Epoxidation caryophyllene

Menthol (hRf 15) and menthyl acetate hRt 55) yielded blue chromatogram zones caryophyllene hRf 90) and caryophyllene epoxide hRf 20 — 25) appeared red-violet and thymol hRf 40 — 45) appeared brick red in color. 

Fig. 1 Schematic sketch (A) of the separation of essential oil components (ca. 500 ng of each component) and reflectance scan of the mixture (B). Menthol (1), caryophyllene epoxide (2), thymol (3), menthyl acetate (4), caryophyllene (5), mixture (G).

Bromisoval (h/ f 15-20) yielded dark brown chromatogram zones on a light brown background. Bromopride, bromazepam, bromhexine, bromocriptine, caryophyllene epoxide and rose oxide did not react. 

SYNS CARYOPHYLLENE EPOXIDE CARYOPHYLLENE OXIDE (-)-CARYOPHYLLENE OXIDE P-CARYOPHYLLENE OXIDE EPOXY-CARYOPHYLLENE (-)-EPOXYDIHYDROCARY-OPHYLLENE 5-OXATRICYCLO(8.2.0.0 > DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R,4R,6R,10S)- 4.11.11-TRIMETHYL-8-METHYLENE-50XATRI-CYCL0-(8.2.0.0(4,6))DODECANE... 

Group 32 shows various epoxides like p-caryophyllene epoxide (Flavis 16.043). 

Using the most active catalyst (CoNaY) we have studied the oxidation of olefins of different structure and size of molecules, including a number of natural terpenes, namely, (+)-a-pinene (1), (+)-3-carene (2), (-)-caryophyllene (3) and dipentene (4). We have found that even acid-sensitive epoxides that are known to be prone to ring cleavage (caryophyllene epoxide, for example) can be obtained with high-to-exceUent selectivity (Table 2). It is noteworthy that neither allylic oxidation nor overoxidation occurs in the systems studied. Diolefins give mono-... 

Linalyl acetate (30%-55%), linalool (20%-3,5%), with small quantitie.5 of nerol, borneol, fVocimeii, geraniol, dneole, caryophyllene-epoxide, camphene... 

P-Caryophyllene alcohol acetate. See Caryophyllene alcohol acetate Caryophyllene epoxide p-Caryophyllene epoxide. See P-Caryophyllene oxide P-Caryophyllene oxide CAS 1139-30-6 EINECS/ELINCS 214-519-7 Synonyms Caryophyllene epoxide p-Caryophyllene epoxide Epoxycaryophyllene (-... 

Leaf cutter ants, abundant from Texas to Argentina, are polyphagous herbivores, but will not attack several plants. The ant, Atta cephalotes, for example, does not feed on Lasi-anthaea fruticosa (Asteraceae). The active repellent substance is lasidiol angelate (51) (Wiemer and Ales, 1981). Three of four other inhibitory compounds to ant feeding, nerolidol (7), caryophyllene epoxide (52), kolavenol (a diter-pene), and caiyophyllene (not active), either produced dramatic effects on the ants or the fungus cultivated by the ants (Howard et al., 1988). 

FIGURE 20.133 Biotransformation of (-)-P-caryophyllene epoxide (453) by various fungi. 

The structure of the frequently occurring bicyclic sesquiterpene 6-caryophyllene was for many years a matter of doubt. After numerous investigations W. Treibs (1952) has been able to isolate the crystalline caryophyllene epoxide from the autoxidation products of clove oil and F. Sorm et al. (1950) suggested caryophyllene to have a 4- and 9-membered ring on bases of infrared (IR) investigations. This suggestion was later confirmed by the Fnglish chemist D. H. R. Barton (Barton and Lindsay, 1951), who was awarded the Nobel Prize in Chemistry in 1969. 

Roots of Echinacea purpurea contain up to 0.2% essential oil [4, 14,15, 21, 67, 69, 74]. According to Becker [75] and Martin [76] it is composed of 2.1% caryophyl-lene, 0.6% humulene and 1.3% caryophyllene epoxide. Heinzer et al. [14] have analyzed the essential oil by gas chromatography-mass spectrometry (GC-MS) and found compounds of the type dodeca-2,4- dien-l-yl-isovalerate, as well as palmitic and linolenic acid, vanillin, p-hydroxycinnamic acid methyl ester and germacrene D, which had already been reported by Bohlmann and Hoffmann [27] for the aerial parts of the plant. Nevertheless, . purpurea roots are not a typical essential oil drug, and therefore analysis of the essential oil has not been used often for standardization purposes of phytopreparations. However, gas chromatography of the essential oil can be used for the discrimination of the species (see Fig. 1) [14]. 

Flowering aerial parts of E. purpurea contain less than 0.1% essential oil [14, 21, 67, 69, 74]. Bos et al. [96] showed that it contains borneol, bornyl acetate, pen-tadeca-8-en-2-one, germacrene D, caryophyllene, caryophyllene epoxide and palm-... 

Hashizume, T., and I. Sakata Constituents of Japanese Peppermint Oil. II. Isolation and Identification of ( —)-p-Caryophyllene Epoxide from Okako No. 6 . Agric. Biol. Chem. 34, 638 (1970). 

Thappa, R. K., V. N. Vashist, J. Singh, and R. K. Sharma Caryophyllene Epoxide from the Oil of Artemisia scoparia, Elsholtzia polystacha, Piper hookeri, and Piper... 

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