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Linalool structure

These regular monoterpenes constitute a small class which includes the trienes myrcene 4 and ocimenes (5-7) and the alcohols geraniol 15, nerol 16, citronel-lol 17, linalool 18, etc (Structure 4.5). [Pg.48]

Single receptor neurons were tuned to a few structurally related components [383-384], while neurons in the antennae of individual insects were more responsive to speciflc enantiomers, e.g. (-i-)-linalool [377, 386]. [Pg.101]

Using a chiral column, coated with a definite modified cyclodextrin as the chiral stationary phase, the elution orders of furanoid and pyranoid linalool oxides are not comparable [11, 12]. Consistently, the chromatographic behaviour of diastereomers and/or enantiomers on modified cyclodextrins is not predictable (Fig. 17.1, Table 17.1). Even by changing the non-chiral polysiloxane part of the chiral stationary phase used, the order of elution may significantly be changed [13]. The reliable assignment of the elution order in enantio-cGC implies the coinjection of structurally well defined references [11-13]. [Pg.380]

Kreis P, Dietrich A, Mosandl A (1996) Elution order of the furanoid linalool oxides on common gas chromatographic phases and modified cyclodextrin phases. J Essent Oil Res 8 339 Weinert B, Wiist M, Mosandl A Hanssum H (1998) Stereoisomeric flavour compounds LXX-Vlff. Separation and structure elucidation of the pyranoid linalool oxide stereoisomers using common gas chromatographic phases, modified cyclodextrin phases and nuclear magnetic resonance spectroscopy. Phytochem Anal 9.T0... [Pg.403]

As mentioned before, a Pseudomonas incognita was isolated by enrichment technique on the monoterpene alcohol linalool that was also able to grow on geraniol, nerol and limonene [36]. The metabolism of limonene by this bacterium was also investigated [37]. After fermentation the medium yielded as main product a crystallic acid, perillic acid, together with unmetabolised limonene, and some oxygenated compounds dihydrocarvone, carvone, carveol, p-menth-8-en-1 -ol-2-one, p-menth-8-ene-1,2-diol or p-menth-1 -ene-6,9-diol (structure not fully elucidated) and finally / -isopropenyl pimelic acid. [Pg.147]

Ethyl acetate, which is a comparatively small molecule, has the typical fruity character associated with all the lower esters, and a more or less equal balance between the influence of the two structural units, derived from ethyl alcohol and acetic acid. Linalyl acetate and geranyl acetate, however, although retaining the typical character of an acetate have much less of the ester fruitiness and are more closely related to the corresponding alcohols, linalool, and geraniol. The dominance of the alcohol appears to be even greater in phenylethyl acetate and paracresyl acetate (a phenolic ester). [Pg.218]

As a further Wittig synthon isopropylidene-triphenylphosphorane was used for the preparation of trans 2,6-famesol and trans-nerolidol 236) which are structurally related to one another like linalool and geraniol. [Pg.140]

During distillation of the spice, a number of transformations may occur in the composition of the volatile oil. Small quantities of p-cymene may be produced as an artefact, linalyl acetate and some other esters may be hydrolysed and d-linalool may rearrange to its optically inactive isomer geraniol. Potter et al. (1993) found structural similarity in the compounds of Polygonum odoratum to that of C. sativum. [Pg.197]

Oxides in essential oils have an oxygen atom within a ring structure, usually made from an alcohol, and are named after the alcohol with the termination oxide, e.g. linalool oxide (Fig. 3.12). They are found in a wide range of essences, especially those of a camphoraceous nature, e.g. eucalyptus, rosemary, tea tree and cajeput. [Pg.75]

