3877-67-6

Basic information

• Product Name: (E)-1-(6-hydroxy-2,3,4-triMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one
• Synonyms: (E)-1-(6-hydroxy-2,3,4-triMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one;1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS NO: 3877-67-6
• Molecular Formula: C₁₉H₂₀O₆
• Molecular Weight: 344.3585
• EINECS: -0
• Mol File: 3877-67-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 558.5°Cat760mmHg
• Flash Point: 200.2°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 4.43E-13mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: (E)-1-(6-hydroxy-2,3,4-triMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(6-hydroxy-2,3,4-triMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one(3877-67-6)
• EPA Substance Registry System: (E)-1-(6-hydroxy-2,3,4-triMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one(3877-67-6)

Safety Data

• Hazardous Substances Data: 3877-67-6(Hazardous Substances Data)

Usage

General Description

(E)-1-(6-hydroxy-2,3,4-triMethoxyphenyl)-3-(4-Methoxyphenyl)prop-2-en-1-one, also known as curcumin, is a natural compound found in the rhizome of the turmeric plant. It is a polyphenolic compound with a bright yellow color and is widely used as a food colorant and flavor. Curcumin has also been studied for its potential therapeutic effects, including anti-inflammatory, antioxidant, and anti-cancer properties. It has been used in traditional medicine for centuries and is currently being researched for its potential benefits in a variety of health conditions. Its chemical structure contains a combination of phenolic rings and a β-diketone moiety, which contribute to its biological activity.

InChI:InChI=1/C19H20O6/c1-22-13-8-5-12(6-9-13)7-10-14(20)17-15(21)11-16(23-2)18(24-3)19(17)25-4/h5-11,21H,1-4H3

Upstream product

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• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 138008-76-1 3,4,4,5-Tetramethoxy-2-[(E)-3-(4-methoxy-phenyl)-acryloyl]-cyclohexa-2,5-dienone 
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• 33507-92-5 7-(benzyloxy)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one 
• 33507-93-6 7-hydroxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 676536-34-8 scutellarein 7-O-glucuronopyranoside 
• 529-53-3 scutellarein 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 138008-78-3 3-hydroxy-4,4,5-trimethoxy-2-<3-(4-methoxyphenyl)acryloyl>cyclohexa-2,5-dienone 
• 57197-19-0 4-Hydroxy-3,4,5-trimethoxy-2-[(E)-3-(4-methoxy-phenyl)-acryloyl]-cyclohexa-2,5-dienone 

Relevant articles and documents

Note concerning the synthesis of the mikanins, a flavonol from Mikania cordata (Burm. f.) B.L. Robinson

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Activities of Wogonin Analogs and Other Flavones against Flavobacterium columnare

In our on-going pursuit to discover natural products and natural product-based compounds to control the bacterial species Flavobacterium columnare, which causes columnaris disease in channel catfish (Ictalurus punctatus), we synthesized flavone and chalcone analogs, and evaluated these compounds, along with flavonoids from natural sources, for their antibacterial activities against two isolates of F. columnare (ALM-00-173 and BioMed) using a rapid bioassay. The flavonoids chrysin (1a), 5,7-dihydroxy-4′-methoxyflavone (11), isorhamnetin (26), luteolin (27), and biochanin A (29), and chalcone derivative 8b showed strong antibacterial activities against F. columnare ALM-00-173 based on minimum inhibition concentration (MIC) results. Flavonoids 1a, 8, 11, 13 (5,4′-dihydroxy-7-methoxyflavone), 26, and 29 exhibited strong antibacterial activities against F. columnare BioMed based upon MIC results. The 24-h 50% inhibition concentration (IC50) results revealed that 27 and 29 were the most active compounds against F. columnare ALM-00-173 (IC50 of 7.5 and 8.5 mg/l, resp.), while 26 and 29 were the most toxic compound against F. columnare BioMed (IC50 of 9.2 and 3.5 mg/l, resp.). These IC50 results were lower than those obtained for wogonin against F. columnare ALM-00-173 and F. columnare BioMed (28.4 and 5.4 mg/l, resp.). However, based on MIC results, none of the compounds evaluated in this study were as active as wogonin (MIC 0.3 mg/l for each F. columnare isolate). Further modification of the wogonin structure to enhance antibacterial is of interest.

4',5,6,7-OXYGENATED FLAVONES AND FLAVANONES.

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