Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae
Authors
Nytoft, Hans PeterKildahl-Andersen, Geir
Lindström, Sofie
Rise, Frode
Bechtel, Achim
Mitrović, Danica D.
Đoković, Nataša
Životić, Dragana R.
Stojanović, Ksenija A.
Article (Accepted Version)
Metadata
Show full item recordAbstract
Two previously unidentified dehydroabietane isomers were isolated from Miocene Serbian
lignite and Rhaetian (Late Triassic) coaly mudstones from South Sweden and characterized using
NMR-spectroscopy as cis- and trans-dehydroicetexane. Both have a 9(10→20)-abeo-abietane or
icetexane skeleton consisting of a 6-7-6 tricyclic framework with seven carbons in ring B instead of
the usual six in common diterpanes of the abietane-type. Dehydroicetexanes can be detected using GC-MS-MS in m/z 270 → 146 chromatograms without interference from dehydroabietane or other isomers. Dehydroicetexanes are often abundant in high latitude coals and mudstones ranging fromTriassic to Miocene, and in high latitude oils (Canada and Greenland) sourced from terrigenous organic matter. The trans/(cis+ trans) dehydroicetexane ratio is low in immature sediments, but usually around 0.83 in oils and mature sediments with vitrinite reflectance (%Rr) above 0.5 suggesting an equilibrium from the start of the oil wind...ow. Dehydroicetexanes are more stable than dehydroabietane and some oils, rich in dehydroicetexanes, contain no dehydroabietane. Precursors could be plant diterpenoids having the icetexane structure, which have been known for more than 40 years and isolated from a variety of higher plant sources, including some angiosperms. Many of the relatively simple icetexanes were isolated for the first time from Chamaecyparis pisifera and related species where they seem to be particularly abundant, suggesting that dehydroicetaxanes may be used as markers for the genus Chamaecyparis or for Cupressoideae in general.
Keywords:
dehydroicetexane / dehydroabietane / coal / crude oil / Triassic-Jurassic boundary / NMR / HPLC / GC-MS / GC-MS-MSSource:
Organic Geochemistry, 2019Publisher:
- Elsevier
Funding / projects:
- Geochemical investigations of sedimentary rocks - fossil fuels and environmental pollutants (RS-MESTD-Basic Research (BR or ON)-176006)
Note:
- This is the peer-reviewed version of the following article: Nytoft, H. P.; Kildahl-Andersen, G.; Lindström, S.; Rise, F.; Bechtel, A.; Mitrović, D.; Đoković, N.; Životić, D.; Stojanović, K. A. Dehydroicetexanes in Sediments and Crude Oils: Possible Markers for Cupressoideae. Organic Geochemistry 2019, 129, 14–23. https://doi.org/10.1016/j.orggeochem.2019.01.001
DOI: 10.1016/j.orggeochem.2019.01.001
ISSN: 0146-6380
WoS: 000460896700002
Scopus: 2-s2.0-85061249011
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Institution/Community
Inovacioni centar / Innovation CentreTY - JOUR AU - Nytoft, Hans Peter AU - Kildahl-Andersen, Geir AU - Lindström, Sofie AU - Rise, Frode AU - Bechtel, Achim AU - Mitrović, Danica D. AU - Đoković, Nataša AU - Životić, Dragana R. AU - Stojanović, Ksenija A. PY - 2019 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2811 AB - Two previously unidentified dehydroabietane isomers were isolated from Miocene Serbian lignite and Rhaetian (Late Triassic) coaly mudstones from South Sweden and characterized using NMR-spectroscopy as cis- and trans-dehydroicetexane. Both have a 9(10→20)-abeo-abietane or icetexane skeleton consisting of a 6-7-6 tricyclic framework with seven carbons in ring B instead of the usual six in common diterpanes of the abietane-type. Dehydroicetexanes can be detected using GC-MS-MS in m/z 270 → 146 chromatograms without interference from dehydroabietane or other isomers. Dehydroicetexanes are often abundant in high latitude coals and mudstones ranging fromTriassic to Miocene, and in high latitude oils (Canada and Greenland) sourced from terrigenous