Abietane

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
3D model (JSmol)
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 checkY
    Key: STIVVCHBLMGYSL-ZYNAIFEFSA-N checkY
  • [H][C@]12[C@@](C[C@@H](C(C)C)CC2)([H])CC[C@@]3([H])C(C)(C)CCC[C@@]31C
Properties
C20H36
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).
☒N verify (what is checkY☒N ?)

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]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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
  5. ^ 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.
  6. ^ Cite error: The named reference :9 was invoked but never defined (see the help page).
  7. ^ 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.
  8. ^ Cite error: The named reference :4 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).