Characterization of volatiles and aroma-active compounds in honeybush (Cyclopia subternata) by GC-MS and GC-O analysis

Volatile organic compounds (VOCs) in fermented honeybush, Cyclopia subternata, were sampled by means of a high-capacity headspace sample enrichment probe (SEP) and analyzed by gas chromatography-mass spectrometry (GC-MS). Stereochemistry was determined by means of enantioselective GC-MS with derivatized β-cyclodextrin columns as chiral selectors. A total of 183 compounds, the majority of which are terpenoids (103; 56%), were identified by comparing their mass spectra and retention indices with those of reference compounds or tentatively identified by comparison with spectral library or literature data. Of these compounds, 37 were determined by gas chromatography-olfactometry (GC-O), using detection frequency (DF) and aroma extract dilution analysis (AEDA), to be odor-active (FD ≥ 2). (E)-β-Damascenone, (R/S)-linalool, (E)-β-damascone, geraniol, (E)-β-ionone, and (7E)-megastigma-5,7,9-trien-4-one were identified with the highest FD factors (≥512). The odors of certain compounds, that is, (6E,8Z)-megastigma-4,6,8-trien-3-one, (6E,8E)-megastigma-4,6,8-trien-3-one, (7E)-megastigma-5,7,9-trien-4-one, 10-epi-γ-eudesmol, epi-α-muurolol, and epi-α-cadinol, were perceived by GC-O assessors as typically honeybush-like.     

Characterization of the key aroma compounds in apricots (Prunus armeniaca) by application of the molecular sensory science concept

An aroma extract dilution analysis applied on an aroma distillate prepared from fresh apricots revealed (R)-gamma-decalactone, (E)-beta-damascenone, delta-decalactone, and (R/S)-linalool with the highest flavor dilution (FD) factors among the 26 odor-active compounds identified. On the basis of quantitative measurements performed by application of stable isotope dilution assays, followed by a calculation of odor activity values (OAVs), beta-ionone, (Z)-1,5-octadien-3-one, gamma-decalactone, (E,Z)-2,6-nonadienal, linalool, and acetaldehyde appeared with OAVs >100, whereas in particular certain lactones, often associated with an apricot aroma note, such as gamma-undecalactone, gamma-nonalactone, and delta-decalactone, showed very low OAVs (<5). An aroma recombinate prepared by mixing the 18 most important odorants in concentrations as they occurred in the fresh fruits showed an overall aroma very similar to that of apricots. Omission experiments indicated that previously unknown constituents of apricots, such as (E,Z)-2,6-nonadienal or (Z)-1,5-octadien-3-one, are key contributors to the apricot aroma.     

Gas chromatographic-olfactometric characterization of aroma compounds in two types of cashew apple nectar

Cashew apple nectar is a secondary product from the production of cashew nuts and possesses an exotic tropical aroma. Aroma volatiles in pasteurized and reconstituted (from concentrate) Brazilian cashew apple nectars were determined using GC-MS and split, time-intensity GC-olfactometry (GC-O)/GC-FID. Methional, (Z)-1,5-octadien-3-one, (Z)-2-nonenal, (E,Z)-2,4-decadienal, (E,E)-2,4-decadienal, beta-damascenone, and delta-decalactone were identified for the first time in cashew apple products. These compounds plus butyric acid, ethyl 3-methylbutyrate, 2-methylbutyric acid, acetic acid, benzaldehyde, homofuraneol, (E)-2-nonenal, gamma-dodecalactone, and an unknown were the most intense aroma volatiles. Thirty-six aroma volatiles were detected in the reconstituted sample and 41 in the pasteurized sample. Thirty-four aroma active components were common to both samples. Ethyl 3-methylbutyrate and 2-methylbutyric acid were character impact compounds of cashew apple (warm, fruity, tropical, sweaty). Using GC-pFPD, 2-methyl-3-furanthiol and bis(2-methyl-3-furyl) disulfide were identified for the first time in cashew apple. Both were aroma active (meaty).     

