Tinkturenpresse

Vitis vinifera L. - Vitaceae - grape, common grape vine, Wein, Weinstock, Weinrebe

Deciduous woody climber (up to 10m), only known in culture, cultivated worldwide; leaves opposite, palmately lobed; wheel-shaped bisexual flowers in racemes; berries green, red or dark blue.

„The wild grape is often classified as V. vinifera subsp. sylvestris (in some classifications considered Vitis sylvestris), with V. vinifera subsp. vinifera restricted to cultivated forms. Domesticated vines have hermaphrodite flowers, but subsp. sylvestris is dioecious (male and female flowers on separate plants) and pollination is required for fruit to develop.“ http://en.wikipedia.org/wiki/Vitis_vinifera

Of the 20 odour-active volatiles with OAVs >1 found in berries (Merlot and Cabernet Gernischt), 7 odour-active volatiles had OAVs higher than 20: (E)-2-nonenal, decanal, hexanal, (E)-2-hexenal, (E,Z)-2,6-nonadienal, (E)-β-damascenone and β-ionone and are considered to be potent aroma contributors to grapes.
[MLA Xie, Sha, et al. „Influence of natural variation in berry size on the volatile profiles of Vitis vinifera L. cv. Merlot and Cabernet Gernischt grapes.“ PloS one 13.9 (2018): e0201374] https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0201374

wine

„… the common pattern typical for wines derived from Vitis vinifer, which, quantitatively, is usually dominated by isoamyl alcohol, ethyl caproate, ethyl caprylate, diethyl succinate, caproic acid, 2-phenylethyl alcohol, caprylic acid, caprinic acid, monoethyl succinate, and some others. These compounds may together represent 90-98% of the volatiles forming the wine's bouquet and are certainly important as a skeleton, but such a wine you would not just not drink. There are many more minor and trace constituents that characterize a wine, giving these elegant associations with flowers, fruits, and other natural scents, in our case, elderflower, lychee, roses, honey, cinnamon, and other spices…
The most variety-typical compound [of Gewürztraminer] is cis-rose oxide, but it needs to be accompanied by nerol oxide and linalool to form this distinct Gewürztaminer accord, which I have also encountered several times in flower and fruit scents…
…the famous damascenone - first discovered as an olfactory key component of Bulgarian rose oil and since than found in many natural scents, but never in that of fresh rose flowers - is of eminent importance in all white and red wines. I have found no wine made from Vitis vinifera in which it is not present. Exactly the same is true for 3-sulfanylhexan-1-ol, discovered for the first time in yellow passion fruit and later as an important impact chemical in the bouquet of Sauvignon Blanc wines.“
[Meaningful Scents around the World, Roman Kaiser, Zürich 2006, 183-193]

Solerone (5-oxo-4-hydroxyhexanoic acid γ-lactone) has been identified as an almost racemic mixture of (4R)- and (4S)-solerone from commercially available sherry; within the solerole series, the (4R,5R)- and (4S,5R)-configurated isomers of 4,5-dihydroxyhexanoic acid γ-lactone have been detected predominantly.
[Chiral aroma compounds of sherry., Hollnagel, A., Menzel, E.M., Mosandl, A., Zeitschrift für Lebensmittel-Untersuchung und Forschung, 193(3), 1991, 234-236.]

„Forty-four odor-active compounds were quantified in Scheurebe and Gewürztraminer wines, respectively. Calculation of odor activity values (OAVs) of odorants showed that differences in odor profiles of both varieties were mainly caused by cis-rose oxide in Gewürztraminer and by 4-mercapto-4-methylpentan-2-one in Scheurebe. On the basis of their high OAVs, ethyl octanoate, ethyl hexanoate, 3-methylbutyl acetate, ethyl isobutyrate, (E)-β-damascenone, and 3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (wine lactone) were further potent odorants in both varieties. The compounds were dissolved in a water/ethanol mixture in various combinations and in concentration levels equal to those in wine. The results indicated that the aromas of Gewürztraminer and Scheurebe models were in good agreement with the original wines.“
[Quantitation and sensory studies of character impact odorants of different white wine varieties., Guth, H., Journal of Agricultural and Food Chemistry, Vol.45(8), 1997, 3027-3032]

