- Effects of intact glucosinolates and products produced from glucosinolates in myrosinase-catalyzed hydrolysis on the potato cyst nematode (Globodera rostochiensis cv. Woll)
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The potato cyst nematode (Globodera rostochiensis cv. Woll) is responsible for large yield losses in the potato crop, and opportunities for reducing the attack of these plant nematode species are, therefore, important. This study has been devoted to the testing of the in vitro effects on the potato cyst nematode of eight glucosinolates [prop-2-enyl-, but-3-enyl-, (R)-4-methylsulfinylbut-3-enyl-, benzyl-, phenethyl-, 4-hydroxybenzyl-, (2S)-2-hydroxybut-3-enyl-, and (2R)-2-hydroxy-2-phenylethylglucosinolate] as well as the effects of the products of this myrosinase-catalyzed hydrolysis. The glucosinolates were used at three concentrations, 0.05, 0.3, and 1.0 mg/mL, in the presence or absence of the enzyme myrosinase. The effects of the compounds on the mortality were monitored every 8 h for a 72 h period. No effects were found for any of the intact glucosinolates. However, when active myrosinase was included with 1 mg/mL phenethylglucosinolate at pH 6.5, 100% mortality was observed within just 16 h. A similar effect was achieved at the same concentration of benzyl-and prop-2-enylglucosinolates in the myrosinase-containing solutions, although longer exposures were required (24 and 40 h, respectively). The main aglucone products released from the glucosinolates with pronounced effects on the nematodes were shown to be the corresponding isothiocyanates. The results suggest that mixtures of these specific glucosinolates and active myrosinase or autolysis of plant materials containing these enzymes and glucosinolates might be used to control the potato cyst nematode in the soil.
- Buskov,Serra,Rosa,Sorensen,Sorensen
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Read Online
- 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
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In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.
- Gavara, Laurent,Legru, Alice,Verdirosa, Federica,Sevaille, Laurent,Nauton, Lionel,Corsica, Giuseppina,Mercuri, Paola Sandra,Sannio, Filomena,Feller, Georges,Coulon, Rémi,De Luca, Filomena,Cerboni, Giulia,Tanfoni, Silvia,Chelini, Giulia,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois
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- HIGH-PURITY ISOTHIOCYANATE COMPOUND PREPARATION METHOD FOR INDUSTRIAL PRODUCTION
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The present invention provides a high-purity isothiocyanate compound preparation method for industrial production. Specifically, in the method, organic amine and CS2 are used as raw materials to prepare the thiocarbamate, and then desulfurization is carried out, and the high-purity isothiocyanate compound is obtained by using purification, post-processing and other methods. The method in the present invention is suitable for industrial production, is simple in the post-processing, has a high yield rate, and allows the product to have a high purity, and is suitable for the production of the isothiocyanate compound in the pharmaceutical industry.
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Paragraph 0104-0117
(2020/04/09)
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- Synthesis method for high purity allyl isothiocyanate and cosmetic composition comprising high purity allyl isothiocyanate
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The present invention relates to a synthesis method for a high-purity allyl isothiocyanate compound, and a functional cosmetic composition containing the allyl isothiocyanate compound according to the synthesis method as an active ingredient. More particularly, as it has been confirmed that the purity of allyl isothiocyanate synthesized through a three-step synthesis method using allylamine as a starting material is 99%, high-purity allyl isothiocyanate synthesized by the synthesis method may be provided as a functional cosmetic composition for preventing or ameliorating atopic dermatitis or acne.COPYRIGHT KIPO 2020
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Paragraph 0048-0052
(2020/08/26)
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- Preparation method of allyl isothiocyanate
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The invention discloses a method for preparing allyl isothiocyanate. The preparation method of allyl isothiocyanate is divided into two steps of allyl isothiocyanate synthesis and allyl isothiocyanaterectification. According to the present invention, the allyl isothiocyanate is synthesized under the solvent condition, the allyl isothiocyanate synthesis process has advantages of mild reaction, lowtemperature, simple operation, no wastewater and the like, the organic solvent is firstly removed during the rectification process, and then rectification is performed to obtain the qualified allyl isothiocyanate standard product.
