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Beer and wine are popular beverages with clearly different aroma characters, the molecular background of which has not yet been systematically investigated. A comprehensive literature survey returned 14 845 concentration values obtained from 160 beer and 904 wine samples, covering 42 basic beer and 42 basic wine odorants, among which 40 were common to both beverages. Based on mean concentrations and a comparison with threshold data, 29 beer and 32 wine odorants were finally selected to build aroma base models that reflected the basic olfactory difference between beer and wine. Orthonasal concentration leveling tests applied to groups of odorants with similar odor characteristics finally revealed the crucial role of fruity smelling compounds. When 11 fruity compounds, predominantly esters, in the beer aroma base model were adjusted to the respective concentration levels in the wine aroma base model, the sensory panel no longer described the sample as beer-like but as wine-like.

Geosmin, a ubiquitous volatile sesquiterpenoid of microbiological origin, is causative for deteriorating the quality of many foods, beverages, and drinking water, by eliciting an undesirable "earthy/musty" off-flavor. Moreover, and across species from worm to human, geosmin is a volatile, chemosensory trigger of both avoidance and attraction behaviors, suggesting its role as semiochemical. Volatiles typically are detected by chemosensory receptors of the nose, which have evolved to best detect ecologically relevant food-related odorants and semiochemicals. An insect receptor for geosmin was recently identified in flies. A human geosmin-selective receptor, however, has been elusive. Here, we report on the identification and characterization of a human odorant receptor for geosmin, with its function being conserved in orthologs across six mammalian species. Notably, the receptor from the desert-dwelling kangaroo rat showed a more than 100-fold higher sensitivity compared to its human ortholog and detected geosmin at low nmol/L concentrations in extracts from geosmin-producing actinomycetes.

Mead was analyzed by using the concept of molecular sensory science for the identification of key odorants. A total of 29 odor-active compounds were identified in mead by using gas chromatography olfactometry (GCO). Flavor dilution (FD) factors of identified compounds ranged from 1 to 16,384, compounds with FD factors ≥32 were quantitated by using stable isotopically substituted odorants as internal standards or external standard method, and odor activity values (OAVs) were calculated. Fifteen compounds showed OAVs ≥1: aldehydes (2-phenylacetaldehyde, 3-(methylsulfanyl)propanal), 4-hydroxy-3-methoxybenzaldehyde), esters (ethyl 3-methylbutanoate, ethyl propanoate, ethyl octanoate), alcohols (2-phenylethan-1-ol, 3- and 2-methylbutan-1-ol, 3-(methylsulyfanyl)propan-1-ol), furanons (4-hydroxy-2,5-dimethylfuran-3(2 H )-one, 3-hydroxy-4,5-dimethylfuran-2(5 H )-one), acids (3- and 2-methylbutanoic acid, acetic acid), 1,1-diethoxyethane, and 4-methylphenol. 2-Phenylacetaldehyde (OAV, 3100) was suggested as the compound with the biggest influence on the aroma of mead, followed by 4-hydroxy-2,5-dimethylfuran-3(2 H )-one (OAV, 1900), 3-(methylsulfanyl)propanal (OAV, 890), and 2-phenylethan-1-ol (OAV, 680). Quantitative olfactory profile analysis revealed strong honey, malty, and alcoholic impressions. Omission experiments revealed that 3-(methylsulfanyl)propanal, 2-phenylethan-1-ol, 4-hydroxy-2,5-dimethylfuran-3(2 H )-one, ethyl propanoate, ethyl 3-methylbutanoate, 2-phenylacetaldehyde, 3- and 2-methylbutanoic acid, 3-hydroxy-4,5-dimethylfuran-2(5 H )-one, and 4-hydroxy-3-methoxybenzaldehyde were the key odorants in the mead. Determining concentrations of key odorants in important production steps showed that the fermentation and maturation stages had the strongest effect on the formation of mead aroma.

Some truffles are expensive and, therefore, are prone to food fraud. A particular problem is the differentiation of high-priced Tuber magnatum truffles from cheaper Tuber borchii truffles, both of which are white truffles with similar morphological characteristics. Using an untargeted approach, the volatiles isolated from samples of both species were screened for potential marker compounds by comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC×GC-TOFMS) and statistical analysis of the obtained semiquantitative data. Results suggested bis(methylsulfanyl)methane and furan-2(5 H )-one as compounds characterizing T. magnatum and T. borchii , respectively. Exact quantitation of both volatiles by conventional one-dimensional gas chromatography-mass spectrometry in combination with stable isotopologues of the target compounds as internal standards confirmed both as marker compounds. The method is suitable to be used in the routine analysis for the objective species differentiation of T. magnatum and T. borchii .

Muscaris is a modern white grape variety with good fungal resistance and a pleasant aroma, the molecular background of which was unknown. A comparative aroma extract dilution analysis applied to Muscaris grapes and grapes of the father variety Muskateller revealed little differences and resulted in 39 and 35 odorants, respectively. Sixteen odorants exceeded their odor threshold concentrations. Odor reconstitution and omission experiments showed that the distinct lychee note in the aroma of the Muscaris grapes was generated by the combination of (2 S ,4 R )-rose oxide and geraniol. This finding will guide further molecular research on the transfer of the lychee note into wine and may also be helpful for the targeted breeding of new grape varieties.

