The steam-volatile constituents of Melaleuca viridiflora Sol. ex Gaertn

Australian Journal of Chemistry
1968.0

Abstract

Melaleuca viridi$ora Sol. ex Gaertn. belongs to the group of broad-leaved tea-trees of northern Australia. It occurs from Maryborough in Queensland into New Guinea and across northern Australia into the 15-in, rainfall regi0n.l It is quite distinct from ~Melaleuca quinquenervia (Cav.) S. T. Blake, formerly designated as,Melaleuca viridi$ora Gaertn.2 The steam-volatile oils of this latter species, which exists in two morphologically indistinguishable forms, are characterized by the presence of either nerolidol and linalool or 1,8-cineole and viridiflorol.3 The steam-volatile oils of.Melaleuca vi~idi$ora obtained from foliage collected in two different localities on the Cape York Peninsula in northern Queensland were shown to consist of methyl cinnamate (c. 75%) and trans-p-ocimene (I) (c. 20%), with only small amounts of other components. Amongst these, only eugenol (c. 1%) and linalool (c. 0.5%) were identified with certainty. The identification of transp-ocimene was based on spectral and other physical data (see Table 1). This identification was confirmed by the preparation of 7-carboxy-2-isopropylidene-4-n1ethyl-2,3,3a,G,7,7a-hexahydroindanone (11) from its n~aleic anhydride adduct according to the method of Joseph and Rae.* The indanone derivative (11) was obtained in a high yield (c. 70%). It also has a high melting point (m.p. 213-214") and thus appears suitable for the purpose of identifying trans-p-ocimene, a hydrocarbon otherwise difficult to characterize. However, the possibility that transa-ocimene (111) would yield the same indanone derivative (11) at the high temperature used cannot be ruled out completely. Reinvestigation of the steam-volatile oil of Homoranthus Jlavescens A. Cunn. showed that the ocimene previously reported5 is, in fact, trans-p-ocimene.

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