[Phenol compounds of cymene and their biological activity].
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Phenols↗
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[Local anesthetics derived from p-cymene and cumene].
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Anesthetics, Local↗
[Surface active antiseptics, derivatives of p-cymene].
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Anti-Infective Agents, Local↗
[Local anesthetics derived from p-cymene and mesitylene].
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Anesthetics, Local↗
Microbial models of mammalian metabolism. Fungal metabolism of phenolic and nonphenolic p-cymene-related drugs and prodrugs. I. Metabolites of thymoxamine.
This study was undertaken to validate the use of microbial biotransformation systems for drug metabolism studies. Thymoxamine 1 was rapidly hydrolyzed to desacetylthymoxamine (DAT) 2 by numerous fungi. Other known animal metabolites, such as N-desmethyl-desacetylthymoxamine 3 and desacetylthymoxamine-O-sulfate 6, were produced from DAT by Mucor rouxii and Mortierella isabellina. DAT-N-oxide 5, a putative animal microsomal metabolite, was also produced by M. isabellina, in addition, a few strains (such as Actinomucor elegans, Mucor hiemalis, and Mucor janssenii) produced a glycosylated metabolite that was identified by high-resolution 1H- and 13C-NMR, MS, and enzymatic hydrolysis as the corresponding [4-(2-dimethylaminoethoxy)-5-isopropyl-2-methyl-phenyl]-1-beta-D- glucopyranoside 7. A similar glucosylation reaction was observed when thymohydroquinone 10 was incubated with A. elegans. Several strains were able to produce transiently thymohydroquinone from DAT-N-oxide 5, possibly through a beta-elimination mechanism.
Adrenergic alpha-Antagonists↗
Ruthenium(II) and ruthenium(IV) complexes containing kappa1-P-, kappa2-P,O-, and kappa3-P,N,O-iminophosphorane-phosphine ligands Ph2PCH2P[=NP(=O)(OR)2]Ph2 (R = Et, Ph): synthesis, reactivity, theoretical studies, and catalytic activity in transfer hydrogenation of cyclohexanone.
[(Ru(eta(6)-p-cymene)(mu-Cl)Cl)(2)] and [(Ru(eta(3):eta(3)-C(10)H(16))(mu-Cl)Cl)(2)] react with Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2) (R = Et (1a), Ph (1b)) affording complexes [Ru(eta(6)-p-cymene)Cl(2)(kappa(1)-P-Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2))] (R = Et (2a), Ph (2b)) and [Ru(eta(3):eta(3)-C(10)H(16))Cl(2)(kappa(1)-P-Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2))] (R = Et (6a), Ph (6b)). While treatment of 2a with 1 equiv of AgSbF(6) yields a mixture of [Ru(eta(6)-p-cymene)Cl(kappa(2)-P,O-Ph(2)PCH(2)P[=NP(=O)(OEt)(2)]Ph(2))][SbF(6)] (3a) and [Ru(eta(6)-p-cymene)Cl(kappa(2)-P,N-Ph(2)PCH(2)P[=NP(=O)(OEt)(2)]Ph(2))][SbF(6)] (4a), [Ru(eta(6)-p-cymene)Cl(kappa(2)-P,O-Ph(2)PCH(2)P[=NP(=O)(OPh)(2)]Ph(2))][SbF(6)] (3b) and [Ru(eta(3):eta(3)-C(10)H(16))Cl(kappa(2)-P,O-Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2))][SbF(6)] (R = Et (7a), Ph (7b)) are selectively formed from 2b and 6a,b. Complexes [Ru(eta(6)-p-cymene)(kappa(3)-P,N,O-Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2))][SbF(6)](2) (R = Et (5a), Ph (5b)) and [Ru(eta(3):eta(3)-C(10)H(16))(kappa(3)-P,N,O-Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2))][SbF(6)](2) (R = Et (8a), Ph (8b)) have been prepared using 2 equiv of AgSbF(6). The reactivity of 3-5a,b has been explored allowing the synthesis of [Ru(eta(6)-p-cymene)X(2)(kappa(1)-P-Ph(2)PCH(2)P[=NP(=O)(OR)(2)]Ph(2))] (R = Et, Ph; X = Br, I, N(3), NCO (9-12a,b)). The catalytic activity of 2-8a,b in transfer hydrogenation of cyclohexanone, as well as theoretical calculations on the models [Ru(eta(6)-C(6)H(6))Cl(kappa(2)-P,N-H(2)PCH(2)P[=NP(=O)(OH)(2)]H(2))]+ and [Ru(eta(6)-C(6)H(6))Cl(kappa(2)-P,O-H(2)PCH(2)P[=NP(=O)(OH)(2)]H(2))]+, has been also studied.
