147556-16-9

Basic information

• Product Name: 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,4Z,6E)-
• CAS NO: 147556-16-9
• Molecular Formula: C21H20O6
• Molecular Weight: 368.386
• Mol File: 147556-16-9.mol

Chemical Properties

• CAS DataBase Reference: 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,4Z,6E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,4Z,6E)-(147556-16-9)
• EPA Substance Registry System: 1,4,6-Heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,4Z,6E)-(147556-16-9)

Safety Data

• Hazardous Substances Data: 147556-16-9(Hazardous Substances Data)

Upstream product

• 121-33-5 vanillin 
• 884506-54-1 (3Z,5E)-4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)hexa-3,5-dien-2-one 
• 123-54-6 acetylacetone 
• 15390-25-7 (acetylacetonato)borondifluoride 
• 458-37-7 curcumin 
• 704885-44-9 β-D-glucopyranosiduronic acid 4-formyl-2-methoxyphenyl methyl ester triacetate 
• 30802-02-9 feruloyl-CoA 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 23598-07-4 4-formyl-2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β?D?galactopyranoside 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 76474-56-1 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4,6-heptadiene-3-one 

Downstream Products

• 98886-38-5 [2-methoxy-4-[(1E,6E)-7-(3-methoxy-4-propanoyloxyphenyl)-3,5-dioxohepta-1,6-dienyl]phenyl] propanoate 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 121-33-5 vanillin 
• 36062-04-1 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione 
• 52328-98-0 O,O-dimethyl-curcumin 
• 2309-07-1 Methyl ferulate 
• 60831-46-1 bisdemethylcurcumin 
• 52552-50-8 (1E,4Z,6E)-1,7-bis(3,4-dimethoxyphenyl)-5-hydroxy-4-methylhepta-1,4,6-trien-3-one 
• 70727-06-9 (Z)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one 
• 36062-05-2 hexahydrocurcumin 
• 114380-40-4 Isoxazole-curcumin 
• 19697-86-0 [4-[(1E,6E)-7-(4-acetyloxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] acetate 
• 70727-06-9 1,7-bis(3-hydroxy-4-methoxyphenyl)heptane-3,5-dione 

Relevant articles and documents

Mechanochemical synthesis of 2,2-difluoro-4, 6-bis(β-styryl)-1,3,2-dioxaborines and their use in cyanide ion sensing

The conversion of arylaldehydes to 1,7-diaryl-5-hydroxyhepta-1,4,6-trien-3-ones (curcuminoids) and the mechanochemical cyclization of these products to 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines using BF3-Et2O are described. Investigation of the cyanide ion sensing ability of the 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines, in relation to the substituent groups on the aryl ring, showed that a hydroxy susbstituent is required, preferably para to the intervening carbon bridge.

Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors

Series of curcumin derivatives were synthesized; the inhibitory activities on thioredoxin reductase (TrxR) of all analogues were evaluated by DTNB assay in vitro. It is found that most of the analogues can inhibit TrxR in the low micromolar range; Structure-activity relationship analysis reveals that analogues with furan moiety have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogues with TrxR. The effect of selected curcuminoids on growth of different TrxR overexpressed cancer cell lines was also investigated and discussed.

Synthesis, anticancer activity, and preliminary pharmacokinetic evaluation of 4,4-disubstituted curcuminoid 2,2-bis(hydroxymethyl)propionate derivatives

Compound 1 is a curcumin di-O-2,2-bis(hydroxymethyl)propionate that shows significant in vitro and in vivo inhibitory activity against MDA-MB-231 cells with eight to ten-fold higher potency than curcumin. Here, we modified the α-position (C-4 position) of the central 1,3-diketone moiety of 1 with polar or nonpolar functional groups to afford a series of 4,4-disubstituted curcuminoid 2,2-bis(hydroxymethyl)propionate derivatives and evaluated their anticancer activities. A clear structure–activity relationship of compound 1 derivatives focusing on the functional groups at the C-4 position was established based on their anti-proliferative effects against the MDA-MB-231 and HCT-116 cell lines. Compounds 2–6 are 4,4-dimethylated, 4,4-diethylated, 4,4-dibenzylated, 4,4-dipropargylated and 4,4-diallylated compound 1, respectively. Compounds 2m–6m, the ester hydrolysis products of compounds 2–6, respectively, were synthesized and assessed for anticancer activity. Among all compound 1 derivatives, compound 2 emerged as a potential chemotherapeutic agent for colon cancer due to the promising in vivo anti-proliferative activities of 2 (IC50 = 3.10 ± 0.29 μM) and its ester hydrolysis product 2m (IC50 = 2.17 ± 0.16 μM) against HCT-116. The preliminary pharmacokinetic evaluation of 2 implied that 2 and 2m are main contributors to the in vivo efficacy. Compound 2 was further evaluated in an animal study using HCT-116 colon tumor xenograft bearing nude mice. The results revealed a dose-dependent efficacy that led to tumor volume reductions of 27%, 45%, and 60% at 50, 100, and 150 mg/kg doses, respectively. The established structure–activity relationship and pharmacokinetic outcomes of 2 is the guidance for future development of 4,4-disubstituted curcuminoid 2,2-bis(hydroxymethyl)- propionate derivatives as anticancer drug candidates.

