56766-77-9Relevant articles and documents
Biomimetic regioselective and high-yielding Cu(i)-catalyzed dimerization of sinapate esters in green solvent Cyrene: Towards sustainable antioxidant and anti-UV ingredients
Mention, Matthieu M.,Flourat, Amandine L.,Peyrot, Cédric,Allais, Florent
supporting information, p. 2077 - 2085 (2020/04/08)
Naturally occurring sinapic acid and its esters are anti-UV and antiradical chemicals. This work aimed at designing an industrially relevant sustainable synthetic pathway allowing their selective β-β′ dimerization to enhance their properties with a view to use them in commercial applications such as functional additives for cosmetics, plastics and food/feed. A copper(i)-catalyzed procedure involving pyridine and O2 from air was developed and greened up using the REACH-compliant bio-based solvent Cyrene. Upon optimizing further through design of experiments, this sustainable synthetic process was successfully implemented to various sinapate esters and was validated on the multigram scale. Antiradical activities of the resulting β-β′ disinapate esters were benchmarked against commercial antioxidants, whereas their UV absorbance was compared to that of sinapoyl malate, a natural anti-UV compound found in plants and that of Octinoxate, a widely used commercial sunscreen ingredient. Results showed that these dimers were better radical scavengers, and not only exhibited a better UV absorbance but also covered both UV-A and UV-B regions.
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students
Chen, Hui-Zhen,Chen, You-Bao,Lv, Ya-Ping,Zeng, Fang,Zhang, Juan,Zhou, Yong-Lie,Li, Han-Bing,Chen, Li-Fei,Zhou, Bin-Jie,Gao, Jian-Rong,Xia, Chun-Nian
supporting information, p. 4367 - 4371 (2015/02/06)
We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.
Development of an enantioselective, kilogram-scale, rhodium-catalysed 1,4-addition
Brock, Sally,Hose, David R.J.,Moseley, Jonathan D.,Parker, Alexandra J.,Patel, Ian,Williams, Andrew J.
, p. 496 - 502 (2013/01/03)
A rhodium-catalysed 1,4-addition of an arylboron species to an α,β-unsaturated ester was the key chirality-inducing step in the synthesis of an API. We describe herein the development of this chemistry, including optimization of reagent charges, reaction