98886-01-2

Basic information

• Product Name: 5-hydroxy-1,7-bis (3,4-dimethoxyphenyl)hepta-1,4,6-trien-3-one
• CAS NO: 98886-01-2
• Molecular Weight: 396.44
• Mol File: 98886-01-2.mol

Chemical Properties

• CAS DataBase Reference: 5-hydroxy-1,7-bis (3,4-dimethoxyphenyl)hepta-1,4,6-trien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-1,7-bis (3,4-dimethoxyphenyl)hepta-1,4,6-trien-3-one(98886-01-2)
• EPA Substance Registry System: 5-hydroxy-1,7-bis (3,4-dimethoxyphenyl)hepta-1,4,6-trien-3-one(98886-01-2)

Safety Data

• Hazardous Substances Data: 98886-01-2(Hazardous Substances Data)

Upstream product

• 98885-93-9 curcumin 
• 67-68-5 dimethyl sulfoxide 
• 458-37-7 curcumin 
• 74-88-4 methyl iodide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 123-54-6 acetylacetone 

Downstream Products

• 1118765-46-0 (E,E)-3,5-bis(3,4-dimethoxystyryl)isoxazole 
• 1384274-56-9 (1E,6E)-4,4-difluoro-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione 

Relevant articles and documents

A new family of homoleptic copper complexes of curcuminoids: Synthesis, characterization and biological properties

We report herein the synthesis and crystal structures of five new homoleptic copper complexes of curcuminoids. The scarcity of reports of homoleptic complex structures of curcuminoids is attributed to the lack of crystallinity of such derivatives, and therefore, their characterization by single crystal X-ray diffraction is rare. The ligand design suppressing the phenolic interaction by esterification or etherification has afforded a significant increase in the number of known crystal structures of homoleptic metal complexes of curcuminoids revealing more favorable crystallinity. The crystal structures of the present new copper complexes show four-fold coordination with a square planar geometry. Two polymorphs were found for DiBncOC-Cu when crystallized from DMF. The characterization of these new complexes was carried out using infrared radiation (IR), nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), and single crystal X-ray diffraction (SCXRD) and the antioxidant and cytotoxic activity of the obtained complexes was evaluated.

Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin

Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.

Design, synthesis, and evaluation of curcumin analogues as potential inhibitors of bacterial sialidase

Sialidases are key virulence factors that remove sialic acid from the host cell surface glycan, unmasking receptors that facilitate bacterial adherence and colonisation. In this study, we developed potential agents for treating bacterial infections caused by Streptococcus pneumoniae Nan A that inhibit bacterial sialidase using Turmeric and curcumin analogues. Design, synthesis, and structure analysis relationship (SAR) studies have been also described. Evaluation of the synthesised derivatives demonstrated that compound 5e was the most potent inhibitor of S. pneumoniae sialidase (IC50 = 0.2 ± 0.1 μM). This compound exhibited a 3.0-fold improvement in inhibitory activity over that of curcumin and displayed competitive inhibition. These results warrant further studies confirming the antipneumococcal activity 5e and indicated that curcumin derivatives could be potentially used to treat sepsis by bacterial infections.

Kinetics of curcumin oxidation by 2,2-diphenyl-1-picrylhydrazyl (DPPH): An interesting case of separated coupled proton-electron transfer

The decay of dpph in absolute ethanol at 25 °C and in the presence of curcumin (1), 4-methylcurcumin (3), 4,4-dimethylcurcumin (4) or curcumin 4′-methyl ether (5) follows bi-exponential kinetics. These unusual reaction kinetics are compatible with a two-step process in which an intermediate accumulates in a reversible first step followed by an irreversible process. As in other similar cases (Foti et al., Org. Lett., 2011, 13, 4826-4829), we have hypothesised that the intermediate is a π-stacked complex, formed between one curcumin anion (in the case of 1, 3 and 5 the enolate anion) and the picryl moiety of dpph, in which an intra-complex electron transfer from the (enolate) anion takes place. By comparing the kinetics of curcumin 4′,4′′-dimethyl ether (2) (no phenolic OH), (5) (one phenolic OH) and (1) (two phenolic OHs), we have deduced that the electron transfer process must be accompanied by a simultaneous proton transfer from the phenolic OHs to the bulk solvent (separated coupled proton-electron transfer). The rate constants kα for the forward reaction of 2, 5 and 1 with dpph are in fact ～0, 7.5 × 103 and 1.8 × 104 M-1 s-1, respectively, in a clear dependence on the number of phenolic OHs.

Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway

Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/β-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of β-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of β-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than 1a (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma.

Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor

Inhibition of the amyloid β aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid β aggregation activity. Compound 7, the ideal amyloid β aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid β aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed.