Abietane
Names
IUPAC name
Abietane
Systematic IUPAC name
(4aR ,4bS ,7S ,8aS ,10aS )-1,1,4a-Trimethyl-7-(propan-2-yl)tetradecahydrophenanthrene
Other names
13α-Isopropylpodocarpane
Identifiers
ChEBI
ChemSpider
InChI=1S/C20H36/c1-14(2)15-7-9-17-16(13-15)8-10-18-19(3,4)11-6-12-20(17,18)5/h14-18H,6-13H2,1-5H3/t15-,16-,17-,18-,20+/m0/s1
Y Key: STIVVCHBLMGYSL-ZYNAIFEFSA-N
Y
[H][C@]12[C@@](C[C@@H](C(C)C)CC2)([H])CC[C@@]3([H])C(C)(C)CCC[C@@]31C
Properties
C 20 H 36
Molar mass
276.508 g·mol−1
Density
0.876 g/ml
Boiling point
338
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Abietane is a diterpene that forms the structural basis for a variety of natural chemical compounds such as abietic acid ,[ 1] carnosic acid , and ferruginol which are collectively known as abietanes or abietane diterpenes .
Abietanes are found in the tissues and resins of certain higher plants, particularly gymnosperms .[ 2] [ 3] Although the functions of terpenes are not fully understood, conifers appear to produce abietane diterpenoids as a form of defense against insect and microbial attack.[ 4] [ 5] Some abietane diterpenoids, especially aromatic abietenes, are of interest to the pharmacology and natural products communities for their potential biological activities.[ 6] In the rock record, abietanes are commonly found in amber as well as in fossil wood , sometimes in the form of the mineral fichtelite . Additionally, abietanes are observed in sediments—both riverine and marine—and in coals , where they are often interpreted as geochemical biomarkers for terrestrial input from conifers.[ 2] [ 7] [ 4] [ 8] [ 9]
^ San Feliciano, Arturo; Gordaliza, Marina; Salinero, Miguel A.; Miguel del Corral, Jose M (1993). "Abietane acids: sources, biological activities, and therapeutic uses" . Planta Medica . 59 (6): 485–490. doi :10.1055/s-2006-959744 . PMID 8302943 .
^ a b Otto, A.; Walther, H.; Püttmann, W. (January 1997). "Sesqui- and diterpenoid biomarkers preserved in Taxodium-rich Oligocene oxbow lake clays, Weisselster basin, Germany" . Organic Geochemistry . 26 (1–2): 105–115. Bibcode :1997OrGeo..26..105O . doi :10.1016/s0146-6380(96)00133-7 . ISSN 0146-6380 .
^ Diefendorf, Aaron F.; Freeman, Katherine H.; Wing, Scott L. (2012-05-15). "Distribution and carbon isotope patterns of diterpenoids and triterpenoids in modern temperate C3 trees and their geochemical significance" . Geochimica et Cosmochimica Acta . 85 : 342–356. Bibcode :2012GeCoA..85..342D . doi :10.1016/j.gca.2012.02.016 . ISSN 0016-7037 .
^ a b Freeman, K.H.; Pancost, R.D. (2014), "Biomarkers for Terrestrial Plants and Climate" , Treatise on Geochemistry , Elsevier, pp. 395–416, doi :10.1016/b978-0-08-095975-7.01028-7 , ISBN 978-0-08-098300-4 , retrieved 2021-05-10
^ Mason, Charles J.; Klepzig, Kier D.; Kopper, Brian J.; Kersten, Philip J.; Illman, Barbara L.; Raffa, Kenneth F. (June 2015). "Contrasting Patterns of Diterpene Acid Induction by Red Pine and White Spruce to Simulated Bark Beetle Attack, and Interspecific Differences in Sensitivity Among Fungal Associates" . Journal of Chemical Ecology . 41 (6): 524–532. Bibcode :2015JCEco..41..524M . doi :10.1007/s10886-015-0588-4 . ISSN 0098-0331 . PMID 26003180 . S2CID 1506353 .
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^ Simoneit, Bernd R.T.; Grimalt, J.O.; Wang, T.G.; Cox, R.E.; Hatcher, P.G.; Nissenbaum, A. (January 1986). "Cyclic terpenoids of contemporary resinous plant detritus and of fossil woods, ambers and coals" . Organic Geochemistry . 10 (4–6): 877–889. Bibcode :1986OrGeo..10..877S . doi :10.1016/s0146-6380(86)80025-0 . ISSN 0146-6380 .
^ Cite error: The named reference :4
was invoked but never defined (see the help page ).
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