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Compound "J'' in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18 beta(H)-oleanane

Samo za registrovane korisnike
2014
Autori
Nytoft, Hans Peter
Kildahl-Andersen, Geir
Šolević Knudsen, Tatjana
Stojanović, Ksenija
Rise, Frode
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
A C-30 pentacyclic triterpane eluting slightly after 18 alpha(H)-oleanane in the m/z 191 mass chromatograms of Late Cretaceous/Tertiary terrigenous oils (peak "J'' in the early literature) has been isolated from a Niger Delta oil and identified using NMR spectroscopy as 3 beta-methyl-24-nor-18 alpha(H)-oleanane. The previous assignment as 18 beta(H)-oleanane is therefore partly erroneous. 3 beta-Methyl-24-nor-18 alpha(H)-oleanane affords a larger m/z 412 -> 356 response than the oleananes and the relative contribution of 3 beta-methyl-24-nor-18 alpha(H)-oleanane to the 412 -> 191 "oleanane peak'' can be roughly estimated from comparison of the 412 -> 356/412 -> 191 ratio from the oleanane peak with that of the pure compounds. 3 beta-Methyl-24-nor-18 alpha(H)-oleanane can be as abundant as 18a(H)-oleanane in oils having a high concentration of early eluting rearranged oleananes. 3 beta-Methyl-24-nor-19 alpha(H)-taraxastane was also tentatively assigned in the oils on the basis of its ma...ss spectrum as well as its gas chromatography and high performance liquid chromatography retention times. 3 beta-Methyl-24-nor-gammacerane was tentatively assigned in a similar way in an oil containing gammacerane. All 3 beta-methyl-24-nor-triterpanes could be formed via dehydration, rearrangement and hydrogenation of triterpenoids having an OH group at C-3.

Ključne reči:
Biomarkers / Oleananes / Rearranged oleananes / Crude oil / NMR / HPLC / GC-MS
Izvor:
Organic Geochemistry, 2014, 77, 89-95
Izdavač:
  • Pergamon-Elsevier Science Ltd, Oxford
Projekti:
  • Geohemijska ispitivanja sedimentnih stena - fosilna goriva i zagađivači životne sredine (RS-176006)
  • Organisation for the Prohibition of Chemical Weapons (OPCW)

DOI: 10.1016/j.orggeochem.2014.09.010

ISSN: 0146-6380

WoS: 000345430500008

Scopus: 2-s2.0-84908328465
[ Google Scholar ]
8
7
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1470
Kolekcije
  • Radovi istraživača / Researchers' publications
Institucija
IHTM
TY  - JOUR
AU  - Nytoft, Hans Peter
AU  - Kildahl-Andersen, Geir
AU  - Šolević Knudsen, Tatjana
AU  - Stojanović, Ksenija
AU  - Rise, Frode
PY  - 2014
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/1470
AB  - A C-30 pentacyclic triterpane eluting slightly after 18 alpha(H)-oleanane in the m/z 191 mass chromatograms of Late Cretaceous/Tertiary terrigenous oils (peak "J'' in the early literature) has been isolated from a Niger Delta oil and identified using NMR spectroscopy as 3 beta-methyl-24-nor-18 alpha(H)-oleanane. The previous assignment as 18 beta(H)-oleanane is therefore partly erroneous. 3 beta-Methyl-24-nor-18 alpha(H)-oleanane affords a larger m/z 412 -> 356 response than the oleananes and the relative contribution of 3 beta-methyl-24-nor-18 alpha(H)-oleanane to the 412 -> 191 "oleanane peak'' can be roughly estimated from comparison of the 412 -> 356/412 -> 191 ratio from the oleanane peak with that of the pure compounds. 3 beta-Methyl-24-nor-18 alpha(H)-oleanane can be as abundant as 18a(H)-oleanane in oils having a high concentration of early eluting rearranged oleananes. 3 beta-Methyl-24-nor-19 alpha(H)-taraxastane was also tentatively assigned in the oils on the basis of its mass spectrum as well as its gas chromatography and high performance liquid chromatography retention times. 3 beta-Methyl-24-nor-gammacerane was tentatively assigned in a similar way in an oil containing gammacerane. All 3 beta-methyl-24-nor-triterpanes could be formed via dehydration, rearrangement and hydrogenation of triterpenoids having an OH group at C-3.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Organic Geochemistry
T1  - Compound "J'' in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18 beta(H)-oleanane
VL  - 77
SP  - 89
EP  - 95
DO  - 10.1016/j.orggeochem.2014.09.010
ER  - 
@article{
author = "Nytoft, Hans Peter and Kildahl-Andersen, Geir and Šolević Knudsen, Tatjana and Stojanović, Ksenija and Rise, Frode",
year = "2014",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/1470",
abstract = "A C-30 pentacyclic triterpane eluting slightly after 18 alpha(H)-oleanane in the m/z 191 mass chromatograms of Late Cretaceous/Tertiary terrigenous oils (peak "J'' in the early literature) has been isolated from a Niger Delta oil and identified using NMR spectroscopy as 3 beta-methyl-24-nor-18 alpha(H)-oleanane. The previous assignment as 18 beta(H)-oleanane is therefore partly erroneous. 3 beta-Methyl-24-nor-18 alpha(H)-oleanane affords a larger m/z 412 -> 356 response than the oleananes and the relative contribution of 3 beta-methyl-24-nor-18 alpha(H)-oleanane to the 412 -> 191 "oleanane peak'' can be roughly estimated from comparison of the 412 -> 356/412 -> 191 ratio from the oleanane peak with that of the pure compounds. 3 beta-Methyl-24-nor-18 alpha(H)-oleanane can be as abundant as 18a(H)-oleanane in oils having a high concentration of early eluting rearranged oleananes. 3 beta-Methyl-24-nor-19 alpha(H)-taraxastane was also tentatively assigned in the oils on the basis of its mass spectrum as well as its gas chromatography and high performance liquid chromatography retention times. 3 beta-Methyl-24-nor-gammacerane was tentatively assigned in a similar way in an oil containing gammacerane. All 3 beta-methyl-24-nor-triterpanes could be formed via dehydration, rearrangement and hydrogenation of triterpenoids having an OH group at C-3.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Organic Geochemistry",
title = "Compound "J'' in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18 beta(H)-oleanane",
volume = "77",
pages = "89-95",
doi = "10.1016/j.orggeochem.2014.09.010"
}
Nytoft HP, Kildahl-Andersen G, Šolević Knudsen T, Stojanović K, Rise F. Compound "J'' in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18 beta(H)-oleanane. Organic Geochemistry. 2014;77:89-95
Nytoft, H. P., Kildahl-Andersen, G., Šolević Knudsen, T., Stojanović, K.,& Rise, F. (2014). Compound "J'' in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18 beta(H)-oleanane.
Organic GeochemistryPergamon-Elsevier Science Ltd, Oxford., 77, 89-95.
https://doi.org/10.1016/j.orggeochem.2014.09.010
Nytoft Hans Peter, Kildahl-Andersen Geir, Šolević Knudsen Tatjana, Stojanović Ksenija, Rise Frode, "Compound "J'' in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18 beta(H)-oleanane" 77 (2014):89-95,
https://doi.org/10.1016/j.orggeochem.2014.09.010 .

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