Sabinene hydrate, trans

The use of enantiomers as additional markers for taxonomic characterization of aromatic plants may be very helpful. The differences in the enantiomeric distribution of trans- and cis- sabinene hydrates in two Origanum species enable the species to be distinguished in spite of their similar essential oil compositions. A further study on the natural variation of the enantiomeric composition within a wild population may be carried out in order to examine the stability in a taxon (including the possible presence of chemotypes). The enantiomeric ratio of essential oil components is a reliable parameter for assessing quality because it may be indicative of adulteration, contamination, aging, shelf life, technological process and the botanical source of a specific chiral compound. ... 

The bicyclic monoterpenes cis-sabinene hydrate and cit-sabinene hydrate acetate are known as the major and original flavor compounds of marjoram Origanum majorand) Relatively large quantities of cis- and trans-sabinene hydrate were detected in the genus Origanum m-Sabinene hydrate acetate was found in relatively large amounts in solvent and CO2 extracts of O. and as a minor component in hydro-... 

Larkov O, Dunkelblum E, Zada A, Lewinsohn E, Freiman L, Dudai N, Ravid U, Enantiomeric composition of trans- and cis- sabinene hydrate and their acetates in five Origanum spp., Flavour Fragr/22 109—114, 2005. 

Galopin, C. C. A short and efficient synthesis of ( )-trans-sabinene hydrate. Tetrahedron Lett. 2001,42, 5589-5591. 

Composition 30-55% (-)-menthol, 14-32% (-)-menthone, 1.5-10% (-i-)-iso menthone, 2.8-10% menthyl acetate, 3.5-14% 1,8-cineole, 1-9% menthofuran, up to 4% pule-gone [220], as well as 3-octanol, trans-sabinene hydrate, piperitone, viridrflorol, mono- and sesquiterpene hydrocarbons. For further constituents see [221, 222, 223[. On the differentiation between peppermint oils and the detection of dementholised commint oil as a major adulterant see the results of Lawrence et al. [224], The ratio of 1,8-cineole limonene (min. 2) was even implemented in the European Pharmacopoeia. The latter also limits the isopulegol content for Mentha piperita oil to 0.2%. 

Bicydo[3,l)0]hexanes.—Acid-catalysed ethanolysis (80% EtOH) of cis-sabinene hydrate (28) and its trans-isomer (of unspecified chiralities) yields 30% of p-menth-l-en-4-ol it would be of interest to know its optical purity in view of the reports that (+)-trans-sabinene hydrate may be isomerized to p-menth-1- ... 

The GCxGC resolution advantage is known to improve the efficiency of enantioselective essential oil analysis (in contrast to one-dimensional analysis). In a single temperature-programmed analysis, the individual antipodes of optically active components can be separated and are effectively free from matrix interferences. The enantiomeric compositions of a number of monoterpene hydrocarbons and oxygenated monoterpenes in Australian tea tree Melaleuca alternifolia), including sabinene, a-pinene, (3-phellandrene, limonene, trans-sabinene hydrate, ds-sabinene hydrate, linalool, terpinen-4-ol, and a-terpineol shown in Figure 7,... 

Cis- and trans-sabinene hydrate, formerly called thujanol, are the two main tertiary alcohols. They are t5rpical compounds in the marjoram oil Origanum majorana) and a specific chemot5tpe of thyme oils Thymus vulgaris). Sabinol is found in the oil of Juniperus sabina and other Juniperus species. These alcohols occur as free compounds or as acetates. 

Owing to its long-standing limitations, the Stetter reaction has been utQized in a limited number of syntheses (Figure 18.4). P-Unsubstituted acceptors have been used en route to cis-jasmone and dihydrojasmone [57], roseophilin (81) [58], ( )-trans-sabinene hydrate [59], monomorine I [60], and haloperidol [61], while a doubly activated Michael acceptor was used to access an intermediate in the synthesis of atorvastatin [62]. Less reactive P-substituted acceptors could be used intramolecularly in the syntheses of ( )-hirsutic acid C (82) [63], ( )-platensimycin (83) [64], and polycyclic ether arrays [65], as well as in the enantioselective formation of a spirocyclic intermediate toward FD-838 (84) [66]. 

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