Zur Kenntnis der Bestandteile ätherischer Öle. (Über Elemol, ein in der Natur vorkommender monocyclischer Sesquiterpenalkohol, C₁₅ H₂₆ O.)

Abstract

7Y4riolette Farbe, die beim E r w h m e u niit steigender Temperatur inimer mehr in rotviolett iibergeht. Beiiii Erkalten findet wieder Ruckkelir der ursprunglichen Flirbung stntt. In der Farbe der Losungen besteht sonlit. ein bernerkenswerter Gegensatz bei hydrasylfreien und bei Iiytlrosylhaltigen Losungsmitteln. J)ns Azin hat einerseits sehr schwach basische >Sigenschst'ten, cs bildet niit Scturen blaugefiirbte Snlze, die leicht wieder hydrolytisclt gespalten werden, andererseits ist es auch in Nstronlauge mit intensiv tliinkelblauer Farbe Ioslich, die beim Verdiinnen niit Wnsser i n brlunlichgriiu Uhergeht.

Hedycaryol – Central Intermediates in Sesquiterpene Biosynthesis, Part II

“…Without detailed knowledge about its structure, in 1916 Semmler and Liao discovered the first monocyclic sesquiterpene alcohol elemol (2, Scheme 2A) that was isolated from a fraction of the essential oil of the Philippine tree Canarium luzonicum (elemi) obtained by fractional distillation. [19] After establishment of its constitution by Sorm and coworkers, [20] the compound was also found to be the main constituent (60 %) of the essential oil from Hedycarya angustifolia, a small tree native to Australia. [21] The missing optical activity of the chiral compound geijerene (4), the main constituent in the steam distillates from Geijera parviflora, was explained by Jones and Sutherland through their discovery that pregeijerene (3) is the true plant natural product that undergoes a Cope rearrangement during compound isolation.…”

“…[76] All three eudesmols 14-16 yield the same hydrogenation product (+)-18, confirming their consistent absolute configurations. [75] Further proof for this assignment was obtained by synthesis of eudesmols 14-16 from (+)-dihydrocarvone (19). [77,78] The alcohols 14-16 were frequently obtained as a mixture from various plants including different Eucalyptus species, [79,80] Thuja occidentalis [81] and Phebalium ozothamnoides, [50] while the pure compounds were isolated from Callitropsis araucarioides, [82] Cordia trichotoma, [83] and Cryptomeria japonica.…”

“…At the same time the isolation of a compound from Pluchea arguta with same 13 C NMR data (apart from C4, this is likely a typographical error), but with a cisdecalin structure (10-epi-36) was reported ([α] D 29 = + 66.66). [138] This erroneous structural assignment was later corrected based on a total synthesis of (+)-36 ([α] D 29 = + 73.3) from (+)-dihydrocarvone (19). [139] Pterodondiol from Laggera pterodonta for which initially a structure with 7S configuration was published, [140,141] is identical to 36 (with its 7R configuration), as was later demonstrated by X-ray crystallography.…”

The Essential Oil of Dacrydium Kirkii

“…Analysis showed it to be a sesquiterpene alcohol, CibHsbOH, which may be new, since the combined physical properties and dehydrogenation products of fractions 31-34 do not agree with any known compound. Elemol (13,14) is the only sesquiterpene alcohol of similar melting point, values 42°to 52°b eing recorded, but whereas it gives eudalene on dehydrogenation with selenium, fraction 34, from which the solid alcohol had separated gives an azulene and Z-cadinene dihydrochloride (a trace of the latter was also obtained from fraction 33). Elemol also is monocyclic whereas the constants of fraction 34 indicate a dicyclic compound.…”

Monoterpene, Sesquiterpene und dimere Phellandrene aus Manila-Elemi*

“…Em weiterer Sesquiterpen-Alkohol lieB sich nicht soweit anreichern, um Aussagen zu seiner Struktur machen zu kOnnen. Alkohol 29 war als Bestandteil des Manila-Elemi (10) und von drei weiteren Elemiarten bereits bekannt (11)(12)(13).…”