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Planta Med 2002; 68(10): 949-950
DOI: 10.1055/s-2002-34931
DOI: 10.1055/s-2002-34931
Letter
© Georg Thieme Verlag Stuttgart · New York
The Guaiol Color Reaction
Further Information
Publication History
Received: March 8, 2002
Accepted: June 15, 2002
Publication Date:
21 October 2002 (online)
![](https://www.thieme-connect.de/media/plantamedica/200210/lookinside/thumbnails/10.1055-s-2002-34931-1.jpg)
Abstract
The common and biogenetically important sesquiterpene guaiol yields a deep purple color when treated with electrophilic bromine reagents. This interesting color reaction was observed over fifty years ago, but the chemistry of this process has not been investigated. Herein, we present the chemistry of the guaiol color reaction.
References
- 1 Yan X, Zhou J, Xie G. Traditional Chinese Medicines: molecular structures, natural sources, and applications. In: Milne GWA, editor Ashgate Publishing Brookfield VT; 1999
- 2 Krishnan S, Paknikar S K, Bates R B, Bhattacharya S C. Oxidation products of guaiol. Indian Journal of Chemistry. 1972; 10 320-1
- 3 Winter R EK, Baker J A, Lam B V, Breite A G, Rath N. On guaiol oxidation products. Natural Products Letters. 1997; 10 105-9
- 4 Waddell T G, Carter A D, Miller T J, Pagni R M. Chromium(VI) oxidation of tertiary unsaturated alcohols. Oxidative fragmentation of 2-substituted bicyclo[2.2.1]hept-5-en-2-ols. Journal of Organic Chemistry. 1992; 57 381-3
- 5 Neuhaus J WG, Reuter F H. A note on some minor constituents of the wood oil of Callitris glauca . Australian Chemical Institute Journal & Proceedings. 1948; 15 185-9
- 6 Harris C M, McKern H HG. Occurrence of guaiol in some essential oils of Eucalyptus citridora . Museum of Technology and Applied Science. 1950; 2 15-6
- 7 Geissman T A, Griffin T S. Sesquiterpene lactones: Acid-catalysed color reactions as an aid in structure determination. Phytochemistry. 1971; 10 2475-85
- 8 Griffin T S, Geissman T A, Winters T E. The chemistry of a structurally diagnostic color reaction of xanthinin and related sesquiterpene lactones. Phytochemistry. 1971; 10 2487-95
- 9 . CAChe Scientific, Computer-aided chemistry from the Oxford Molecular Group.
- 10 Bates R B, Slagel R C. β-Bulnesene, α-guaiene, β-patchoulene, and guaioxide in essential oils. Chemistry and Industry 1962: 1715-6
- 11 Ishii H, Tozyo T, Minato H. Structure elucidation of guaioxide by microbial oxidation. Chemical Communications 1968: 649-51
- 12 Kadival M V, Nair M SR, Bhattacharya S C. Terpenoids - XCVI: Dehydration reaction of guaiol and dihydroguaiols and transformation of 1α, 5α-dihydroguaiol to 1α, 5α-hexahydrodehydrocostus lactone. Tetrahedron. 1967; 23 1241-9
Thomas G. Waddell
Department of Chemistry
University of Tennessee, Chattanooga
Chattanooga, TN 37403
U.S.A.
Email: Thomas-Waddell@utc.edu
Fax: +1-423-755-5234