Journal Article↗
Synthetic, spectroscopic, computational and structural studies of some 13-vertex ruthenacarboranes.
Reduction of 1,2-closo-C2B10H12 followed by treatment with [RuCl2(p-cymene)]2(p-cymene = C6H4MeiPr-1,4) affords the 13-vertex ruthenacarborane 4-(p-cymene)-4,1,6-closo-RuC2B10H12, characterised both spectroscopically and, in two crystalline forms, crystallographically. Although asymmetric in the solid state, having a docosahedral cage architecture with cage C atoms at vertices 1 and 6, this species clearly has Cs symmetry on the NMR timescale at room temperature. However, the fluctional process in operation can be arrested at low temperature, and an activation energy of 43.1 kJ mol(-1) is estimated. A computational study of the related species 4-(eta-C6H6)-4,1,6-closo-RuC2B10H12 reveals that the fluctionality is due to a double diamond-square-diamond process, first suggested by Hawthorne et al for the analogous CpCo species. These calculations yield an activation energy of 40.4 kJ mol(-1), in excellent agreement with that derived from experiment. Reduction of 1,2-Ph(2)-1,2-closo-C2B10H10 followed by treatment with [RuCl2(eta-C6H6)]2 or [RuCl2(p-cymene)]2 yields the analogous species 1,6-Ph2-4-(eta-C6H6)-4,1,6-closo-RuC2B10H10 and 1,6-Ph2-4-(p-cymene)-4,1,6-closo-RuC2B10H10, respectively. These C,C-diphenyl compounds were again studied spectroscopically and crystallographically, the p-cymene species again showing two crystalline modifications. In contrast to their CpCo and Cp*Co analogues all three ruthenacarboranes do not undergo isomerisation in refluxing toluene.
Journal Article↗
Bioluminescent bioreporter integrated-circuit sensing of microbial volatile organic compounds.
A bioluminescent bioreporter for the detection of the microbial volatile organic compound p-cymene was constructed as a model sensor for the detection of metabolic by-products indicative of microbial growth. The bioreporter, designated Pseudomonas putida UT93, contains a Vibrio fischeri luxCDABE gene fused to a p-cymene/p-cumate-inducible promoter derived from the P. putida F1 cym operon. Exposure of strain UT93 to 0.02-850 ppm p-cymene produced self-generated bioluminescence in less than 1.5 h. Signals in response to specific volatile organic compounds (VOCs) such as m- and p-xylene and styrene, also occurred, but at two-fold lower bioluminescent levels. The bioreporter was interfaced with an integrated-circuit microluminometer to create a miniaturized hybrid sensor for remote monitoring of p-cymene signatures. This bioluminescent bioreporter integrated-circuit device was capable of detecting fungal presence within approximately 3.5 h of initial exposure to a culture of p-cymene-producing Penicillium roqueforti.
Air Microbiology↗
Seasonal, populational and ontogenic variation in the volatile oil content and composition of individuals of Origanum vulgare subsp. Hirtum, assessed by GC headspace analysis and by SPME sampling of individual oil glands.
Small-scale GC headspace analyses combined with SPME sampling of individual oil glands have been used to measure the variation in volatile content and composition in and within different oregano plants as affected by age, season and developmental state. The main monoterpenes found were p-cymene, carvacrol and their precursor gamma-terpinene. The early season preponderance of p-cymene over carvacrol was reversed as the season progressed and this pattern could also be seen at any time within the plant, from the latest leaves to be produced (low in cymene) to the earliest (high in cymene). Seedlings from the same mother plant developed this pattern at different rates. Within individual leaves the pattern was not observed, even within the youngest developing leaves. However it was found that the oil composition of individual glands within a single leaf varied considerably, most notably in respect of the production of carvacrol and its isomer thymol.
Chromatography, Gas↗
Structural requirements for the antimicrobial activity of carvacrol.
