Ferruginol

Ferruginol
Names
IUPAC name
Abieta-8,11,13-trien-12-ol
Systematic IUPAC name
(4bS,8aS)-4b,8,8-Trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1 checkY
    Key: QXNWVJOHUAQHLM-AZUAARDMSA-N checkY
  • InChI=1/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1
    Key: QXNWVJOHUAQHLM-AZUAARDMBU
  • Oc1c(cc2c(c1)[C@]3(CCCC([C@@H]3CC2)(C)C)C)C(C)C
Properties
C20H30O
Molar mass 286.459 g·mol−1
Density 1.0±0.1 g/cm3
Melting point 56-57 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ferruginol is a natural phenol with a terpenoid substructure. Specifically, it is a diterpene of the abietane chemical class, meaning it is characterized by three fused six-membered rings and alkyl functional groups. Ferruginol was first identified in 1939 by Brandt and Neubauer as the main component in the resin of the Miro tree (Podocarpus ferrugneus)[1] and has since been isolated from other conifer species in the families Cupressaceae and Podocarpaceae. As a biomarker, the presence of ferruginol in fossils, mainly resin, is used to describe the density of these conifers in that particular biosphere throughout time.

  1. ^ Brandt, C. W.; Neubauer, L. G. (1939-01-01). "221. Miro resin. Part I. Ferruginol". Journal of the Chemical Society (Resumed): 1031–1037. doi:10.1039/JR9390001031. ISSN 0368-1769.