(3R,4S,5S,8S,10R,13R)-3-Hydroxykaura-9(11),16-dien-18-oic acid

Beattie, Karren D. and Bhadbhade, Mohan M. and Craig, Donald C. and Leach, David N. (2012) (3R,4S,5S,8S,10R,13R)-3-Hydroxykaura-9(11),16-dien-18-oic acid. Acta Crystallographica Section E: Structure Reports Online, 68 (2). o526-o527.


The title compound, C(20)​H(28)​O(3)​, was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae)​. The enanti-​opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-​membered rings in chair, twist-​boat, half-​chair and envelope conformations, respectively. Each mol-​ecule makes one intra- and one inter-​molecular O-​H(midline ellipsis)​O hydrogen bond in the crystal lattice, forming hydrogen-​bonded chains along [010]​. The absolute configuration of the compound was assigned on the basis of optical rotation measurements.

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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Faculty/School / Institute/Centre: No Faculty
Faculty/School / Institute/Centre: No Faculty
Date Deposited: 17 Aug 2014 12:25
Last Modified: 02 Feb 2017 05:03
Uncontrolled Keywords: kaurane diterpene, crystal structure, Centipeda cunninghamii
Fields of Research (2008): 03 Chemical Sciences > 0306 Physical Chemistry (incl. Structural) > 030606 Structural Chemistry and Spectroscopy
03 Chemical Sciences > 0305 Organic Chemistry > 030502 Natural Products Chemistry
Fields of Research (2020): 34 CHEMICAL SCIENCES > 3403 Macromolecular and materials chemistry > 340399 Macromolecular and materials chemistry not elsewhere classified
34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340502 Natural products and bioactive compounds
Socio-Economic Objectives (2008): E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences
Identification Number or DOI: https://doi.org/10.1107/S1600536812002206
URI: http://eprints.usq.edu.au/id/eprint/25712

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