24903-95-5Relevant articles and documents
Scale-Up of Ozonolysis using Inherently Safer Technology in Continuous Flow under Pressure: Case Study on β-Pinene
Courboin, Daniel,Roth, Philippe M. C.,Vaz, Margaux,Winter, Marc
, p. 1589 - 1597 (2021)
Despite its synthetic relevance, ozonolysis is still an underused reaction in the synthetic chemistry industries. This can be attributed to safety issues while handling the ozone itself, alongside extra hazard related to unstable reaction intermediates. Flow chemistry is inherently safer as it involves a small volume of reagent at any given time. Here, to address safety and technical issues, we describe the design and testing of an ozone dosing line. A global risk assessment and the description of the setup, the analytics, are presented in detail. This new dosing line enabled the successful scale-up of β-pinene ozonolysis in flow, with a productivity of over 16 g/h.
Trost,B.M. et al.
, p. 3407 - 3415 (1978)
Design, synthesis and biological evaluation of novel β-pinene-based thiazole derivatives as potential anticancer agents via mitochondrial-mediated apoptosis pathway
Wang, Yunyun,Wu, Chenliang,Zhang, Qiangjian,Shan, Yu,Gu, Wen,Wang, Shifa
, p. 468 - 477 (2019/01/03)
A series of novel β-pinene-based thiazole derivatives were synthesized and characterized by HRMS, 1H NMR, and 13C NMR analyses as potential antineoplastic agents. Derivatives were evaluated for their anticancer activities in vitro, and the data manifested that most target compounds showed potent anti-proliferative activities against three human cancer cell lines. Especially, compound 5g displayed excellent cytotoxic activity against Hela, CT-26, and SMMC-7721 cell lines with IC50 values of 3.48 ± 0.14, 8.84 ± 0.16, and 6.69 ± 0.15 μM, respectively. To determine the underlying mechanism of compound 5g on cell viability, DAPI staining, Annexin-V/PI staining, JC-1 staining, DCFDA staining, and Western blot analysis were performed. Our data showed that compound 5g inhibited cell proliferation by inducing apoptosis and cell cycle arrest of Hela cells at the G0/G1 phase in a dose dependent manner. Further studies revealed that compound 5g enhanced levels of reactive oxygen species (ROS), caused a decrease in mitochondrial membrane potential, increased the release of mitochondrial cytochrome C, and affected the expression of Bax, Bcl-2, caspase-3 and caspase-9. Thus, our findings indicated that compound 5g induced apoptosis in Hela through ROS-mediated mitochondrial dysfunction signaling pathways.
Synthesis and surface spectroscopy of α-pinene isotopologues and their corresponding secondary organic material
Upshur, Mary Alice,Vega, Marvin M.,Bé, Ariana Gray,Chase, Hilary M.,Zhang, Yue,Tuladhar, Aashish,Chase, Zizwe A.,Fu, Li,Ebben, Carlena J.,Wang, Zheming,Martin, Scot T.,Geiger, Franz M.,Thomson, Regan J.
, p. 8390 - 8398 (2019/09/30)
Atmospheric aerosol-cloud interactions remain among the least understood processes within the climate system, leaving large uncertainties in the prediction of future climates. In particular, the nature of the surfaces of aerosol particles formed from biogenic terpenes, such as α-pinene, is poorly understood despite the importance of surface phenomena in their formation, growth, radiative properties, and ultimate fate. Herein we report the coupling of a site-specific deuterium labeling strategy with vibrational sum frequency generation (SFG) spectroscopy to probe the surface C-H oscillators in α-pinene-derived secondary organic aerosol material (SOM) generated in an atmospheric flow tube reactor. Three α-pinene isotopologues with methylene bridge, bridgehead methine, allylic, and vinyl deuteration were synthesized and their vapor phase SFG spectra were compared to that of unlabeled α-pinene. Subsequent analysis of the SFG spectra of their corresponding SOM revealed that deuteration of the bridge methylene C-H oscillators present on the cyclobutane ring in α-pinene leads to a considerable signal intensity decrease (ca. 30-40%), meriting speculation that the cyclobutane moiety remains largely intact within the surface bound species present in the SOM formed upon α-pinene oxidation. These insights provide further clues as to the complexity of aerosol particle surfaces, and establish a framework for future investigations of the heterogeneous interactions between precursor terpenes and particle surfaces that lead to aerosol particle growth under dynamically changing conditions in the atmosphere.
