Enantiomeric composition and prevalence of some bicyclic monoterpenoids in amber

Chirality

Volumn 8, Issue 1, 1996, Pages 39-48

  Armstrong, Daniel W ^a   Zhou, Eve Y ^a   Zukowski, Janusz ^a,b   Kosmowska Ceranowicz, Barbara ^a,c  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

^c POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

pinene; pinene; borneol; camphene; geochemistry; isoborneol; limonene; pine resins; stereochem istry; succinite

Indexed keywords

AMBER; BETA PINENE; BICYCLO COMPOUND; BORNEOL; CAMPHENE; ISOBORNEOL; LIMONENE; MONOTERPENOID; PINENE; RESIN; TERPENOID; UNCLASSIFIED DRUG;

CONFERENCE PAPER; ENANTIOMER; FOSSIL; NONHUMAN; PINE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029919064     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:1<39::AID-CHIR9>3.0.CO;2-B     Document Type: Conference Paper

References (19)

1. Langenheim, J.H. Amber: A botanical inquiry. Science 163:1157-1169, 1969.
2. Langenheim, J.H. Plant resins. Am. Sci. 78:16-24, 1990.
3. Kosmowska-Ceranowicz, B., Kulicka, R., Leciejewicz, K., Mierzejewski, P. Pietrzak, T. Amber in nature. Polish Academy of Sciences. Warsaw: Museum of the Earth, Wydawnictwa Geologiczne, 1984.
4. Gough, L.J., Mills, J.S. The composition of succinite (Baltic amber). Nature 239:527-528, 1972.
5. Mills, J.S., White, R., Gough, L.J. The chemical composition of Baltic amber. Chem. Geol. 47:15-39, 1984/85.
6. Simoneit, B.R.T., Grimait, J.O., Wang, T.G., Cox, R.E., Hatcher, P.G., Nissenbaum, A. Cyclic terpenoids of contemporary resinous plant detritus and of fossil woods, ambers and coals. Org. Geochem. 10:877-889, 1986.
7. Anderson, K.B., Winans, R.E. Nature and fate of natural resins in the geosphere. 1. Evaluation of pyrolysis-gas chromatography/mass spectrometry for the analysis of natural resins and resinites. Anal. Chem. 63:2901-2908, 1991.
8. Mosini, V., Forcellese, M.L., Nicoletti, R. Presence and origin of volatile terpenes in succinite. Phytochemistry 19:679-680, 1980.
9. Eglinton, G., Calvin, M. Chemical fossils. Sci. Am. 32-46, 1967.
10. Didyk, B.M., Simoneit, B.R.T., Brassell, S.C., Eglinton, G. Organic geochemical indicators of paleoenvironmental conditions of sedimentation. Nature 272:216-222, 1978.
11. Radke, M., Willsch, H., Leythaeuser, D., Teichmuller, M. Aromatic components of coal: Relation of distribution pattern to rank. Geochim. Cosmochim. Acta 46:1831-1848, 1982.
12. Fowland, S.J., Yon, D.A., Lewis, C.A., Maxwell, J.R. Occurrence of 2,6,10-trimethyl-7-(3-methylbutryl)-dodecane and related hydrocarbons in the green alga Enteromorpha prolifera and sediments. Org. Geochem. 8:207-213, 1985.
13. Philp, R.P. Geochemistry in the search for oil. Chem. Eng. News 64:28-43, 1986.
14. Cox, R.E., Maxwell, J.R., Ackman, R.G., Hooper, S.N. Stereochemical studies of acyclic isoprenoid compounds. III. The stereochemistry of naturally occurring (Manne) 2,6,10,14-tetramethylpentadecane. Can. J. Biochem. 50:1238-1241, 1972.
15. Krumbiegel, G., Kosmowska-Ceranowicz, B. Fossile Harze der Umgebung von Halle (Saale) in der Sammbung des Geiseltalmuseums. Wiss. Z. Univ. Halle. 6:5-35, 1992.
16. Trevoy, L.W., Brown, W.G. Mechanism of lithium aluminum hydride reactions. J. Am. Chem. Soc. 71:1657-1678, 1949.
17. Rottlander, R.C.A. On the formation of amber from Pinus resin. Archaeometry 12:35-51, 1970.
18. Erman, W.F. Chemistry of the monoterpenes, an encyclopedic handbook, Gassman, P.G., ed. Studies in Org. Chem. New York; Marcel Dekker, 1985.
19. Armstrong, D.W., Tang, Y., Zukowski, J. Resolution of enantiomeric hydrocarbon biomarkers of geochemical importance. Anal. Chem. 63: 2858-2861, 1991.