Skip to Main Content
U.S. Forest Service
Caring for the land and serving people

United States Department of Agriculture

Home > Search > Publication Information

 Due to a lapse in federal funding, this USDA website will not be actively updated. Once funding has been reestablished, online operations will continue.


  1. Share via EmailShare on FacebookShare on LinkedInShare on Twitter
    Dislike this pubLike this pub
    Author(s): Thomas Elder; Laura Berstis; Gregg T. Beckham; Michael F. Crowley
    Date: 2016
    Source: Journal of Agricultural and Food Chemistry
    Publication Series: Scientific Journal (JRNL)
    Station: Southern Research Station
    PDF: View PDF  (1.0 MB)

    Description

    The catechol alcohols, caffeyl and 5-hydroxyconiferyl alcohol, may be incorporated into lignin either naturally or through genetic manipulation. Due to the presence of o-OH groups, these compounds form benzodioxanes, a departure from the interunit connections found in lignins derived from the cinnamyl alcohols. In nature, lignins composed of caffeyl and 5- hydroxyconiferyl alcohol are linear homopolymers and, as such, may have properties that make them amenable for use in valueadded products, such as lignin-based carbon fibers. In the current work, results from density functional theory calculations for the reactions of 5-hydroxyconiferyl alcohol, taking stereochemistry into account, are reported. Dehydrogenation and quinone methide formation are found to be thermodynamically favored for 5-hydroxyconiferyl alcohol, over coniferyl alcohol. The comparative energetics of the rearomatization reactions suggest that the formation of the benzodioxane linkage is under kinetic control. Ring-opening reactions of the benzodioxane groups show that the bond dissociation enthalpy of the α-O cleavage reaction is lower than that of the β-O reaction. The catechol lignins represent a novel form of the polymer that may offer new opportunities for bioproducts and genetic targets.

    Publication Notes

    • You may send email to pubrequest@fs.fed.us to request a hard copy of this publication.
    • (Please specify exactly which publication you are requesting and your mailing address.)
    • We recommend that you also print this page and attach it to the printout of the article, to retain the full citation information.
    • This article was written and prepared by U.S. Government employees on official time, and is therefore in the public domain.

    Citation

    Elder, Thomas; Berstis, Laura; Beckham, Gregg T.; Crowley, Michael F. 2016. Coupling and reactions of 5- hydroxyconiferyl alcohol in lignin formation. Journal of Agricultural and Food Chemistry, Vol. 64(23): 9 pages.: 4742-4750.  10.1021/acs.jafc.6b02234

    Cited

    Google Scholar

    Keywords

    5-hydroxyconiferyl alcohol, coniferyl alcohol, lignin, benzodioxane, stereochemistry

    Related Search


    XML: View XML
Show More
Show Fewer
Jump to Top of Page
https://www.fs.usda.gov/treesearch/pubs/52254