Carvacrol is a component of several essential oils and has been shown to exert antimicrobial activity. The structural requirements for the activity of carvacrol were determined by comparison to structurally related (nonessential oil) compounds. Removal of the aliphatic ring substituents of carvacrol slightly decreased the antimicrobial activity. The effect of the hydroxyl group of carvacrol on activity could not be determined by simply comparing it to p-cymene, because this compound is immiscible with water; therefore, 2-amino-p-cymene, the amino analogue of carvacrol, which has a similar hydrophobicity and structural characteristics, was used. 2-Amino-p-cymene had similar membrane disruption and bacterial killing characteristics as carvacrol showing that, contrary to previous reports, the hydroxyl group of carvacrol itself is not essential for the antimicrobial activity. However, the observed 3-fold lower activity for 2-amino-p-cymene as compared to carvacrol indicates special features in the antimicrobial mode of action of carvacrol due to the hydroxyl group.
Anti-Infective Agents↗
The phenolic hydroxyl group of carvacrol is essential for action against the food-borne pathogen Bacillus cereus.
The natural antimicrobial compound carvacrol shows a high preference for hydrophobic phases. The partition coefficients of carvacrol in both octanol-water and liposome-buffer phases were determined (3.64 and 3.26, respectively). Addition of carvacrol to a liposomal suspension resulted in an expansion of the liposomal membrane. Maximum expansion was observed after the addition of 0.50 micromol of carvacrol/mg of L-alpha-phosphatidylethanolamine. Cymene, a biological precursor of carvacrol which lacks a hydroxyl group, was found to have a higher preference for liposomal membranes, thereby causing more expansion. The effect of cymene on the membrane potential was less pronounced than the effect of carvacrol. The pH gradient and ATP pools were not affected by cymene. Measurement of the antimicrobial activities of compounds similar to carvacrol (e.g., thymol, cymene, menthol, and carvacrol methyl ester) showed that the hydroxyl group of this compound and the presence of a system of delocalized electrons are important for the antimicrobial activity of carvacrol. Based on this study, we hypothesize that carvacrol destabilizes the cytoplasmic membrane and, in addition, acts as a proton exchanger, thereby reducing the pH gradient across the cytoplasmic membrane. The resulting collapse of the proton motive force and depletion of the ATP pool eventually lead to cell death.
Adenosine Triphosphate↗
Antimicrobial activity of carvacrol toward Bacillus cereus on rice.
The antimicrobial activity of carvacrol, a compound present in the essential oil fraction of oreganum and thyme, toward the foodborne pathogen Bacillus cereus on rice was studied. Carvacrol showed a dose-related inhibition of growth of the pathogen. Concentrations of 0.15 mg/g and higher inhibited the growth and the extent of inhibition depended on the initial inoculum size. To decrease the input of carvacrol on the taste and flavor of the product, a combined treatment with the structure analog cymene was tested. Due to the smell and taste of carvacrol at high concentrations, carvacrol was combined with cymene, a natural antimicrobial compound with a similar structure. A synergistic effect was observed when 0.30 mg/g carvacrol was combined with 0.27 mg/g cymene. Finally it was demonstrated that a common taste enhancer like soya sauce also increased the antimicrobial action of carvacrol toward B. cereus. The antimicrobial activity of carvacrol with cymene or soya sauce was influenced by the addition of NaCl.
Anti-Bacterial Agents↗
Self-assembled organometallic [12]metallacrown-3 complexes.
The reaction of [(arene)RuCl2]2 (arene = C6H6, cymene, C6H3Et3, or C6Me6) or [Cp*RhCl2]2 with 3-hydroxy-2-pyridone in the presence of Cs2CO3 gives trinuclear metallamacrocyclic complexes. The self-assembly process was shown to be completely diastereoselective, and a racemic mixture of complexes with M(R)M(R)M(R) or MsMsMs (M=Ru, Rh) configuration was obtained. Plausible mononuclear intermediates of the formula [(arene)RuCl(C5H4NO2)] (arene = cymene, C6Me6) have been isolated and characterized. A structurally related trimer was synthesized by using [(cymene)RuCl2]2 and 3-acetamido-2-pyridone instead of 3-hydroxy-2-pyridone. The macrocycles were shown to be highly potent ionophores for Na+ and/or Li+ with negligible affinities for the larger cation K+. The selectivities of the receptors depend on the pi-ligand present: whereas the (C6H6)Ru- and (cymene)Ru complexes bind both Li+ and Na+, the (C6Me6)Ru-, (C6H3Et3)Ru-, and Cp*Rh complexes bind exclusively Li+. For all receptors, the presence of alkali metal ions can be detected electrochemically: the peak potential is shifted by > 300 mV toward anionic potential upon binding. This behavior was utilized to detect Li+ and Na+ colorimetrically. Single crystal X-ray analyses have been carried out on eight complexes, four of which are bound to an alkali metal halide ion pair. Structural parameters, which affect the affinity and selectivity are discussed. A computational study on [[MX][12]crown-3] complexes (M =Li, Na; X=Cl, Br, I) was performed in order to compare relevant bond lengths and angles of the energy-minimized structures with those of the organometallic receptors.
