Arthur B. Anderson

Monoterpenes, fatty and resin acids of Pinus ponderosa and Pinus jeffreyi

Abstract The sapwood and heartwood of ponderosa pine ( Pinus ponderosa ) and Jeffrey pine ( P. jeffreyi ) have been examined for monoterpenes, fatty and resin acids. The composition of the fatty and resin acids is comparable in each species. The principal qualitative differences between these two species is the presence of the hydrocarbons n -heptane, n -nonane, and n -undecane in the steam volatiles from Jeffrey pine and their apparent absence in ponderosa pine.

The structure of δ-cadinol

Abstract Albicaulol, a crystalline cadinol isolated from the oleoresin of Pinus albicaulis and Pinus armandi, has been found to be identical with δ-cadinol. The structure of δ-cadinol has been shown to be Δ8-cadinene-3-ol rather than the Δ9-structure assigned by Motl, Sýkora, Herout and Sorm.

Chemistry of the genus Sequoia—II : Isolation of sequirins, new phenolic compounds from the coast redwood (Sequoia sempervirens)

Abstract New phenolic compounds, sequirins A, B, and C were isolated from the extractives of redwood heartwood. These compounds account for the durability and staining of redwood, and they are probably the precursors of polymers present in redwood.

Monoterpenes, fatty and resin acids of pinus contorta and pinus attenuata

Abstract The sapwood and heartwood of lodgepole pine ( Pinus contorta ) and knobcone pine ( P. attenuata ) have been examined for monoterpenes, fatty and resin acids. While eleven monoterpenes were identified as common to both species, the principal difference in the monoterpenes is in their major components, namely β-phellandrene (71 per cent) in lodgepole pine and α-pinene (72 per cent) in knobcone pine. Four fatty acids and eight resin acids were identified as common to both species.

Monoterpenes, fatty and resin acids of Pinus lambertiana and Pinus monticola☆

Abstract The sapwood and heartwood of sugar pine ( Pinus lambertiana ) and western white pine ( Pinus monticola ) have been examined for monoterpenes, fatty and resin acids. The principal qualitative differences between the terpene composition are the presence of Δ 3 -carene in significant amounts in sugar pine and its apparent absence in western white pine and the presence of n -decane in western white pine and its absence in sugar pine. While the seldom reported trans -cinnamic acid was found in each of these pines, the recently reported sugar pine resin acid, lambertianic, was not found in western white pine.

Chemistry of the genus Sequoia—IV. : The Structures of the C17 Phenols from Sequoia sempervirens

Abstract Further structural investigation was carried out on the recently isolated C 17 polyphenolic materials from California redwood ( Sequoia sempervirens ) heartwood extract. Structures for these compounds are proposed on the basis of chemical and spectral evidence.

Chemistry of genus Pinus. VII. Monoterpenes, fatty and resin acids of Pinus monophylla and Pinus quadrifolia.

Schlüsselwörter (Sachgebiete) Haploxylon Monoterpene Harzsäuren z!()-Isopimarsäure Chemotaxonomie Pinus monophylla Pinus quadrifolia Chemistry of Genus Pinus. VII. Monoterpenes, Fatty and Resin Acids of Pinus monophylla and Pinus quadrifolia Summary Sapwood and Heartwood of singleleaf pine (Pinus monophylla) and Parry pinyon pine (Pinus quadrifolia) were examined for monoterpenes and fatty and resin acids. The principal qualitative difference between terpene compositions of these two pines appears to be the presence of ßphellandrene, terpinolene, and camphene in singleleaf pine and their apparent absence in Parry pinyon pine. Two fatty acids and nine resin acids were identified as common to both species. The principal resin acid in each species is z!<-isopimaric acid, which has not been detected in six pine species belonging to the subgenus Diploxylon we have examined to date.

