23731-65-9

Upstream product

• 23731-64-8 3,4-dimethoxy-1,2-methylenedioxybenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 484-31-1 dillapiole 
• 17672-89-8 4.5-Dimethoxy-6-(1-propenyl)-1,3-benzodioxol 
• 23731-63-7 4,5-dimethoxy-6-(prop-1-en-1-yl)benzo[1,3]dioxole 
• 23504-78-1 5-Hydroxy-4-methoxybenzo<1,3>dioxol 
• 344599-82-2 6-(1,3-Diphenylimidazolidin-2-yl)-4,5-dimethoxy-1,3-benzodioxol 

Downstream Products

• 1293408-38-4 C₂₃H₃₀O₇Si 
• 1293408-43-1 (3-hydroxy-4-methoxyphenyl)(2,3-dimethoxy-4,5-methylenedioxyphenyl)methanone 
• 1221719-44-3 3-(2,3-dimethoxy-4,5-methylenedioxyphenyl)-5-(4-hydroxyphenyl)-1,2,4-oxadiazole 
• 1285164-03-5 C₁₉H₁₆O₇ 
• 1240114-31-1 2-(4-methoxyphenyl)-3-oxo-3-(2,3-dimethoxy-4,5-methylenedioxyphenyl)propanenitrile 
• 1449420-90-9 3-(4-methoxyphenyl)-3-oxo-2-(2,3-dimethoxy-4,5-methylenedioxyphenyl)propanenitrile 
• 1301743-23-6 4-(4-methoxyphenyl)-5-(2,3-dimethoxy-4,5-methylenedioxyphenyl)-1H-pyrazol-3-amine 
• 1449420-94-3 5-(4-methoxyphenyl)-4-(2,3-dimethoxy-4,5-methylenedioxyphenyl)-1H-pyrazol-3-amine 
• 1257321-01-9 4,5-methylenedioxy-2,3,4'-trimethoxy-3'-O-t-butyldimethylsilylstilbene 
• 1257321-02-0 4,5-methylenedioxy-2,3,4'-trimethoxy-3'-O-t-butyldimethylsilylstilbene 
• 22027-56-1 dillapionic acid 

Relevant academic research and scientific papers

A PROCESS FOR THE PREPARATION OF VANILLIN AND OTHER SUBSTITUTED PHENYLALDEHYDES

The present invention relates to a chemical process for the production of substituted phenylaldehydes such as vanillin (1a) from substituted phenylpropenes or substituted phenylpropenes enriched essential oils such as eugenol (2a) or eugenol rich essential oils indiscriminately through either cis or trans or a mixture of cis and trans isomer(s) of substituted phenylprop-2-enes such as isoeugenol, an intermediate compound. The invention relates to the conversion of substituted phenylpropenes to other substituted phenylaldehydes, particularly vanillin without the protection of the phenolic group, therefore, it offers a step economy. The present chemical process involves the use of class 3 and 4 solvents thereby devoid of the use of any chlorinated solvent.

Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues

A technologically advanced protocol has been developed for converting plant allyl(polyalkoxy)benzenes to methyl- and propyl(polyalkoxy)benzenes being intermediates in the syntheses of coenzyme Q0 analogues. The key stage of allyl and benzaldehyde moieties hydrogenation was carried out in a periodical autoclave mode on highly porous ceramic block Pd-catalysts. These catalysts possess large surface area, low hydraulic resistance, significant thermal and mechanical stabililty, multiple cycling and easy regeneration, which can dramatically reduce Pd consumption.

Dill and parsley seed extracts in scale up synthesis of aminopolyalkoxybenzenes - Beneficial synthons for fused nitrogen polyalkoxyheterocycles

Ecologically friendly transformation of readily accessible plant allylpolyalkoxybenzenes to hardly available aminotetraalkoxybenzenes has been developed. The efficacy of hydrogenation stage is substantially increased by the application of highly porous ceramic block Pd-catalysts featuring a large surface area, low hydraulic resistance, significant thermal and mechanical stabililty, multiple cycling and easy regeneration.

Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity

A concise six-step protocol for the synthesis of isoflavone glaziovianin A (GVA) and its alkoxyphenyl derivatives 9 starting with readily available plant metabolites from dill and parsley seeds was developed. The reaction sequence involved an efficient conversion of the key intermediate epoxides 7 into the respective β-ketoaldehydes 8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure-activity relationship studies suggested that compounds 9cd and 9cf substituted with trimethoxy- and dillapiol-derived B-rings, respectively, were less active than the parent 9cg. Of the evaluated human cancer cell lines, the A375 melanoma cell line was the most sensitive to the tested molecules. Notably, the target compounds were not cytotoxic against human peripheral blood mononuclear cells up to 10 μM concentration. Phenotypic readouts from the sea urchin assay unequivocally suggest a direct microtubule-destabilizing effect of isoflavones 9cg, 9cd, and 9cf.

Synthesis of analogues of natural antimitotic glaziovianin A based on dill and parsley seed essential oils

Glaziovianin A and its analogues were synthesized in six steps starting from allylpolyalkoxybenzenes separated from essential oils of dill (Anetum graviolens) and parsley (Petro-selinum sativum) seeds.

Cis -restricted 3-aminopyrazole analogues of combretastatins: Synthesis from plant polyalkoxybenzenes and biological evaluation in the cytotoxicity and phenotypic sea urchin embryo assays

We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl- 3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multi-drug-resistant cancer cells.

Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues

Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent.

Polyalkoxybenzenes from plants. 5. parsley seed extract in synthesis of azapodophyllotoxins featuring strong tubulin destabilizing activity in the sea urchin embryo and cell culture assays

A series of 4-azapodophyllotoxin derivatives with modified rings B and E have been synthesized using allylpolyalkoxybenzenes from parsley seed oil. The targeted molecules were evaluated in vivo in a phenotypic sea urchin embryo assay for antimitotic and tubulin destabilizing activity. The most active compounds identified by the in vivo sea urchin embryo assay featured myristicin-derived ring E (4e, 6e, and 8e). These molecules were determined to be more potent than podophyllotoxin. Cytotoxic effects of selected molecules were further confirmed and evaluated by conventional assays with A549 and Jurkat human leukemic T-cell lines including cell growth inhibition, cell cycle arrest, cellular microtubule disruption, and induction of apoptosis. The ring B modification yielded 6-OMe substituted molecule 8e as the most active compound. Finally, in Jurkat cells, compound 8e induced caspase-dependent apoptosis mediated by the apical caspases-2 and -9 and not caspase-8, implying the involvement of the intrinsic caspase-9-dependent apoptotic pathway.

Polyalkoxybenzenes from plant raw materials 1. Isolation of polyalkoxybenzenes from CO2 extracts of Umbelliferae plant seeds

For the search for a domestic natural source of allylpolyalkoxybenzenes and development of an effective process for their isolation, CO2 extracts of several varieties of parsley, dill, celery, caraway, and nutmeg were analyzed systematically for the first time by GC/MS and GLC techniques. The varieties with high contents of myristicin, elemicin, allyltetramethoxybenzene, apiol, and dillapiol were identified. The conditions of CO2 extraction for obtaining concentrates with minimum contents of the distillation residues were selected. Using high performance fractional distillation, polyalkoxyallylbenzenes with 98-99% purity were isolated from the concentrates on a pilot unit. By isomerization of some allylbenzenes followed by ozonolysis under specially selected conditions, apiol-and dillapiolaldehydes were obtained in 75-80% yields.