Identification of two isomers of 4,5-dihydroxyhexanoic acid gamma lactone in Californian and Spanish flor sherries

Müller, Carlos J.; Maggiora, Linda; Kepner, Richard E.; Webb, A. Dinsmoor

doi:10.1021/jf60166a013

Cited by 36 publications

(20 citation statements)

References 3 publications

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“…In the V2 wines, the variation of 4-carbethoxy-c-butyrolactone (sweet, coconut aroma) could have influence on the sensory properties of Amarone wine, since in those produced by mixed cultures, the content exceeded the threshold (400 lg L -1 ). The effect of T. delbrueckii was particularly evident analysing sherry lactones [28], where the amount produced differed up to almost 3-folds higher than the control, as the case of sherry lactone 2 in V1 wines (Table 1). Different metabolic yield between T. delbrueckii and S. cerevisiase on the production of these compounds could explain these data.…”

Section: Aroma Analysismentioning

confidence: 94%

Effects of Torulaspora delbrueckii and Saccharomyces cerevisiae mixed cultures on fermentation and aroma of Amarone wine

Azzolini¹,

Fedrizzi

Tosi³

et al. 2012

Eur Food Res Technol

118

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The impact of Torulaspora delbrueckii has been investigated for the first time in the production of Amarone wine, a high-alcohol dry red wine obtained from withered grapes. In two different vinifications, winery trials were inoculated by a selected strain of T. delbrueckii simultaneously and/or sequentially to Saccharomyces cerevisiae. Implantation analysis demonstrated T. delbrueckii was able to rapidly colonise the must remaining in wine up to 16.5 % v v -1 of ethanol. The effects of T. delbrueckii on the aroma of Amarone wine were linked to its persistence during the fermentation and a great number of compounds varied in wine obtained with mixed cultures. The most significant changes were observed among alcohols, fermentative esters, fatty acids and lactones, which are important in the Amarone wine flavour. This study confirms the role of T. delbrueckii on wine aroma and the potential of non-Saccharomyces use in winemaking.

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Section: Aroma Analysismentioning

confidence: 94%

Effects of Torulaspora delbrueckii and Saccharomyces cerevisiae mixed cultures on fermentation and aroma of Amarone wine

Azzolini¹,

Fedrizzi

Tosi³

et al. 2012

Eur Food Res Technol

118

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“…This paper reports on 5-0x0-4-hydroxyhexanoic acid y-lactone (solerone) and 4,5-dihydroxyhexanoic acid y-lactone (solerole), both well-known characteristic flavour components of the sherry aroma, although knowledge of their stereochemistry and their sensory qualities did not exist until now. (1)(2)(3)(4)(5)(6) Even if the description of sensory experiences remains incomplete in principle, optically pure stereoisomers 1-6 have been generated (ee > 99.5%) for sensory evaluation. Characteristic odour qualities have been found (Table 3).…”

Section: Discussionmentioning

confidence: 99%

“…RT: 36.60 min (R)-solerone 1 Program: 120°C for 2 min isothermal, then rising at 3"C/min to 240°C ( Table 1).…”

Section: Methodsmentioning

confidence: 99%

“…As the influence of chirality on odour quality is well appreciated t~day,'~-*'' the aim of our research on structure-activity relationships of stereoisomeric flavour compounds is (1) to study sensory properties of enantiomerically pure isomers and (2) to examine the optical purity of naturally occurring chiral flavour compounds.…”

Section: Introductionmentioning

confidence: 99%

“…In this paper we report the generation of the optically pure enantiomers of solerone (1,2) and the stereoisomers of solerole (3)(4)(5)(6).…”

Section: Introductionmentioning

confidence: 99%

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Stereoisomeric flavour compounds XXXV: Chiral aroma compounds of sherry I. Optically pure stereoisomers of solerone and solerole

Mosandl

Hollnagel

1989

Chirality

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The enantioseparation of the sherry aroma components 5-0x04-hydroxyhexanoic acid y-lactone (solerone) and 4,5-dihydroxyhexanoic acid y-lactone (solerole) is achieved, using Chiraspher (Merck) as the chiral HPLC phase and the optical purity ascertained directly by HRGC with heptakis(3-O-acetyl-2,6-di-Openty1)-8-cyclodextrin (Lipodex D) as the chiral stationary phase. The absolute configurations of 4,5-dihydroxyhexanoic acid y-lactones are assigned by H-NMR spectral data of diastereomeric a-methoxy-a-trifluoromethylphenylacetic acid (MTPA) esters, according to Mosher's model. Sensory qualities of the isomers are given.

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Aroma of sherry wines

Webb

Noble

1976

Biotech & Bioengineering

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SummaryOver 130 volatile components have been identified in aromas of film (F), submerged-culture flor (S), and baked (B) sherries. The composition of these volatiles, which include more than 25 alcohols, five carbonyls, ten acetals, three amides, 35 esters, and five lactones, is influenced by the variety of grape used, the nature of the primary alcoholic fermentation, type oE cooperage, aging and blending system, and film-phase yeast metabolism in (F) and (S) or reactions occurring during "baking" in (B). The influence of these factors on the aroma and several volatile formation mechanisms which contribute to the characteristic flavor of sherry, particularly during the film growth and during baking, are discussed.

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Identification of two isomers of 4,5-dihydroxyhexanoic acid gamma lactone in Californian and Spanish flor sherries

Cited by 36 publications

References 3 publications

Effects of Torulaspora delbrueckii and Saccharomyces cerevisiae mixed cultures on fermentation and aroma of Amarone wine

Effects of Torulaspora delbrueckii and Saccharomyces cerevisiae mixed cultures on fermentation and aroma of Amarone wine

Stereoisomeric flavour compounds XXXV: Chiral aroma compounds of sherry I. Optically pure stereoisomers of solerone and solerole

Aroma of sherry wines

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