Investigations on lignins and lignification Pt. xxxi characterization of metasequoia 'milled-wood' lignin / By Michael J. Reale, Donald D. Clarke, Walter J. Schubert and F. F. Nord Laboratory of Organic Chemistry and Enzymology), Fordham University, Bronx, New York
A young Metasequoia tree was debarked; its branches and heartwood were removed. The branches, sapwood and heartwood were separately ground to 8o mesh and air-dried. The moisture and lignin contents of these were determined. "Milled-wood" lignin was isolated from the sapwood sawdust, and was characterized by means of its ultraviolet and infrared absorption spectra. As a means of determining the empirical formula and the number of certain functional groups present in this lignin, an acetylated derivative and a phenylhydrazone were prepared. These were also studied spectroscopically. Elemental, methoxyl and acetoxyl analyses were performed on the original lignin and on its derivatives. The solubility of Metasequoia Bjorkman lignin in various solvents and its color reactions were also determined. Alkaline nitrobenzene oxidation was applied to the lignin, and the average yield of vanillin present in the oxidation mixture was 22.0 ± 1.2 %. Neither p-hydroxybenzaldehyde nor syringaldehyde was detected. Hydrogenation-hydrogenolysis of Metasequoia sawdust was also conducted. The products were separated by gas-liquid chromatography, and the following compounds were identified by their retention times and/or infrared absorption spectra: guaiacol, 4 -methylguaiacol, 4-ethylguaiacol, 4-n-propylguaiacol and dihydroconiferyl alcohol. Thus all the chemical evidence supports the previous biological classification of Metasequoia glyptostroboides as a member of the class Gymnospermae
Reale, Michael J.; Clarke, Donald Dudley PhD; Schubert, Walter J.; and Nord, Friedrich F., "Investigations on lignins and lignification Pt. xxxi characterization of metasequoia 'milled-wood' lignin / By Michael J. Reale, Donald D. Clarke, Walter J. Schubert and F. F. Nord Laboratory of Organic Chemistry and Enzymology), Fordham University, Bronx, New York" (1966). Chemistry Faculty Publications. Paper 75.