1119-63-7Relevant academic research and scientific papers
Influence of terminal branching on the transdermal permeation-enhancing activity in fatty alcohols and acids
Klimentova, Jana,Kosak, Petr,Vavrova, Katerina,Holas, Tomas,Hrabalek, Alexandr
, p. 7681 - 7687 (2006)
In order to investigate the effect of terminal chain branching in the skin permeation enhancers, seven alcohols and seven acids with the chain length of 8-12 carbons and terminal methyl or ethyl branching were prepared. Their transdermal permeation-enhancing activities were evaluated in vitro using theophylline as a model permeant and porcine skin, and compared to those of the linear standards. Terminal methyl branching increased the enhancing activity only in 12C acid, no effect was seen in the shorter ones. Terminal ethyl however produced a significant increase in activity. In the alcohols, the branching was likely to change the mode of action, due to a different relationship between the activity and the chain length.
Method for preparing alkane carboxylic acid by increasing alkane carbon chains
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Paragraph 0031; 0055; 0058, (2021/06/09)
The invention discloses a method for preparing alkane carboxylic acid by increasing alkane carbon chains. The method comprises the following steps: (1) carrying out Stork enamine alkylation on cyclopentanone or cyclohexanone and a secondary amine compound to generate a corresponding 1-position secondary amine substituted cyclopentene or cyclohexene crude product, namely Stork enamine; (2) carrying out electrophilic reagent reaction on the Stork enamine and acyl halide to form a 2-acyl cyclic ketone compound; and (3) carrying out ring opening on the 2-acyl cyclic ketone compound under the action of alkali to generate a carbonyl carboxylic acid compound, and carrying out a Wolff-Huang Minglong reduction reaction on the carbonyl carboxylic acid compound to obtain the corresponding alkane carboxylic acid. According to the method disclosed by the invention, cyclopentanone or cyclohexanone can be flexibly selected to meet the requirement of increasing different carbon numbers according to the required carbon number and different sources of target carburant alkane carboxylic acid or corresponding acyl halide. The method has the advantages of simple reaction process and no complex operation difficulty, and is suitable for industrial mass production.
PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION, STABILIZING METHOD OF CAPSINOID, AND CAPSINOID COMPOSITION
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Page/Page column 50-51, (2008/06/13)
In the production methods of capsinoid by esterification using an enzyme, a method of conveniently obtaining capsinoid in a high yield in a short time without using a dehydrating agent is provided. In addition, a method of stable preservation of produced capsinoid by purifying the obtained capsinoid under stable conditions is provided. A fatty acid represented by the formula (1) and a hydroxymethylphenol represented by the formula (2) are condensed without solvent or in a low-polar solvent, using an enzyme as a catalyst to give an ester compound represented by the formula (3). In addition, a fatty acid represented by the formula (4) is added to the ester compound represented by the formula (3) for stabilization. wherein each symbol is as defined in the specification.
Transannular vs intramolecular insertion reactions of transition metal carbenes: Evaluation of a transannular approach to cyclooctane ring synthesis
Dudones, James D.,Sampson, Paul
, p. 9555 - 9567 (2007/10/03)
The efficacy of closing cyclooctane rings via transannular metal-stabilized carbene insertion reactions within an 11-membered macrocyclic lactone ring was explored. The impact of performing these reactions in a transannular fashion was evaluated via a comparative study of closely analogous intramolecular (but not transannular) processes. Closure of a γ-lactone ring via intramolecular cyclopropanation on a moderately electron-deficient alkene proceeded in good yield under Cu(acac)2 catalysis, whereas analogous transannular cyclopropanation was thwarted by competitive β-hydride migration. In contrast, use of a more electron-rich methoxy-substituted alkene resulted in successful transannular cyclopropanation to afford the desired cyclooctane ring-containing product. (C) 2000 Elsevier Science Ltd.
First total synthesis of N-4909 and its diastereomer; A stimulant of apolipoprotein E secretion in human hepatoma Hep G2 cells
Yanai, Makoto,Hiramoto, Shigeru
, p. 150 - 159 (2007/10/03)
Both (R)- and (S)-3-hydroxy-13-methyltetradecanoic acids were prepared via a lipase-catalyzed enantioselective acylation. The total synthesis of N-4909 and its diastereomer were achieved by a coupling of either (R)- or (S)-3-hydroxy-13-methyltetradecanoic acid moiety with a hexapeptide moiety and by a cyclization with HATU (O-(7-azabenzotriazol-1-yl)- 1,1,3,3-tetramethyluronium hexafluorophosphate) and HOAt (1-hydroxy-7-azabenzotriazole) in a high dilution condition. The R configuration of 3-hydroxy-13-methyltetradecanoic acid was found to be important for stimulating the activity of apolipoprotein E secretion in human hepatoma Hep G2 cells.
A Short Route to Dihydrocapsaicinoids
Kaga, Harumi,Miura, Masakatsu,Orito, Kazuhiko
, p. 864 - 866 (2007/10/02)
Huang-Minlon reduction of 8-methyl-7-oxononanoic acid (4ba), obtained by the acylation of cyclohexanone enamine 2a with 2-methylpropanoyl chloride (1b) followed by ring cleavage of the resultant β-diketone 3ba affords 8-methylnonanoic acid (5ba), the chloride of which reacts readily with 4-hydroxy-3-methoxybenzylamine to give dihydrocapsaicin (7ba).This reaction sequence works also efficiently for other dihydrocapsaicinoids such as 7aa and 7bb.