Journal Article↗
Eta6-mesityl,eta1-imidazolinylidene-carbene-ruthenium(II) complexes: catalytic activity of their allenylidene derivatives in alkene metathesis and cycloisomerisation reactions.
The reaction of electron-rich carbene-precursor olefins containing two imidazolinylidene moieties [(2,4,6-Me(3)C(6)H(2)CH(2))NCH(2)CH(2)N(R)Cdbond;](2) (2a: R=CH(2)CH(2)OMe, 2 b R=CH(2)Mes), bearing at least one 2,4,6-trimethylbenzyl (R=CH(2)Mes) group on the nitrogen atom, with [RuCl(2)(arene)](2) (arene=p-cymene, hexamethylbenzene) selectively leads to two types of complexes. The cleavage of the chloride bridges occurs first to yield the expected (carbene) (arene)ruthenium(II) complex 3. Then a further arene displacement reaction takes place to give the chelated eta(6)-mesityl,eta(1)-carbene-ruthenium complexes 4 and 5. An analogous eta(6)-arene,eta(1)-carbene complex with a benzimidazole frame 6 was isolated from an in situ reaction between [RuCl(2)(p-cymene)](2), the corresponding benzimidazolium salt and cesium carbonate. On heating, the RuCl(2)(imidazolinylidene) (p-cymene) complex 8, with p-methoxybenzyl pendent groups attached to the N atoms, leads to intramolecular p-cymene displacement and to the chelated eta(6)-arene,eta(1)-carbene complex 9. On reaction with AgOTf and the propargylic alcohol HCtbond;CCPh(2)OH, compounds 4-6 were transformed into the corresponding ruthenium allenylidene intermediates (4-->10, 5-->11, 6-->12). The in situ generated intermediates 10-12 were found to be active and selective catalysts for ring-closing metathesis (RCM) or cycloisomerisation reactions depending on the nature of the 1,6-dienes. Two complexes [RuCl(2)[eta(1)-CN(CH(2)C(6)H(2)Me(3)-2,4,6)CH(2)CH(2)N- (CH(2)CH(2)OMe)](C(6)Me(6))] 3 with a monodentate carbene ligand and [RuCl(2)[eta(1)-CN[CH(2)(eta(6)-C(6)H(2)Me(3)-2,4,6)]CH(2)CH(2)N-(CH(2)C(6)H(2)Me(3)-2,4,6)]] 5 with a chelating carbene-arene ligand were characterised by X-ray crystallography.
Journal Article↗
Hybrid cluster-cages formed via cyanometalate condensation: Cs subset Co(4)Ru(6)S(2)(CN)(12), Co(4)Ru(9)S(6)(CN)(9), and Rh(4)Ru(9)S(6)(CN)(9) frameworks.
Condensation of cyanometalates and cluster building blocks leads to the formation of hybrid molecular cyanometalate cages. Specifically, the reaction of [Cs subset [CpCo(CN)(3)](4)[CpRu](3)] and [(cymene)(2)Ru(3)S(2)(NCMe)(3)]PF(6) produced [Cs subset [CpCo(CN)(3)](4)[(cymene)(2)Ru(3)S(2)][CpRu](3)](PF(6))(2), Cs subset Co(4)Ru(6)S(2)(2+). Single-crystal X-ray diffraction, NMR spectroscopy, and ESI-MS measurements show that Cs subset Co(4)Ru(6)S(2)(2+ ) consists of a Ru(4)Co(4)(CN)(12) box fused with a Ru(3)S(2) cluster via a common Ru atom. The reaction of PPN[CpCo(CN)(3)] and 0.75 equiv of [(cymene)(2)(MeCN)(3)Ru(3)S(2)](PF(6))(2) in MeCN solution produced [[CpCo(CN)(3)](4)[(cymene)(2)Ru(3)S(2)](3)](PF(6))(2), Co(4)Ru(9)S(6)(2+). Crystallographic analysis, together with NMR and ESI-MS measurements, shows that Co(4)Ru(9)S(6)(2+ ) consists of a Ru(3)Co(4)(CN)(9) "defect box" core, wherein each Ru is fused to a Ru(3)S(2) clusters. The analogous condensation using [CpRh(CN)(3)](-) in place of [CpCo(CN)(3)](-) produced the related cluster-cage Rh(4)Ru(9)S(6)(2+). Electrochemical analyses of both Co(4)Ru(9)S(6)(2+) and Rh(4)Ru(9)S(6)(2+) can be rationalized in the context of reduction at the cluster and the Co(III) subunits, the latter being affected by the presence of alkali metal cations.
