Composition of Gum Turpentines of Pines*

Abstract

contained some a-pinene and the tails contained A3-carene. A heart cut (22%) had the following properties: b760, 165-166"; d:4, 0.8609; n ' : . ' , 1.4772; [a]"D4, -16.2". I-p-Pinene was identified in this fraction by preparation of nopinic acid melting a t 126". No depression in melting point occurred upon admixture with authentic nopinic acid.Fraction 7 was a mixture of 8-pinene and A3carene. Fraction 8 was mainly A3-carene. The nitrosate of Fraction 8 was prepared and after 3 recrystallizations melted a t 144.5'. A mixed melting point determination with authentic d-A3-carene nitrosate showed no depression. The optical rotation of Fractions 11 and 12 were negative, apparently due to the presence of E-limonene, but A3-carene nitrosate was prepared from fraction 12.Fraction 13 was redistilled over sodium in a Claisen flask yielding a heart cut with the properties 1.4785. Preparation of a tetrabromide was attempted but no crystalline derivative was obtained.Fractions 18 and 19 contained an unidentified sesquiterpene. On attempting to prepare a hydrochloride from fraction 19, no solid derivative was obtained.From 2 ml. of fraction 21. one Gm. of a crude b760, 174-177"; [a]":, -58.2'; d i a " , 0.8465; n ' : , hydrochloride was obtained treatment with dry -HCl gas in ether solution. After two recrystallizations from glacial acetic acid the crystals melted a t 59" and showed no depression on admixture with longifolene hydrochloride derived from P. pcnderosa of the Black Hills. It is estimated that about 4% of the original turpentine is d-longifolene. To sum up, the gum turpentine from P. ponderosa from McNary, Ariz., contains approximately: 34% d-and dl-a-pinene; 14% 1-p-pinene; 31% d-A3-careue; 4% 1-limonene (suspected but not identified) ; 4% d-longifolene and 4-5% unidentified sesquiterpene. inus chihuahuana Engelmann is essentially a pMexican pine . It is known under the name of Pino prieto, P. saguaco, or P. chamonque and i t occurs as far south as the states of Nayarit, Zacatecas, and the northern part of Jalisco. It grows chiefly in the states of Durango, Chihuahua, and Sonora. I n the United States i t occurs in southeastern Arizona and southwestern New Mexico. Botanically it is related to P i n u s leiophylla and P. lumholtzii (8). From its discovery in 1848, for over 60 years, Chihuahua pine was considered as a valid species (9); in 1909 Shaw (8) designated i t as a variety of P. Liophylla. Martinez (5) is of the opinion t h a t P. chihuahu-* Received December 23 1953 from the Iustitute of Forest Genetics, California Forest and 'Range Experiment Station, maintained by the Forest Service, U S Divartmrnt of Agriculture, in cooperation with the University of California, Berkeley. grant from the Rockefeller Foundation. The work reported in this paper was aided through a ana deserves a specific rank. Analysis of turpentine of P. chihuahuana reported in this paper seems t o substantiate Sudworth's and Martinez's contention : while the turpentine obtained by Mirov ( 6 ) from P. leiophylla (in Michoacan) consisted ...

Developments in Multiple Comparisons 1966–1976

“…Our results are inconsistent with those of Pitman (197 I) who demonstrated that apinene was more effective than myrcene in attracting D. ponderosae in stands of western white pine and are surprising since a-pinene is the most common monoterpene in the resin of western white pine, which has low amounts of myrcene (Mirov 1961). The relative proportion of myrcene is higher in the resin of' lodgepole and ponderosa pines with amounts of myrcene greater than or equal to amounts of a-pinene (Mirov 196 1;Shrimpton 1973).…”

Southern Pine Beetle, Dendroctonus frontalis, Antennal and Behavioral Responses to Nonhost Leaf and Bark Volatiles

“…For example, one or more of the nonhost species sampled contained volatiles identified in the resin of host pines of D. frontalis (including the aggregation synergist α-pinene) as well as D. frontalis pheromone components (trans-verbenol and verbenone) (Mirov, 1961; A. rubrum C. alba L. styraciflua N. sylvatica P. serotina Q. falcata Q. marilandica Q. nigra…”

Host-Tree Chemistry Affecting Colonization in Bark Beetles

“…pini that is responsive only to one of two possible enantiomers (chemicals that cannot be structurally superimposed but otherwise are identical, see a-pinene in Figure 5.4); (2) a pheromone-sensitive type that is also responsive to some other synergists or inhibitors such as the frontalin cells of D. frontalis (the cells have at least two acceptor types each specific for one enantiomer of frontalin, see identical except that they are non-superimposable (mirror images). Carnphene, P-pinene, 3-carene, P-phellandrene, and limonene also have two enantiomers, although only (-)-P-pinene and (+)-3-carene are found in trees (Mirov, 1961). Myrcene and terpinolene are achiral.…”