5676-61-9Relevant academic research and scientific papers
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.
Control of the Solid-state photodimerization of some derivatives and analogs of transcinnamic acid by ethylenediamine
Ito, Yoshikatsu,Borecka, Bozena,Olovsson, Gunnar,Trotter, James,Scheffer, John R.
, p. 6087 - 6090 (2007/10/02)
Some of double salts derived from ethylenediamine (en) and a variety of trans-cinnamic acids and their analogs underwent photodimerization in the solid state, giving predominantly β-truxinic dimers. X-Ray studies demonstrate that (a) the conformation of en is gauche for the highly photoreactive double salts (o-1b·en and m-le·en), whereas it is anti for lessphotoreactive o-la·en or photoinert Id·en and (b) for highly reactive o-lb·en and m-le·en, the monomer acid molecules are arranged in an overlap configuration and a reactive monomer pair is hydrogendashbonded to the same en molecule.
