134447-07-7Relevant academic research and scientific papers
Molecular design of multifunctional food additives: Antioxidative antifungal agents
Nihei, Ken-Ichi,Nihei, Atsuko,Kubo, Isao
, p. 5011 - 5020 (2007/10/03)
A series of alkyl 3,4-dihydroxybenzoates (protocatechuates) was synthesized, and their fungicidal activity against Saccharomyces cerevisiae was assayed using a 2-fold serial broth dilution method. Nonyl and octyl 3,4-dihydroxybenzoate were noted to be the most effective against this yeast with the minimum fungicidal concentration of 12.5 μg/mL each. The activity was found to correlate with the hydrophobic alkyl chain length. The time-kill curve study showed that nonyl 3,4-dihydroxybenzoate was fungicidal against S. cerevisiae at any growth stage and this activity was not influenced by pH values. The fungicidal activity of alkyl 3,4-dihydroxybenzoates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. However, the primary fungicidal activity of nonyl 3,4-dihydroxybenzoate likely comes from its ability to act as a surfactant.
Rational design of antimicrobial agents: Antifungal activity of alk(en)yl dihydroxybenzoates and dihydroxyphenyl alkanoates
Nihei, Ken-Ichi,Nihei, Atsuko,Kubo, Isao
, p. 3993 - 3996 (2007/10/03)
A homologous series (C3-C14) of each alkyl 3,4- and 3,5-dihydroxybenzoates, and 3,4- and 3,5-dihydroxyphenyl alkanoates exhibit similar antifungal activity against Saccharomyces cerevisiae. Their nonyl derivatives exhibit the most potent antifungal activity against this yeast with the minimum fungicidal concentration (MFC) in the range between 12.5 and 50 μg/mL. In addition, various 3,4-dihydroxybenzoates, possessing different side chains, namely unsaturated, branched and alicyclic were synthesized and their activity was compared.
The Effect of Carbonyl Containing Terminal Chains on Mesomorphic Properties in 4,4'-Disubstituted Phenylbenzoates and Thiobenzoates 8. Phenylbenzoates Containing Two Carbonyl Containing Terminal Chains
Neubert, M. E.,Keast, S. S.,Ezenyilimba, M. C.,Greer, P. B.,Jones, W. C.,et al.
, p. 47 - 68 (2007/10/02)
A variety of phenylbenzoates of the type (1) with both X and Y being the carbonyl containing chains (CH2)nCOR (n = 0 - 1), (CH2)nCO2R and (CH2)nOCOR (R = alkyl chain) in various combinations were synthesized and their mesomorphic properties studied to determine if an additive effect occurs when these chains are incorporated into the same molecule.No reliable additive effect could be found.Instead, clearing temperatures often seemed to be closer to the clearing temperature of the parent single carbonyl containing chain ester with the higher clearing temperature.An attempt was also made to improve the properties of the esters 1 with X or Y being I, F, CN or NO2 by using a carbonyl containing chain as the second substituent and assuming an additive effect.However, such an effect was also not observed in these esters.Smectic C phases were found in some of the esters with X = CN which is rare for compounds containing this substituent. - Keywords: liquid crystals, phenylbenzoates, synthesis, NMR, esters, ketones
The Effect of Carbonyl Containing Terminal Chains on Mesomorphic Properties in 4,4'-Disubstituted Phenylbenzoates and Phenylthiobenzoates. 4. Phenylbenzoates Containing A (CH2)nCO2R' Group (n = 0-2) on the Phenolic End
Neubert, M. E.,Leung, K.,Jirousek, M. R.,Ezenylimba, M. C.,Sabol-Keast, S.,et al.
, p. 21 - 41 (2007/10/02)
The effect of a (CH2)nCO2R' group on the mesomorphic properties of the esters where X = alkyl or alkoxy, Y = (CH2)nCO2R'(R' = C7 and C9) and n = 0-2 has been studied by synthesizing these esters and determining their mesomorphic properties by hot-stage polarizing microscopy.The starting phenols were prepared by esterification of 4-hydroxybenzoic, phenylacetic or phenylpropionic acids.Both the benzyl and methoxycarbonyl protecting groups were tried with the latter giving higher yields when n = 0 because of better solubility of the protected acid.No mesophases were observed in the esters when n = 1, nematic and smectic A phases occurred when n = 2 and smectic A and C phases when n = 0.A few 1,4-cyclohexane diesters were also prepared using these phenols.The mesomorphic properties of these esters followed the same trend observed in the phenylbenzoates escept no C phases were observed.Comparisons of the transition temperatures for these esters with those for Y = R' showed that both small increases or decreases were observed for Y = CO2R'.However, the addition of a spacer methylene group (n = 1 and 2) always gave lower temperatures with the amount of lowering being much greater for n = 2 than n = 1.A comparison of transition temperatures for Y = CO2R', OCOR', COR' and OR' indicated that these temperatures were higher when Y = COR' as expected from dipole moment considerations but were lower when Y = CO2R' than when Y = OCOR', the opposite expected from these considerations.This trend was also observed in the cyclohexane diesters.Transition temperatures were always higher for the esters when Y has an oxygen atom adjacent to the benzene ring.Therefore, esters with Y = O(CH2)nCO2R', n = 1 and 2 were also synthesized.The phenols were prepared by alkylation of 4-benzyloxyphenol with the bromo esters followed by hydrogenolysis.However, these esters showed no mesophases except the cyclohexane diester with n = 2.