Analysis of 10 typical Sauvignon blanc wines (Bordeaux, Sancerre) showed that 4-mercapto-4-methylpentan-2-one (catty black currant), 3-mercapto-hexyl acetate (floral-fruity, passionfruit), and 3-mercaptohexan-1-ol (fruity-tropical, grapefruit) are involved in their varietal aroma.
[Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon blanc., Tominaga, T., Murat, M.L., Dubourdieu, D., Journal of Agricultural and Food Chemistry, 46(3), 1998, 1044-1048]

„GC/O analysis of canned lychees indicated that cis-rose oxide, linalool, ethyl isohexanoate, geraniol, furaneol, vanillin, (E)-2-nonenal, β-damascenone, isovaleric acid, and (E)-furan linalool oxide were the most odor potent compounds detected in the fruit extracts. However, on the basis of calculated odor activity values (OAVs), cis-rose oxide, β-damascenone, linalool, furaneol, ethyl isobutyrate, (E)-2-nonenal, ethyl isohexanoate, geraniol, and δ-decalactone were determined to be the main contributors of canned lychee aroma. When these results were compared with GC/O results of fresh lychees and Gewürztraminer wine, 12 common odor-active volatile compounds were found in all three products. These included cis-rose oxide, ethyl hexanoate/ethyl isohexanoate, β-damascenone, linalool, ethyl isobutyrate, geraniol, ethyl 2-methylbutyrate, 2-phenylethanol, furaneol, vanillin, citronellol, and phenethyl acetate. On the basis of OAVs, cis-rose oxide had the highest values among the common odorants in the three products, indicating its importance to the aroma of both lychee fruit and Gewürztraminer wines. Other compounds that had significant OAVs included β-damascenone, linalool, furaneol, ethyl hexanoate, and geraniol. This indicated that while differences exist in the aroma profile of lychee and Gewürztraminer, the common odorants detected in both fruit and wine, particularly cis-rose oxide, were responsible for the lychee aroma in Gewürztraminer wine. When headspace SPME was used as a rapid analytical tool to detect the levels of selected aroma compounds deemed important to lychee aroma in Gewürztraminer-type wines, cis-rose oxide, linalool, and geraniol were found to be at relatively higher levels in Gewürztraminers. No cis-rose oxide was detected in the control wines (Chardonnay and Riesling), while lower levels were detected in the Gewürztraminer-hybrid wine Traminette.“
[Similarities in the aroma chemistry of Gewürztraminer variety wines and lychee (Litchi chinesis Sonn.) fruit. Ong, P. K., Acree, T. E., Journal of agricultural and food chemistry, Vol.47(2), 1999, 665-670]

„The intensity and quality of the aroma constitutes the primary quality factor in a white wine, and a substantial part of such quality is related to the variety of grape from which the wine was made. The importance of the grape variety explains the interest that this issue has aroused among researchers. Previous studies have shown that some odorants are related to the aroma characteristics of a given variety. The first discovery, made more than 30 years ago, was about the role of linalool and other terpenols in the aroma of wines made with muscat-related grapes. Other significant findings about the role of some odorants in the aroma of specific varieties came later, including works on the role of methoxypyrazines in Sauvignon varieties, o-aminoacetophenone in Vitis labrusca or Vitis rotundifolia varieties, cis-rose oxide in Gewürztraminer, 4-methyl-4-mercaptopentanone in Sauvignon blanc and in Scheureube, and 3-mercaptohexanol in Grenache, Merlot, and Cabernet rose ́ wines.“ The aroma profiles of six young monovarietal Spanish white wines showed that the „… main aroma differences between these wines are due to the ratio linalool/3-mercaptohexyl acetate. Floral, sweet, and muscat are positively related to the concentration of linalool and negatively to that of 3-mercaptohexyl acetate. Tropical fruit is related to the wine content in this last odorant. 2-Phenyl acetate, reinforced by other acetates, can also contribute to floral and sweet notes. Alkyl-methoxypyrazines lessen the tropical fruit note, and acetic acid lessens the muscat nuance.“
[Prediction of the wine sensory properties related to grape variety from dynamic-headspace gas chromatography-olfactometry data. Campo, E., Ferreira, V., Escudero, A., Cacho, J., Journal of Agricultural and Food Chemistry, Vol.53(14), 2005, 5682-5690]

