Tetramethylammonium hydroxide (TMAH) thermochemolysis of lignin: Behavior of 4-O-etherified cinnamyl alcohols and aldehydes

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 23, 2005, Pages 8859-8865

  Kuroda, Ken Ichi ^a   Nakagawa Izumi, Akiko ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

4 O etherified cinnamyl alcohols; 4 O etherified cinnamyl aldehydes; Dehydrogenation polymer; Japanese cedar (Cryptomeria japonica) wood; Lignin; Tetramethylammonium hydroxide (TMAH) thermochemolysis

Indexed keywords

ALDEHYDE; CINNAMYL ALCOHOL; CONIFERYL ALCOHOL; ETHER DERIVATIVE; LIGNIN; PHENOL DERIVATIVE; PHENYLPROPIONIC ACID DERIVATIVE; PROPANOL; QUATERNARY AMMONIUM DERIVATIVE; SINAPYL ALCOHOL; TETRAMETHYLAMMONIUM; TRANS CONIFERYL ALDEHYDE; TRANS-CONIFERYL ALDEHYDE;

ARTICLE; CHEMISTRY; CONIFER; DIMERIZATION; MASS FRAGMENTOGRAPHY; METHYLATION; WOOD;

ALDEHYDES; CONIFEROPHYTA; DIMERIZATION; ETHERS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LIGNIN; METHYLATION; PHENOLS; PHENYLPROPIONATES; PROPANOLS; QUATERNARY AMMONIUM COMPOUNDS; WOOD;

CRYPTOMERIA JAPONICA;

EID: 28444494083     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf058085g     Document Type: Article

References (52)

