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.     

Aroma-active components of nonfat dry milk.

Application of aroma extract dilution analysis (AEDA) on the volatile components of low-, medium-, and high-heat-treated nonfat dry milks (NDM) revealed aroma-active compounds in the log(3) flavor dilution (log(3) FD) factor range of 1 to 6. The following compounds contributed the highest log(3) FD factors to overall NDM flavor: 2,5-dimethyl-4-hydroxy-3(2H)-furanone [(Furaneol), burnt sugar-like]; butanoic acid (rancid); 3-(methylthio)propanal [(methional), boiled potato-like]; o-aminoacetophenone (grape-like); delta-decalactone (sweet); (E)-4,5-epoxy-(E)-2-decenal (metallic); pentanoic acid (sweaty); 4,5-dimethyl-3-hydroxy-2(5H)-furanone [(sotolon), curry]; 3-methoxy-4-hydroxybenzaldehyde [(vanillin), vanilla]; 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline (popcorn-like); hexanoic acid (vinegar-like); phenylacetic acid (rose-like); octanoic acid (waxy); nonanal (fatty); and 1-octen-3-one (mushroom-like). The odor intensities of Furaneol, butanoic acid, methional, o-aminoacetophenone, sotolon, vanillin, (E)-4,5-epoxy-(E)-2-decenal, and phenylacetic acid were higher in high-heat-treated samples than others. However, the odor intensities of lactones, 2-acetyl-1-pyrroline, and 2-acetyl-2-thiazoline were not affected by heat treatment. Sensory evaluation results also revealed that heat-generated flavors have a major impact on the flavor profile of NDM.     

Instrumental and sensory characterization of heat-induced odorants in aseptically packaged soy milk

Predominant heat-induced odorants generated in soy milk by ultrahigh-temperature (UHT) processing were evaluated by sensory and instrumental techniques. Soy milks processed by UHT (143 degrees C/14 s, 143 degrees C/59 s, 154 degrees C/29 s) were compared to a control soy milk (90 degrees C/10 min) after 0, 1, and 7 days of storage (4.4 +/- 1 degrees C). Dynamic headspace dilution analysis (DHDA) and solvent-assisted flavor evaporation (SAFE) in conjunction with GC-olfactometry (GCO)/aroma extract dilution techniques and GC-MS were used to identify and quantify major aroma-active compounds. Sensory results revealed that intensities of overall aroma and sulfur and sweet aromatic flavors were affected by the processing conditions. Odorants mainly responsible for the changes in sulfur perception were methional, methanethiol, and dimethyl sulfide. Increases in 2-acetyl-1-pyrroline, 2-acetyl-thiazole, and 2-acetyl-2-thiazoline intensities were associated with roasted aromas. A marginal increase in intensity of sweet aromatic flavor could be explained by increases in 2,3-butanedione, 3-hydroxy-2-butanone, beta-damascenone, and 2- and 3-methylbutanal. Predominant lipid-derived odorants, including (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal, (E,Z)-2,4-decadienal, (E)-2-nonenal, (E)-2-octenal, 1-octen-3-one, 1-octen-3-ol, and (E,Z)-2,6-nonadienal, were affected by processing conditions. Intensities of overall aroma and sulfur notes in soy milk decreased during storage, whereas other sensory attributes did not change. Color changes, evaluated by using a Chroma-meter, indicated all UHT heating conditions used in this study generated a more yellow and saturated color in soy milk in comparison to the control soy milk.     

Identification and quantitation of key aroma compounds formed in Maillard-type reactions of fructose with cysteamine or isothiaproline (1,3-thiazolidine-2-carboxylic acid)

Fructose was reacted in the presence of either cysteamine (model A) or isothiaproline (model B) in aqueous buffer at 145 degrees C and pH 7.0. Application of an aroma extract dilution analysis on the bulk of the volatile compounds formed in model A revealed 5-acetyl-3,4-dihydro-2H-1,4-thiazine (19), N-(2-mercaptoethyl)-1,3-thiazolidine (16), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (15), and 2-acetyl-2-thiazoline (11) as the key aroma compounds among the 10 odorants detected. A similar set of aroma compounds was formed when isothiaproline was reacted (model B), but the flavor dilution factors were generally lower. Substitution of the buffer by silica gel/water (9 + 1 w/w) in both models and application of 150 degrees C for 10 min also gave the same key odorants from both thio compounds; however, under these conditions isothiaproline was the better precursor of, in particular, 19 and 11. Quantitative measurements performed by means of stable isotope dilution assays revealed a significant effect of the pH on odorant formation. For example, in model A, formation of 19 as well as of 11 was suppressed at pH values <5.0. A clear maximum was, however, found for 19 at pH 7.0 (approximately 1 mol % yield), whereas 11 increased with increasing pH from 7.0 to 9.0.     

