- Oxidative Rearrangement of 3,5-Di-tert-butyl-4-hydroxybenzaldehyde Acetals
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3,5-Di-tert-butyl-4-hydroxybenzaldehyde acetals rearrange to various esters when oxidized with potassium ferricyanide in alkaline medium.
- Pugovics, Osvalds,Kauss, Valerjans,Kalvinsh, Ivars,Gold, Markus R.
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- Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains
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Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.
- Lima, Tamires C.,Ferreira, Alana R.,Silva, Daniele F.,Lima, Edeltrudes O.,de Sousa, Dami?o P.
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p. 572 - 575
(2017/09/30)
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- A 3, 5 - di-tert-butyl - 4 - hydroxy-benzoic acid methyl ester (by machine translation)
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The present invention provides anti-oxidant 3, 5 - di-tert-butyl - 4 - hydroxy-benzoic acid methyl ester, which belongs to the field of organic chemical synthesis. In this method the methanol is used as the esterification reaction of the raw material is used as a reaction solvent, in order to sodium methoxide or paratoluene sulfonic acid as catalyst, 3, 5 di-tert-butyl - 4 - hydroxy benzoic acid with methanol in order to 1.0: 2.0 - 1.0: 15.0 molar ratio, in the 60 - 80 °C reflow reaction for 8 - 14h after evaporate the solvent, solid first with sodium carbonate or sodium bicarbonate saturated solution washing, distilled water washing to neutral, filtering, drying, to get the pure product 3, 5 - di-tert-butyl - 4 - hydroxy-benzoic acid methyl ester compound. The process of the invention is simple, mild reaction conditions, which avoids the use of toxic solvents, the cost is reduced, while at the same time favorable to the environment; to obtain high yield, high purity, and has a good industrial application prospect. (by machine translation)
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Paragraph 0014; 0015; 0016; 0017; 0018; 0019; 0020-0027
(2017/06/23)
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- The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors
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A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC50s; 0.0063 and 0.012 μM) and the low-micromolar ranges (IC50s; 2.1 and 1.0 μM), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 μM) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations ≥0.030 μM.
- Minkkilae, Anna,Myllymaeki, Mikko J.,Saario, Susanna M.,Castillo-Melendez, Joel A.,Koskinen, Ari M.P.,Fowler, Christopher J.,Leppaenen, Jukka,Nevalainen, Tapio
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experimental part
p. 2994 - 3008
(2009/10/10)
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- The occurrence of 3-oxo-6-keto-cyclohexa-1,4-diene (p-quinoketene) during an esterification process
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We succeeded in demonstrating the occurrence of a 3-oxo-6-keto-cyclohexa-1,4-diene (also called p-quinoketene) 5 during an esterification process of a p-hydroxy acyl chloride with a hindered phenol, in the presence of triethylamine.
- Badea, Florin,Costea, Ion,Velter, Ingrid,Simion, Alina,Simion, Cristian
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- Triazole derivative and pharmaceutical use thereof
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An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) STR1 or the following formula (III) STR2 wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all, have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.
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- Synthesis of bis(semiquinone)s and their electrochemical and electron paramagnetic resonance spectral characterization
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The syntheses of three new bis(semiquinone)s (2(··2-), 3(··2-), and 5(··2-)) linked through carbon-carbon double bonds in a geminal fashion (2(··2-) and 3(··2-)), and through an sp3 carbon (5(··2-)), are presented, as well as the results of variable-temperature EPR (VT-EPR) spectroscopy on these biradicals and two previously reported bis(semiquinone)s, 1(··2-) and 4(··2-). We suggest that the potential difference in redox couples associated with a biradical is useful for qualitatively assessing changes in the exchange parameter within an isostructural series. The zero-field-splitting parameters for 1(··2-) 5(··2-) are consistent with their electronic structures: biradicals 1(··2-)-3(··2-) which have conjugating groups attached to the semiquinone rings have D-values less than 5(··2-), a bis(semiquinone) that lacks such a conjugating group. Also, the D-value of 3(··2-) is significantly less than those of 1(··2-) and 2(··2-), in agreement with larger interelectron separation in 3(··2-), a biradical with quinone-methide π-system delocalization. Changes in counterion Lewis acidity are not manifested in the D-values of the biradical dianion 4(··2-). The EPR spectrum of biradical 5(··2-) is consistent with the existence of at least two rotamers having different zero-field-splitting parameters. Biradicals 1(··2-)-4(··2-) gave linear Curie plots, consistent with J > 0 (ferromagnetic coupling) or J = 0. The temperature-dependent intensity of EPR signals of 5(··2-) are characteristic of antiferromagnetic coupling. Best fit results give J = -114 ± 6 cal/mol for the |D/hc| = 0.01309 cm-1 rotamer of 5(··2-), and J = -76 ± 3 cal/mol for the |D/hc| = 0.01026 cm-1 rotamer of 5(··2-).