Fresh kernels of the walnut tree ( Juglans regia L.) show a characteristic and pleasant aroma, the molecular basis of which was unknown. The application of an aroma extract dilution analysis resulted in 50 odor-active compounds. Among them, 37 had not been reported as fresh walnut kernel volatiles before, including the two odorants with the highest flavor dilution factors, namely, fenugreek-like smelling 3-hydroxy-4,5-dimethylfuran-2(5 H )-one (sotolon) and oatmeal-like smelling (2 E ,4 E ,6 Z )-nona-2,4,6-trienal. Quantitations revealed 17 odorants with concentrations in the walnuts that exceeded their odor threshold concentrations. Aroma reconstitution and omission experiments finally showed that the characteristic aroma of fresh walnuts is best represented by a binary mixture of sotolon and (2 E ,4 E ,6 Z )-nona-2,4,6-trienal. Of both, the natural concentration was ∼10 μg/kg. Further sensory studies showed that the walnut character is intensified when their concentrations are in parallel increased to ∼100 μg/kg. This finding may guide the future breeding of new walnut cultivars with improved aroma.

In order to analyze the molecular rearrangement of terpenes in wine during aging, the changes in linalool, α-terpineol, nerol, and geraniol in model wine were investigated in the dark at low temperature for 90 days. Headspace-gas chromatograph-mass spectrometer/olfactometry was used for qualitative and relative quantitation of terpenes. Quantum mechanical calculation was used to analyze the Gibbs free energy. The results showed that nerol was converted into d-limonene, terpinolene, linalool, and α-terpineol. Geraniol was converted into β-ocimene, terpinolene, and linalool. Linalool was converted into terpinolene. The conversion rate of nerol to terpinolene was the highest with 5.94%. α-Terpineol was not converted spontaneously into other terpenes due to its lowest Gibbs free energy, indicating that the cyclization and isomerization could occur spontaneously through an exotherm reaction. However, the dehydroxylation of linalool, nerol, and geraniol required an energy source.

Fine flavor properties of chocolates such as fruity, floral, and cocoa-like were decoded on a molecular level for the first time. The molecular compositions of six chocolates made out of liquors that were referenced with specific sensory attributes were analyzed. After the screening for odor-active molecules by aroma extract dilution analysis, selected compounds were quantitated with the overall aim to decode the distinct fine flavor attributes on a molecular level. Acidic and fruity flavor notes were associated with high dose over threshold factors (DoT factors) of acetic acid and fruity smelling esters such as ethyl 2-methylbutanaote, ethyl 3-methylbutanoate, and 3-methylbutyl acetate, respectively. Cocoa-like and roasty flavor notes were associated with high DoT factors for 2-methylbutanal, 3-methylbutanal, 4-hydroxy-2,5-dimethylfuran-3(2 H )-one, and dimethyltrisulfane. The floral and astringent flavors were linked to high DoT factors of (-)-epicatechin, procyanidin B2, procyanidin C1, and 2-phenylethan-1-ol.

Application of gas chromatography-olfactometry and aroma extract dilution analysis to the volatiles isolated from (1) crust and (2) crumb of a wheat bread made with the addition of a dark liquid malt extract (LME) to the dough and (3) crust and (4) crumb of a reference bread made without addition resulted in the identification of 23 major odorants. Their quantitation followed by the calculation of odor activity values (OAV = ratio of concentration to odor threshold value) suggested that LME addition influenced the aroma of the bread predominantly by increasing seasoning-like smelling sotolon in crust and crumb, and caramel-like smelling compounds maltol and 4-hydroxy-2,5-dimethylfuran-3(2 H )-one (HDMF) in the crumb. The increase in sotolon and maltol was explainable by direct transfer from the LME to the bread, whereas HDMF must have been formed from LME-derived precursors. This difference needs to be considered in the targeted optimization of LMEs for bread making.

Volatile compounds of raw and cooked green kohlrabi were investigated using a sensomics approach. A total of 55 odor-active compounds were detected and identified in raw and cooked green kohlrabi using GC-O. Twenty-eight odor-active compounds with high flavor dilution (FD) factors ranging from 64 to 1024 were quantitated, and odor activity values (OAVs) were determined. Eight compounds showed high OAVs in raw and cooked kohlrabi: five sulfur compounds (dimethyl trisulfide, methyl 2-methyl-3-furyl disulfide, and three isothiocyanates (1-isothiocyanato-3-(methylsulfanyl)propane, benzyl isothiocyanate, and 1-isothiocyanato-4-(methylsulfanyl)butane)), two lipid oxidation products (1-octen-3-one and trans -4,5-epoxy-(2 E )-dec-2-enal), and 2-isopropyl-3-methoxypyrazine. Among these, the sulfur compounds contributed most to the overall smell of the raw and cooked vegetables. The quantitation analysis indicates that the eight odorants are the backbone compounds for raw and cooked kohlrabi. The OAVs for the backbone compounds and also for minor odorants are clearly higher in raw kohlrabi than in the cooked one. Differences can be explained by the influence of the cooking process.

