New Polyoxyphenols from Western Hemlock Sapwood

Authors

  • G. M. Barton

Abstract

Mild treatment of western hemlock (Tsuga heterophylla) sapwood sawdust with methanol resulted in extractives largely uncontaminated with colored polymeric material. Further separation into chloroform solubles followed by gel column chromatography and preparative layer chromatography resolved the extractives into cyclitols and sugars (0.66%); unknown phenolics (0.13%); chloroform soluble nonphenolics (0.12%); phenolic glycosides (0.12%); previously reported polyoxyphenolics such as α-conidendrin (0.01%), hydroxymatairesinol (0.10%), matairesinol (0.02%), and catechin (0.05%); and two new compounds, liovil (0.01%) and a coumaran (0.05%). Liovil previously was found only in black spruce (Picea mariana), and the coumaran is a new lignin dimer with a unique β, γ-linkage. Its structure has been determined as 2-(α-hydroxy-vanillyl)-5-(ω-hydroxypropyl)-7-methoxy coumaran by a combination of nuclear magnetic, infrared, and mass spectroscopy as well as chemical analysis and degradation.

The discovery of liovil in western hemlock reinforces the similarity in extractives between hemlock and spruce and should be of interest to taxonomists to reexamine the genetic relationship between the two genera. The new coumaran, on the other hand, will be of particular interest to lignin chemists who have postulated phenylcoumaran linkages in lignin.

References

Adler, E., S. Delin, and K. Lundquist. 1959. Phenylcoumaran elements in spruce lignin. Acta Chem. Scand., 13: 2149-2150.nBarton, G. M. 1967. Application of solutions to preparative chromatoplates using basic thin-layer equipment. Chem. and Ind., 25: 1079.nBarton, G. M. 1968. Significance of western hemlock phenolic extractives in pulping and lumber. Forest Prod. J., 18(5): 76-80.nBarton, G. M. and J. A. F. Gardner. 1962. The occurrence of matairesinol in mountain hemlock, western hemlock and balsam. J. Org. Chem., 27: 322-323.nBarton, G. M. and J. A. F. Gardner. 1966. Brown stain formation and the phenolic extractives of western hemlock. Dept. of Forest. Publ. No. 1147. p 20.nBarton, G. M. R. S. Evans, and J. A. F. Gardner. 1952. Paper chromatography of phenolic substances. Nature, 170: 249-251.nFreudenberg, K., and L. Knof. 1957. Die Lignane des Fichtenholzes. Berichte, 90: 2857-2869.nGoldschmid, O., and H. L. Hergert. 1961. Examination of western hemlock for lignin precursors. Tappi, 44: 858-870.nGierer, J. 1954. Die Reaktion von Chinonmono-chlorimid mit Lignin. Acta Chem. Scand., 8(8): 1319-1331.nNimz, H. 1966. A new type of rearrangement in the lignin field. Angew. Chem. Internat. Edit., 5(9): 843.nSegal, R., I. Milo-Goldzweig, S. Sokoloff, and D. V. Zaitschek. 1967. A new benzofuren from the seeds of styrax officinalis L. J. Chem. Soc., C: 2402-2404.n

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Published

2007-06-19

Issue

Number 2 / Summer 1970

Section

Research Contributions

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