- US $0.00/mg
- Min. Order
- 5mg
- Purity
- ≥98%(HPLC)
- Supply Ability
- 10 g
- Release date
- 2019-12-03