„The characteristic aroma of Petite Arvine, a local white wine specialty prepared from the autochthone grape variety Petite Arvine in Valais, Switzerland, is described as intense in grapefruit and rhubarb flavors. In sensory evaluation by a triangle-test, the impact of thiol compounds on the wine aroma was demonstrated. In gas chromatography-olfactometry and gas chromatography-mass spectrometry analyses, 3-mercaptohexanol was identified as one of the key aroma compounds for the wine aroma. The concentration of 3-mercaptohexanol in 11 Petite Arvine wines was in the range between 210 and 6100 ng/L; all values being above the odor threshold value in aqueous ethanol solutions for this compound.“
[3-Mercaptohexanol: An aroma impact compound of Petite Arvine wine., Fretz, C.B., Luisier, J.L., Tominaga, T., Amadò, R., American journal of enology and viticulture, 56(4), 2005, 407-410]

3-Mercapto-hexanol (3-sulfanyl-hexan-1-ol) with its unique grapefruit/tropical fruit scent is present in all types of white and red wines and in many cases of great importance to their buquets. The most variety-typical compound of Gewürztraminer is cis-rose oxide. Accompanied by nerol oxide, linalool and β-damascenone, it forms this distinct Gewürtraminer accord, which is found also in the scent of elderflower (Sambucus nigra), and in the fruit aroma of lychee (Litchi sinensis).
[Meaningful Scents around the World, Roman Kaiser, Zürich 2006, 69, 184-185]

„The aroma profile of five premium red wines has been studied by sensory descriptive analysis, quantitative gas chromatography−olfactometry (GC-O), and chemical quantitative analysis. The most relevant findings have been confirmed by sensory analysis. Forty-five odorants, including the most intense, were identified. At least 37 odorants can be found at concentrations above their odor threshold. A satisfactory agreement between GC-O and quantitative data was obtained in most cases. Isobutyl-2-methoxypyrazine, (E)-whiskey lactone, and guaiacol were responsible for the veggie, woody, and toasted characters of the wines, respectively. The sweet-caramel notes are related to the presence of at least five compounds with flowery and sweet notes. The phenolic character can be similarly related to the presence of 12 volatile phenols. The berry fruit note of these wines is related to the additive effect of nine fruity esters. Ethanol exerts a strong suppression effect on fruitiness, whereas norisoprenoids and dimethyl sulfide enhance fruity notes.“
[Analytical characterization of the aroma of five premium red wines. Insights into the role of odor families and the concept of fruitiness of wines., Escudero, A., Campo, E., Fariña, L., Cacho, J., Ferreira, V., Journal of Agricultural and Food Chemistry, Vol.55(11), 2007, 4501-4510]

„An obscure sesquiterpene, rotundone, has been identified as a hitherto unrecognized important aroma impact compound with a strong spicy, peppercorn aroma. Excellent correlations were observed between the concentration of rotundone and the mean 'black pepper' aroma intensity rated by sensory panels for both grape and wine samples, indicating that rotundone is a major contributor to peppery characters in Shiraz [Syrah] grapes and wine (and to a lesser extent in wine of other varieties). Approximately 80% of a sensory panel were very sensitive to the aroma of rotundone (aroma detection threshold levels of 16 ng/L in red wine and 8 ng/L in water). Above these concentrations, these panelists described the spiked samples as more 'peppery' and 'spicy'. However, approximately 20% of panelists could not detect this compound at the highest concentration tested (4000 ng/L), even in water. Thus, the sensory experiences of two consumers enjoying the same glass of Shiraz wine might be very different. Rotundone was found in much higher amounts in other common herbs and spices, especially black and white peppercorns, where it was present at approximately 10000 times the level found in very 'peppery' wine. Rotundone is the first compound found in black or white peppercorns that has a distinctive peppery aroma. Rotundone has an odor activity value in pepper on the order of 50000-250000 and is, on this criterion, by far the most powerful aroma compound yet found in that most important spice.“
[From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound. Wood, C., Siebert, T. E., Parker, M., Capone, D. L., Elsey, G. M., Pollnitz, A. P., Herderich, M. J., Journal of agricultural and food chemistry, Vol.56(10), 2008, 3738-3744]