The impact of water on odor-active compounds in fermented and dried cocoa beans as well as in chocolate either produced by a novel processing (NPC) or a traditional processing (TPC) technology from the same batch of cocoa beans was investigated in this study. Quantitation of selected key odorants revealed significantly higher concentrations of Strecker aldehydes such as 3-(methylsulfanyl)propanal (66-fold) and phenylacetaldehyde (50-fold) after water treatment of the cocoa beans. The comparison of the two chocolates showed that higher amounts of the Strecker aldehydes 2-methylbutanal, 3-methylbutanal, and phenylacetaldehyde are released with water in the NPC (24-fold to 39-fold), compared to the TPC (7.3-fold-11-fold). In addition to Strecker aldehydes, the concentrations of many further characteristic key odorants of cocoa and chocolate increased after water treatment. Based on the results, a more intense retronasal odor perception of the analyzed compounds is expected due to their release during consumption in contact with saliva.

Specialty barley malts provide unique aroma characteristics to beer; however, the transfer of specialty malt odorants to beer has not yet been systematically studied. Therefore, three beers were brewed: (1) exclusively with kilned base barley malt, (2) with the addition of a caramel barley malt, and (3) with the addition of a roasted barley malt. Major odorants in the beers were identified by aroma extract dilution analysis followed by quantitation and calculation of odor activity values (OAVs). The caramel malt beer was characterized by outstandingly high OAVs for odorants such as ( E )-β-damascenone, 2-acetyl-1-pyrroline, methionol, 2-ethyl-3,5-dimethylpyrazine, and 4-hydroxy-2,5-dimethylfuran-3(2 H )-one, whereas the highest OAV for 2-methoxyphenol was obtained in the roasted malt beer. Quantifying odorants in the malts revealed that the direct transfer from malt to beer played only a minor role in the amount of malt odorants in the beers, suggesting a substantial formation from precursors and/or a release of encapsulated odorants during brewing.

The parallel application of aroma extract dilution analysis to the volatiles isolated from a sample of fermented cocoa seeds with a pronounced moldy-musty off-flavor and to the volatiles isolated from a flawless reference sample revealed (-)-geosmin, 4-methoxy-2,5-dimethylfuran-3(2 H )-one, 1 H -indole, and 3-methyl-1 H -indole as potential off-flavor compounds on the basis of their odor quality and higher flavor dilution factors in off-flavor cocoa than in the reference sample. Quantitation of the four compounds in nine off-flavor cocoa samples and calculation of odor activity values (ratio of the concentrations to the odor threshold values) suggested the crucial roles of (-)-geosmin and 3-methyl-1 H -indole for the off-flavor. In the chocolate industry, their quantitation can be used to objectively assess the off-flavor at the level of incoming goods inspection. Because both compounds are inhomogeneously distributed between the testa and the embryo, separate quantitation in the two parts of the seeds is required.

Application of an aroma extract dilution analysis in parallel applied to the volatiles isolated from a sample of fermented cocoa with a pronounced smoky off-flavor and a reference sample with flawless aroma revealed seven potential off-flavor compounds with smoky/phenolic odor qualities and higher flavor dilution factors in the off-flavor sample than in the reference sample. These compounds were 2-methoxyphenol, 3- and 4-methylphenol, 3- and 4-ethylphenol, and 3- and 4-propylphenol. Their quantitation in seven off-flavor samples and two reference samples without off-flavor showed that 4-propylphenol did not exceed its odor threshold value. From the concentrations obtained for the other six compounds and their odor threshold values in deodorized cocoa butter, maximum tolerable concentrations were derived for the incoming goods inspection in the chocolate industry. The suggested limits are 2 μg/kg for 3-ethylphenol and 3-propylphenol, 20 μg/kg for 4-methylphenol, 3-methylphenol, and 4-ethylphenol, and 70 μg/kg for 2-methoxyphenol.

On the basis of the following data from the literature, we hypothesized the presence of ethionine in durian pulp: (1) the major odorants in terms of quantity as well as odor potency in durian pulp are ethanethiol and its derivatives; (2) genome analysis of durian assigned methionine γ-lyase (MGL), the enzyme that converts methionine to methanethiol, a key role for durian odor formation; and (3) MGL accepts not only methionine but also ethionine as a substrate. A targeted search by liquid chromatography-tandem mass spectrometry allowed us to confirm the presence of ethionine in durian pulp. Quantitation of ethionine in samples of different varieties (Monthong, Krathum, Chanee, and Kanyao) showed concentrations (621-9600 μg/kg) in the same range but below the methionine concentrations (16100-30200 μg/kg). During fruit ripening, the ethionine concentration increased as well as the ethanethiol concentration. Final evidence for the role of ethionine as an ethanethiol precursor was provided by demonstrating the formation of ( 2 H 5 )ethanethiol after adding ( 2 H 5 )ethionine to durian pulp.

