100613-36-3

Basic information

• Product Name: 1-(3,4,5-TRIMETHOXYPHENYL)BUTANE-1,3-DIONE
• Synonyms: 1-(3,4,5-TRIMETHOXYPHENYL)BUTANE-1,3-DIONE
• CAS NO: 100613-36-3
• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.26
• Product Categories: pharmacetical
• Mol File: 100613-36-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 370.8 °C at 760 mmHg
• Flash Point: 163.6 °C
• Appearance: /
• Density: 1.13 g/cm³
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.499
• CAS DataBase Reference: 1-(3,4,5-TRIMETHOXYPHENYL)BUTANE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4,5-TRIMETHOXYPHENYL)BUTANE-1,3-DIONE(100613-36-3)
• EPA Substance Registry System: 1-(3,4,5-TRIMETHOXYPHENYL)BUTANE-1,3-DIONE(100613-36-3)

Safety Data

• Hazardous Substances Data: 100613-36-3(Hazardous Substances Data)

Usage

General Description

1-(3,4,5-Trimethoxyphenyl)butane-1,3-dione, also known as curcumin, is a natural phenolic compound found in the root of the turmeric plant. It is a bright yellow chemical that has been used for centuries in traditional medicine for its anti-inflammatory and antioxidant properties. Curcumin has gained attention in modern research for its potential therapeutic applications in various diseases including cancer, diabetes, and neurodegenerative disorders. It has been found to exert its effects through multiple molecular pathways, making it a promising compound for the development of new drugs and treatments. Additionally, curcumin is considered safe and well-tolerated, further supporting its potential as a therapeutic agent.

InChI:InChI=1/C13H16O5/c1-8(14)5-10(15)9-6-11(16-2)13(18-4)12(7-9)17-3/h6-7H,5H2,1-4H3

Upstream product

• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 141-78-6 ethyl acetate 
• 118-41-2 Eudesmic acid 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 67-64-1 acetone 
• 68415-05-4 α-(3,4,5-trimethoxyphenyl)-α-morpholinoacetonitrile 

Downstream Products

• 1178542-11-4 1-(1-(3,4,5-trimethoxybenzoyl)cyclopropyl)ethanone 
• 102659-48-3 6,7-dimethoxy-4-(3,4,5-trimethoxy-phenyl)-quinoline-2-carboxylic acid 
• 102659-44-9 6,7-dimethoxy-4-(3,4,5-trimethoxy-phenyl)-quinoline-2-carbaldehyde 
• 7473-33-8 4-(3,5-dimethoxy-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-quinoline 
• 5465-02-1 6,7-dimethoxy-2-methyl-4-(3,4,5-trimethoxy-phenyl)-quinoline 
• 7473-34-9 6,7-dimethoxy-4-(3,4,5-trimethoxy-phenyl)-quinoline 
• 107504-59-6 2-(5,6-Dihydro-imidazo[2,1-b]thiazol-3-yl)-1-(3,4,5-trimethoxy-phenyl)-ethanone; hydrobromide 
• 107504-75-6 2-[5,6-Dihydro-imidazo[2,1-b]thiazol-(3E)-ylidene]-1-(3,4,5-trimethoxy-phenyl)-ethanone 
• 344247-32-1 4-Bromo-1-(3,4,5-trimethoxy-phenyl)-butane-1,3-dione 
• 6630-31-5 3-(3,4-dimethoxy-anilino)-1-(3,4,5-trimethoxy-phenyl)-but-2-en-1-one 

Relevant articles and documents

Propargyl bromide as an excellent α-bromoacetone equivalent: Convenient and new route to α-aroylacetones

A variety of α-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein α-aminonitriles 1a-g as the aryl acyl anion equivalents readily react with propargyl bromide as the α-bromoacetone equivalent. The alkylated product undergoes one-pot unmasking of the keto functionality along with Markovnikov's hydration of the terminal alkyne with CuSO4·5H2O in aqueous methanol at 60 °C to furnish the desired target in excellent isolated yields.

Synthesis and biological evaluation of 3-alkyl-1,5-diaryl-1H-pyrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative activity

A series of novel 3-alkyl-1,5-diaryl-1H-pyrazoles were synthesized as combretastatin A-4 (CA-4) analogues and evaluated for antiproliferative activity against three human cancer cell lines (SGC-7901, A549 and HT-1080). Most of the target compounds displayed moderate to potent antiproliferative activity, and 7k was found to be the most potent compound. Structure-activity relationships indicated that compounds with a trimethoxyphenyl A-ring at the N-1 position of the pyrazole skeleton were more potent than those with the A-ring at the C-5 position. Tubulin polymerization and immunostaining experiments revealed that 7k potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Computational modelling demonstrated that the binding of 7k to the colchicine binding site on microtubules may involve a similar mode as CA-4.