„The premature aging of red Vitis vinifera L. wines is mainly associated with the formation of an intense off-flavor reminiscent of prunes… high-pressure liquid chromatography, gas chromatography, and multidimensional gas chromatography coupled with mass spectrometry (MDGC-MS) were used to identify the odorants reminiscent of prunes in prematurely aged red wines and in the dried fruit. Three compounds were detected with a strong odor of prunes: γ-nonalactone, β-damascenone, and 3-methyl-2,4-nonanedione. The perception threshold of the latter β-diketone in a model hydroalcoholic solution is 16 ng/L. Identified for the first time in aged red wines, this very powerful volatile compound was also suggested to produce the characteristic prune aroma of prematurely aged red wines. The presence of 3-methyl-2,4-nonanedione was also detected in prunes for the first time.“
[Pons, Alexandre, et al. „Identification of volatile compounds responsible for prune aroma in prematurely aged red wines.“ Journal of Agricultural and Food Chemistry 56.13 (2008): 5285-5290]

„Wine lactone (i.e., 3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one, 1a/1b) was formed hydrolytically at wine pH from both racemic (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid (3) and the corresponding glucose ester 2a at 45 °C but at room temperature was only formed from the acid 3. The glucose ester does not appear to be a significant precursor for the formation of wine lactone in wine. The slow formation of wine lactone from the free acid 3 indicates that the acid is not likely to be an important precursor to wine lactone in young wines unless present in high concentration (≫1 mg/L), but could be a significant precursor to wine lactone in wine that is several years old. The wine lactone formed in hydrolysates of the (6R)-enantiomer of 3 was partially enriched in the (3S,3aS,7aR)-enantiomer 1a when the hydrolysis was conducted at pH 3.2 and 100 °C in a closed vessel or under simultaneous distillation-extraction (SDE) conditions, and the enantiomeric excess (ee) varied from 5 to 22%. Hydrolysis of (6R)-3 in sealed ampules at 45 °C and at pH 3.0, 3.2, or 3.4 gave near-racemic wine lactone, but when the hydrolyses were conducted at room temperature, the product was enriched in the (3S,3aS,7aR)-enantiomer 1a and the ee was greater at higher pH (up to 60% at pH 3.4).“
[The formation of wine lactone from grape-derived secondary metabolites., Giaccio, J., Capone, D. L., Hakansson, A. E., Smyth, H. E., Elsey, G. M., Sefton, M. A., Taylor, D. K., Journal of agricultural and food chemistry, 59(2), 2010, 660-664]

Some Italian Schioppettin white wines and Vespolina red wines, known for their special white pepper flavour, contained more than 450ng/L rotundone (max. 561ng/L, Vespolina from 2007 and Schioppettino from 2005, nearly 4 times higher than the maximal value previously reported for the most peppery Shiraz wines.).
[Effective analysis of rotundone at below‐threshold levels in red and white wines using solid‐phase microextraction gas chromatography/tandem mass spectrometry., Mattivi, F., Caputi, L., Carlin, S., Lanza, T., Minozzi, M., Nanni, D., Vrhovsek, U., Rapid communications in mass spectrometry, 25(4), 2011, 483-488]