Identification of potent odorants in different green tea varieties using flavor dilution technique

Two kinds of pan-fired green teas (Japanese Kamairi-cha and Chinese Longing tea) were compared with the common Japanese green tea (Sen-cha). Application of the aroma extract dilution analysis (AEDA) using the volatile fraction of the Sen-cha, Kamairi-cha and Longing tea infusions revealed 32, 51, and 52 odor-active peaks with flavor dilution factors between 16 and 1024, respectively. (Z)-1,5-Octadien-3-one (metallic, geranium-like), 4-mercapto-4-methyl-2-pentanone (meaty, black currant-like), methional (potato-like), (E,Z)-2,6-nonadienal (cucumber-like), and 3-methylnonane-2,4-dione (green, fruity, hay-like) showed high flavor dilution factors in all varieties. In addition, 2-acetyl-1-pyrroline (popcorn-like), 2-ethyl-3,5-dimethylpyrazine (nutty), 2,3-diethyl-5-methylpyrazine (nutty), and 2-acetyl-2-thiazoline (popcorn-like) belonged to the most potent odorants only in the pan-fired green teas. Among these odorants, 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline were identified for the first time among the tea volatiles.     

Characterization of volatile compounds from the reaction of 3-hydroxy-2-butanone and ammonium sulfide model system

The reactions between 3-hydroxy-2-butanone and ammoniun sulfide at 25, 50, 75, 100, 125, and 150 degrees C were studied. Four well-known flavor compounds, 2,4,5-trimethyloxazole, 2,4, 5-trimethyl-3-oxazoline, 2,4,5-trimethylthiazole, and 2,4, 5-trimethyl-3-thiazoline, were identified. Another four interesting intermediate compounds, 2-(1-hydroxyethyl)-2,4, 5-trimethyl-3-oxazoline, 2-(1-mercaptoethyl)-2,4, 5-trimethyl-3-oxazoline, 2-(1-hydroxyethyl)-2,4, 5-trimethyl-3-thiazoline, and 2-(1-mercaptoethyl)-2,4, 5-trimethyl-3-thiazoline, were also identified by GC-EIMS and GC-CIMS. All these intermediate compounds were formed at 25 degrees C. On the other hand, tetramethylpyrazine was the major product with a reaction temperature higher than 100 degrees C.     

Chemoenzymatic synthesis of aroma active 5,6-dihydro- and tetrahydropyrazines from aliphatic acyloins produced by baker's yeast

Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines. Their odor qualities were evaluated, and their odor thresholds were estimated. Among these pyrazine derivatives, 2-ethyl-3,5-dimethyl-5,6-dihydropyrazine (roasted, nutty, 0.002 ng/L air), 2,3-diethyl-5-methyl-5,6-dihydropyrazine (roasted, 0.004 ng/L air), and 2-ethyl-3,5-dimethyltetrahydropyrazine (bread crustlike, 1.9 ng/L air) were the most intensive-smelling aroma active compounds.     

Characterization of the key odorants in raw Italian hazelnuts ( Corylus avellana L. var. Tonda Romana) and roasted hazelnut paste by means of molecular sensory science

The concentrations of 19 odorants, recently characterized by GC-olfactometry and aroma extract dilution analysis as the most odor-active compounds in raw hazelnuts, were quantitated by stable isotope dilution assays (SIDA). Calculation of odor activity values (OAV) on the basis of odor thresholds in oil revealed high OAVs, in particular for linalool, 5-methyl-4-heptanone, 2-methoxy-3,5-dimethylpyrazine, and 4-methylphenol. A model mixture in sunflower oil containing the 13 odorants showing OAVs above 1 in their natural concentrations resulted in a good similarity compared to the overall nut-like, fruity aroma of the raw hazelnuts. Quantitation of the 25 most odor-active compounds in roasted hazelnut paste by SIDA showed clear changes in the concentrations of most odorants, and formation of new odor-active compounds induced by the roasting process was observed. The highest OAVs were calculated for 3-methylbutanal (malty), 2,3-pentanedione (buttery), 2-acetyl-1-pyrroline (popcorn), and (Z)-2-nonenal (fatty), followed by dimethyl trisulfide, 2-furfurylthiol, 2,3-butanedione, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone. The aroma of a model mixture containing the 19 odorants with OAVs above 1 in their actual concentrations in the roasted nut material was judged to elicit a very good similarity to the popcorn-like, coffee-like, and sweet-smoky aroma of the roasted hazelnut paste. New SIDAs were developed for the quantitation of 5-methyl-4-heptanone, 5-methyl-(E)-2-hepten-4-one, 2-thenylthiol, and 3,5,5-trimethyl-2(5H)-furanone.     

Inhibition of key aroma compound generated during ultrahigh-temperature processing of bovine milk via epicatechin addition

The ability of epicatechin (EC) to inhibit the thermal development of aroma compounds (i.e., Maillard reaction products) formed during ultrahigh-temperature (UHT) processing of bovine milk was evaluated. Volatile extracts were prepared for two UHT-processed milk samples made from (1) raw milk and (2) raw milk containing 0.1% EC by solvent-assisted flavor evaporation (SAFE) and subsequently analyzed by aroma extract dilution analysis (AEDA). Sensory evaluation was also conducted by a trained panel on the intensity of cooked flavor and bitterness in four UHT-processed milk samples (0.00, 0.01, 0.10, and 0.20% EC added prior to processing), as well as a commercial pasteurized milk sample for comparison. AEDA indicated that addition of EC to raw fluid milk prior to UHT processing reduced the overall thermal formation of key aroma-active compounds in comparison to the traditional UHT milk sample. The largest changes in FD values were reported for methional, furfural, 2-isopropyl-3-methoxypyrazine, 2-acetyl-1-pyrroline, and 2-acetyl-2-thiazoline (Maillard-type aroma compounds) with 32-, 8-, 8-, 4-, and 4-fold reductions in formation, respectively. Sensory evaluation also revealed that all EC-containing UHT milk samples had statistically (P < 0.05) lower cooked flavor intensity in comparison to the control, whereas the 0.2% EC sample was statistically similar to a pasteurized milk sample. Furthermore, addition of EC at or below 0.1% in UHT fluid milk did not significantly increase the bitterness intensity.     

Studies on the key odorants formed by roasting of wild mango seeds (Irvingia gabonensis)

Application of the aroma extract dilution analysis on a concentrate of volatiles obtained by solvent extraction and high vacuum distillation from roasted seeds (180 degrees C; 15 min) of wild mango (Irvingia gabonensis) revealed 32 odor-active compounds with flavor dilution (FD) factors ranging from 8 (low odor activity) to 2048 (high odor activity). The identification experiments based on the use of reference odorants revealed methional (cooked potato-like) followed by 2-acetyl-1-pyrroline (roasty, popcorn-like), butan-2,3-dione, pentan-2,3-dione, 2-ethyl-3,5-dimethylpyrazine, and 2,3-diethyl-5-methylpyrazine as the key aroma compounds among the 27 odorants identified. All odorants are reported for the first time as components of roasted wild mango seeds.     

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.     

Improved organoleptic and nutritive properties of bakery products supplemented with amino acid overproducing Saccharomyces cerevisiae yeasts

Spontaneous yeast mutants isolated in continuous culture as resistant to toxic amino acid analogues, able to increase up to 40 times their free amino acid pool of Thr, up to 160 times their pool of Met, or up to 20 times their pool of Lys, were characterized with regard to properties of industrial interest. Growth rate, mu (h(-1)), and biomass yield, Y (g/L), of the amino acid overproducing mutants (AA(S)) were in many cases similar to those of the wild type, whereas their free amino acid content was substantially increased in laboratory and industrial media (molasses). Doughs fermented with 3% baker's yeast and 0.5% AA(S) mutants produced bakery products that displayed texture similar to those fermented with 3.5% baker's yeast, but the former had a considerable improvement of their taste and aroma. On the other hand, bread content of the essential amino acids Lys, Met, and Thr provided by yeast was also increased.     

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.     

Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection

Odor volatiles in three major lychee cultivars (Mauritius, Brewster, and Hak Ip) were examined using gas chromatography-olfactometry, gas chromatography-mass spectrometry, and gas chromatography-pulsed flame photometric detection. Fifty-nine odor-active compounds were observed including 11 peaks, which were associated with sulfur detector responses. Eight sulfur volatiles were identified as follows: hydrogen sulfide, dimethyl sulfide, diethyl disulfide, 2-acetyl-2-thiazoline, 2-methyl thiazole, 2,4-dithiopentane, dimethyl trisulfide, and methional. Mauritius contained 25% and Brewster contained 81% as much total sulfur volatiles as Hak Ip. Cultivars were evaluated using eight odor attributes: floral, honey, green/woody, tropical fruit, peach/apricot, citrus, cabbage, and garlic. Major odor differences in cabbage and garlic attributes correlated with cultivar sulfur volatile composition. The 24 odor volatiles common to all three cultivars were acetaldehyde, ethanol, ethyl-3-methylbutanoate, diethyl disulfide, 2-methyl thiazole, 1-octen-3-one, cis-rose oxide, hexanol, dimethyl trisulfide, alpha-thujone, methional, 2-ethyl hexanol, citronellal, (E)-2-nonenal, linalool, octanol, (E,Z)-2,6-nonadienal, menthol, 2-acetyl-2-thiazoline, (E,E)-2,4-nonadienal, beta-damascenone, 2-phenylethanol, beta-ionone, and 4-vinyl-guaiacol.     

Precursors of 2-acetyl-1-pyrroline, a potent flavor compound of an aromatic rice variety

The biological formation of a potent flavor compound, 2-acetyl-1-pyrroline, in the aromatic rice variety (Khao Dawk Mali 105) was studied in seedlings and callus of the rice. Concentrations of 2-acetyl-1-pyrroline were determined by GC-MS-SIM using an isotope dilution method. Increases in concentration occurred when proline, ornithine, and glutamate were present in solution, with proline increasing the concentration by more than 3-fold compared to that of the control. Results of tracer experiments using (15)N-proline, (15)N-glycine, and proline-1-(13)C indicated that the nitrogen source of 2-acetyl-1-pyrroline was proline, whereas the carbon source of the acetyl group was not the carboxyl group of proline. 2-acetyl-1-pyrroline was formed in the aromatic rice at temperatures below that of thermal generation in bread baking, and formed in the aerial part of aromatic rice from proline as the nitrogen precursor.     

Volatiles from roasted byproducts of the poultry-processing industry

Volatiles of roasted chicken breast muscle and byproducts, such as backbones, breastbones, spent bones, and skin, were investigated. Total volatile concentrations ranged from 2030 ppb in the roasted backbones to 4049 ppb in the roasted skin. The major classes of volatile compounds detected in roasted samples were aldehydes (648-1532 ppb) and alcohols (336-1006 ppb). Nitrogen- and/or sulfur-containing compounds were also detected in appreciable quantities (161-706 ppb) in all samples. For all samples, hexanal and 2-methyl-2-buten-1-ol were dominant among the aldehydes and alcohols, respectively. Among the nitrogen- and sulfur-containing compounds, Maillard reaction products, such as tetrahydropyridazines, piperidines, and thiazoles, were the major contributors to the total volatile content in all samples. The composition of volatiles observed in roasted byproducts was markedly different from that of the roasted breast muscle. Therefore, the blending of the byproducts in appropriate proportions or blending of volatile flavor extracts from different byproducts may be necessary to obtain an aroma that mimics roasted chicken aroma.     

Development of a stable isotope dilution assay for the quantification of 5-methyl-(E)-2-hepten-4-one: application to hazelnut oils and hazelnuts.

A stable isotope dilution assay was developed for the quantitation of the hazelnut odorant 5-methyl-(E)-2-hepten-4-one by mass chromatography using synthesized [(2)H](2)-5-methyl-(E)-2-hepten-4-one as the internal standard. Application of the method on two batches of commercial hazelnut oils, processed from either roasted or unroasted nuts, revealed 6.4 microg 5-methyl-(E)-2-hepten-4-one per kg of unroasted oil whereas 315.8 microg per kg was determined in the roasted nut oil. The about 50-fold higher amount of 5-methyl-(E)-2-hepten-4-one in roasted hazelnut oil suggested the necessity of a thermal treatment to generate the flavor compound. Pan frying of raw hazelnuts (9 to 15 min) or boiling of the crushed nut material for 1 h in water led to an increase of 5-methyl-(E)-2-hepten-4-one by factors of 600 and 800, respectively, thereby corroborating that the major part of the nut flavorant is formed during heat treatment from a yet unknown precursor in hazelnuts.