Monoterpenes, fatty and resin acids of pinus edulis and pinus albicaulis☆

Abstract The sapwood and heartwood of pinyon pine ( Pinus edulis ) and whitebark pine ( P. albicaulis ) were examined for monoterpenes, fatty and resin acids. The principal qualitative differences between the terpene composition of these pines are the presence of limonene in pinyon pine and its apparent absence in whitebark pine, and the presence of α-phellandrene in whitebark pine and its possible absence in pinyon pine. Quantitatively, the principal difference appears to be the predominance of α-pinene in pinyon pine, and the high percentage of δ 3 -carene in whitebark pine. Among acidic components, the main qualitative difference is the presence of δ 8,15 -isopimaric acid in pinyon pine, and its apparent absence in whitebark pine.

Chemistry of the Genus Pinus.Part II. Composition of Resin Acids in Ponderosa Pine Heartwood (Pinus Ponderosa Dougl.)

(16) Kratzl, K., Holz als Rohund Werkstoff 11, 269 (1953). (17) Brauns, F. E., The Chemistry of Lignin, Academic Press, Inc., New York, 1952, p. 156; a. pp. 35—39; b. pp. 2iyffo c. p. 245. (18) Björkman, A., Svensk Papperstidn. 59, 1477 (1956). (19) Brauns, F. E., J. Am. Chem. Soc. 61, 2120 (1939)· (193) Nord, F. F., and de Stevens, G., in Handbuch d. Pflanzenphysiologie 10,424 (1958), Springer Verlag, Berlin. (190) F. Schimmel & Co., DRP. 693350 (1940). (20) Stone, J. E., and Blundel, M. J., Anal. Chem. 23, 771 (195l). (21) Reale, M. J., Anal. Biochem., 13, 162 (1965). (22) Thoma, J. A., Anal. Chem. 35, 214 (1963). (23) Browning, B. L., in The Composition and Chemical Reactions of Wood (B. L. Browning, ed.), Interscience Publishers, New York, 1963, p. 69. (24) Crocker, E. C., Ind. Eng. Chem. 13, 625 (1921). (25) Crocker, E. C., Botan. Gaz. 95, 168 (1933)· (26) Adler, E., Björkvist, K. J., and Häggroth, S., Acta Chem. Scand. 2, 93 (1948). (27) Brauns, F. E., and Brauns, D. A., The Chemistry of Lignin, Suppl. Vol., Academic Press, Inc., New York, 1960, p. 39. (28) Hershenson, H. M., Ultraviolet and Visible Absorption Spectra, Index for 1930—1954, Academic Press, Inc., 1956, p. 120. (29) Silverstein, R. M., and Bassler, G. C., Spectrometric Identification of Organic Compounds, John Wiley and Sons, Inc., New York, i063, p. 1005 a. p. 64. (30) Hillmer, Ber. 66, 1600 (1933). (31) Stamm, A. J., Semb, J., and Harris, E. E., J. Phys. Chem. 36, 1574 (1932). (32) Hershenson, H. M., Infrared Absorption Spectra, Index for 1945—1957, Academic Press, Inc., New York, 1959, p. 60. (33) Hershenson, H. M., Infrared Absorption Spectra, Index for 1958—1962, Academic Press, Inc., New York, 1964, P79(34) Hergert, H. L., J. Org. Chem. 25, 405 (1960). (35) Björkman, A., Svensk Papperstidn. 60, 158 (1957). (36) Björkman, A., ibid., p. 243. (37) Leopold, B., and Malmström, I. L., Acta Chem. Scand. 6, 49 (1952). (38) Adler, E., and Yllner, S., Svensk Papperstidn. 55, 238 (1952)· (39) Ishikawa, H., Schubert, W. J., and Nord, F. F., Arch. Biochem. Biophys. 100, 131, 140 (1963). (40) Pepper, J. M., and Steck, W., Can. J. Chem. 41, 2867 (1963). (41) Olcay, A., unpublished observations. (42) Reale, M. J., M. S. Dissertation, Fordham University, Bronx, New York, 1963.

Terpenoid constituents of the pocket resin from coast redwood (Sequoia sempervirens)

Abstract The principal volatile component in the pocket resin of Sequoia sempervirens is α-pinene, while the major resin acids appear to be levopimaric and palustric acids among the five resin acids identified. Abietic acid could not be detected.