17055-09-3Relevant articles and documents
Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata
Newson, Harriet L.,Wild, Duncan A.,Yeung, Sing Yee,Skelton, Brian W.,Flematti, Gavin R.,Allan, Jane E.,Piggott, Matthew J.
, p. 3127 - 3135 (2016)
The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the αD-line.
Polyalkoxybenzenes from plant raw materials 1. Isolation of polyalkoxybenzenes from CO2 extracts of Umbelliferae plant seeds
Semenov,Rusak,Chartov,Zaretskii,Konyushkin,Firgang,Chizhov,Elkin,Latin,Bonashek,Stas'Eva
, p. 2448 - 2455 (2007)
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.
Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents
Samet, Alexander V.,Shevchenko, Oksana G.,Rusak, Vyacheslav V.,Chartov, Eduard M.,Myshlyavtsev, Andrey B.,Rusanov, Daniil A.,Semenova, Marina N.,Semenov, Victor V.
, p. 1451 - 1458 (2019)
Free-radical-scavenging capacity antioxidant and membrane-protective properties of natural and related synthetic allylpolyalkoxybenzenes with different numbers of alkoxy/methoxy groups in the aromatic ring were evaluated using several in vitro models. These included the DPPH assay, inhibition of lipid peroxidation products accumulation, inhibition of H2O2-induced hemolysis, and oxidation of oxyhemoglobin. A synthetic protocol for the synthesis of natural nothoapiol (9) from a parsley seed metabolite, apiol (7), was developed. A structure-activity relationship study revealed that both the methylenedioxy fragment and methoxy groups in the aromatic ring are favorable for antioxidant activity. Hydroxyapiol (14), containing a hydroxy group in the aromatic core, was identified as the most potent compound. The pentaalkoxy-substituted nothoapiol (9) showed antioxidant activity in mouse brain homogenates, whereas in mouse erythrocytes it exhibited a marked pro-oxidant effect. Despite their low free-radical-scavenging capacity, allylpolyalkoxybenzenes can contribute to the total antioxidant potencies of plant essential oils.
Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues
Khrustalev, Victor N.,Muravsky, Egor A.,Semenov, Victor V.,Shinkarev, Ilia Yu.,Varakutin, Alexander E.
, p. 599 - 601 (2020/10/18)
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.
