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ARS Home » Midwest Area » Madison, Wisconsin » U.S. Dairy Forage Research Center » Research » Publications at this Location » Publication #173170
Title: PREPARATION AND RELEVANCE OF A CROSS-COUPLING PRODUCT BETWEEN SINAPYL ALCOHOL AND SINAPYL P-HYDROXYBENXOATE

Author
item LU, FACHUANG - UW-MADISON
item Ralph, John
item MORREEL, KRIS - U. GHENT, BELGIUM
item MESSENS, ERIC - U. GHENT, BELGIUM
item BOERJAN, WOUT - U. GHENT, BELGIUM

Submitted to: Organic and Biomolecular Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/10/2004
Publication Date: 10/13/2004
Citation: Lu, F., Ralph, J., Morreel, K., Messens, E., Boerjan, W. 2004. Preparation and relevance of a cross-coupling product between sinapyl alcohol and sinapyl p-hydroxybenxoate. Organic and Biomolecular Chemistry. 2:2888-2890.

Interpretive Summary: Lignin is a polymer that is mainly present in plant cell walls, where it provides strength and impermeability, allowing transport of water and solutes through the vascular system. There is wide interest in understanding the process of lignin biosynthesis and deposition because of its economic relevance. It is clear that lignin limits the digestibility of forages and must be removed from the wood chips during chemical pulping, a process that is expensive and environmentally hazardous, to produce good quality paper. It has been assumed that lignin is composed of three simple monolignols coupled together into complex structures. This work along with earlier work demonstrates that the lignin molecule contains a much wider range of building blocks resulting in even more complex structures. In the work described here sinapyl p-hydroxybenzoate is incorporated into lignin giving the resulting polymer unique chemical and structural properties. By understanding how these new building blocks impact lignin structure it may be possible to induce plans to produce unique lignins better suited to the ultimate use of the plant, whether it be for digestibility, paper production, or added strengthen for wood fiber construction.

Technical Abstract: Cross-coupling of sinapyl p-hydroxybenzoate and sinapyl alcohol produces an 8'8-cross-coupled product that is also detected in lignifying poplar tissues, implicating sinapyl p-hydroxybenzoate as a lignin precursor.