14737-91-8Relevant articles and documents
Investigation on the aggregation behavior of photo-responsive system composed of 1-hexadecyl-3-methylimidazolium bromide and 2-methoxycinnamic acid
Du, Mingyong,Dai, Caili,Chen, Ang,Wu, Xuepeng,Li, Yuyang,Liu, Yifei,Li, Weitao,Zhao, Mingwei
, p. 68369 - 68377 (2015)
A novel fluid system composed of 2-methoxycinnamic acid (trans-OMCA) and 1-hexadecyl-3-methylimidazolium bromide (C16mimBr) in an aqueous solution was investigated. The compounds trans-OMCA and C16mimBr in an aqueous solution can self-assemble and form viscoelastic worm-like micelles. The concentrations of trans-OMCA and C16mimBr have a significant influence on the rheological properties of the system. The samples were characterized by rheological measurements. The structural isomerization of trans-to-cis for trans-OMCA occurred after UV light irradiation. The transformation of the system after UV light irradiation was determined by UV-vis absorption spectroscopy, rheological measurement and cryo-TEM observation. Surface tension measurements were carried out to investigate the role of trans-OMCA and UV light in C16mimBr aqueous solution. Critical aggregation concentration (cac), effectiveness of surface tension reduction (Πcac), maximum excess surface concentration (Γmax) and minimum area occupied per surfactant molecule (as) were investigated. Critical packing parameter was introduced to express the mechanism of aggregation behavior transition.
Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
Nishikawa, Keisuke,Fukuda, Hiroshi,Abe, Masato,Nakanishi, Kazunari,Taniguchi, Tomoya,Nomura, Takashi,Yamaguchi, Chihiro,Hiradate, Syuntaro,Fujii, Yoshiharu,Okuda, Katsuhiro,Shindo, Mitsuru
, p. 132 - 147 (2014/01/06)
1-O-cis-Cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA.
Photocyclization of Ortho-Substituted Cinnamic Acids
Terrian, Deborah L.,Mohammad, Taj,Morrison, Harry
, p. 1981 - 1984 (2007/10/02)
Mono and di (i.e. 2,6) o-chloro- and o-methoxycinnamic acids undergo photocyclization to give the corresponding coumarins.The reaction occurs in aqueous and organic media, with a prototypical reaction giving evidence of being favored at pH > 6.Cyclization of the dimethoxy acid is relatively inefficient (Φ for the PSS = 0.0015), and a photostationary state of the cis/trans acids is formed early into the reaction.The photocyclization of the dichloro analog is more efficient (Φ exceeds 0.04) and therefore time dependent since product formation competes with trans/cis isomerization.Methyl o-chlorocinnamate also photocyclizes (Φ for the PSS = 0.0022 in acetonitrile) but the o-methoxy ester is virtually photoinert.It is proposed that the acid photocyclizes through intramolecular nucleophilic attack by the carboxylate group followed by heterolysis of the nucleofuge.Methyl o-chlorocinnamate appears to photocyclize through a cycloaddition of the carbonyl group followed by homolysis of the Cl and Me moieties, possibly through the intermediacy of a ketene as proposed by earlier workers.