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Paragraph 0038-0129
(2020/08/25)
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- Preparation method of isothiocyano compound
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The invention discloses a preparation method of an isothiocyano compound. An ammonium thiocyanate, sodium thiocyanate or potassium thiocyanate water solution and a halide are used as raw materials, and an isothiocyano compound is synthesized under the action of a phase transfer catalyst. The requirements that the thiocyanate radical in each batch of reaction is excessive by 10% and the yield is high are met, the purpose that the concentration of thiocyanic acid in wastewater is very low is realized, complex wastewater treatment equipment and treatment operation are avoided, and environmental protection pressure is reduced. The preparation method is a green preparation method, and solves the problems of extremely difficult degradation and high biotoxicity of thiocyanate-containing wastewater in conventional isothiocyano compound production. The method is simple to operate and is suitable for industrial production.
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Paragraph 0012
(2019/10/29)
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- Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
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We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
- Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
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supporting information
p. 4484 - 4491
(2018/10/17)
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- A pharmaceutical intermediate propenyl thiourea synthesis method (by machine translation)
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A pharmaceutical intermediate propenyl thiourea synthesis method, comprises the following steps: in the reaction container by adding 5 L sodium chloride solution, 4 μM of 3 - methyl isobutyl ketone sulfur cyanic acid benzene, raising the temperature of the solution to 60 - - 65 °C, adding 5 — 6 μM of acrylamide and 6 L acetone solution, reflux 90 - 120 min, layered, take out the oil layer, potassium bromide solution for washing 5 — 7 times, be propylene isothiocyanate, desiccant dehydration, filtering, the filtrate is distilled under reduced pressure, collecting 80 — 86 °C fraction, obtained propylene thiocyanate; the resulting thiocyanate of propylene added to the 5 — 6 μM benzene acetamide, adding 2 L aqueous solution, raising the temperature of the solution to 50 — 60 °C, reaction 50 — 70 min, reduce the temperature of the solution to 10 — 15 °C, separating out crystal, filtering, washing toluene solution, butanone solution washing, dehydrating agent dehydration, to get finished propenyl thiourea. (by machine translation)
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Paragraph 0011; 0013; 0014; 0015
(2018/07/30)
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- Synthesis of novel dithiocarbamates and xanthates using dialkyl azodicarboxylates: S–N bond formation
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A one?pot three?component route for the synthesis of a novel category of dithiocarbamates or xanthates is developed by a reaction of in-situ generated dithiocarbamic acids or xanthates with dialkyl azodicarboxylates under mild and catalyst-free conditions. The reaction is characterized by a wide scope, high efficiency and straightforward isolation protocol. The synthetic utility of the dithiocarbamates and xanthates was demonstrated on the preparation of symmetrical and unsymmetrical thioureas, isothiocyanates, and thiocarbamates.
- Ziyaei Halimehjani, Azim,Klepetá?ová, Blanka,Beier, Petr
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p. 1850 - 1858
(2018/03/06)
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- T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates
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A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.
- Janczewski, ?ukasz,Gajda, Anna,Frankowski, Sebastian,Goszczyński, Tomasz M.,Gajda, Tadeusz
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p. 1141 - 1151
(2017/12/06)
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- Synthesis of 2-sulfanylidene-1,3-thiazolidin-4-one derivatives
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Three-component condensation of primary amines with carbon disulfide and dialkyl maleates afforded the corresponding alkyl (3-R-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl)acetates whose structure was confirmed by independent synthesis and IR and 1/s
- Mustafaev,Efendieva, Kh. K.,Akchurina, T. Kh.
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p. 1860 - 1863
(2018/02/06)
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- Synthesis, characterization, and antibacterial activity of some thiazoles derived from allyl thioureas
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Synthesis of thiazoles was carried out from allyl thioureas using different cyclizing agents such as hydrogen chloride gas and bromine. Synthesized compounds were characterized by IR, 1H and 13C NMR, mass spectrometry, and elemental analysis. The synthesized thiazoles were evaluated for their antibacterial activity against Gram postitive (Lactobacillus bulgaris and Streptococcus mitis) and Gram negative (Yersinia) as well as antifungal activity against Aspergillus niger fungi.