Identification of characteristic aroma-active compounds from water dropwort (Oenanthe javanica DC.)

Characteristic aroma components of water dropwort (Oenanthe javanica DC.) were evaluated by aroma extract dilution analysis and solid-phase microextraction-gas chromatography-olfactometry. Alpha-Terpinolene (plastic/cucumber-like) was the most intense aroma-active compound in water dropwort. Other potent aroma-active compounds included p-cymene (kerosene-like), alpha-terpinene (lemon), (E)-caryophyllene (woody), (Z,E)-alpha-farnesene (woody), hexanal (green), (Z)-3-hexenol (green), phenylacetaldehyde (honey), (E)-2-nonenal (cucumber), bornyl acetate (cooked vegetable), and gamma-terpinene (lemon). Of these, p-cymene was believed to be primarily responsible for the distinct kerosene-like aroma note of water dropwort. The aroma property of p-cymene was dependent on its concentration and was described as kerosene-like at relatively high concentrations but changed to citrus and green aroma notes at low concentrations.     

Identification of potent odorants in Chinese jasmine green tea scented with flowers of Jasminum sambac

The odorants in Chinese jasmine green tea scented with jasmine flowers (Jasminum sambac) were separated from the infusion by adsorption to Porapak Q resin. Among the 66 compounds identified by GC and GC/MS, linalool (floral), methyl anthranilate (grape-like), 4-hexanolide (sweet), 4-nonanolide (sweet), (E)-2-hexenyl hexanoate (green), and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (sweet) were extracted as potent odorants by an aroma extract dilution analysis and sensory analysis. The enantiomeric ratios of linalool in jasmine tea and Jasminum sambac were determined by a chiral analysis for the first time in this study: 81.6% ee and 100% ee for the (R)-(-)-configuration, respectively. The jasmine tea flavor could be closely duplicated by a model mixture containing these six compounds on the basis of a sensory analysis. The omission of methyl anthranilate and the replacement of (R)-(-)-linalool by (S)-(+)-linalool led to great changes in the odor of the model. These two compounds were determined to be the key odorants of the jasmine tea flavor.     

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.     

Characteristic odor components of kumquat (Fortunella japonica Swingle) peel oil

This study was conducted to determine the composition of kumquat (Fortunella japonica Swingle) cold-pressed peel oil and to determine which volatile components are primarily responsible for the aroma of this oil. Eighty-two compounds were identified in the oil by GC and GC-MS. The major compounds were limonene (93.73%), myrcene (1.84%), and ethyl acetate (1.13%). Flavor dilution (FD) factors and relative flavor activities (RFA) of volatile constituents were evaluated by aroma extract dilution analysis with gas chromatography-olfactometry (GC-O). Camphene, terpinen-4-ol, citronellyl formate, and citronellyl acetate showed high FD factors (>/=5) and RFA (>20). Citronellyl formate and citronellyl acetate were regarded as the characteristic odor components of the kumquat peel oil from the results of FD factor, RFA, and GC-sniffing. Citronellyl acetate is considered to be the odor component most similar to kumquat by organoleptic evaluation with GC-O.     

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.     

Characterization of the most odor-active compounds of Iberian ham headspace

Gas chromatography-olfactometry (GC-O) based on detection frequency (DF) was used to characterize the most odor-active compounds from the headspace of Iberian ham. Twenty-eight odorants were identified by GC-O on two capillary columns, including aldehydes (11), sulfur-containing compounds (7), ketones (5), nitrogen-containing compounds (2), esters (2), and an alcohol. Among them, the highest odor potencies (DF values) were found for 2-methyl-3-furanthiol, 2-heptanone, 3-methylbutanal, methanethiol, hexanal, hydrogen sulfide, 1-penten-3-one, 2-methylpropanal, ethyl 2-methylbutyrate, and (E)-2-hexenal. Nine of the 28 most odor-active compounds were identified for the first time as aroma components of dry-cured ham, including hydrogen sulfide, 1-penten-3-one, (Z)-3-hexenal, 1-octen-3-one, and the meaty-smelling compounds 2-methyl-3-furanthiol, 2-furfurylthiol, 3-mercapto-2-pentanone, 2-acetyl-1-pyrroline, and 2-propionyl-1-pyrroline.     

Characterization of (E,E,Z)-2,4,6-nonatrienal as a character impact aroma compound of oat flakes

To identify the compounds evoking the characteristic cereal-like, sweet aroma of oat flakes, an aroma extract dilution analysis (AEDA) was applied to a distillate prepared by solvent extraction/vacuum distillation from commercial oat flakes. Among the nine aroma-active compounds detected by gas chromatography-olfactometry and AEDA in the flavor dilution (FD) factor range of 4-1024, eight odorants, for example, (E)-beta-damascenone, (Z)-3-hexenal, and butanoic acid, showed only low FD factors. However, one odorant eliciting the typical cereal, sweet aroma of the flakes was detected with the highest FD factor of 1024. By mass spectrometry and nuclear magnetic resonance measurements followed by a synthesis, (E,E,Z)-2,4,6-nonatrienal, exhibiting an intense oat flake-like odor at the extremely low odor threshold of 0.0002 ng/L in air, was identified as the key odorant of the flakes. By means of a newly developed stable isotope dilution analysis using synthesized, carbon-13-labeled nonatrienal as the internal standard, a concentration of 13 mug of (E,E,Z)-2,4,6-nonatrienal per kilogram of the flakes was measured. Model studies suggested linolenic acid as the precursor of nonatrienal in oats.     

Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim)

Volatile flavor compounds of miniature beefsteakplant (Mosla dianthera Maxim.) from Vietnam were analyzed through gas chromatography-mass spectrometry-olfactometry (GC-MS-O). Sixty-two compounds were identified by GC-MS. Of these, (+/-)-carvone and (+/-)-limonene were the most abundant, followed by (Z)-limonene oxide, beta-caryophyllene, and alpha-humulene. Twenty aroma-active compounds were detected by aroma extract dilution analysis conducted on two GC columns of different polarities (DB-5MS and DB-Wax). The most intense aroma-active compounds were linalool (floral/sweet/lemon), (-)-carvone (spearminty), and 1-octen-3-one (mushroom/earthy). Other predominant aroma-active compounds included (Z)-3-hexenol (grassy/leafy/metallic), (Z)-limonene oxide (lemon/floral), myrcene (plastic/sweet), (+)-limonene (orange/lemon), alpha-thujene (soy sauce/grassy), and (Z)-dihydrocarvone (spearminty/pepperminty). On the basis of the aroma characteristics and intensity, it was concluded that (-)-carvone was responsible for the characteristic aroma of miniature beefsteakplant.     

Comparison of odor-active compounds from six distinctly different rice flavor types

Using a dynamic headspace system with Tenax trap, GC-MS, GC-olfactometry (GC-O), and multivariate analysis, the aroma chemistry of six distinctly different rice flavor types (basmati, jasmine, two Korean japonica cultivars, black rice, and a nonaromatic rice) was analyzed. A total of 36 odorants from cooked samples were characterized by trained assessors. Twenty-five odorants had an intermediate or greater intensity (odor intensity >or= 3) and were considered to be major odor-active compounds. Their odor thresholds in air were determined using GC-O. 2-Acetyl-1-pyrroline (2-AP) had the lowest odor threshold (0.02 ng/L) followed by 11 aldehydes (ranging from 0.09 to 3.1 ng/L), guaiacol (1.5 ng/L), and 1-octen-3-ol (2.7 ng/L). On the basis of odor thresholds and odor activity values (OAVs), the importance of each major odor-active compound was assessed. OAVs for 2-AP, hexanal, ( E)-2-nonenal, octanal, heptanal, and nonanal comprised >97% of the relative proportion of OAVs from each rice flavor type, even though the relative proportion varied among samples. Thirteen odor-active compounds [2-AP, hexanal, ( E)-2-nonenal, octanal, heptanal, nonanal, 1-octen-3-ol, ( E)-2-octenal, ( E, E)-2,4-nonadienal, 2-heptanone, ( E, E)-2,4-decadienal, decanal, and guaiacol] among the six flavor types were the primary compounds explaining the differences in aroma. Multivariate analysis demonstrated that the individual rice flavor types could be separated and characterized using these compounds, which may be of potential use in rice-breeding programs focusing on flavor.     

The compositions of volatiles and aroma-active compounds in dried omija fruits (Schisandra chinensis Baillon) according to the cultivation areas

Differences in the compositions of volatiles from dried omija fruits (Schisandra chinensis Baillon) cultivated in different areas (Mungyeong, Jangsu, Jechon, and Hoengseong) in South Korea were determined by applying principal component analysis to gas chromatography-mass spectrometry data sets. Quantitative assessments revealed that terpene hydrocarbons, such as germacrene D, β-selinene, α-ylangene, β-elemene, α-selinene, and (E)-β-farnesene, were the main volatiles in all omija fruit samples. On the other hand, (E)-β-ocimene, calarene, (E)-β-farnesene, β-selinene, nonanal, 2-methylbutanoic acid, benzoic acid, 2,3-butanediol, and phenethyl alcohol were the major volatile components that contributed to the discrimination between omija fruit samples from the four cultivation areas. In addition, aroma-active compounds in four dried omija fruits were investigated and compared by gas chromatography-olfactometry using aroma extract dilution analysis. (E)-β-Ocimene (floral and herbaceous), α-pinene (pine-like and woody), hexanal (cut grass-like), 5-methylfurfural (burnt sugar-like and sweet), and α-terpinene (minty, green, and fresh) were important aroma-active compounds in all omija samples. Interestingly, the flavor dilution factors of most aroma-active compounds were lower for omija sample cultivated in Hoengseong than for those cultivated in Mungyeong, Jangsu, and Jechon.     

Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis

Application of the aroma extract dilution analysis (AEDA) on the volatile fraction carefully isolated from an American Bourbon whisky revealed 45 odor-active areas in the flavor dilution (FD) factor range of 32-4096 among which (E)-beta-damascenone and delta-nonalactone showed the highest FD factors of 4096 and 2048, respectively. With FD factors of 1024, (3S,4S)-cis-whiskylactone, gamma-decalactone, 4-allyl-2-methoxyphenol (eugenol), and 4-hydroxy-3-methoxy-benzaldehyde (vanillin) additionally contributed to the overall vanilla-like, fruity, and smoky aroma note of the spirit. Application of GC-Olfactometry on the headspace above the whisky revealed 23 aroma-active odorants among which 3-methylbutanal, ethanol, and 2-methylbutanal were identified as additional important aroma compounds. Compared to published data on volatile constituents in whisky, besides ranking the whisky odorants on the basis of their odor potency, 13 aroma compounds were newly identified in this study: ethyl (S)-2-methylbutanoate, (E)-2-heptenal, (E,E)-2,4-nonadienal, (E)-2-decenal, (E,E)-2,4-decadienal, 2-isopropyl-3-methoxypyrazine, ethyl phenylacetate, 4-methyl acetophenone, alpha-damascone, 2-phenylethyl propanoate, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, trans-ethyl cinnamate, and (Z)-6-dodeceno-gamma-lactone.     

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.     

Key odorants of Oscypek, a traditional Polish ewe's milk cheese

The unique flavor of Oscypek, a Polish ewe's milk smoked cheese, is described as slightly sour, piquant, salted, and smoked. In this paper with the application of gas chromatography-olfactometry (GC-O) and combination of aroma extract dilution analysis (AEDA) 20 potent odorants of this cheese have been identified within the flavor dilution factor (FD) range of 4-2048. Among them, 2-methoxyphenol, 2-methoxy-4-methylphenol, 4-methylphenol, and butanoic acid showed the highest FD factors. Quantification results based on labeled standard addition followed by calculation of odor activity values (OAV) of 13 compounds with the highest FD factors revealed that 11 compounds were present at concentrations above their odor threshold values and therefore mostly contribute to the overall aroma of smoked ewe's milk cheese. Six of those compounds were represented by phenolic derivatives, with the highest OAV for 2-methoxyphenol (1280). Analysis of key odorants of an unsmoked cheese sample showed that the smoking process had a fundamental influence on Oscypek aroma formation.     

Characterization of aroma compounds of chinese "Wuliangye" and "Jiannanchun" liquors by aroma extract dilution analysis

Aroma compounds in Chinese "Wuliangye" liquor were identified by gas chromatography-olfactometry (GC-O) after fractionation. A total of 132 odorants were detected by GC-O in Wuliangye liquor on DB-wax and DB-5 columns. Of these, 126 aromas were identified by GC-mass spectrometry (MS). Aroma extract dilution analysis (AEDA) was further employed to identify the most important aroma compounds in "Wuliangye" and "Jiannanchun" liquors. The results showed that esters could be the most important class, especially ethyl esters. Various alcohols, aldehydes, acetals, alkylpyrazines, furan derivatives, lactones, and sulfur-containing and phenolic compounds were also found to be important. On the basis of flavor dilution (FD) values, the most important aroma compounds in Wuliangye and Jiannanchun liquors could be ethyl butanoate, ethyl pentanoate, ethyl hexanoate, ethyl octanoate, butyl hexanoate, ethyl 3-methylbutanoate, hexanoic acid, and 1,1-diethoxy-3-methylbutane (FD > or = 1024). These compounds contributed to fruity, floral, and apple- and pineapple-like aromas with the exception of hexanoic acid, which imparts a sweaty note. Several pyrazines, including 2,5-dimethyl-3-ethylpyrazine, 2-ethyl-6-methylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, and 3,5-dimethyl-2-pentylpyrazine, were identified in these two liquors. Although further quantitative analysis is required, it seems that most of these pyrazine compounds had higher FD values in Wuliangye than in Jiannanchun liquor, thus imparting stronger nutty, baked, and roasted notes in Wuliangye liquor.     

Aroma components of cooked tail meat of American lobster (Homarus americanus)

Key aroma components of cooked tail meat of American lobster (Homarus americanus) were studied by gas chromatography-olfactometry (GCO) techniques. Components of low and intermediate volatility were evaluated by aroma extract dilution analysis of solvent extracts prepared by direct solvent extraction-high vacuum distillation and vacuum steam distillation-solvent extraction, whereas headspace volatile components were assessed by GCO of decreasing headspace (static and dynamic modes) samples. Forty-seven odorants were detected by all techniques. 3-Methylbutanal (chocolate, malty), 2,3-butanedione (buttery), 3-(methylthio)propanal (cooked potato), 1-octen-3-one (mushroom), 2-acetyl-1-pyrroline (popcorn), and (E,Z)-2,6-nonadienal (cucumber), were identified as predominant odorants by all four isolation methods. The highly volatile compounds methanethiol (rotten, sulfurous) and dimethyl sulfide (canned corn) were detected by headspace methods only. These eight odorants along with three unknown compounds with crabby, amine, fishy odors were found to predominate in the overall aroma of cooked lobster tail meat.     

Characterization of odor-active compounds in extracts obtained by simultaneous extraction/distillation from moroccan black olives

"Greek-style" Moroccan black table olives were screened for potent odorants by GC/olfactometry/aroma extract dilution analysis of representative Likens-Nickerson extracts and compared with "Spanish-style" green fruits. ( Z)-3-Hexenal, ( E, E)-2,4-decadienal, ( E, Z)-2,4-decadienal, guaiacol, and methional were found in both green and black olives, but with significant differences in concentration according to the fruit ripening degree (the first was lower and the last two were higher in black fruits). Specific compounds not previously detected in green olives (gamma-deca- and dodecalactones, delta-decalactone, and 2-methyl-3-furanthiol) proved to be, with methional, the strongest odors in black olive extracts. These extracts were also distinguishable from green olive extracts by the presence of new sulfur compounds and fewer terpenes.