New Method to Isolate Gamma-Thujaplicin from Western Red Cedar (Thuja plicata Donn.)

Western red cedar (WRC) (Thuja plicata Donn.) is one of the most durable softwoods in North America, and this durability has largely been attributed to its tropolone content. Further studies on factors contributing to the durability of this species require isolation of substantial quantities of the...

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Bibliographic Details
Published in:Journal of wood chemistry and technology 2010-07, Vol.30 (3), p.299-314
Main Authors: Liu, Zhi-Ming, Daniels, C. R., Morris, Paul I.
Format: Article
Language:English
Subjects:
Byproducts
Cedar
Durability
Gamma-thujaplicin
GC-MS
Hexanes
High performance liquid chromatography
HPLC
identification
isolation
Magnetic resonance
Spectroscopy
western red cedar
Wood
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Summary:Western red cedar (WRC) (Thuja plicata Donn.) is one of the most durable softwoods in North America, and this durability has largely been attributed to its tropolone content. Further studies on factors contributing to the durability of this species require isolation of substantial quantities of the active components. Wood meal from the heartwood butt of a WRC tree was extracted with hexane for 24 hours. The thujaplicin mixture was obtained by chloroform extraction of the alkali solution adjusted to a pH of 6.5. With chemical conversion and regeneration, the selected compound, "gamma-thujaplicin," was isolated from the thujaplicin mixture and characterized by Fourier transform infra-red (FTIR) spectroscopy, High Performance Liquid Chromatography (HPLC), Mass Spectroscopy (MS), 1 H-nuclear magnetic resonance (NMR), Gas Chromatography-Mass Spectroscopy (GC-MS), a color test, and comparison with standard gamma-thujaplicin. Relative purity reached up to 99%. Additionally, a by-product, nezukone, could be also isolated from the hexane extractives.
ISSN:0277-3813
1532-2319
DOI:10.1080/02773810903537101