The three most abundant free odorants, linalool (OAV 1-60), geraniol (OAV 1-13) and nerol (OAV 0.2-0.7), making the major contribution to berry Muscat flavour, however, their presence is not sufficient to produce a complete Muscat flavour. There is a significant correlation between the presence/absence of rose oxide (OAV 3-20) in grapes and the presence/absence of Muscat flavour.
[Ruiz-García, Leonor, et al. „Prediction of Muscat aroma in table grape by analysis of rose oxide.“ Food Chemistry 154 (2014): 151-157]

„Megastigmatrienone is a key flavor compound in tobacco. It has also been detected in wine, where it may contribute to a tobacco/incense aroma, but its importance and concentration in wines had never previously been evaluated… Megastigmatrienone isomers were extracted by headspace solid-phase microextraction (HS-SPME)… The LOQ were between 0.06 μg L−1 and 0.49 μg L−1 for white wine and 0.11 μg L−1 and 0.98 μg L−1 for red wine, repeatability in both types of wine was less than 10% and recovery ranged from 96% for white wine to 94% for red wine. The five isomers of megastigmatrienone were quantified in red and white wines for the first time. Concentrations ranged from 2 μg L−1 to 41 μg L−1 in both red and white wines. Initial results revealed a link between wine aging and megastigmatrienone levels, indicating that megastigmatrienone may be a component in wine “bouquet”.“
[Quantitative solid phase microextraction – Gas chromatography mass spectrometry analysis of five megastigmatrienone isomers in aged wine., Davide Slaghenaufia, Marie-Claire Perelloa, Stéphanie Marchand-Mariona, Sophie Temperea, Gilles de Revel, Analytica Chimica Acta, Vol.813, 2014, 63-69]

„For instance, the 28 key food odorants recombined in natural concentrations to match the odor percept of a Dornfelder red wine ranged from 0.9µg/l for the cooked apple-like smelling (E)-1-(2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one, known as (E)-β-damascenone, over 79040 µg/l for the flowery smelling 2-phenylethanol up to 641900 µg/l for the vinegar-like smelling acetic acid. Considering their odor detection thresholds of 0.01, 18, and 5600 µg/l (Table 1), respectively, (E)-β-damascenone, 2-phenylethanol, and acetic acid show largely different odor activity values (OAVs) of 90, 4391, and 115, thus demonstrating that the key food odorants in a natural food setting show huge differences in their individual odor impact and flavor contribution and are far from being present in equal intensity.“
[Dunkel, Andreas, et al. „Nature’s chemical signatures in human olfaction: a foodborne perspective for future biotechnology.“ Angewandte Chemie International Edition 53.28 (2014): 7124-7143]

„VvSTO2 as a α-guaiene 2-oxidase which can transform α-guaiene to (−)-rotundone in the grape cultivar Syrah. It is a cytochrome P450 (CYP) enzyme belonging to the CYP 71BE subfamily… VvSTO2 was expressed at a higher level in the Syrah grape exocarp (skin) in accord with the localization of (−)-rotundone accumulation in grape berries. α-Guaiene was also detected in the Syrah grape exocarp at an extremely high concentration. These findings suggest that (−)-rotundone accumulation is regulated by the VvSTO2 expression along with the availability of α-guaiene as a precursor… VvSTO2 may be a key enzyme in the biosynthesis of (−)-rotundone in grapevines by acting as a α-guaiene 2-oxidase.“
[Cytochrome P450 CYP71BE5 in grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound (−)-rotundone., Takase, H., Sasaki, K., Shinmori, H., Shinohara, A., Mochizuki, C., Kobayashi, H., Takata, R., Journal of experimental botany, 67(3), 2016, 787-798] http://jxb.oxfordjournals.org/content/67/3/787.full
A review shows rotundone concentration in grapes at harvest and in commercial (C) or experimental (E) single-variety wine: [Geffroy, Olivier, Didier Kleiber, and Alban Jacques. „May peppery wines be the spice of life? A review of research on the ‘pepper’aroma and the sesquiterpenoid rotundone.“ OENO One 54.2 (2020): 245-262]
https://oeno-one.eu/article/view/2947