Figure 9. Structures of additional glycoconjugates isolated from Riesling wine during this study B-D-glucopyranosides of 3-methylbutanol 21, 2-methyl-butanol 22, benzyl alcohol 23, 2-phenylethanol 24, furanoid linalool oxides (two diastereoisomers) 25, pyranoid linalool oxides (two diastereoisomers) 27, 3-oxo-7,8-dihydrc>-a-ionol 28, 3-oxo-a-ionol 29, 4,5-dihydro-vomifoliol 30, vomifoliol 31, and 7,8-dihydro-vomifoliol as well as the 6-O-B-D-apiofurano-syl-fi-D-glucopyranosides of furanoid linalool oxides (two diastereoisomers). Figure 9. Structures of additional glycoconjugates isolated from Riesling wine during this study B-D-glucopyranosides of 3-methylbutanol 21, 2-methyl-butanol 22, benzyl alcohol 23, 2-phenylethanol 24, furanoid linalool oxides (two diastereoisomers) 25, pyranoid linalool oxides (two diastereoisomers) 27, 3-oxo-7,8-dihydrc>-a-ionol 28, 3-oxo-a-ionol 29, 4,5-dihydro-vomifoliol 30, vomifoliol 31, and 7,8-dihydro-vomifoliol as well as the 6-O-B-D-apiofurano-syl-fi-D-glucopyranosides of furanoid linalool oxides (two diastereoisomers).
Scheme 2) 84 treatment of (24) and its analogues with dissolving metals or peracids also led to novel, functionalized but regular structures.85 Methods for the formation of allylsilanes from geraniol, linalool, and myrtenol86 and... [Pg.10]

The odorless polyols appear to be derived from four "parent" monoterpenes - linalool, citronellol, nerol and geraniol by hydration and oxidation reactions (6,22). Figure 3 lists the polyols identified in grapes and also shows structures of components not yet found but likely to be observed should polyol formation from each parent molecule follow an analogous route. [Pg.226]

Techniques were developed for the isolation of monoterpene glycosides (23) and structural studies on those with aglycons at the linalool oxidation state were carried out (24). These compounds... [Pg.226]

Figure 2. Structures of terpenoids chemically formed from linalool (1 ) at pH 3.5 (cf. Fig.1-4). (2) 2,4(8)-p-menthadiene (3) B-myrcene (4) a-phellandrene (5) cx-terpinene (6) limonene (7) B-phellandrene (8) (Z)-ocimene (9) y-terpinene (10) (E)-ocimene (11) p-cymene (12) terpinolene (13) (E,Z)-alloocimene (14) (E,E)-alloocimene (15) a-terpineol (16) 3,7-dimethyl-l-oct-ene-3,7-diol (17) 1,8-cineole (18) 2,2,6-trimethyl-2-vinyl-te-trahydropyran. Figure 2. Structures of terpenoids chemically formed from linalool (1 ) at pH 3.5 (cf. Fig.1-4). (2) 2,4(8)-p-menthadiene (3) B-myrcene (4) a-phellandrene (5) cx-terpinene (6) limonene (7) B-phellandrene (8) (Z)-ocimene (9) y-terpinene (10) (E)-ocimene (11) p-cymene (12) terpinolene (13) (E,Z)-alloocimene (14) (E,E)-alloocimene (15) a-terpineol (16) 3,7-dimethyl-l-oct-ene-3,7-diol (17) 1,8-cineole (18) 2,2,6-trimethyl-2-vinyl-te-trahydropyran.
Figure 4. Structures of terpenoids formed from linalool (1) by Botrytis cinerea. (19)>(20) (E)- and (Z)-2,6-dimethyl-2,7-octadie-ne-l,6-diol (21),(22) (Z)- and (E)-linalool oxides, furanoid (23),(24) (Z)- and (E)-linalool oxides, pyranoid (25),(26) (Z)-and (E)-linalool oxide acetates, pyranoid (27) 3,9-epoxy-p-menth-1-ene (28) 2-vinyl-2-methyl-tetrahydrofuran-5-one. Figure 4. Structures of terpenoids formed from linalool (1) by Botrytis cinerea. (19)>(20) (E)- and (Z)-2,6-dimethyl-2,7-octadie-ne-l,6-diol (21),(22) (Z)- and (E)-linalool oxides, furanoid (23),(24) (Z)- and (E)-linalool oxides, pyranoid (25),(26) (Z)-and (E)-linalool oxide acetates, pyranoid (27) 3,9-epoxy-p-menth-1-ene (28) 2-vinyl-2-methyl-tetrahydrofuran-5-one.
Geraniol-nerol, linalool, citronellol, citronellal and citral are five of the most important terpenes as far as the perfume industry is concerned. Apart from citral, all are used as such in perfumes, and the alcohols and their esters are particularly important. All of them are key starting materials for other terpenes, as discussed later. Scheme 4.1 shows the structures of these materials and how they can be interconverted simply by isomerization, hydrogenation and oxidation. The ability to manufacture any one of these, therefore, opens up the potential to produce all of them and, hence, a wide range of other terpenes. Obviously, if one company produces geraniol-nerol initially and another linalool and both do so at the same cost per kilogramme, then they will not be able... [Pg.54]


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Linalool

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