- Khare,Sharma,Sharma
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p. 702 - 707
(2016/06/01)
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- ISOTHIOCYANATE PRODUCTION METHOD, COMPOSITION FOR TRANSPORTING AND STORING N-SUBSTITUTED O-SUBSTITUTED THIOCARBAMATE, AND ISOTHIOCYANATE COMPOSITION
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The present invention relates to an isothiocyanate production method using an organic primary amine and thiourea as starting materials; to a composition for transporting and storing an N-substituted O-substituted thiocarbamate that includes an N-substituted O-substituted thiocarbamate and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the carbamate groups of the N-substituted O-substituted thiocarbamate being in the range of 1 to 100; to a composition for transporting and storing a compound with a thioureido group that includes a compound with a thioureido group and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the thioureido groups of the compound with a thioureido group being in the range of 1 to 100; and to an isothiocyanate composition containing an isothiocyanate and a compound with a specific functional group.
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Paragraph 0279
(2016/02/12)
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- ISOTHIOCYANATE PRODUCTION METHOD, COMPOSITION FOR TRANSPORTING AND STORING N-SUBSTITUTED O-SUBSTITUTED THIOCARBAMATE, AND ISOTHIOCYANATE COMPOSITION
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The present invention relates to an isothiocyanate production method using an organic primary amine and thiourea as starting materials; to a composition for transporting and storing an N-substituted O-substituted thiocarbamate that includes an N-substituted O-substituted thiocarbamate and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the carbamate groups of the N-substituted O-substituted thiocarbamate being in the range of 1 to 100; to a composition for transporting and storing a compound with a thioureido group that includes a compound with a thioureido group and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the thioureido groups of the compound with a thioureido group being in the range of 1 to 100; and to an isothiocyanate composition containing an isothiocyanate and a compound with a specific functional group.
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Paragraph 0381-0383
(2016/10/10)
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- High-performance liquid chromatography-based method to evaluate kinetics of glucosinolate hydrolysis by Sinapis alba myrosinase
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Isothiocyanates (ITCs) are one of several hydrolysis products of glucosinolates, plant secondary metabolites that are substrates for the thioglucohydrolase myrosinase. Recent pursuits toward the development of synthetic non-natural ITCs have consequently led to an exploration of generating these compounds from non-natural glucosinolate precursors. Evaluation of the myrosinase-dependent conversion of select non-natural glucosinolates to non-natural ITCs cannot be accomplished using established ultraviolet-visible (UV-Vis) spectroscopic methods. To overcome this limitation, an alternative high-performance liquid chromatography (HPLC)-based analytical approach was developed where initial reaction velocities were generated from nonlinear reaction progress curves. Validation of this HPLC method was accomplished through parallel evaluation of three glucosinolates with UV-Vis methodology. The results of this study demonstrate that kinetic data are consistent between both analytical methods and that the tested glucosinolates respond similarly to both Michaelis-Menten and specific activity analyses. Consequently, this work resulted in the complete kinetic characterization of three glucosinolates with Sinapis alba myrosinase, with results that were consistent with previous reports.
- Vastenhout, Kayla J.,Tornberg, Ruthellen H.,Johnson, Amanda L.,Amolins, Michael W.,Mays, Jared R.
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p. 105 - 113
(2015/01/08)
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- Chemical transformations of N-morpholinylacetic acid hydrazide and steric structure of its derivatives
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The reaction of N-morpholinylacetic acid hydrazide with various isothiocyanates and potassium thiocyanate resulted in the corresponding potentially biologically active thiosemicarbazide derivatives. Potassium N′-(2-morpholin-4-ylacetyl)hydrazinocarbothioate was synthesized and involved into heterocyclization in acidic environment to yield cyclic 5-(morpholinomethyl)-1,3,4-thiadiazole-2-thione. The structure of the synthesized compounds was established by IR, 1H NMR spectroscopy, mass spectrometry, and XRD analysis.
