6951-17-3

Basic information

• Product Name: 1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(pyridin-3-yl)propane-1,3-dione
• CAS NO: 6951-17-3
• Molecular Formula: C₁₆H₁₅NO₅
• Molecular Weight: 301.294
• Mol File: 6951-17-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 516.6°C at 760 mmHg
• Flash Point: 266.2°C
• Density: 1.273g/cm³
• Vapor Pressure: 2.72E-11mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(pyridin-3-yl)propane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(pyridin-3-yl)propane-1,3-dione(6951-17-3)
• EPA Substance Registry System: 1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(pyridin-3-yl)propane-1,3-dione(6951-17-3)

Safety Data

• Hazardous Substances Data: 6951-17-3(Hazardous Substances Data)

Usage

General Description

1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(pyridin-3-yl)propane-1,3-dione, also known as Curcumin III, is a chemical compound found in turmeric, a popular spice. It is a derivative of curcumin, which is known for its anti-inflammatory and antioxidant properties. Curcumin III has been studied for its potential health benefits, including its potential role in the treatment of various diseases, such as cancer, diabetes, and neurodegenerative disorders. Its chemical structure contains a hydroxy and methoxy group on the phenyl ring, as well as a pyridin-3-yl group, and a propane-1,3-dione moiety, which contribute to its biological activity. Further research is needed to fully understand the potential therapeutic applications of this compound.

Upstream product

• 94299-22-6 3,4-Dimethoxy-2-nicotinoyloxi-acetophenon 
• 5396-18-9 2'-hydroxy-3',4'-dimethoxyacetophenone 

Downstream Products

• 6622-57-7 7,8-Dimethoxy-2-pyridyl-(3)-chromon 

Relevant articles and documents

Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity

With many cancers showing resistance to current chemotherapies, the search for novel anti-cancer agents is attracting considerable attention. Natural flavonoids have been identified as useful leads in such programmes. However, since an in-depth understanding of the structural requirements for optimum activity is generally lacking, further research is required before the full potential of flavonoids as anti-proliferative agents can be realised. Herein a broad library of 76 methoxy and hydroxy flavones, and their 4-thio analogues, was constructed and their structure-activity relationships for anti-proliferative activity against the breast cancer cell lines MCF-7 (ER +ve), MCF-7/DX (ER +ve, anthracycline resistant) and MDA-MB-231 (ER -ve) were probed. Within this library, 42 compounds were novel, and all compounds were afforded in good yields and >95% purity. The most promising lead compounds, specifically the novel hydroxy 4-thioflavones 15f and 16f, were further evaluated for their anti-proliferative activities against a broader range of cancer cell lines by the National Cancer Institute (NCI), USA and displayed significant growth inhibition profiles (e.g. compound-15f: MCF-7 (GI50 = 0.18 μM), T-47D (GI50 = 0.03 μM) and MDA-MB-468 (GI50 = 0.47 μM) and compound-16f: MCF-7 (GI50 = 1.46 μM), T-47D (GI50 = 1.27 μM) and MDA-MB-231 (GI50 = 1.81 μM)). Overall, 15f and 16f exhibited 7-46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure-activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality, and incorporation of electron withdrawing groups at C-4′ of the B-ring phenyl, also enhanced activity. Molecular docking and mechanistic studies suggest that the anti-proliferative effects of flavones 15f and 16f are mediated via ER-independent cleavage of PARP and downregulation of GSK-3β for MCF-7 and MCF-7/DX cell lines. For the MDA-MB-231 cell line, restoration of the wild-type p53 DNA binding activity of mutant p53 tumour suppressor gene was indicated.