DNA-binding and in vitro cytotoxic activity of platinum(II) complexes of curcumin and caffeine

Three Pt(II) complexes containing the natural ligands curcumin and caffeine, namely [Pt(curc)(PPh3)2]Cl (1), [PtCl(curc)(DMSO)] (2) (curc = deprotonated curcumin) and trans-[Pt(caffeine)Cl2(DMSO)] (3), were synthesized and

Mining Plants for Bacterial Quorum Sensing Modulators

The bacterial plant pathogen Agrobacterium tumefaciens uses quorum sensing (QS) in order to regulate the transfer of DNA into the host plant genome, and this results in the induction of crown gall tumors. The deleterious results of these infections are wi

A curcumin-diglutaric acid conjugated prodrug with improved water solubility and antinociceptive properties compared to curcumin

In this work, a curcumin-diglutaric acid (CurDG) prodrug was synthesized by conjugation of curcumin with glutaric acid via an ester linkage. The water solubility, partition coefficient, release characteristics, and antinociceptive activity of CurDG were compared to those of curcumin. The aqueous solubility of CurDG (7.48 μg/mL) is significantly greater than that of curcumin (0.068 μg/mL). A study in human plasma showed that the CurDG completely releases curcumin within 2 h, suggesting the ability of CurDG to serve as a prodrug of curcumin. A hot plate test in mice showed the highest antinociceptive effect dose of curcumin at 200 mg/kg p.o., whereas CurDG showed the same effect at an effective dose of 100 mg/kg p.o., indicating that CurDG significantly enhanced the antinociceptive effect compared to curcumin. The enhanced antinociceptive effect of CurDG may be due to improved water solubility and increased oral bioavailability compared to curcumin.

Structure-activity relationship studies of 1,7-diheteroarylhepta-1,4,6-trien-3-ones with two different terminal rings in prostate epithelial cell models

To systematically investigate the structure-activity relationships of 1,7-diheteroarylhepta-1,4,6-trien-3-ones in three human prostate cancer cell models and one human prostate non-neoplastic epithelial cell model, thirty five 1,7-diarylhepta-1,4,6-trien-

Method for artificially synthesizing curcumin and derivative thereof

The invention discloses a method for artificially synthesizing curcumin and a derivative thereof. The method comprises the steps of adopting calcium acetylacetonate as a acetylacetone supply source, carrying out claisen-schmidt ester condensation reaction on the calcium acetylacetonate and a corresponding benzaldehyde derivative, and dehydrating under the catalysis of a dehydrating agent which is tributyl borate to obtain a product intermediate (I) which is curcumin calcium salt; then hydrolyzing the intermediate (I) through a one-pot method to obtain a crude product, and purifying the crude product so as to obtain the final product curcumin and the derivative thereof. Compared with a acetylacetone boric acid complex method, according to the method provided by the invention, the calcium acetylacetonate is used, so that active sites of acetylacetonate during a reaction process are more accurate and activated, the generation of by-products is reduced, and the yield of the curcumin and the derivative thereof is improved.

Synthesis of Unnatural 2-Substituted Quinolones and 1,3-Diketones by a Member of Type III Polyketide Synthases from Huperzia serrata

A curcuminoids, benzalacetone-, and quinolone-producing type III polyketide synthase (HsPKS3) from Huperzia serrata uniquely catalyzes the formation of unnatural 2-substituted quinolones and 1,3-diketones via head-to-head condensation of two completely different substrates. The broad range of substrate tolerance of HsPKS3 facilitates accessing structurally diverse 2-substituted quinolones and 1,3-diketones.

Novel Dialkyl Curcumin Derivatives and Uses Thereof

The present invention provides novel dialkyl curcumin derivatives. The dialkyl curcumin derivatives according to the present invention have significant effects in vascularization and tumor growth when compared to curcumin. The dialkyl curcumin derivatives according to the present invention may be used for preventing and curing various vascularization-related diseases and tumor diseases. The dialkyl curcumin derivatives are expressed by chemical formula 1. In the chemical formula 1, R_1 to R_4 are each independently H or C_1-C_5 alkyl; R_5 and R_6 are each independently OH, C_1-C_5 haloalkoxy, polyethyleneoxy, halopolyethyleneoxy, amino, monoalkylamino, dialkylamino, piperidine, piperazine, morpholin, pyrrole, imidazole, benzimidazole, or indole; and R_7 and R_8 are each independently H, OH, or C_1-C_5 alkoxy, wherein the polyethyleneoxy is (ethoxy)_n-OH and n is an integer of 1 to 5.COPYRIGHT KIPO 2016