- Nurkenov,Fazylov,Satpaeva, Zh. B.,Kulakov,Turdybekov,Turdybekov,Talipov,Ibragimov
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p. 520 - 525
(2013/08/23)
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- Substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one as CB 1 cannabinoid receptor ligands: Synthesis and pharmacological evaluation
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A set of 30 substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one (thiohydantoins) derivatives was synthesized, and their affinity for the human CB1 cannabinoid receptor has been evaluated. These compounds are derived from the previously described cannabinoid ligands 5,5′- diphenylimidazolidine-2,4-dione (hydantoins). The replacement of the oxygen by a sulfur leads to an increase of the affinity while the function-i.e., inverse agonism-determined by [35S]-GTPγS experiments remains unaffected. Finally, to evaluate the molecular parameters that could influence the affinity of the thiohydantoins, molecular electrostatic potential as well as lipophilicity calculations were undertaken on representative thiohydantoins and hydantoins derivatives. In conclusion, 5,5′-bis-(4-iodophenyl)-3-butyl-2- thioxoimidazolidin-4-one (31) and 3-allyl-5,5′-bis(4-bromophenyl)-2- thioxoimidazolidin-4-one (32) possess the highest affinity for the CB 1 cannabinoid receptor described to date for the hydantoin and thiohydantoins series when compared in a same bioassay.
- Muccioli, Giulio G.,Martin, Diana,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Wouters, Johan,Lambert, Didier M.
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p. 2509 - 2517
(2007/10/03)
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- Study of the products of iodocyclization of 4-allyl-5-phenyl-1,2,4- triazole-3-thione
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The interaction of 4-allyl-5-phenyl-1,2,4-triazole-3-thione with iodine proceeds with the formation of a mixture of 6-iodomethyl-3-phenyl-5,6- dihydrothiazolo[2,3-c]-1,2,4-triazole and 6-iodo-3-phenyl-6,7-dihydro-5H-1,2,4- triazolo[3,4-b]-1,3-thiazine. The structures of the cyclization products obtained were established on the basis of the 1H NMR spectra of their dehydroiodinated derivatives. 6-Methyl-3-phenylthiazolo[2,3-c]-1,2,4-triazole, 3-phenyl-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine, and 3-phenyl-7H-1,2,4- triazolo[3,4-b]-1,3-thiazine are formed on eliminating HI from the cyclization products.
- Shmygarev,Kim
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p. 1077 - 1082
(2007/10/03)
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- Biopesticides related to natural sources
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The present invention provides novel biopesticides which can replace commercial pesticides and biopesticides which have been banned, restricted, or are being phased out, including, but not limited to chloropicrin, dichlorvos and methyl bromide. Many of the biopesticides of the present invention are excellent fumigants, possessing quick action and volatility, while posing less risk than currently used pesticides to humans and the environment. The biopesticides of the present invention are natural and closely-related synthetic derivatives or analogs related to two classes of natural compounds, namely glucosinolates and monoterpenoids.
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- Inter- and intramolecular isotopic correlations in some cyanogenic glycosides and glucosinolates and their practical importance
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Sinalbin is a complex organic salt from white mustard. The δ 13C- values of the aromatic parts of the anion glucosinalbin (p- hydroxyphenylacetic acid) and of the cation sinapin (sinapic acid) are identical (-32.2‰) and both aromatic compounds are depleted by 6.4‰ with respect to the glucose moiety (-25.8‰) bound in glucosinalbin. The δ 13C value of the choline part of the molecule can be correlated to its metabolic origin from glucose. However, there is an unexpected dramatic 13C- enrichment in the first C atom of glucosinalbin, originally the C-2 of tyrosine. This enrichment of approximately 11% relative to the mean value of the aglycone is found in the same position of four other glucosinolates and cyanogenic glycosides derived from phenylalanine or tyrosine. An isotope effect on the phenylalanine-ammonia-lyase reaction is discussed as the most probable cause for this finding. In contrast, sinigrin, the glucosinolate from black mustard, shows a relative 13C-depletion of 6.5‰ in the corresponding first C-atom of the aglycone allyl mustard oil. The proposed reason for this depletion is an isotope effect on an aldol reaction during the biosynthetic introduction of this C-atom into the aglycone skeleton. Synthetic allyl mustard oil is depleted by 14% in the same position relative to the δ 13C-value of the whole molecule, probably owing to an isotope effect on the first step of its chemical synthesis, the binding of allyl amine to CS2. This difference can be used to detect adulterations of mustard.
- Butzenlechner, Maria,Thimet, Susanne,Kempe, Klaus,Kexel, Hugo,Schmidt, Hanns-Ludwig
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p. 585 - 592
(2007/10/03)
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- Novel selenium catalyzed synthesis of isothiocyanates from isocyanides and elemental sulfur
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A variety of aliphatic and aromatic isothiocyanates were synthesized in good to excellent yields from corresponding isocyanides and elemental sulfur under mild conditions by use of catalytic amounts of elemental selenium.