The volatiles isolated by solvent extraction and solvent-assisted flavor evaporation (SAFE) from roasted barley tea, prepared from either hulled barley or naked barley, were subjected to a comparative aroma extract dilution analysis, which resulted in 27 odor-active compounds with flavor dilution factors (FD factors) of 64-1024. An additional 5 odorants were detected by static headspace analysis. Quantitation of these 32 compounds revealed 22 and 23 odorants in the naked barley tea and in the hulled barley tea, respectively, that exceeded their odor-threshold values. On the basis of these data, the aromas of both barley tea variants were successfully reconstituted with reference compounds. The calculation of odor-activity values (OAVs = concentration/odor-threshold value) and omission tests suggested 2-methoxyphenol (OAVs 69 and 160) and trans -isoeugenol (OAVs 1.4 and 31) as key compounds responsible for the stronger smoky note in the hulled barley tea. Further important odorants in the naked and hulled barley teas included 2-acetylpyrazine (OAVs 23 and 16), 2-acetyl-1-pyrroline (OAVs 19 and 16), and 3-methylbutanal (OAVs 12 and 15).

Screening the volatiles of cempedak [ Artocarpus integer (Thunb.) Merr.] pulp for odor-active compounds by aroma extract dilution analysis and gas chromatography (GC)-olfactometry of static headspace samples revealed a total of 55 odorants, among which 47 were identified. Using stable isotopically substituted odorants as internal standards, these compounds were quantitated by GC-mass spectrometry, and odor activity values (OAVs) were calculated as ratios of the natural concentrations in cempedak pulp to the orthonasal odor detection thresholds. An aroma reconstitution model based on the 41 compounds with OAVs >1 in their natural concentrations successfully mimicked the characteristic aroma of cempedak pulp including the pronounced sulfury, oniony note which is intense in cempedak pulp but absent in jackfruit pulp. Further sensory tests finally showed that 2-(methylsulfanyl)propane, 2-(methylsulfanyl)butane, and 2-(methylsulfanyl)pentane are the key compounds responsible for this unique aroma note in cempedak pulp and vitally contribute to the aroma difference between cempedak pulp and jackfruit pulp.

An aroma extract dilution analysis applied to the volatiles isolated from jackfruit ( Artocarpus heterophyllus Lam.) pulp by solvent extraction and solvent-assisted flavor evaporation resulted in the detection of 48 odorants with flavor dilution (FD) factors between 1 and ≥8192. Application of gas chromatography-olfactometry to static headspace samples revealed additional five highly volatile odorants. The structures of 44 out of the 53 detected odorants could be assigned. These 44 compounds were quantitated using stable isotopically substituted odorants as internal standards, and their odor activity values (OAVs) were calculated as the ratio of the natural concentrations in jackfruit pulp and the odor threshold values in water. High OAVs were in particular obtained for ethyl 3-methylbutanoate (74000), ethyl butanoate (1800), 3-methylbutanal (1500), and 2-methylpropanal (1400). An aroma model solution based on the natural concentrations of the 35 compounds for which OAVs > 1 had been calculated fully mimicked the characteristic jackfruit pulp aroma.

Propolis is a fragrant material produced by bees and is commonly used as an ingredient in food, beverage, and consumer goods industries. Application of a comparative aroma extract dilution analysis (cAEDA) to volatiles isolated from propolis over three consecutive years afforded 48 odorants with flavor dilution (FD) factors ≥ 4, including 21 compounds not previously reported in propolis. Despite differences in FD factors of some compounds, the overall temporal variation in the odorants was low. Compounds with FD ≥ 64 were quantitated by stable isotope dilution assays (SIDAs), and odor activity values (OAVs) were calculated. A total of 22 compounds showed OAVs ≥ 1, including ( E)-isoeugenol (clove; OAV 3700), linalool (floral; OAV 380), butanoic acid (sweaty, rancid; OAV 370), and 3-phenylpropanoic acid (floral; OAV 270). An odor reconstitution model prepared from deodorized beeswax and the 22 odorants in their natural concentrations closely matched the olfactory profile of authentic propolis. The results of this study will help to establish a basis for future research on the variability of propolis sourced from different geographical locations, produced by different bee species, and collected from different botanical sources, all of which are largely unknown.

Bottom-fermented and top-fermented beers, both either late or dry hopped with Huell Melon hops, and respective reference beers without late or dry hopping were subjected to a comparative odorant screening by aroma extract dilution analyses. On the basis of differences in the FD factors, 14 odorants were identified as hop-derived. Among them were ethyl 2-methylpropanoate, methyl 2-methylbutanoate, ethyl 2-methylbutanoate, propyl 2-methylbutanoate, myrcene, linalool, and geraniol. Differences between late hopped, dry hopped, and reference beers were substantiated by quantitation. Results showed minimal transfer of myrcene from hops into beer. Moderate transfer was observed for propyl 2-methylbutanoate, geraniol, and linalool. Process-induced changes of ethyl 2-methylpropanoate, ethyl 2-methylbutanoate, and methyl 2-methylbutanoate were beyond a direct transfer from hops into beer, suggesting a formation from the corresponding hop-derived carboxylic acids by yeast. Spiking experiments revealed that linalool and propyl 2-methylbutanoate contributed particularly to the characteristic aroma of beers flavored with Huell Melon hops.

The volatiles isolated from samples of the special flavor hop varieties, Huell Melon and Polaris, and from the aroma hop variety, Hallertau Tradition, by solvent extraction and solvent-assisted flavor evaporation (SAFE) were subjected to a comparative aroma extract dilution analysis (cAEDA), which resulted in 46 odor-active compounds in the flavor dilution (FD) factor range of 16 to 2048. On the basis of high FD factors, myrcene, (3R)-linalool, and 2- and 3-methylbutanoic acid were confirmed as important variety-independent hop odorants. (1R,4S)-Calamenene was identified for the first time as an odor-active compound in hops. Clear differences in the FD factors and their subsequent objectification by stable isotope dilution quantitation suggested that high concentrations of the esters ethyl 2-methylbutanoate, ethyl 2-methylpropanoate, and propyl 2-methylbutanoate cause the characteristic fruity, cantaloupe-like odor note in Huell Melon hops, whereas the fruity and minty odor notes in Polaris are associated with high amounts of 3-methylbutyl acetate and 1,8-cineole.

A stable isotope dilution assay was developed for quantitation of 4-methyl-4-sulfanylpentan-2-one (4MSP) in hops. The approach included the use of 4-( 13 C)methyl-4-sulfanyl(1,3,5- 13 C 3 )pentan-2-one as internal standard, selective isolation of hop thiols by mercurated agarose, and GC×GC-TOFMS analysis. Application of the method to 53 different hop samples revealed 4MSP concentrations between <1 and 114 μg/kg. Notably high concentrations were associated with United States varieties such as Citra, Eureka, Simcoe, and Apollo, whereas 4MSP was absent from traditional German and English varieties. Further experiments showed that besides the variety, also harvest year and storage vitally influenced 4MSP concentrations, whereas the impact of provenance was less pronounced. Hop processing such as drying and pelletizing had only a minor impact on 4MSP concentrations. Like the majority of other hop volatiles, 4MSP is predominantly located in the lupulin glands.

The most odor-active compounds previously identified by application of an aroma extract dilution analysis were quantitated in freshly picked curry leaves, either by stable isotope dilution assays in combination with GC-GC-MS or by GC-FID after simultaneous extraction/fractionation. Odor activity values (OAVs) were calculated as ratios of concentrations to odor threshold values. The topmost OAVs were obtained for (3Z)-hex-3-enal (grassy; OAV 180 000), (1S)-1-phenylethane-1-thiol (sulfury, burnt; OAV 150 000), (1R)-1-phenylethane-1-thiol (sulfury, burnt; OAV 120 000), (3R)-linalool (citrusy; OAV 58 000), and myrcene (geranium leaf-like; OAV 23 000). The high OAVs calculated for its enantiomers confirmed 1-phenylethane-1-thiol as character impact compound of the typical sulfury and burnt aroma of curry leaves. The 1-phenylethane-1-thiol concentration in curry leaves decreased upon tissue disruption and drying, as well as upon frying of fresh leaves. By contrast, frying of dried leaves led to an increase of 1-phenylethane-1-thiol, indicating a yet unknown thermolabile precursor.

Sixteen compounds, previously identified as potent odorants by application of an aroma extract dilution analysis and the gas chromatography-olfactometry analysis of static headspace samples, were quantitated in the pulp of durians, variety Monthong, and odor activity values (OAVs) were calculated by dividing the concentrations obtained by the odor thresholds of the compounds in water. In combination with data recently reported for hydrogen sulfide and short-chain alkanethiols, OAVs > 1 were obtained for 19 compounds, among which ethyl (2S)-2-methylbutanoate (fruity; OAV 1700000), ethanethiol (rotten onion; OAV 480000), and 1-(ethylsulfanyl)ethane-1-thiol (roasted onion; OAV 250000) were the most potent, followed by methanethiol (rotten, cabbage; OAV 45000), ethane-1,1-dithiol (sulfury, durian; OAV 23000), and ethyl 2-methylpropanoate (fruity; OAV 22000). Aroma simulation and omission experiments revealed that the overall odor of durian pulp could be mimicked by only two compounds, namely, ethyl (2S)-2-methylbutanoate and 1-(ethylsulfanyl)ethane-1-thiol, when combined in their natural concentrations.

