60525-32-8Relevant articles and documents
Compositional analysis of organosolv poplar lignin by using high-performance liquid chromatography/high-resolution multi-stage tandem mass spectrometry
Zhang, Jifa,Jiang, Yuan,Easterling, Leah F.,Anstner, Anton,Li, Wanru,Alzarieni, Kawthar Z.,Dong, Xueming,Bozell, Joseph,Kentt?maa, Hilkka I.
, p. 983 - 1000 (2021/02/09)
Organosolv treatment is an efficient and environmentally friendly process to degrade lignin into small compounds. The capability of characterizing the individual compounds in the complex mixtures formed upon organosolv treatment is essential for the optimization of the further lignin conversion processes and for the rational genetic engineering of plants used to produce lignin in order to improve lignin properties. In this study, an organosolv poplar lignin sample was initially analyzed by high-resolution mass spectrometry coupled with negative-ion mode electrospray ionization ((?)ESI HRMS). Lignin monomers and dimers were found to constitute the majority of the compounds in the organosolv lignin sample. Larger lignin oligomers, such as trimers and tetramers, and some not lignin-related compounds, were also detected. A high-performance liquid chromatograph/linear quadrupole ion trap/orbitrap mass spectrometer capable of multi-stage high-resolution tandem mass spectrometry experiments (HRMSn), equipped with an (?)ESI source (HPLC/(?)ESI HRMSn), was employed to separate the unknown compounds in the organosolv mixture and to obtain structural information for the deprotonated compoundsviacollision-activated dissociation (CAD) HRMSnexperiments. To improve the understanding of the CAD behavior of deprotonated lignin-related compounds, 16 deprotonated model compounds with different functionalities and linkage types were examined. This approach enabled the assignment of likely structures for several lignin monomers, dimers, trimers, and tetramers, and some not lignin-related compounds, most likely fatty acids. Based on the proposed structures, compounds in the organosolv lignin sample contain β-O-4, 5-5, β-5, and possibly also 4-O-5 linkages. Most compounds contain G- and S-monomeric units although a small amount of H-units were also detected.
An efficient and flexible synthesis of model lignin oligomers
Graham Forsythe,Garrett, Mark D.,Hardacre, Christopher,Nieuwenhuyzen, Mark,Sheldrake, Gary N.
supporting information, p. 3031 - 3038 (2013/11/06)
The use of model compounds in the development of selective lignin depolymerisation processes has been limited by the lack of complexity of these models compared with lignin itself. In this paper we report a convergent and efficient synthetic method for th
Synthesis and N.m.r. Spectra of 2,6- and 2,4-Diaryl-3,7-dioxabicyclooctanes
Pelter, Andrew,Ward, Robert S.,Watson, Derrick J.,Jack, Ibiba R.
, p. 183 - 190 (2007/10/02)
A series of isomeric 2,6- and 2,4-diaryl-3,7-dioxabicyclooctanes have been prepared via the corresponding threo, and erythro-dioxo-diesters.Comparison of their 1H and 13C n.m.r. spectra reveals small differences in chemical shifts and coupling constants which could be diagnostic in assigning structures to such compounds.The structure of 4-hydroxysesamin has been confirmed by direct correlation with sesamin.