108439-88-9

Usage

Appearance

Yellow crystalline solid

Chemical structure

Contains two 1,3-benzodioxole groups and a pentadienone group

Main use

Fragrance ingredient in perfumes and personal care products

Potential applications

Building block for the synthesis of more complex molecules in organic chemistry

Safety precautions

Handle and use with caution in a controlled laboratory or industrial setting due to chemical properties and potential health hazards

Upstream product

• 120-57-0 piperonal 
• 67-64-1 acetone 
• 3160-37-0 4-(benzo[d][1,3]dioxol-5-yl)but-3-en-2-one 

Downstream Products

• 41296-80-4 5-benzo[1,3]dioxol-5-yl-3-(2-benzo[1,3]dioxol-5-yl-vinyl)-1-phenyl-4,5-dihydro-1H-pyrazole 
• 41186-48-5 2,5-bis-benzo[1,3]dioxol-5-yl-1-phenyl-1,2,3,5,6,7-hexahydro-pyrazolo[1,5-a]pyridine-6,7-dicarboxylic acid anhydride 

Relevant academic research and scientific papers

TERMITE ANTIFEEDANT ACTIVITY IN AFRAMOMUM MELEGUETA

n-Hexane and methanolic seed extracts of Aframomum melegueta were studied for termite antifeedant activity against workers of Reticulitermes speratus.Strong antifeedant activity was observed when the termite workers were tested in a choice filter paper di

Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant Candida spp.

Twenty-three monoketone derivatives of curcumin were synthesized to investigate the synergy with fluconazole against fluconazole-resistant Candida spp. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant C. albicans, C. tropicalis and C. krusei in vitro. Most of these compounds showed good synergistic activities against C. tropicalis. Among them, compound 9 exhibited significant synergistic activities against Candida spp. SARs were also discussed. In particular, a cell growth test exhibited that a combination of 1 μg ml-1 fluconazole and 64 μg ml-1 or 128 μg ml-1 compound 9 showed the most potent fungicidal effect against C. tropicalis. The synergistic effect may be associated with the changes of the intracellular ATP content and cell membrane permeability. Our results provided a basis for future evaluation and development of these compounds as leads for therapeutics for fluconazole-resistant candidiasis.

Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)- hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation

Amidinohydrazone compounds are very important synthetic intermediates and can serve as versatile precursors in synthesis of many natural products and drug molecules. The use of ultrasound, p-dodecylbenzenesulfonic acid (DBSA) and water as solvent improved the synthesis of different 2-(1,5-diaryl-1,4- pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction conditions for the condensation of 1,5-diphenyl-1,4-pentadien-3-one with aminoguanidine hydrochloride were as follows: 1,5-diphenyl-1,4-pentadiene-3-one (1, 1 mmol), aminoguanidine hydrochloride (1.1 mmol), DBSA (0.5 mmol), water 10 mL, reaction temperature 25-27°C, irradiation frequency 25 kHz. 2a was achieved in 94% yield within 2 h. The other seven amidinohydrazones were obtained in 84-94% yield within 2-3 h under the same conditions. Compared to the method involving catalysis by hydrochloric acid in refluxing EtOH, the advantages of present procedure are milder conditions, shorter reaction times, higher yields, and environmental friendly conditions, which make it a useful strategy for the synthesis of analogues.

Lewis acid mediated diastereoselective synthesis of fused fluorinated spiroketal as potential biologically active compounds

A series of substituted dibenzalacetones prepared using standard procedures were condensed with 5-methyl, 5-phenyl, and 5-trifluoromethyl-1,3- cyclohexanediones respectively, in toluene containing BF3·OEt as the Lewis acid catalyst. The reaction was found to be highly diastereoselective (dr, 9:1). The resulting spiroketals 1a-r were formed in moderate to good yields. In addition, a synthetically and biologically useful by-product identified as chromenone 7 was observed.

BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER

It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents

Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modifications of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive β-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically.

Synthesis of some 3-(4-styryl-6-aryl-pyridin-2-yl)- and 3-(6-styryl-4-aryl-pyridin-2-yl) coumarins

Various 3-(4-styryl-6-aryl-pyridin-2-yl) coumarins 4a-f and 3-(6-styryl-4-aryl-pyridin-2-yl) coumarins 5a-f have been synthesized by the reaction of 3-coumarinoyl methyl pyridinium salt I with pentadienones 2a-f and 3a-f respectectively in the presence of ammonium acetate in refluxing acetic acid.

Improved microwave-induced synthesis of chalcones and related enones

Various chalcones and related enones have been synthesised in unsealed vessels in a domestic microwave oven.Considerable increase in the reaction rate has been observed with better yields.

Efficient Wittig-Horner and Improved Claisen-Schmidt Synthesis of Acyclic α-Enones with a 2-Furyl or 3,4-Methylenedioxyphenyl Group at the β-Position.

The Wittig-Horner and Claisen-Schmidt syntheses of acyclic α-enanes bearing a 2-furyl or 3,4-methylenedioxyphenyl group in the β-position have been achieved using activated barium hydroxide C-200 with good yields.The Wittig-Horner reaction in homogeneous phase is shown to be more efficient than the Claisen-Schmidt condensation under interfacial solid-liquid conditions.The 1H and the 13C megnetic parameters of compounds 5 and 6 are described.The use of 1H-13C correlation spectra helped in the unambiguous assignment of the olefinic and aromatic carbons of α-enones 5a and 6a.