organic matter. The trans/(cis+ trans) dehydroicetexane ratio is low in immature sediments, but usually around 0.83 in oils and mature sediments with vitrinite reflectance (%Rr) above 0.5 suggesting an equilibrium from the start of the oil window. Dehydroicetexanes are more stable than dehydroabietane and some oils, rich in dehydroicetexanes, contain no dehydroabietane. Precursors could be plant diterpenoids having the icetexane structure, which have been known for more than 40 years and isolated from a variety of higher plant sources, including some angiosperms. Many of the relatively simple icetexanes were isolated for the first time from Chamaecyparis pisifera and related species where they seem to be particularly abundant, suggesting that dehydroicetaxanes may be used as markers for the genus Chamaecyparis or for Cupressoideae in general. PB - Elsevier T2 - Organic Geochemistry T1 - Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae DO - 10.1016/j.orggeochem.2019.01.001 ER -
@article{ author = "Nytoft, Hans Peter and Kildahl-Andersen, Geir and Lindström, Sofie and Rise, Frode and Bechtel, Achim and Mitrović, Danica D. and Đoković, Nataša and Životić, Dragana R. and Stojanović, Ksenija A.", year = "2019", abstract = "Two previously unidentified dehydroabietane isomers were isolated from Miocene Serbian lignite and Rhaetian (Late Triassic) coaly mudstones from South Sweden and characterized using NMR-spectroscopy as cis- and trans-dehydroicetexane. Both have a 9(10→20)-abeo-abietane or icetexane skeleton consisting of a 6-7-6 tricyclic framework with seven carbons in ring B instead of the usual six in common diterpanes of the abietane-type. Dehydroicetexanes can be detected using GC-MS-MS in m/z 270 → 146 chromatograms without interference from dehydroabietane or other isomers. Dehydroicetexanes are often abundant in high latitude coals and mudstones ranging fromTriassic to Miocene, and in high latitude oils (Canada and Greenland) sourced from terrigenous organic matter. The trans/(cis+ trans) dehydroicetexane ratio is low in immature sediments, but usually around 0.83 in oils and mature sediments with vitrinite reflectance (%Rr) above 0.5 suggesting an equilibrium from the start of the oil window. Dehydroicetexanes are more stable than dehydroabietane and some oils, rich in dehydroicetexanes, contain no dehydroabietane. Precursors could be plant diterpenoids having the icetexane structure, which have been known for more than 40 years and isolated from a variety of higher plant sources, including some angiosperms. Many of the relatively simple icetexanes were isolated for the first time from Chamaecyparis pisifera and related species where they seem to be particularly abundant, suggesting that dehydroicetaxanes may be used as markers for the genus Chamaecyparis or for Cupressoideae in general.", publisher = "Elsevier", journal = "Organic Geochemistry", title = "Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae", doi = "10.1016/j.orggeochem.2019.01.001" }
Nytoft, H. P., Kildahl-Andersen, G., Lindström, S., Rise, F., Bechtel, A., Mitrović, D. D., Đoković, N., Životić, D. R.,& Stojanović, K. A.. (2019). Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae. in Organic Geochemistry Elsevier.. https://doi.org/10.1016/j.orggeochem.2019.01.001
Nytoft HP, Kildahl-Andersen G, Lindström S, Rise F, Bechtel A, Mitrović DD, Đoković N, Životić DR, Stojanović KA. Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae. in Organic Geochemistry. 2019;. doi:10.1016/j.orggeochem.2019.01.001 .
Nytoft, Hans Peter, Kildahl-Andersen, Geir, Lindström, Sofie, Rise, Frode, Bechtel, Achim, Mitrović, Danica D., Đoković, Nataša, Životić, Dragana R., Stojanović, Ksenija A., "Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae" in Organic Geochemistry (2019), https://doi.org/10.1016/j.orggeochem.2019.01.001 . .