2-Exo-Hydroxy-1,8-cineole: a new component from grape var. Sauvignon

Bitteur, Sylvaine; Baumes, Raymond; Bayonove, Claude; Versini, G.; Martin, C. A.; Serra, A. Dalla

doi:10.1021/jf00095a011

Cited by 24 publications

(16 citation statements)

References 12 publications

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“…These measurements are in agreement with other reports. 30 ) Consequently, a large part of the phenolic extract is represented by benzoic and hydroxycinnamic acids (p-coumaric, o-coumaric, and others).…”

Section: Resultsmentioning

confidence: 99%

Fluorometric Analysis of Phenolics in Persimmons

Gorinstein

Zemser

Weisz

et al. 1994

Bioscience, Biotechnology, and Biochemistry

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Section: Resultsmentioning

confidence: 99%

Fluorometric Analysis of Phenolics in Persimmons

Gorinstein

Zemser

Weisz

et al. 1994

Bioscience, Biotechnology, and Biochemistry

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“…These were accompanied by smaller amounts of 2-au-hydroxy-1,8-cineole (14) and the two isomers (83 and 84) of the minor constituent pmenth-1-ene-6,8-diol (Table 2). The three p-menthene diols (25, 83 and 84) (Versini et al, 1991) and 2-euo-hydroxy-1,8cineole (14) (Bitteur et al, 1990) were previously identified as new grape components in Sauvignon Blanc juices. A fourth p-menthene diol, tentatively identified in this study as p-menth-2-ene-1,8-diol (81), was seen in acid hydrolysates only ( Table 2).…”

Section: Monoterpenesmentioning

confidence: 99%

“…origin of varietal aromas of Sauvignon Blanc wines. Only a small number of such volatiles have been reported in free and/ or bound form in juices of this variety (Baumes et al, 1986;Versini et al, 1988;Williams et al, 1989;Bitteur et al, 1990;Versini et al, 1991).…”

mentioning

confidence: 99%

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

Sefton

Francis

Williams

1994

Journal of Food Science

100

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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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“…In contrast, naturally occurring oxygenated derivatives have been reported sporadically, mainly as metabolites from living organisms fed on cineole containing food [8][9][10][11] such as in the urine of some mammals as brush-tail opossums, male koalas [9a-d], rabbits [9e], and humans after oral administration of medication containing 1 [12]. Microbial hydroxylation of 1 using Bacillus cereus [8c] and Pseudomonas flava [8b] yielded optically pure hydroxycineole derivatives, while biotransformation of 1 by a Rhodococcus species, in addition to hydroxycineole derivatives, yielded optically active 2-oxocineole [13,14] of undetermined absolute configuration or enantiomeric purity.…”

mentioning

confidence: 99%

Preparation and Absolute Configuration of (1R,4R)-(+)-3-Oxo-, (1S,4S)-(-)-3-Oxo- and (1R,3S,4R)-(+)-3-Acetyloxy-5-oxo-1,8-cineole

Loandos

Villecco

Burgueño‐Tapia

et al. 2009

Natural Product Communications

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Enantiomerically pure (1S,4S)-(-)-3-oxo-1,8-cineole (-)-2 and (1R,4R)-(+)-3-oxo-1,8-cineole (+)-2 were prepared for the first time and their absolute configurations assigned by vibrational circular dichroism (VCD) measurements. Thus, treatment of cineole 1 with chromyl acetate gave rac-2 which after sodium borohydride reduction and acetylation provided racemic 3-endo-acetyloxy-1,8-cineole, rac-4. Enantioselective hydrolysis using porcine liver esterase (PLE) gave a mixture of 3-endo-hydroxy-1,8-cineole (-)-3 and 3-endo-acetyloxy-1,8-cineole (+)-4. After chromatographic separation, (-)-3 was oxidized to (+)-2, while (+)-4 was hydrolysed to (+)-3 and then oxidized to (-)-2. The absolute configuration of either ketone 2 was established by VCD spectroscopy in combination with density functional theory (DFT) calculations at the B3LYP/DGDZVP level of theory, from where it followed that the (+)-2 enantiomer corresponds to (1R,4R)-1,3,3-trimethyl-5oxo-2-oxabicyclo[2.2.2]octane and the (-)-2 enantiomer to the (1S,4S) molecule which is also in agreement with the absolute configuration deduced by the Mosher method for the starting chiral alcohols. Some literature inconsistencies are clarified. In addition, the enantiomerically pure monoester (1S,3S,4R,5R)-(-)-3-acetyloxy-5-hydroxy-1,8-cineole 6 and the ketoester (1R,3S,4R)-(+)-3-acetyloxy-5-oxo-1,8-cineole 7 were prepared from meso-diacetate 5 by enantioselective asymmetrization also using PLE.

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2-Exo-Hydroxy-1,8-cineole: a new component from grape var. Sauvignon

Cited by 24 publications

References 12 publications

Fluorometric Analysis of Phenolics in Persimmons

Fluorometric Analysis of Phenolics in Persimmons

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

Preparation and Absolute Configuration of (1R,4R)-(+)-3-Oxo-, (1S,4S)-(-)-3-Oxo- and (1R,3S,4R)-(+)-3-Acetyloxy-5-oxo-1,8-cineole

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