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Biologically Important Eremophilane Sesquiterpenes from Alaska Cedar Heartwood Essential Oil and Their Semi-Synthetic Derivatives

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Author(s): Mohammad A. Khasawneh | Yeping Xiong | Javier Peralta-Cruz | Joe J. Karchesy

Journal: Molecules
ISSN 1420-3049

Volume: 16;
Issue: 6;
Start page: 4775;
Date: 2011;
Original page

Keywords: eremophilane sesquiterpenes | nootkatol | valencene-13-ol | stereochemistry | Chamaecyparis nootkatensis

ABSTRACT
The essential oil of Alaska cedar heartwood is known to contain compounds which contribute to the remarkable durability of this species. While previous research has identified several compounds, a complete description of this oil has not been undertaken. In this research a profile of the oil is given in which the major components are identified by GC, isolation and spectroscopic techniques. The major components of the steam distilled essential oil were identified as nootkatin, nootkatone, valencene, nootaktene, carvacrol, methyl carvacrol, nootkatol (2), and eremophil-1(10),11-dien-13-ol (3). The last two compounds were isolated for the first time from Alaska cedar in this research. The absolute stereochemistry at C-2 of nootkatol was shown to have the (S) configuration using the Mosher ester method. Assignment of stereochemistry for valencene-13-ol (3) was established by synthesis from valencene (6). Finally, two related sesquiterpenoids were synthesized from nootkatone and valencene. These sesquiterpenoids were nootkatone-1,10-11,12-diepoxide (5) and valencene-13-aldehyde (4), respectively.

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