1. Sarkanen, K. V.; Ludwig, C. H. Definition and nomenclature. In Lignins: Occurrence, Formation, Structure and Reactions; Sarkanen, K. V., Ludwig, C., Eds.; Wiley: New York, 1971; pp 1-18.
2. Goldschmid, O. Ultraviolet spectra. In Lignins: Occurrence, Formation, Structure and Reactions; Sarkanen, K. V., Ludwig, C., Eds.; Wiley: New York, 1971; pp 241-266.
3. Adler, E. Lignin chemistry - past, present and future. J. Wood Sci. Technol. 1977, 11, 169-218.
4. Lai, Y.-Z.; Sarkanen, K. V. Isolation and structural studies. In Lignins: Occurrence, Formation, Structure and Reactions; Sarkanen, K. V., Ludwig, C. H., Eds.; Wiley: New York, 1971; pp 165-240.
5. Marton, J.; Adler, E. Carbonyl groups in lignin. III. Mild catalytic hydrogenation of Björkman lignin. Acta Chem. Scand. 1961, 15, 370-387.
6. Lindgren, B. O.; Mikawa, H. The presence of cinnamyl alcohol groups in lignin. Acta Chem. Scand. 1957, 11, 826-835.
7. 13C-enriched lignin in wheat straw from coniferin. Phytochemistry 1997, 46, 863-870.
8. Zhang, L.; Gellerstedt, G. Detection and determination of carbonyls and quinones by modern NMR techniques. Proceedings of the 10th International Symposium on Wood and Pulping Chemistry; Japan Tappi: Yokohama, Japan, 1999; Vol. II, pp 164-170.
9. Lundquist, K.; Olsson, T. NMR studies of lignins. 1. Signals due to protons in formyl groups. Acta Chem. Scand. 1977, B31, 788-792.
10. Lu, F.; Ralph, J. The DFRC method for lignin analysis. 7. Behavior of cinnamyl end groups. J. Agric. Food Chem. 1999, 47, 1981-1987.
11. Rolando, C.; Monties, B.; Lapierre, C. Thioacidolysis. In Methods in Lignin Chemistry; Lin, S. Y., Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 334-349.
12. MacKay, J.; Dimmel, D. R.; Boon, J. J. Pyrolysis mass spectral characterization of wood from CAD-deficient pine. J. Wood Chem. Technol. 2001, 21, 19-29.
13. Ralph, J.; MacKay, J. J.; Hatfield, R. D.; Omalley, D. M.; Whetten, R. W.; Sederoff, R. R. Abnormal lignin in a loblolly pine mutant. Science 1997, 277, 235-239.
14. Kim, H.; Ralph, J.; Yahiaoui, N.; Pean, M.; Boudet, A. M. Cross-coupling of hydroxycinnamyl aldehydes into lignins. Org. Lett. 2000, 2, 2197-2200.
15. Dimmel, D. R.; MacKay, J. J.; Althen, E. M.; Parks, C.; Sederoff, R. R. Pulping and bleaching of CAD-deficient wood. J. Wood Chem. Technol. 2001, 21, 1-17.
16. Ito, T.; Hayase, R.; Kawai, S.; Ohashi, H.; Higuchi, T. Coniferyl aldehyde dimers in dehydrogenative polymerization: model of abnormal lignin formation in cinnamyl alcohol dehydrogenase-deficient plants. J. Wood Sci. 2002, 48, 216-221.
17. Pomar, F.; Merino, F.; Barcelo, A. R. O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. Protoplasma 2002, 220, 17-38.
18. Li, L.; Zhou, Y. H.; Cheng, X. F.; Sun, J. Y.; Marita, J. M.; Ralph, J.; Chiang, V. L. Combinatorial modification of multiple lignin traits in trees through multigene cotransformation. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 4939-4944.
19. Kim, H.; Ralph, J.; Lu, F.; Ralph, S. A.; Boudet, A.-M.; MacKay, J. J.; Sederoff, R. R.; Ito, T.; Kawai, S.; Ohashi, H.; Higuchi, T. NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins. Org. Biomol. Chem. 2003, 1, 268-281.
20. Barriere, M.; Ralph, J.; Mechin, V.; Guillaumie, S.; Grabber, J.; Argillier, O.; Chabbert, B.; Lapierre, C. Genetic and molecular basis of grass cell wall biosynthesis and degradability. II. Lessons from brown-midrib mutants. C. R. Biol. 2004, 327, 847-860.
21. Challinor, J. M. A pyrolysis-derivatisation-gas chromatography technique for the structural elucidation of some synthetic polymers. J. Anal. Appl. Pyrolysis 1989, 16, 323-333.
22. Challinor, J. M. Characterisation of wood by pyrolysis derivatisation-gas chromatography/mass spectrometry. J. Anal. Appl. Pyrolysis 1995, 35, 93-107.
23. Clifford, D. J.; Carson, D. M.; McKinney, D. E.; Bortiatynski, J. M.; Hatcher, P. G. A new rapid technique for the characterization of lignin in vascular plants: thermochemolysis with tetramethylammonium hydroxide (TMAH). Org. Geochem. 1995, 23, 169-175.
24. 13C-labeled TMAH to a synthetic model lignin dimer. Org. Geochem. 1999, 30, 607-621.
25. Challinor, J. M. Review: The development and applications of thermally assisted hydrolysis and methylation reactions. J. Anal. Appl. Pyrolysis 2001, 61, 3-34.
26. Hatcher, P. G.; Minard, R. D. Comparison of dehydrogenase polymer (DHP) lignin with native lignin from gymnosperm wood by thermochemolysis using tetramethylammonium hydroxide (TMAH). Org. Geochem. 1996, 24, 593-600.
27. Hardell, H.-L.; Nilvebrant, N.-O. Analytical pyrolysis of spruce milled wood lignins in the presence of tetramethylammonium hydroxide. Nord. Pulp Pap. Res. J. 1996, 2, 121-126.