„High sun exposure of the vines and long-term storage of the wines cause formation of the C13-norisoprenoid 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) eliciting a kerosene-like flavor in Riesling wines… While trained panelists were able to distinguish Riesling wines with TDN levels of 2.3 µg/L, consumer detection threshold of 14.7 µg/L TDN determined with 156 consumers exceeded the threshold of the trained panel by a factor of five and varied by consumers’ gender. Rejecting a Riesling wine due to its petrol off-flavor, 60 µg/L TDN were required in a young and 91 µg/L in an eight-year-old Riesling wine.“
[Ziegler, Michael. 1,1,6-Trimethyl-1,2-dihydronaphthalin (TDN) in Riesling - Sensorische Relevanz und Minimierungsstrategie. Diss. Technische Universität Kaiserslautern, 2020.] Dissertation (PDF)

„Application of the aroma extract dilution analysis (AEDA) on a distillate prepared from freshly squeezed juice of Dornfelder grapes revealed (3Z)-hex-3-enal and trans-4,5-epoxy-(2E)-dec-2-enal with the highest flavor dilution (FD) factors. In contrast, in the final Dornfelder wine prepared thereof, the highest FD factors were found for 2-phenylethyl acetate, 2-phenylethan-1-ol, and (E)-β-damascenone. However, for example, among others, (3Z)-hex-3-enal no longer appeared as an important odorant.“
[Frank, Stephanie, and Peter Schieberle. „Changes in the Major Odorants of Grape Juice during Manufacturing of Dornfelder Red Wine.“ Journal of Agricultural and Food Chemistry 70.43 (2022): 13979-13986]

raisins

The main free volatiles of air-dried raisins from China „…were ethyl acetate, hexanoic acid, (E,E)-2,4-heptadienal and geraniol, with β-damascenone, 3-ethyl-2,5-dimethylpyrazine, 1-octen-3-ol and hexanal making the highest contribution to the aroma. Fruity and floral were the main characteristics of the free-form aromas in raisins. The main bound-form volatiles were benzyl alcohol and acetoin, with β-damascenone contributing most to the bound-form aromas, enhancing the floral, fruity and fatty aroma.“
[Wang, Dong, et al. „Study of free and glycosidically bound volatile compounds in air-dried raisins from three seedless grape varieties using HS–SPME with GC–MS.“ Food chemistry 177 (2015): 346-353]

cognac

„…(E)-β-damascenone showed the highest flavor dilution (FD) factor of 2048 followed by 2- and 3-methylbutanol, (S)-2-methylbutanol, 1,1-diethoxyethane, ethyl methylpropanoate, and ethyl (S)-2-methylbutanoate, as well as 4-hydroxy-3-methoxybenzaldehyde (vanilla-like) and 2-phenylethanol. The quantitation of 37 odorants by stable isotope dilution assays and a calculation of odor activity values (OAV; ratio of concentration to odor threshold) resulted in 34 odorants with OAVs > 1. Among them (E)-β-damascenone, methylpropanal, ethyl (S)-2-methylbutanoate, ethyl methylpropanoate, and ethyl 3-methylbutanoate together with ethanol were established as key contributors to the Cognac aroma.“
[Uselmann, Verena, and Peter Schieberle. „Decoding the combinatorial aroma code of a commercial cognac by application of the Sensomics concept and first insights into differences from a German brandy.“ Journal of agricultural and food chemistry 63.7 (2015): 1948-1956]

Together with guaiacol, cis-whisky lactone, trans-whisky lactone, γ-nonalactone, eugenol, vanillin, and acetovanillone, especially the megastigmatrienones play an important role in the aroma of oak-barrel-ripened spirits like Armagnac, Cognac, and Rum.
[Slaghenaufi, Davide, et al. „Quantification of megastigmatrienone, a potential contributor to tobacco aroma in spirits.“ Food Chemistry 203 (2016): 41-48]

Köhler,F.E., Medizinal Pflanzen, vol.1 t.51 (1887) [W.Müller]
http://plantgenera.org/species.php?id_species=1068564

Vitis vinifera, CC BY-SA 3.0, Author: Andreas Kraska