Transformations of monoterpenoids in aqueous acids

Baxter, Robert L.; Laurie, W. A.; McHale, D.

doi:10.1016/0040-4020(78)89026-7

Cited by 55 publications

(24 citation statements)

References 9 publications

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“…Stability studies -Robustness of the analytical method Geraniol (1), nerol (2), linalool (3), and α-terpineol (4) undergo a variety of transformations, even in dilute acidic media [12,20,23,27,34,35,36]. Thus, Skouroumounis and Sefton [34] hydrolysed geraniol (1) in 10% ethanol/ water at pH 3.0 at 50°C.…”

Section: Resultsmentioning

confidence: 99%

“…Geraniol (1) and linalool (3) are considered to be the most important of the monoterpene alcohols as they are present in greater concentrations, and have lower flavour thresholds than other major wine monoterpenes [22]. Geraniol (1), nerol (2), linalool (3), α-terpineol (4) and related compounds are also considered to be important to the flavour of other alcoholic beverages [23,24], soft drinks [20] and are widely used in the perfume and flavour industries [25].…”

Section: Introductionmentioning

confidence: 99%

“…When present in young wines, geraniol (1) and nerol (2) decrease in concentration as wine is aged [3,14,15,16,17,18,19] and are usually present in no more than trace amounts after two to three years in the bottle. The concentration of linalool (3) and α-terpineol (4) can initially increase during bottle storage, but decreases afterwards, as they are converted mainly to terpin hydrate [12,20]. Traces of linalool (3) and α-terpineol (4) are still detectable in aged Riesling wine [21].…”

Section: Introductionmentioning

confidence: 99%

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Quantitative analysis of geraniol, nerol, linalool, and α-terpineol in wine

et al. 2003

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A mixture of [(2)H(7)]-geraniol, [(2)H(7)]-nerol, [(2)H(7)]-linalool and [(2)H(7)]-alpha-terpineol was prepared for use as internal standards in a rapid and accurate analytical method, employing gas chromatography-mass spectrometry (GC/MS), to determine the concentration of geraniol, nerol, linalool and alpha-terpineol in wine. The method avoids the possible formation, degradation and interconversion of these compounds during their analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantitative analysis of geraniol, nerol, linalool, and α-terpineol in wine

et al. 2003

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“…Apart from the enediol17 the major components of these hydrolysates were a-terpineol (ll), and the p-menthane diols 19 and 20. Mild acid treatment of the acyclic compounds geraniol, nerol and linalool leads mainly to a-terpineol (Baxter et al, 1978). The hydration experiment we carried out (see below) showed that cw-terpineol in turn, can be almost exclusively converted to thep-menthane-1,8-diols 19 and 20 at grape and wine pH.…”

Section: Monoterpenesmentioning

confidence: 96%

Free and Bound Volatile Secondary Metabolites of Vitis Vhifera Grape cv. Sauvignon Blanc

Sefton

Francis

Williams

1994

Journal of Food Science

102

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Free volatiles, and those hydrolytically released from glycosidic forms, were analyzed for Sauvignon Blanc juices from three successive vintages. Most of the 213 compounds identified were in one of the biogenetic categories: norisoprenoids, benzene derivatives, monoterpenes or aliphatics. Several have not been previously reported as grape components. Monoterpenes were in lower concentration than normally found in floral grape varieties, but at higher levels than reported in Chardonnay juices. A notable proportion (40-50%) of the bound monoterpenes were monocyclic. Hydration of a-terpineol at pH 3 gave c-4

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“…Elution with a mixture of petroleum ether and AcOEt (9 : 1) gave 71 mg (91%) of hydroxydiacetate 7c (a colorless viscous liquid). Found (/%): C, 61.8l; H, 8 …”

Section: Methodsmentioning

confidence: 99%

Electrophilic cyclization of α- and β-geranyl acetates by mercury(II) trifluoroacetate

1997

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Etectrophilic cyclization of !3-geranyl acetate promoted by mercury(u) trifluoroacctate leads to mixtures of ct-and 7-5ctH-eyclogeranyl acetate derivatives and 6a-hydroxy-Sc~//-and 6~-hydroxy-513H-cyclogeranyl acetate derivatives mereurated at the C-3 atom. The ratio of the unsaturated and hydroxymercurated products depends on the reaction conditions. cL-Geranyl acetate reacts with mercury(u) trifluoroacetate to give a mixture of 6c~-hydroxy5all-and 6a-hydroxy-513H-geranyt acetates, mereurated at C-9, with an equatorial mercurated methylene group at C-4. The mercury-containing groups in mercurated cyclogeranyl derivatives can easily be reduced or replaced by an oxygen-containing functional group; this constitutes a convenient route to polyfunctional cyclogeranyl derivatives that are difficult to obtain.Key words: electrophilic cyclization, ct-and 13-geranyl acetates, mercury(n) trffiuoroacetate, cyclogeranyl derivatives.Electrophilic cyclization of ct-(1) and J3-geranyl acetates (2) promoted by mercury salts is of certain synthetic interest, because, owing to the possibility of easy replacement of the mercury-containing residue by an oxygen-containing functional group, 1 it opens a way to difficultly accessible cyclogeranyl derivatives with functional groups in the gem-dimethyl position or at the C-3 atom (from here on, the steroid numbering of atoms is used). The alternative pathway to cyclogeranyl derivatives hydroxylated at the above-mentioned positions, which involves cyclization of the corresponding atiphatic epoximonoterpenoids with a terminal epoxide ring is of low efficiency. [2][3][4][5] In this paper, we report the results of a study of the cyclization of ct-and 13-geranyl acetates 1 and 2 promoted by Hg(OCOCF3)2. It should be noted that cyclization of 13-geranyl acetate 2 in the presence of this reagent has been carried out earlier; 6 ct-(3a) and , [-(4a) cyclogeranyl acetates mercurated at the C-3 atom were isolated in an overall yield of 24%.By the reaction of 13-geranyl acetate 2 with Hg(OCOCF3) 2 at room temperature in l-nitropropane followed by treatment of the reaction mixture with a solution of NaCI, we obtained a mixture of compounds, which was separated by chromatography on a column with silica gel. The least polar fraction contained unreacted geranyl acetate 2. The next fraction in order of polarity consisted of a mixture (1 : 7) of mercurated cyclic compounds 3b and 4b (overall yield 45.7%) (Scheme I), whose structures are confirmed by the fact that the mixture of 3b and 4b was reduced by NaBH4 under standard conditions 7 to give a mixture (1 : 7,

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Transformations of monoterpenoids in aqueous acids

Cited by 55 publications

References 9 publications

Quantitative analysis of geraniol, nerol, linalool, and α-terpineol in wine

Quantitative analysis of geraniol, nerol, linalool, and α-terpineol in wine

Free and Bound Volatile Secondary Metabolites of Vitis Vhifera Grape cv. Sauvignon Blanc

Electrophilic cyclization of α- and β-geranyl acetates by mercury(II) trifluoroacetate

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