28. del Rio, J. C.; McKinney, D. E.; Knicker, H.; Nanny, M. A.; Minard, R. D.; Hatcher, P. G. Structural characterization of bio-and geo-macromolecules by off-line thermochemolysis with tetramethylammonium hydroxide. J. Chromatogr. A 1998, 823, 433-448.
29. Kuroda, K.; Ozawa, T.; Ueno, T. Characterization of sago palm (Metroxylon sagu) lignin by analytical pyrolysis. J. Agric. Food Chem. 2001, 49, 1840-1847.
30. Kuroda, K.; Izumi, A.; Mazumder, B. B.; Ohtani, Y.; Sameshima, K. Characterization of kenaf (Hibiscus cannabinus) lignin by pyrolysis - gas chromatography - mass spectrometry in the presence of tetramethylammonium hydroxide. J. Anal. Appl. Pyrolysis 2002, 64, 453-463.
31. Kuroda, K.; Nishimura, N.; Nakagawa, A.; Dimmel, D. R. Pyrolysis of lignin in the presence of tetramethylammonium hydroxide (TMAH): a convenient method for S/G ratio determination. J. Agric. Food Chem. 2002, 50, 1022-1027.
32. Fu, S. Y.; Lucia, L. A. TMAH-pyrolysis-gas chromatography - mass spectrometry analysis of residual lignin changes in softwood kraft pulp during oxygen delignification. Can. J. Chem. 2004, 82, 1197-1202.
33. Kuroda, K.-I.; Nakagawa-izumi, A. Tetramethylammonium hydroxide (TMAH) thermochemolysis of guaiacyl-syringyl and guaiacyl dehydrogenation polymers. Org. Geochem. 2005, 36, 53-61.
34. 13C-TMAH) thermochemolysis to the study of fungal degradation of wood. Org. Geochem. 2000, 31, 181-198.
35. Filley, T. R.; Cody, G. D.; Goodell, B.; Jellison, J.; Noser, C.; Ostrofsky, A. Lignin demethylation and polysaccharide decomposition in spruce sapwood degraded by brown rot fungi. Org. Geochem. 2002, 33, 111-124.
36. Vane, C. H. The molecular composition of lignin in spruce decayed by white-rot fungi (Phanerochaete chrysosporium and Trametes versicolor) using pyrolysis-GC-MS and thermochemolysis with tetramethylammonium hydroxide. Int. Biodeterior. Biodegrad. 2003, 51, 67-75.
37. Chefetz, B.; van Heemst, J. D. H.; Chen, Y.; Romaine, C. P.; Chorover, J.; Rosario, R.; Gui, M. X.; Hatcher, P. G. Organic matter transformations during the weathering process of spent mushroom substrate. J. Environ. Qual. 2000, 29, 592-602.
38. Chen, Y.; Chefetz, B.; Rosario, R.; van Heemst, J. D. H.; Romaine, C. P.; Hatcher, P. G. Chemical nature and composition of compost during mushroom growth. Compost Sci. Util. 2000, 8, 347-359.
39. 13C NMR. J. Agric. Food Chem. 2001, 49, 2709-2716.
40. Vane, C. H.; Drage, T. C.; Snape, C. E. Biodegradation of oak (Quercus alba) wood during growth of the shiitake mushroom (Lentinula edodes): a molecular approach. J. Agric. Food Chem. 2003, 51, 947-956.
41. 13C NMR and off-line TMAH thermochemolysis with GC-MS. Int. Biodeterior. Biodegrad. 2005, 55, 175-185.
42. Nakagawa-izumi, A.; Kuroda, K.; Ozawa, T. Thermochemolytic behavior of β-β lignin structures in the presence of tetramethylammonium hydroxide (TMAH). Org. Geochem. 2004, 35, 763-774.
43. Kuroda, K.; Nakagawa-izumi, A.; Dimmel, D. R. Pyrolysis of lignin in the presence of tetramethylammonium hydroxide (TMAH): products stemming from β-5 substructures. J. Agric. Food Chem. 2002, 50, 3396-3400.
44. Martin, F.; del Rio, J. C.; Gonzalez-Vila, F. J.; Verdejo, T. Thermally assisted hydrolysis and alkylation of lignins in the presence of tetra-alkylammonium hydroxides. J. Anal. Appl. Pyrolysis 1995, 35, 1-13.
45. del Rio, J. C.; Martin, F.; Gonzalez-Vila, F. J. Thermally assisted hydrolysis and alkylation as a novel pyrolytic approach for the structural characterization of natural biopolymers and geomacromolecules. Trends Anal. Chem. 1996, 15, 70-79.
46. Erdtman, H.; Leopold, B. Aromatic keto and hydroxy polyethers as lignin models. II. Acta Chem. Scand. 1949, 3, 1358-1378.
47. Kulkarni, M. G.; Sebastian, M. T. 1,4-Benzoquinone: a new reagent for oxidation of alcohols. Tetrahedron Lett. 1990, 31, 4497-4500.
48. Kuroda, K. Electron-impact (EI) mass spectra of 1,2-dimethoxybenzenes related to the pyrolysis products of guaiacyl lignin in the presence of tetramethylammonium hydroxide (TMAH). J. Anal. Appl. Pyrolysis 2002, 64, 433-451.
49. Tong, H. Y.; Karasek, F. W. Flame ionization detector response factors for compound classes in quantitative analysis of complex organic mixtures. Anal. Chem. 1984, 56, 2124-2128.
50. Kuroda, K. Analytical pyrolysis products derived from cinnamyl alcohol-end groups in lignins. J. Anal. Appl. Pyrolysis 2000, 53, 123-134.
51. 1H NMR spectroscopy. Paperi ja puu 1980, 62, 669-672.
52. Nakagawa-izumi, A.; Kuroda, K. Analysis of cinnamyl alcohol-and cinnamyl aldehyde end groups in lignin by trimethylsilylation/pyrolysis-gas chromatography. Bunseki Kagaku 2003, 52, 1159-1166.