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Mass spectrometric characteristics of two novel series of ring‐C monounsaturated tricyclic terpenes found in Tasmanian tasmanite
Author(s) -
de Almeida Azevedo Débora,
de Aquino Neto Francisco Radler,
Simoneit Bernd Rolf Tatsuo
Publication year - 1995
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1190300204
Subject(s) - chemistry , terpene , tricyclic , homologous series , mass spectrum , ring (chemistry) , diastereomer , stereochemistry , electron ionization , isomerization , organic chemistry , computational chemistry , mass spectrometry , chromatography , ionization , ion , catalysis
Electron impact and methane chemical ionization mass spectra were measured for two homologous series of monounsaturated tricyclic terpenes, Δ 9(11) and Δ 13(14) . The double bond position was inferred by interpretation of their mass spectra, comparisons with the known saturated and ring‐C monoaromatic series, published mass spectrometric data on other terpenoids and MM2 calculations. The distributions of Δ 13(14) ‐ and Δ 9(11) ‐monounsaturated tricyclic terpene isomers were shown by theory and from experimental data to be dependent on the chain length at position 14. These two series coexist in the same geological sample. Δ 9(11) ‐monounsaturated tricyclic terpenes can be derived from the Δ 13(14) compounds by isomerization of the double bond. The Δ 9(11) ‐monounsaturated tricyclic terpene series extends from C 19 to C 40 and the Δ 13(14) series from C 21 to C 40 . The diastereomers >C 28 for both series could be resolved by gas chromatography.