- Fujiwara, Shin-Ichi,Shin-Ike, Tsutomu,Sonoda, Noboru,Aoki, Minoru,Okada, Kazuhiro,Miyoshi, Noritaka,Kambe, Nobuaki
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p. 3503 - 3506
(2007/10/02)
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- Preparation of Defatted Mustard by Extraction with Supercritical Carbon Dioxide
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The preparation of defatted mustard by extraction with supercritical carbon dioxide (SC-CO2) is described.Oil was not extracted from native mustard seeds but was extracted from compressed mustard seeds with SC-CO2 at 300 atm and 40 deg C.When the extraction time and temperature were kept constant at 3 hr and 40 deg C, 8090 percent of the oil in the compressed mustard seeds could be extracted with SC-CO2 at more than 300 atm.The solubility of the mustard seed oil in SC-CO2 at 300atm and 40 deg C was estimated to be about 0.48 percent.The synigrin content and myrosinase activity in the defatted mustard seeds with SC-CO2 at 300 atm and 40 deg C for 3 hr were comparable to those in native seeds.Thus, the extraction with SC-CO2 made it possible to prepare defatted mustard of high quality without decreasing the synigrin content and myrosinase activity.
- Taniguchi, Masayuki,Nomura, Ryuji,Kijima, Isao,Kobayashi, Takeshi
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p. 413 - 418
(2007/10/02)
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- Effects of pH and Ferrous Ion on the Degradation of Glucosinolates by Mirosinase
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During the enzymatic degradation of sinigrin, the relase of glucose and the formation of allyl isothiocyanate via subsequent cleavage of the aglucon were studied in the presence or absence of ferrous ion over a pH range of 3.5-7.5.The liberation of glucose increased linearly with the time of enzymatic cleveage of sinigrin for the first 20 min at the pHs used, and no inhibition of glucose liberation was caused by ferrous ion at the concentration tried.On the other hand, the effects of ferrous ion on the formation of the isothiocyanate changed greatly with changes of pH of the reaction medium.At pH 4.5 and 5.5, formation of isothiocyanate was strongly inhibited by ferrous ion, while such an effect of ferrous ion was notably depressed at pH 6.5 and disappeared at pH 7.5.These results were also confirmed by gas chromatographic analysis of the volatile cleveage products of the glucosinolates prepared from the seed meal of hakuran (an artificial variety of Brassica napus).From these results, it was suggested that ferrous ion is not involved in the enzymatic liberation of glucose from glucosinolate but in the subsequent degradation of the aglucon.
- Uda, Yasushi,Kurata, Tadao,Arakawa, Nobuhiko
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p. 2735 - 2740
(2007/10/02)
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- DI-2-PYRIDYL THIONOCARBONATE. A NEW REAGENT FOR THE PREPARATION OF ISOTHIOCYANATES AND CARBODIIMIDES.
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Reaction of amines with di-2-pyridyl thionocarbonate affords the corresponding isothiocyanates at room temperature, while reaction of N,N'-disubstituted thioureas with di-2-pyridyl thionocarbonate in the presence of 4-dimethylaminopyridine as a catalyst affords the corresponding carbodiimides in high yields.
- Kim, Sunggak,Yi, Kyu Yang
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p. 1661 - 1664
(2007/10/02)
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- INTERACTIONS OF A FUNGAL THIOGLUCOSIDE GLUCOHYDROLASE AND CRUCIFEROUS PLANT EPITHIOSPECIFIER PROTEIN TO FORM 1-CYANOEPITHIOALKANES: IMPLICATIONS OF AN ALLOSTERIC MECHANISM
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Allylglucosinolate is converted to 1-cyano-2,3-epithiopropane by interaction of the thioglucoside glucohydrolase from the fungus Aspergillus sydowi QM 31c and the epithiospecifier protein from Crambe abyssinica.The kinetic evidence presented supports the hypothesis that the epithiospecifier protein interacts with thioglucoside glucohydrolase in allosteric manner.Key Word Index - Crambe abyssinica; Cruciferae; Aspergillus sydowi; thioglucoside glucohydrolase; thioglucosidase; epithiospecifier protein; crucifer; glucosinolate; 1-cyanoepithioalkanes; 1-cyano-2,3-epithiopropane.
