ChemicalBook > CAS DataBase List > eupatilin

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

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1689
Product name: Eupatilin
Purity: ≥98% (HPLC)
Packaging: 5 mg
Price: $111
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML1689
Product name: Eupatilin
Purity: ≥98% (HPLC)
Packaging: 25 mg
Price: $422.41
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHL80337
Product name: Eupatilin
Purity: phyproof? Reference Substance
Packaging: 10MG
Price: $717
Updated: 2025/07/31

TCI Chemical

Product number: E1409
Product name: Eupatilin
Packaging: 10MG
Price: $59
Updated: 2025/07/31

TCI Chemical

Product number: E1409
Product name: Eupatilin
Packaging: 50MG
Price: $177
Updated: 2025/07/31

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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

Raw materials

Preparation Products

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View Lastest Price from eupatilin manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd

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

Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd.

Product: Eupatilin 22368-21-4
Price: US $400.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 10kg
Release date: 2020-06-13

Shanghai Standard Technology Co., Ltd.

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

22368-21-4, eupatilinRelated Search:

lithospermic acid MONOCROTALINE Isochlorogenic Acid B Cupric hydroxide ISOSAKURANETIN acevaltrate ISOBERGAPTEN HOMOORIENTIN isomangiferin 8-O-acetylharpagide Isocorynoxeine Isoliensinine ISORHYNCHOPHYLLINE ISOLIQUIRITIN Isoginkgetin SAUCHINONE Jaceosidin Breviscapinun

2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one

5,7-Dihydroxy-3',4',6-trimethoxyflavone

2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one

4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy-

eupatilin

Eupatilin 2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxychromen-4-one

2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one

2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one (EUPATILIN)

NSC 122413

Eupatilin 22368-21-4

Eupatilin, BR

Eupatilin-RM

Eupatilin, 10 mM in DMSO

Isozepin

22368-21-4

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract