Characterization of the key aroma compounds in an american bourbon whisky by quantitative measurements, aroma recombination, and omission studies

Thirty-one of the 45 odor-active compounds previously identified by us in an American Bourbon whisky were quantified by stable isotope dilution assays. Also for this purpose, new synthetic pathways were developed for the synthesis of the deuterium-labeled whisky lactone as well as for gamma-nona- and gamma-decalactone. To obtain the odor activity values (OAVs), the concentrations measured were divided by the odor thresholds of the odorants determined in water/ethanol (6:4 by vol.). Twenty-six aroma compounds showed OAVs >1, among which ethanol, ethyl (S)-2-methylbutanoate, 3-methylbutanal, 4-hydroxy-3-methoxybenzaldehyde, (E)-beta-damascenone, ethyl hexanoate, ethyl butanoate, ethyl octanoate, 2-methylpropanal, (3S,4S)- cis-whiskylactone, (E, E)-2,4-decadienal, 4-allyl-2-methoxyphenol, ethyl-3-methylbutanoate, and ethyl 2-methylpropanoate showed the highest values. The overall aroma of the Bourbon whisky could be mimicked by an aroma recombinate consisting of the 26 key odorants in their actual concentrations in whisky using water/ethanol (6:4 by vol.) as the matrix. Omission experiments corroborated the importance of, in particular, 4-hydroxy-3-methoxybenzaldehyde, (3S,4S)-cis-whiskylactone, ethanol, and the entire group of esters for the overall aroma of the Bourbon whisky.     

Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science

Application of aroma extract dilution analysis (AEDA) to the volatiles isolated from a commercial Japanese soy sauce revealed 30 odor-active compounds in the flavor dilution (FD) factor range of 8-4096, among which 2-phenylethanol showed the highest FD factor of 4096, followed by 3-(methylsulfanyl)propanal (methional), the tautomers 4-hydroxy-5-ethyl-2-methyl- and 4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone (4-HEMF), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (4-HDF), and 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone), all showing FD factors of 1024. Thirteen odorants were quantified by stable isotope dilution assays, and their odor activity values (OAVs) were calculated as ratio of their concentrations and odor thresholds in water. Among them, 3-methylbutanal (malty), sotolone (seasoning-like), 4-HEMF (caramel-like), 2-methylbutanal (malty), methional (cooked potato), ethanol (alcoholic), and ethyl 2-methylpropanoate (fruity) showed the highest OAVs (>200). An aqueous model aroma mixture containing 13 odorants, which had been identified with the highest OAVs, in concentrations that occur in the soy sauce showed a good similarity with the overall aroma of the soy sauce itself. Heat treatment of the soy sauce resulted in a clear change of the overall aroma. Quantitation of selected odorants revealed a significant decrease in sotolone and, in particular, increases in 2-acetyl-1-pyrroline, 4-HDMF, and 4-HEMF induced by heating.     

Changes in key aroma compounds of Criollo cocoa beans during roasting

Application of a comparative aroma extraction dilution analysis on unroasted and roasted Criollo cocoa beans revealed 42 aroma compounds in the flavor dilution (FD) factor range of 1-4096 for the unroasted and 4-8192 for the roasted cocoa beans. While the same compounds were present in the unroasted and roasted cocoa beans, respectively, these clearly differed in their intensity. For example, 2- and 3-methylbutanoic acid (rancid) and acetic acid (sour) showed the highest FD factors in the unroasted beans, while 3-methylbutanal (malty), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), and 2- and 3-methylbutanoic acid (sweaty) were detected with the highest FD factors in the roasted seeds. Quantitation of 30 odorants by means of stable isotope dilution assays followed by a calculation of odor activity values (ratio of the concentration/odor threshold) revealed concentrations above the odor threshold for 22 compounds in the unroasted and 27 compounds in the roasted cocoa beans, respectively. In particular, a strong increase in the concentrations of the Strecker aldehydes 3-methylbutanal and phenylacetaldehyde as well as 4-hydroxy-2,5-dimethyl-3(2H)-furanone was measured, suggesting that these odorants should contribute most to the changes in the overall aroma after roasting. Various compounds contributing to the aroma of roasted cocoa beans, such as 3-methylbutanoic acid, ethyl 2-methylbutanoate, and 2-phenylethanol, were already present in unroasted, fermented cocoa beans and were not increased during roasting.     

Identification of the key aroma compounds in cocoa powder based on molecular sensory correlations

Isolation of the volatile fraction from cocoa powder (50 g; 20% fat content) by a careful extraction/distillation process followed by application of an aroma extract dilution analysis revealed 35 odor-active constituents in the flavor dilution (FD) factor range of 8-4096. Among them, 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), 2- and 3-methylbutanoic acid (sweaty, rancid), dimethyl trisulfide (cooked cabbage), 2-ethyl-3,5-dimethylpyrazine (potato-chip-like), and phenylacetaldehyde (honey-like) showed the highest FD factors. Quantitation of 31 key odorants by means of stable isotope dilution assays, followed by a calculation of their odor activity values (OAVs) (ratio of concentration to odor threshold) revealed OAVs>100 for the five odorants acetic acid (sour), 3-methylbutanal (malty), 3-methylbutanoic acid, phenylacetaldehyde, and 2-methylbutanal (malty). In addition, another 19 aroma compounds showed OAVs>1. To establish their contribution to the overall aroma of the cocoa powder, these 24 compounds were added to a reconstructed cocoa matrix in exactly the same concentrations as they occurred in the cocoa powder. The matrix was prepared from deodorized cocoa powder, which was adjusted to 20% fat content using deodorized cocoa butter. The overall sensory evaluation of this aroma recombinate versus the cocoa powder clearly indicated that the 24 compounds represented the typical sweet, cocoa-like odor of the real sample.     

Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays

Application of the aroma extract dilution analysis on a flavor distillate prepared from freshly ground rye flour (type 1150) revealed 1-octen-3-one (mushroom-like), methional (cooked potato), and (E)-2-nonenal (fatty, green) with the highest flavor dilution (FD) factors among the 26 odor-active volatiles identified. Quantitative measurements performed by stable isotope dilution assays and a comparison to the odor thresholds of selected odorants in starch suggested methional, (E)-2-nonenal, and hexanal as contributors to the flour aroma, because their concentrations exceeded their odor thresholds by factors >100. Application of the same approach on a rye sourdough prepared from the same batch of flour revealed 3-methylbutanal, vanillin, 3-methylbutanoic acid, methional, (E,E)-2,4-decadienal, 2,3-butanedione, and acetic acid as important odorants; their concentrations exceeded their odor thresholds in water and starch by factors >100. A comparison of the concentrations of 20 odorants in rye flour and the sourdough made therefrom indicated that flour, besides the fermentation process, is an important source of aroma compounds in dough. However, 3-methylbutanol, acetic acid, and 2,3-butanedione were much increased during fermentation, whereas (E,E)-2,4-decadienal and 2-methylbutanal were decreased. Similar results were obtained for five different flours and sourdoughs, respectively, although the amounts of some odorants in the flour and the sourdough differed significantly within batches.     

Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. variety spalter select) based on GC-olfactometry and odor dilution techniques

Application of aroma extract dilution analysis on the volatiles obtained from dried cones of Spalter Select hops grown in the German hop-growing area of Hallertau revealed 23 odorants in the flavor dilution (FD) factor range of 16-4096, 20 of which could be identified. On the basis of high FD factors, trans-4, 5-epoxy-(E)-2-decenal, linalool, and myrcene were identified as the most potent odorants, followed by ethyl 2-methylpropanoate, methyl 2-methylbutanoate, (Z)-1,5-octadien-3-one, nonanal, (E,Z)-1,3, 5-undecatriene, 1,3(E),5(Z),9-undecatetraene, propyl 2-methylbutanoate, 4-ethenyl-2-methoxyphenol, and 1-octen-3-one. Ten of the high-impact hop aroma compounds had previously not been identified as hop constituents and, in particular, 1,3(E),5(Z), 9-undecatetraene has not yet been reported as a food odorant. In an extract obtained from fresh hops, in addition to the odorants found in dry hops, (Z)-3-hexenal was characterized as a further key odorant rendering an additional green aroma note to the fresh material.     

Comparison of the key aroma compounds in organically grown, raw West-African peanuts (Arachis hypogaea) and in ground, pan-roasted meal produced thereof

Application of an aroma extract dilution analysis on an aroma distillate prepared from organically grown, raw West-African peanuts (Cameroon) revealed 36 odor-active areas in the flavor dilution (FD) factor range of 1 to 2048. The identification experiments, which were all performed by using the respective reference chemicals, revealed 2-isopropyl-3-methoxypyrazine (earthy, pea-like), 2-isobutyl-3-methoxypyrazine (bell pepper-like, earthy), and trans-4,5-epoxy-(E)-2-decenal (metallic) with the highest FD factors among the 36 aroma compounds identified. The two last mentioned odorants and another set of 22 further odorants were identified for the first time in raw peanuts. A comparative aroma extract dilution analysis applied on distillates prepared from either the raw peanuts or ground peanut meal roasted in a pan showed 52 odor-active areas in the FD factor range of 8 to 2048 in the roasted nut material. The identification experiments in combination with the FD factors revealed that among them, 2-acetyl-1-pyrroline and 4-hydroxy-2,5-dimethyl-3-(2H)-furanone showed the most significant contribution to the overall aroma, followed by 1-octen-3-one, 2-isopropyl-3-methoxypyrazine, (E, E)-2,4-decadienal, and trans-4,5-epoxy-(E)-2-decenal. As a further result, 20 aroma compounds were newly identified in roasted peanuts, such as 2-propionyl-1-pyrroline and 2-acetyltetrahydropyridine (both popcorn-like). In particular, 2-acetyl-1-pyrroline and 4-hydroxy-2,5-dimethyl-3(2 H)-furanone showed the most pronounced increase after roasting.     

Identification based on quantitative measurements and aroma recombination of the character impact odorants in a Bavarian Pilsner-type beer

Application of aroma extract dilution analysis on the volatiles isolated from a Bavarian Pilsner-type beer revealed 40 odor-active constituents in the flavor dilution (FD) factor range of 16-2048, among which ethyl octanoate, (E)-beta-damascenone, 2- and 3-methylbutanoic acid, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone showed the highest FD factor of 2048. After quantitation of the 26 odorants showing FD factors > or =128 by stable isotope dilution analysis and determination of their odor thresholds in water, odor acitivity values (OAVs) were calculated. The results indicated ethanol, (E)-beta-damascenone, (R)-linalool, acetaldehyde, and ethyl butanoate with the highest OAVs, followed by ethyl 2-methylpropanoate and ethyl 4-methylpentanoate, which was previously unknown in beer. Finally, the overall aroma of the beer could be mimicked for the first time by recombining 22 reference odorants in the same concentrations as they occurred in the beer using ethanol/water as the matrix.     

Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable isotope dilution assays and sensory studies

An investigation of the volatile fraction of a freshly prepared sourdough rye bread crumb by means of the aroma extract dilution analysis (AEDA), followed by identification experiments, revealed 22 flavor compounds in the flavor dilution (FD) factor range of 128 to 2048. Quantitations performed by stable isotope dilution assays (SIDA) and a calculation of odor activity values (OAV; ratio of concentration to odor threshold) revealed the following as contributors to the overall crumb flavor: 3-methylbutanal (malty), (E)-2-nonenal (green, fatty), (E,E)-2,4-decadienal (fatty, waxy), hexanal (green), acetic acid (sour, pungent), phenylacetaldehyde (honey-like), methional (boiled potato-like), vanillin (vanilla-like), 2,3-butandione (buttery), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (spicy), and 2- and 3-methylbutanoic acid (sweaty). Using either citrate buffer, starch, or deodorized crumb as model matrixes, the typical malty and sour rye bread crumb flavor was reproduced by adding a mixture of 20 reference odorants in the "natural" concentrations as quantitatively determined in the fresh crumb.     

Change in the flavor of black tea drink during heat processing.

Heat processing during canning is responsible for the change in flavor of black tea infusion. The quantitative change in the volatile components of the black tea infusion during heat processing is not sufficient for explaining the sensory evaluation. In this study, application of aroma extract dilution analysis using the volatile fraction before and after black tea (Darjeeling) samples were heat processed resulted in the detection of 10 odor-active peaks for which flavor dilution (FD) factors changed. Seven potent odorants were identified from these peaks by gas chromatography-mass spectrometry. Among these components, 3-methylbutanal (stimulus), methional (potato-like), beta-damascenone (sweet), dimethyl trisulfide (putrid), and 2-methoxy-4-vinylphenol (clove-like) showed the highest FD factors after heat processing of the black tea sample. Therefore, these odorants were the most important components involved in changing the black tea odor during heat processing. In addition, the precursor of beta-damascenone in black tea infusion was investigated, and 3-hydroxy-7,8-didehydro-beta-ionol was determined to be one of the beta-damascenone-generating compounds for the first time.     

Characterization of the key aroma compounds in the beverage prepared from Darjeeling black tea: quantitative differences between tea leaves and infusion

By application of the aroma extract dilution analysis on the volatile fraction isolated from a black tea infusion (Darjeeling Gold Selection), vanillin (vanilla-like), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel), 2-phenylethanol (flowery), and (E,E,Z)-2,4,6-nonatrienal (oat-flake-like) were identified with the highest flavor dilution (FD) factors among the 24 odor-active compounds detected in the FD factor range of 4-128. Quantitative measurements performed by means of stable isotope dilution assays and a calculation of odor activity values (OAVs; ratio of concentration to odor threshold in water) revealed, in particular, the previously unknown tea constituent (E,E,Z)-2,4,6-nonatrienal as a key odorant in the infusion and confirmed the important role of linalool and geraniol for the tea aroma. An aroma recombinate performed by the 18 odorants for which OAVs > 1 were determined in their "natural" concentrations matched the overall aroma of the tea beverage. In the black tea leaves, a total of 42 odorants were identified, most of which were identical with those in the beverage prepared thereof. However, quantitative measurements indicated that, in particular, geraniol, but also eight further odorants were significantly increased in the infusion as compared to their concentration in the leaves.     

Identification of potent odorants in Japanese green tea (Sen-cha)

Application of aroma extract dilution analysis using the volatile fraction of a Japanese green tea (Sen-cha) sample resulted in the detection of 36 odor-active peaks with flavor dilution (FD) factors between 10 and 5000. Thirty-six potent odorants were identified from 36 odor-active peaks by gas chromatography/mass spectrometry (GC/MS) and/or the multidimensional GC/MS (MDGC/MS) system. Among these components, 4-methoxy-2-methyl-2-butanethiol (meaty), (Z)-1, 5-octadien-3-one (metallic), 4-mercapto-4-methyl-2-pentanone (meaty), (E,E)-2,4-decadienal (fatty), beta-damascone (honey-like), beta-damascenone (honey-like), (Z)-methyl jasmonate (floral), and indole (animal-like) showed the highest FD factors. Therefore, these odorants were the most important components of the Japanese green tea odor. In addition, 4-methoxy-2-methyl-2-butanethiol, 4-mercapto-4-methyl-2-pentanone, methional, 2-ethyl-3, 5-dimethylpyrazine, (Z)-4-decenal, beta-damascone, maltol, 5-octanolide, 2-methoxy-4-vinylphenol, and 2-aminoacetophenone were newly identified compounds in the green tea.     

Aroma components of acid-hydrolyzed vegetable protein made by partial hydrolysis of rice bran protein

Hydrolyzed vegetable protein (HVP) was prepared from rice bran protein concentrate (RBPc) by partial hydrolysis with aqueous 0.5 N HCl at 95 degrees C for 12 or 36 h (H-RBPc-12 and H-RBPc-36, respectively). Aroma components of the RBPc and the HVPs were characterized by gas chromatography-olfactometry, gas chromatography-mass spectrometry, aroma extract dilution analysis, and calculation of odor activity values (OAVs). The predominant odorants in RBPc were 3-methylbutanal, hexanal, 2-aminoacetophenone, (E)-2-nonenal, phenylacetaldehyde, and beta-damascenone. Among these, the odor of 2-aminoacetophenone, present at 59 ng/g in RBPc, was reminiscent of the typical odor of RBPc. Most of the predominant odorants had higher log3FD factors in the H-RBPc-36 as compared to H-RBPc-12. Aroma impact compounds of H-RBPc-12 and H-RBPc-36 were 2-methoxyphenol (guaiacol), 4-hydroxy-2,5-dimethyl-3(2H)furanone, 3-hydroxy-4,5-dimethyl-2(5H)furanone (sotolon), vanillin, 3-methylbutanal, (E)-2-nonenal, 4-vinyl-2-methoxyphenol (p-vinylguaiacol), and beta-damascenone. Guaiacol had the highest OAV values of 2770 and 17650 in H-RBPc-12 and H-RBPc-36, respectively.     

Important aroma compounds in freshly ground wholemeal and white wheat flour-identification and quantitative changes during sourdough fermentation

An investigation on the odor-active compounds of wholemeal (WWF) and white wheat flour (WF 550) by aroma extract dilution analysis (AEDA) and by quantitative studies using stable isotope dilution assays (SIDA) revealed a significant number of odor-active compounds, such as (E)-2-nonenal, (E,Z)- and (E,E)-2,4-decadienal, (E)-4,5-epoxy-(E)-2-decenal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, and vanillin, with high odor activities in both wheat flours. The amounts and, consequently, the aroma potencies of vanillin, (E,E)-2,4-decadienal, and 3-(methylthio)propanal were much higher in the WWF than in the WF 550 samples. Fermentation of suspensions of both flours with lactic acid bacteria did not generate new odorants; however, many compounds, such as acetic acid or 3-methylbutanal, were increased, whereas aldehydes (formed from the degradation of unsaturated fatty acids) were decreased. Comparing the odorant concentrations present before and after fermentation gave evidence that the main influence of the microorganisms on sourdough aroma is to either enhance or decrease specific volatiles already present in the flour. A comparison with literature data indicated that most of these odorants are also important for the bread crumb aroma present after baking of the dough.     

Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey

Characteristic aroma components of buckwheat honey were studied by combined sensory and instrumental techniques. Relative aroma intensity of individual volatile components was evaluated by aroma extract dilution analysis (AEDA) of solvent extracts and by gas chromatography-olfactometry (GCO) of decreasing headspace samples (GCO-H). Results indicated that 3-methylbutanal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon), and (E)-beta-damascenone were the most potent odorants in buckwheat honey, with 3-methylbutanal being primarily responsible for the distinct malty aroma. Other important aroma-active compounds included methylpropanal, 2,3-butanedione, phenylacetaldehyde, 3-methylbutyric acid, maltol, vanillin, methional, coumarin, and p-cresol.     

Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. laciniatus L.) blackberries

Cultivar Marion and Evergreen blackberry aromas were analyzed by aroma extract dilution analysis. Sixty-three aromas were identified (some tentatively) by mass spectrometry and gas chromatography-retention time; 48 were common to both cultivars, and 27 have not been previously reported in blackberry fruit. A comparison of cultivars shows that both have comparable compound types and numbers but with widely differing aroma impacts, as measured by flavor dilution (FD) factors. Ethyl 2-methylbutanoate, ethyl 2-methylpropanoate, hexanal, furanones (2,5-dimethyl-4-hydroxy-3-(2H)-furanone, 2-ethyl-4-hydroxy-5-methyl-3-(2H)-furanone, 4-hydroxy-5-methyl-3-(2H)-furanone, 4,5-dimethyl-3-hydroxy-2-(5H)-furanone, and 5-ethyl-3-hydroxy-4-methyl-2-(5H)-furanone), and sulfur compounds (thiophene, dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, 2-methylthiophene, and methional) were prominent in Evergreen (FD 512-2048). Except for ethyl 2-methylpropanoate, these same compounds were also prominent in Marion, but the FD factors varied significantly (FD 8-256) from Evergreen. The aroma profile of blackberry is complex, as no single volatile was unanimously described as characteristically blackberry.     