- Shultz, David A.,Boal, Andrew K.,Farmer, Gary T.
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p. 9462 - 9469
(2007/10/03)
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- NUCLEOPHILIC SUBSTITUTION AT SILICON: SYNTHESIS OF STERICALLY-HINDERED BIS(2,6-DI-t-BUTYLARYLOXY)SILANES
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The reaction of the monomethylsilane (8a) with two equivalents of the 4-carboalkoxy)-2,6-di-t-butyl-substituted phenol (7b) in toluene using triethylamine as an acid acceptor gave the bis(aryloxy) adduct (9a).The analogous reaction of the dimethylsilane (8b) with sodium 2,6-di-t-butyl-4-(methoxycarboxyl)-phenolate (7a) gave only the monosubstitution product (10a).The raction of the corresponding phenolate (7e) with 8b gave a mixture of 7a, 10a, and bis-adduct (9b), whereas, in the presence of 15-crown-5, the bis adduct 9b was obtained.The bis-adducts 9c-e were prepared in an analogous manner.The reaction of n-hexyl 3,5-di-t-butyl-4-hydroxylbenzoate (7h) with the diphenylsilane (8c) gave only the monosubstitution product 12, while forcing conditions gave, unexpectedly, the methyl ether 13.The reaction of 4-(carboalkoxyethyl)-2,6-di-t-butylphenol (16a) with 8a gave the bis adduct.The reaction af 16a with 8b in THF, without a crown ether, gave a low yield of the monosubstitution product.The bis-adducts 17b-c were obtained by the reaction of 8b with the corresponding phenolates (16a-b) in tetraglyme.Compound 17b was also obtained by the reaction of 8b with 16a in THF with a crown ether.These results are discussed in terms of charge dispersal in the phenolate ion and the corresponding effect upon both ion-pairing and aggregation in solution.
- Pastor, Stephen D.,Hessell, Edward T.
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p. 263 - 274
(2007/10/02)
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- Electrochemical Oxidation of 2,6-Di-tert-butyl-4-methylphenol in Basic Methanol
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Electrochemical oxidation of 2,6-di-tert-butyl-4-methylphenol (1) in methanol containing sodium methoxide gave side-chain-oxidized phenols, ArCH2OMe, ArCHO, and ArCOOMe (Ar=3,5-di-tert-butyl-4-hydroxyphenyl), together with 2,6-di-tert-butylbenzoquinone and 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone.The product distribution varied with the electricity consumption.Based on the results obtained, a simple electrochemical transformation of 1 to the hydroxybenzaldehyde ArCHO was effected.Keywords --- electrochemical oxidation; cyclic voltammetry; controlled potential electrolysis; 2,6-di-tert-butyl-4-methylphenol; 3,5-di-tert-butyl-4-hydroxybenzaldehyde
- Ohmori, Hidenobu,Ueda, Chihiro,Tokuno, Yoshimi,Maeda, Hatsuo,Masui, Masaichiro
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p. 4007 - 4011
(2007/10/02)
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- REACTION OF SUPEROXO Co(III) COMPLEX WITH STABLE PHENOXY RADICALS
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A typical superoxo complex +=PPh3>3 combines with stable phenoxy radicals in CH2Cl2 leading to selective formation of peroxy-p-quinols except for 2,4,6-tri-t-butylphenoxy radical, representing radical reactivity of the complex
- Nishinaga, A.,Tomita, H.,Matsuura, T.
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p. 3407 - 3408
(2007/10/02)
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- Polyalkylene glycol esters of hindered phenols substituted alkanoic acid
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Compounds of the formula: EQU1 WHEREIN X is oxygen or sulfur, a is an integer from 2 to 6, b is an integer from 3 to 40, and R is SPC1 Wherein R1 is an alkyl group of 1 to 8 carbon atoms, R2 is hydrogen or an alkyl group of 1 to 8 carbon atoms, and X is an integer from 0 to 6 Are useful as antioxidants for organic materials normally subject to oxidative deterioration, such as polyacetals, polypropylene, and nylon, in amounts of from about 0.005 to about 5% by weight of the composition.
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- Insect control employing certain benzoates
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3,5-DIALKYL-4-HYDROXYBENZOATES, 3,5-DIALKYL-4-HYDROXYTHIONOBENZOATES, 3,5-DIALKYL-4-HYDROXOTHIOLOBENZOATES AND 3,5-DIALKYL-4-HYDROXYDITHIOBENZOATES HAVE MORPHOGENETIC HORMONAL MIMETIC ACTIVITY ON INSECTS.
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