Journal Article↗
Synthesis of Heterobimetallic Fe-M (M = Ni, Pd, Pt) Complexes Containing the 1,1'-Ferrocenedithiolato Ligand and Their Conversion to Trinuclear Complexes.
The reaction of [NiCl(2)(PMe(2)Ph)(2)] with fc(SH)(2) (fcS(2) = 1,1'-ferrocenedithiolato) afforded the Ni-Fe heterobimetallic complex containing an Fe-->Ni dative bond [Ni(S(2)fc)(PMe(2)Ph)] (1) with concurrent liberation of one of the PMe(2)Ph ligands. In contrast, similar treatment of [MCl(2)(dppe)] (M = Ni, Pd, Pt; dppe = Ph(2)PCH(2)CH(2)PPh(2)) gave a series of group 10 metal-ferrocenedithiolato complexes [M(S(2)fc)(dppe)] (2) which do not contain such a dative bond. Furthermore, oxidation of complexes 2 with 1 equiv of [(eta(5)-C(5)H(5))(2)Fe][PF(6)] resulted in the formation of 1,1'-ferrocenedithiolato-bridged complexes [{M(dppe)}(2)(&mgr;-S(2)fc)][PF(6)](2) (3) along with poly(1,1'-ferrocenylene disulfide). Complexes 2 were also converted into the Fe-Ru-M heterotrimetallic complexes [(p-cymene)RuCl(&mgr;-S(2)fc)M(dppe)][PF(6)] (4; p-cymene = 4-isopropyltoluene) by the reaction of 2 with [(p-cymene)RuCl(2)](2) and NH(4)PF(6) in acetonitrile. The detailed structures of 1, [Ni(S(2)fc)(dppe)] (2a), [Pd(S(2)fc)(dppe)] (2b), [{Ni(dppe)}(2)(&mgr;-S(2)fc)][PF(6)](2) (3a), and [(p-cymene)RuCl(&mgr;-S(2)fc)Ni(dppe)][PF(6)] (4a) have been determined by X-ray crystallography.
Journal Article↗
Formation mechanism of p-methylacetophenone from citral via a tert-alkoxy radical intermediate.
The aim of this study was to clarify the formation mechanism of a potent off-odorant, p-methylacetophenone, from citral under acidic aqueous conditions. An acidic aqueous solution (pH 3.0) containing 10 mg/L of citral was stored at 40 degrees C for 2 weeks. Among the compounds detected in the stored citral solution, 4-(2-hydroxy-2-propyl)benzaldehyde was identified for the first time as a degradation product from citral. The formation of p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde behaved the same when antioxidants were added to the citral solution. In addition, both compounds were formed by the Fe(2+)-induced decomposition of 8-hydroperoxy-p-cymene, another compound identified in the stored citral solution. These results suggested that both p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde can be formed via the same radical intermediate [p-CH3C6H4C(CH3)2O*] that can be derived from the O-O bond homolysis of 8-hydroperoxy-p-cymene. On the other hand, the degradation of 8-hydroperoxy-p-cymene without Fe2+ under acidic aqueous conditions did not yield p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde, but the degradation of citral without Fe2+ did. Therefore, other than the decomposition of 8-hydroperoxy-p-cymene, a mechanism to generate the tert-alkoxy radical intermediate was proposed for the formation of p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde in the citral solution.
Acetophenones↗
Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor.
Pseudomonas putida GS1 is able to convert limonene to perillic acid (up to 64 mM,(11 g/l) when the bacteria is cultivated in fed-batch culture with non-limiting amounts of glycerol. ammonium, and limonene. P. putida GS1 can use p-cymene as a single source of carbon and energy, and the enzymes that are responsible for the conversion of limonene to perillic acid belong to the degradation pathway of p-cymene. The p-cymene pathway of P putida GS1 is very similar, if not identical, to the cym pathway of P. putida F1. The latter strain, and a recombinant Escherichia coli strain that carried the genes of the cym pathway of P. putida Fl, also converted limonene to perillic acid. However, the final concentrations that were obtained in batch cultures with these two strains were lower than those obtained with P. putida GS1.
Bioreactors↗