Studies on the key aroma compounds in soy milk made from three different soybean cultivars

An investigation by aroma extract dilution analysis (AEDA) of the aroma concentrate of soy milk made from a major Japanese soybean cultivar, Fukuyutaka (FK), revealed 20 key aroma compounds having flavor dilution (FD) factors of not less than 64. Among them, 2-isopropyl-3-methoxypyrazine, cis-4,5-epoxy-(E)-2-decenal, trans-4,5-epoxy-(E)-2-decenal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, and 2'-aminoacetophenone were identified as the key aroma compounds in soy milk for the first time. (E,E)-2,4-Decadienal exhibiting a fatty note and trans-4,5-epoxy-(E)-2-decenal exhibiting a metallic/sweet note were detected as having the highest FD factors of 4096, followed by hexanal (green), (E)-2-nonenal (fatty), and (E,E)-2,4-nonadienal (fatty) having FD factors of 1024. Although all of these compounds might be generated from lipids, various aroma components, which were thought to be generated from amino acids, sugars, and ferulic acid, were detected having FD factors of 64-256. Investigation by comparative AEDA experiments of the soy milk aroma concentrates of two cultivars for soybean curd and soy milk, FK and Vinton81 (VT), and one cultivar for boiled beans, Miyagishirome (MY), revealed that most of the key aroma compounds were common to all of them, but 2-isopropyl-3-methoxypyrazine, exhibiting a pea-like/earthy note, was detected only in FK and VT. In addition, a sensory experiment revealed that the pea-like/earthy notes in FK and VT were significantly stronger than that in MY. These results demonstrated that a pea-like/earthy note contributed by 2-isopropyl-3-methoxypyrazine might be one of the essential characteristics to describe soy milk aromas.     

Chemical characterization of commercial Sherry vinegar aroma by headspace solid-phase microextraction and gas chromatography-olfactometry

The sensorial representativeness of the headspace solid-phase microextraction (HS-SPME) aroma extract from commercial Sherry vinegars has been determined by direct gas chromatography-olfactometry (D-GCO). Extracts obtained under optimal conditions were used to characterize the aroma of these vinegars by means of GCO and aroma extract dilution analysis (AEDA). Among the 37 different odorants determined, 13 of them were identified for the first time in Sherry vinegars: 2 pyrazines (3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine), 2 sulfur compounds (methanethiol, dimethyl trisulfide), 1 unsaturated ketone (1-octen-3-one), 1 norisoprenoid (β-damascenone), 1 ester (ethyl trans-cinnamate) and 6 aldehydes (2- and 3-methylbutanal, octanal, nonanal, (E)-2-nonenal and (E,E)-2,4-decadienal). The determination of the odor thresholds in a hydroacetic solution together with the quantitative analysis-which was also performed using the simple and fast SPME technique-allowed obtaining the odor activity values (OAV) of the aromatic compounds found. Thus, a first pattern of their sensory importance on commercial Sherry vinegar aroma was provided.     

Characterization of the most odor-active volatiles in fresh, hand-squeezed juice of grapefruit (Citrus paradisi Macfayden)

By application of the aroma extract dilution analysis on an extract prepared from fresh grapefruit juice, 37 odor-active compounds were detected in the flavor dilution (FD) factor range of 4-256 and subsequently identified. Among them the highest odor activities (FD factors) were determined for ethyl butanoate, p-1-menthene-8-thiol, (Z)-3-hexenal, 4,5-epoxy-(E)-2-decenal, 4-mercapto-4-methylpentane-2-one, 1-heptene-3-one, and wine lactone. Besides the 5 last mentioned compounds, a total of 13 further odorants were identified for the first time as flavor constituents of grapefruit. The data confirmed results of the literature on the significant contribution of 1-p-menthene-8-thiol in grapefruit aroma but clearly showed that a certain number of further odorants are necessary to elicit the typical grapefruit flavor.