- Petroski, Richard J.,Kwolek, William F.
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p. 213 - 216
(2007/10/02)
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- COMPARISON OF UNSTIRRED, SONICATED AND STIRRED MIXTURES ON THE TWO-PHASE DISPLACEMENT OF HALIDE BY THIOCYANATE ION
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The two-phase catalytic reaction of alkyl halides with aqueous thiocyanate ion has been found to proceed readily in stirred, unstirred, and sonicated solutions.
- Reeves, W. Preston,McClusky, John V.
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p. 1585 - 1588
(2007/10/02)
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- THE INTRAMOLECULAR FORMATION OF EPITHIOALKANENITRILES FROM ALKENYLGLUCOSINOLATES BY CRAMBE ABYSSINICA SED FLOUR
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Enzymatic degradations of mixtures of potassium 3-butenylglucosinolate and allylglucosinolate by aqueous suspensions of Crambe abyssinica seed flour led to the formation of 4,5-epithiopentanenitrile and essentially unlabelled 3,4-epithiobutanenitrile.The formation of epithioalkanenitriles from alkenylglucosinolates is, therefore deduced to be an intramolecular process. -- Key Word Index - Crambe abyssinica; Cruciferae; allylglucosinolate; 3-butenylglucosinolate; 3,4-epithiobutanenitrile; 4,5-epithiopentanenitrile; sinigrin; episulphide; thiirane; biosynthesis.
- Brocker, Erich R.,Benn, M. H.
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p. 770 - 772
(2007/10/02)
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- THERMAL DEGRADATION OF GLUCOSINOLATES
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Three glucosinolates (allyl-, benzyl- and 2-phenethyl-) were shown to degrade thermally in a GC column to yield products identical with those obtained conventionally on enzymic decomposition, namely nitriles and isothiocyanates.Nitriles were formed more readily at 125 deg but the facility for isothiocyanate production varied slightly with the glucosinolate; 2-phenethylglucosinolate was the most labile of those studied yielding isothiocyanate at a column temperature of 150 deg.Temperature was confirmed as the cause of degradation by isolated heated-tube experiments.The results have significance both with regard to analytical methodology for glucosinolates and their products, and with regard to furthering understanding of the mechanisms of glucosinolate degradation.Key Word Index- Criciferae; glucosinolates; nitriles; isothiocyanates; thermal degradation.
- Macleod, Alexander J.,Panesar, Satwinder S.,Gil, Victor
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p. 977 - 980
(2007/10/02)
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- The chemistry of small ring compounds. Part 45. Thermolysis and photolysis of 1-(alkylthio)cyclopropyl azides
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1-(Alkylthio)cyclopropyl azides - readily accessible from the corresponding chlorides and bromides - are smoothly decomposed at 70 deg C with nitrogen evolution.The main process is a ring enlargement to 2-(alkylthio)azetines 2, accompanied by cleavage to thiocyanate and alkene.Reaction parameters for the thioazetine formation suggest a two-step mechanism involving an intermediate cyclopropylnitrene.Ring enlargement can be averted if the alkylthio group contains a double bond.Thus, the allylthiocyclopropyl azide 8 gives a nitrene that can interact not only with the three-membered ring but also with the double bond, leading to spirocyclic products (15 and 16 in Scheme 1).The photolysis (300 nm) of these azides gives exclusively the fragmentation products thiocyanate and olefin.
- Jorritsma, R.,Steinberg, H.,Boer, Th. J. de
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p. 307 - 312
(2007/10/02)
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- Nonsteroid regulators of ovarian cycles. I. 1, 2-bis-(thiocarbamoyl) hydrazines
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24 New 1,2-bis-(thiocarbamoyl)hydrazines were administered (60 mg/kg of feed) to hens in their laying period. Egg-laying was followed before, during, and after the 21-day administration. In the group of N-(allylthiocarbamoyl)hydrazines the biological activity regularly increased, a further increase being achieved by incorporating oxygen into the nitrogen heterocycle. The incorporation of sulphur caused a strong decrease in the inhibitory activity.
- Budesinsky,Roubinek,Kral,Nemcova,Janata
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p. 200 - 206
(2007/10/05)
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