70727-06-9

Basic information

• Product Name: 4-Hepten-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-
• CAS NO: 70727-06-9
• Molecular Formula: C21H24O6
• Molecular Weight: 372.418
• Mol File: 70727-06-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 4-Hepten-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hepten-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-(70727-06-9)
• EPA Substance Registry System: 4-Hepten-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-(70727-06-9)

Safety Data

• Hazardous Substances Data: 70727-06-9(Hazardous Substances Data)

Upstream product

• 458-37-7 curcumin 
• 98885-93-9 5-hydroxy-1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,4,6-trien-3-one 
• 123-54-6 acetylacetone 
• 121-33-5 vanillin 
• 98885-93-9 curcumin 
• 1420899-25-7 (1E,4Z,6E)-1,7-bis(3-chloro-4-hydroxy-5-methoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one 

Downstream Products

• 36062-07-4 3,5-dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 
• 36062-05-2 hexahydrocurcumin 

Relevant articles and documents

Anti-allergic principles from Thai zedoary: Structural requirements of curcuminoids for inhibition of degranulation and effect on the release of TNF-α and IL-4 in RBL-2H3 cells

The 80% aqueous acetone extract of the rhizomes of Curcuma zedoaria cultivated in Thailand (Thai zedoary) was found to inhibit release of β-hexosaminidase, as a marker of antigen-IgE-mediated degranulation, in RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice. Effects of four curcuminoids from Thai zedoary and several related compounds on the degranulation were examined. Among them, curcumin showed the highest activity against β-hexosaminidase release with IC50 of 5.3 μM, followed by bisdemethoxycurcumin (IC50 = 11 μM). With regard to the structural requirements of curcuminoids for the activity, the conjugated olefins at the 1-7 positions and the 4′- or 4″-hydroxyl groups of curcuminoids were suggested to be essential for the strong activity, whereas the 3′- or 3″-methoxyl group only enhanced the activity. Furthermore, effects of curcumin and bisdemethoxycurcumin on calcium ionophores (A23187 and ionomycin)-induced degranulation and antigen-induced release of TNF-α and IL-4 were examined. The 80% aqueous acetone extract of the rhizomes of Curcuma zedoaria cultivated in Thailand (Thai zedoary) was found to inhibit release of β-hexosaminidase, as a marker of antigen-IgE-mediated degranulation, in RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice. From the active fraction, four curcuminoids (curcumin, dihydrocurcumin, tetrahydrodemethoxycurcumin, and tetrahydrobisdemethoxycurcumin) were isolated together with two bisabolane-type sesquiterpenes, and the effects of four curcuminoids from Thai zedoary and several related compounds on the degranulation were examined. Among them, curcumin showed the highest activity against β-hexosaminidase release with IC50 of 5.3 μM, followed by bisdemethoxycurcumin (IC50 = 11 μM). With regard to the structural requirements of curcuminoids for the activity, the conjugated olefins at the 1-7 positions and the 4′- or 4″-hydroxyl groups of curcuminoids were suggested to be essential for the strong activity, whereas the 3′- or 3″-methoxyl group only enhanced the activity. Furthermore, effects of curcumin and bisdemethoxycurcumin on calcium ionophores (A23187 and ionomycin)-induced degranulation and antigen-induced release of TNF-α and IL-4 were examined.

Synergistic antifungal effects of curcumin derivatives as fungal biofilm inhibitors with fluconazole

Lack of novel antifungal agents and severe drug resistance has led to high incidence and associated mortality of invasive fungal infections. To tackle the challenges, novel antifungal agents with anti-resistant potency are highly desirable. Thus, derivati

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.

Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1

To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp2 carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation.