80-57-9Relevant articles and documents
Synthesis and biological activity of novel (Z)- and (E)-verbenone oxime esters
Hu, Qiong,Lin, Gui-Shan,Duan, Wen-Gui,Huang, Min,Lei, Fu-Hou
, (2017)
Twenty-seven (Z)- and (E)-verbenone derivatives bearing an oxime ester moiety were designed and synthesized in search of novel bioactive molecules. Their structures were confirmed by UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal and herbicidal activities of the target compounds were preliminarily evaluated. As a result, compound (E)-4n (R = b-pyridyl) exhibited excellent antifungal activity with growth inhibition percentages of 92.2%, 80.0% and 76.3% against Alternaria solani, Physalospora piricola, and Cercospora arachidicola at 50 g/mL, showing comparable or better antifungal activity than the commercial fungicide chlorothalonil with growth inhibition of 96.1%, 75.0% and 73.3%, respectively, and 1.7 5.5-fold more growth inhibition than its stereoisomer (Z)-4n (R = b-pyridyl) with inhibition rates of 22.6%, 28.6% and 43.7%, respectively. In addition, seven compounds displayed significant growth inhibition activity of over 90% against the root of rape (Brassica campestris) at 100 g/mL, exhibiting much better herbicidal activity than the commercial herbicide flumioxazin with a 63.0% growth inhibition. Among these seven compounds, compound (E)-4n (R = b-pyridyl) inhibited growth by 92.1%, which was 1.7-fold more than its stereoisomer (Z)-4n (R = b-pyridyl) which inhibited growth by 54.0%.
Individual stereoisomers of verbenol and verbenone express bioactive features
Ivanov, Marija,Kovalenko, Vitaly,Svirid, Anastasia,Kosti?, Marina,Petrovi?, Jovana,Stojkovi?, Dejan
, (2021/12/13)
Naturally occurring terpene core compounds have been used extensively in both pharmaceutical and cosmetic industry. However, since chirality of these compounds has profound influence on the level of their bioactivity, the aim of the present study was to a
Development of rapid and selective epoxidation of α-pinene using single-step addition of H2O2in an organic solvent-free process
Eze, Valentine C.,Harvey, Adam P.,López Fernández, Ana María,Mukhtar Gunam Resul, Mohamad Faiz,Rehman, Abdul
, p. 33027 - 33035 (2021/12/07)
This study reports substantial improvement in the process for oxidising α-pinene, using environmentally friendly H2O2 at high atom economy (～93%) and selectivity to α-pinene oxide (100%). The epoxidation of α-pinene with H2O2 was catalysed by tungsten-based polyoxometalates without any solvent. The variables in the screening parameters were temperatures (30-70 °C), oxidant amount (100-200 mol%), acid concentrations (0.02-0.09 M) and solvent types (i.e., 1,2-dichloroethane, toluene, p-cymene and acetonitrile). Screening the process parameters revealed that almost 100% selective epoxidation of α-pinene to α-pinene oxide was possible with negligible side product formation within a short reaction time (～20 min), using process conditions of a 50 °C temperature in the absence of solvent and α-pinene/H2O2/catalyst molar ratio of 5?:?1?:?0.01. A kinetic investigation showed that the reaction was first-order for α-pinene and catalyst concentration, and a fractional order (～0.5) for H2O2 concentration. The activation energy (Ea) for the epoxidation of α-pinene was ～35 kJ mol-1. The advantages of the epoxidation reported here are that the reaction could be performed isothermally in an organic solvent-free environment to enhance the reaction rate, achieving nearly 100% selectivity to α-pinene oxide.
Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst
Aberkouks, Abderrazak,Mekkaoui, Ayoub Abdelkader,Ait Ali, Mustapha,El Firdoussi, Larbi,El Houssame, Soufiane
, (2020/02/15)
Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.
