Incensole oxide

The chemical composition of B. papyrifera olibanum is markedly different from that of other Boswellia, with small amounts of monoterpenes and sesquiterpenes, large amounts of w-octanol (18) and -octy I acetate (40), with the latter being the major compound, and the presence of particular diterpenes [incensole (127), incen-sole acetate (129), incensole oxide (130) and incensole oxide acetate (131)] and the absence of both isoincensole and isoincensole acetate (128). Linear carboxylic acids from hexanoic acid (10) to lauric acid (93) were also identified in B. papyrifera olibanum exclusively. 

Figure 10.7 Total ion current chromatograms obtained after headspace SPME for (a) incense from Mount Athos and (b) B. papyrifera olibanum. Peak labels correspond to compound identification given in Table 10.3. The occurrence of the following biomarkers of B. papyrifera olibanum in the incense from Mount Athos are a clear indication of its botanical origin n octanol (18), n octylacetate (40), incensole (127), incensole acetate (129), incensole oxide (130) and incensole oxide acetate (131). Artefacts. Reproduced from S. Hamm, J. Bleton,). Connan, A. Tchapla, Phytochemistry, 66, 1499 1514. Copyright 2005 Elsevier Limited...

Frankincense, also called olibanum, is a natural oleo gum resin that exudes from incisions in the bark of Boswellia trees [46, 47]. Diterpenes like incensole or isoincensole and their oxide or acetate derivatives (see Figure 10.3) are characteristic biomarkers of olibanum [48]. Although diterpenoid hydrocarbons possessing the cembrane skeleton have been isolated from a variety of terrestrial and marine organisms, their occurrence and particularly that of cembrenes A and C (see Figure 10.3) is supplementary proof of the presence of olibanum in a sample. Optimisation of the SPME conditions was done with the aim of trapping these low volatile diterpenes. 

The samples coming from Eritrea, Jerusalem and Liban could be undoubtedly attributed to B. papyrifera, because of their characteristic constituents octanol (18), octyl acetate (40), linear caboxylic acids (10, 20, 36, 49, 63), incensole (127) and its acetate and oxide derivatives (129-131). 

Incensole (113) and isoincensole oxide (114) have been synthesized from muku-lol by methods which allow the determination of their stereochemistry. The X-ray analysis of a thunbergadienediol (115), obtained from Greek tobacco, has been described. ... 

A small amount of isoincensole oxide (116) has been isolated from frankincense, the resin of Boswellia carteri. It is also a minor product of the epoxidation of incensole. The epoxide ring is very inert in this compound. 

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