Thirty-four aroma-active compounds, previously identified with high flavor dilution factors by application of an aroma extract dilution analysis, were quantified in tree-ripened fruits of mango (Mangifera indica L. 'Haden'). From the results, the odor activity value (OAV) was calculated for each compound as the ratio of its concentration in the mangoes to its odor threshold in water. OAVs > 1 were obtained for 24 compounds, among which ethyl 2-methylbutanoate (fruity; OAV 2100), (3E,5Z)-undeca-1,3,5-triene (pineapple-like; OAV 1900), ethyl 3-methylbutanoate (fruity; OAV 1600), and ethyl butanoate (fruity; OAV 980) were the most potent, followed by (2E,6Z)-nona-2,6-dienal (cucumber-like), ethyl 2-methylpropanoate (fruity), (E)-β-damascenone (cooked apple-like), ethyl hexanoate (fruity), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), 3-methylbut-2-ene-1-thiol (sulfurous), γ-decalactone (peach-like), β-myrcene (terpeny), (3Z)-hex-3-enal (green), 4-methyl-4-sulfanylpentan-2-one (tropical fruit-like), and ethyl octanoate (fruity). Aroma simulation and omission experiments revealed that these 15 compounds, when combined in a model mixture in their natural concentrations, were able to mimic the aroma of the fruits.

The sensory impact of thiols in Vitis vinifera 'Carmenere' red wines was evaluated. For this purpose, aroma extract dilution analysis was applied to the thiols isolated from a Carmenere red wine by affinity chromatography with a mercurated agarose gel. Results revealed the presence of four odorants, identified as 2-furanylmethanethiol, 3-sulfanylhexyl acetate, 3-sulfanyl-1-hexanol, and 2-methyl-3-sulfanyl-1-butanol, with the latter being described here for the first time in Carmenere red wines. Quantitation of the four thiols in the Carmenere wine screened by aroma extract dilution analysis and in three additional Carmenere wines by stable isotope dilution assays resulted in concentrations above the respective orthonasal odor detection threshold values. Triangle tests applied to wine model solutions with and without the addition of the four thiols showed significant differences, thus suggesting that the compounds do have the potential to influence the overall aroma of red wine.

Curry leaves are a popular seasoning herb with a pronounced sulfury and burnt odor, the molecular background of which was yet unclear. Application of an aroma extract dilution analysis to the volatile fraction of curry leaves isolated by solvent extraction and solvent-assisted flavor evaporation afforded 23 odor-active compounds with flavor dilution (FD) factors ranging from 1 to 8192. On the basis of the comparison of their retention indices, mass spectra, and odor properties with data of reference compounds, the structures of 22 odorants could be assigned, 15 of which had not been reported in curry leaves before. Odorants with high FD factors included 1-phenylethanethiol (FD factor 8192), linalool (4096), α-pinene (2048), 1,8-cineole (1024), (3Z)-hex-3-enal (256), 3-(methylsulfanyl)propanal (128), myrcene (64), (3Z)-hex-3-en-1-ol (32), and (2E,6Z)-nona-2,6-dienal (32). The unique sulfury and burnt odor exhibited by 1-phenylethanethiol in combination with its high FD factor suggested that it constitutes the character impact compound of fresh curry leaf aroma.

The aroma-active compounds present in tree-ripened fruits of the five mango (Mangifera indica L.) cultivars Haden, White Alfonso, Praya Sowoy, Royal Special, and Malindi were isolated by solvent extraction followed by solvent-assisted flavor evaporation (SAFE) and analyzed by gas chromatography-olfactometery (GC-O). Application of a comparative aroma extract dilution analysis (cAEDA) afforded 54 aroma-active compounds in the flavor dilution (FD) factor range from 4 to ≥2048, 16 of which are reported for the first time in mango. The results of the identification experiments in combination with the FD factors revealed 4-hydroxy-2,5-dimethyl-3(2H)-furanone as an important aroma compound in all cultivars analyzed. Twenty-seven aroma-active compounds were present in at least one mango cultivar at an FD factor ≥128. Clear differences in the FD factors of these odorants between each of the mango cultivars suggested that they contributed to the unique sensory profiles of the individual cultivars.

An aroma extract dilution analysis applied on the volatile fraction isolated from Thai durian by solvent extraction and solvent-assisted flavor evaporation resulted in 44 odor-active compounds in the flavor dilution (FD) factor range of 1-16384, 41 of which could be identified and 24 that had not been reported in durian before. High FD factors were found for ethyl (2S)-2-methylbutanoate (fruity; FD 16384), ethyl cinnamate (honey; FD 4096), and 1-(ethylsulfanyl)ethanethiol (roasted onion; FD 1024), followed by 1-(ethyldisulfanyl)-1-(ethylsulfanyl)ethane (sulfury, onion), 2(5)-ethyl-4-hydroxy-5(2)-methylfuran-3(2H)-one (caramel), 3-hydroxy-4,5-dimethylfuran-2(5H)-one (soup seasoning), ethyl 2-methylpropanoate (fruity), ethyl butanoate (fruity), 3-methylbut-2-ene-1-thiol (skunky), ethane-1,1-dithiol (sulfury, durian), 1-(methylsulfanyl)ethanethiol (roasted onion), 1-(ethylsulfanyl)propane-1-thiol (roasted onion), and 4-hydroxy-2,5-dimethylfuran-3(2H)-one (caramel). Among the highly volatile compounds screened by static headspace gas chromatography-olfactometry, hydrogen sulfide (rotten egg), acetaldehyde (fresh, fruity), methanethiol (rotten, cabbage), ethanethiol (rotten, onion), and propane-1-thiol (rotten, durian) were found as additional potent odor-active compounds. Fourteen of the 41 characterized durian odorants showed an alkane-1,1-dithiol, 1-(alkylsulfanyl)alkane-1-thiol, or 1,1-bis(alkylsulfanyl)alkane structure derived from acetaldehyde, propanal, hydrogen sulfide, and alkane-1-thiols. Among these, 1-(propylsulfanyl)ethanethiol, 1-{[1-(methylsulfanyl)ethyl]sulfanyl}ethanethiol, and 1-{[1-(ethylsulfanyl)ethyl]sulfanyl}ethanethiol were reported for the first time in a natural product.

Eleven odor-active thiols, namely, 2-methyl-1-propene-1-thiol, (Z)-3-methyl-1-butene-1-thiol, (E)-3-methyl-1-butene-1-thiol, (Z)-2-methyl-1-butene-1-thiol, (E)-2-methyl-1-butene-1-thiol, 2-methyl-3-furanthiol, 3-mercapto-2-pentanone, 2-mercapto-3-pentanone, 4-mercapto-3-hexanone, 3-mercapto-3-methylbutyl formate, and 2-methyl-3-thiophenethiol, recently identified in an extract prepared from white sesame seeds, were quantitated in sesame using stable isotope dilution analyses. For that purpose, the following deuterium-labeled compounds were synthesized and used as internal standards in the quantitation assays: [2H6]-2-methyl-1-propene-1-thiol, [2H3]-(E)- and [2H3]-(Z)-2-methyl-1-butene-1-thiol, [2H3]-2-methyl-3-furanthiol, [2H2]-3-mercapto-2-pentanone, [2H3]-4-mercapto-3-hexanone, [2H6]-3-mercapto-3-methylbutyl formate, and [2H3]-2-methyl-3-thiophenethiol. On the basis of the results obtained, odor activity values (OAVs) were calculated as ratio of the concentration and odor threshold of the individual compounds in cooking oil. According to their high OAVs, particularly the 3-methyl-1-butene-1-thiols (OAV: 2400) and the 2-methyl-1-butene-1-thiols (OAV: 960) were identified as the most odor-active compounds in pan-roasted white sesame seeds. These compounds were therefore suggested to be mainly responsible for the characteristic but rather unstable sulfury aroma of freshly pan-roasted white sesame seeds.

Screening for aroma-active compounds in an aroma distillate obtained from freshly pan-roasted sesame seeds by aroma extract dilution analysis revealed 32 odorants in the FD factor range of 2-2048, 29 of which could be identified. The highest FD factors were found for the coffee-like smelling 2-furfurylthiol, the caramel-like smelling 4-hydroxy-2,5-dimethyl-3(2H)-furanone, the coffee-like smelling 2-thenylthiol (thiophen-2-yl-methylthiol), and the clove-like smelling 2-methoxy-4-vinylphenol. In addition, 9 odor-active thiols with sulfurous, meaty, and/or catty, black-currant-like odors were identified for the first time in roasted sesame seeds. Among them, 2-methyl-1-propene-1-thiol, (Z)-3-methyl-1-butene-1-thiol, (E)-3-methyl-1-butene-1-thiol, (Z)-2-methyl-1-butene-1-thiol, (E)-2-methyl-1-butene-1-thiol, and 4-mercapto-3-hexanone were previously unknown as food constituents. Their structures were confirmed by comparing their mass spectra and retention indices as well as their sensory properties with those of synthesized reference compounds. The relatively unstable 1-alkene-1-thiols represent a new class of food odorants and are suggested as the key contributors to the characteristic, but quickly vanishing, aroma of freshly ground roasted sesame seeds.

Seventeen aroma-active volatiles, previously identified with high flavor dilution factors in fresh, pink Colombian guavas (Psidium guajava L.), were quantified by stable isotope dilution assays. On the basis of the quantitative data and odor thresholds in water, odor activity values (OAV; ratio of concentration to odor threshold) were calculated. High OAVs were determined for the green, grassy smelling (Z)-3-hexenal and the grapefruit-like smelling 3-sulfanyl-1-hexanol followed by 3-sulfanylhexyl acetate (black currant-like), hexanal (green, grassy), ethyl butanoate (fruity), acetaldehyde (fresh, pungent), trans-4,5-epoxy-(E)-2-decenal (metallic), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel, sweet), cinnamyl alcohol (floral), methyl (2S,3S)-2-hydroxy-3-methylpentanoate (fruity), cinnamyl acetate (floral), methional (cooked potato-like), and 3-hydroxy-4,5-dimethyl-2(5H)-furanone (seasoning-like). Studies on the time course of odorant formation in guava puree or cubes, respectively, showed that (Z)-3-hexenal was hardly present in the intact fruits, but was formed very quickly during crushing. The aroma of fresh guava fruit cubes, which showed a very balanced aroma profile, was successfully mimicked in a reconstitute consisting of 13 odorants in their naturally occurring concentrations. Omission tests, in which single odorants were omitted from the entire aroma reconstitute, revealed (Z)-3-hexenal, 3-sulfanyl-1-hexanol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, hexanal, ethyl butanoate, cinnamyl acetate, and methional as the key aroma compounds of pink guavas.

The volatiles present in fresh, pink-fleshed Colombian guavas ( Psidium guajava, L.), variety regional rojo, were carefully isolated by solvent extraction followed by solvent-assisted flavor evaporation, and the aroma-active areas in the gas chromatogram were screened by application of the aroma extract dilution analysis. The results of the identification experiments in combination with the FD factors revealed 4-methoxy-2,5-dimethyl-3(2 H)-furanone, 4-hydroxy-2,5-dimethyl-3(2 H)-furanone, 3-sulfanylhexyl acetate, and 3-sulfanyl-1-hexanol followed by 3-hydroxy-4,5-dimethyl-2(5 H)-furanone, ( Z)-3-hexenal, trans-4,5-epoxy-( E)-2-decenal, cinnamyl alcohol, ethyl butanoate, hexanal, methional, and cinnamyl acetate as important aroma contributors. Enantioselective gas chromatography revealed an enantiomeric distribution close to the racemate in 3-sulfanylhexyl acetate as well as in 3-sulfanyl-1-hexanol. In addition, two fruity smelling diastereomeric methyl 2-hydroxy-3-methylpentanoates were identified as the ( R,S)- and the ( S,S)-isomers, whereas the ( S,R)- and ( R,R)-isomers were absent. Seven odorants were identified for the first time in guavas, among them 3-sulfanylhexyl acetate, 3-sulfanyl-1-hexanol, 3-hydroxy-4,5-dimethyl-2(5 H)-furanone, trans-4,5-epoxy-( E)-2-decenal, and methional were the most odor-active.

In white pepper samples, directly taken from a retting batch at a pepper production plant in Thailand, 3-methylindole, 4-methylphenol, 3-methylphenol, and butanoic acid, recently confirmed to be responsible for the characteristic fecal off-odor frequently detected in white pepper powders, were quantified by stable isotope dilution analyses. The results clearly showed that, in particular, 3-methylindole (fecal, swine-manure-like), 4-methylphenol (fecal, horse-like), and butanoic acid (cheese-like) were biochemically formed during retting, thus indicating that fermentation is the crucial step for off-odorant formation during white pepper processing. Model fermentation experiments performed with different manufacturing regimens revealed that white pepper, containing no substantial amounts of these odorants, can be produced from ripe starting material by a short fermentation under water and with frequent exchange of water. The overall aroma of such pepper was superior as compared to the aroma of white pepper produced according to the traditional procedure.

Application of the aroma extract dilution analysis on an extract of white pepper powder showing an intense fecal, cowshed-like off-flavor revealed 3-methylindole (fecal, swine-manure) and 4-methylphenol (fecal, horse-like) with the highest flavor dilution (FD) factors among the 22 odor-active compounds detected. In addition, high FD factors and/or undesirable odor qualities suggested 3-methylphenol (phenolic), butanoic acid (cheese-like), and 2- and 3-methylbutanoic acid (cheese-like) as well as pentanoic acid and hexanoic acid (cheese-like odors) as contributors to the malodor. Although the intensities of the off-note were clearly different in 50 commercial samples of white pepper, quantitation of 3-methylindole and 3- and 4-methylphenol as well as of the five short-chain acids by means of stable isotope dilution assays showed similar concentrations in most of the samples. Storage of a freshly ground white pepper powder for up to 7 months revealed a significant decrease in the typical odor qualities of white pepper and an increase in the fecal odor note with storage time. Because the concentrations of the odorants mentioned above were not much changed during storage, possibly very volatile odorants, such as alpha-pinene, which are able to mask the malodor, are lost during storage of, in particular, pepper powders. On the basis of odor activity values, which were calculated using breakthrough thresholds, in particular, 3-methylindole, 4-methylphenol, 3-methylphenol, and butanoic acid could be suggested as the main sources of the fecal off-flavor.

A stable isotope dilution assay (SIDA) was developed for the quantitation of both linalool enantiomers using synthesized [2H(2)]R/S-linalool as the internal standard. For enrichment of the target compound from beer, a solid phase microextraction method (SPME) was developed. In comparison to the more time-consuming extraction/distillation cleanup of the beer samples, the results obtained by SPME/SIDA were very similar, even under nonequilibration conditions. Analysis of five different types of beer showed significant differences in the linalool concentrations, which were clearly correlated with the intensity of the hoppy aroma note as evaluated by a sensory panel. In addition, significant differences in the R/S ratios were measured in the beers. The SPME/SIDA yielded exact data independently from headspace sampling parameters, such as exposure time or ionic strength of the solution.

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.