Characterisation of odour‐active compounds in lupin flour

BACKGROUND: Lupin ingredients are promising alternatives to soybean products owing to their similarly high protein content. Lupin flour exhibits a green and bean‐like off‐flavour in higher amounts. The aim of this study was to characterise and identify the main odour‐active compounds in lupin flour. RESULTS: The orthonasal aroma of lupin flour was evaluated by means of aroma profile analysis and was found to be characterised by grassy‐green, metallic, fatty, fruity, hay‐like, cheese‐like, and meat‐like odour qualities. Volatile compounds of lupin flour of Lupinus angustifolius cv. Boregine were extracted with dichloromethane and isolated by solvent‐assisted flavour evaporation. Aroma extract dilution analysis (AEDA) was carried out with the obtained extract. In total, 50 odorants were detected by high‐resolution gas chromatography–olfactometry. AEDA revealed 26 odour‐active compounds with flavour dilution factors higher or equal to 32. The substances were unequivocally identified by their odour characteristics, their retention indices and their mass spectra using one‐dimensional or two‐dimensional gas chromatography–mass spectrometry, respectively. CONCLUSION: A series of unsaturated and saturated aldehydes, ketones, carboxylic acids, alkyl‐methoxypyrazines and terpenes were identified for the first time as odour‐active contributors to the aroma of lupin flour. Copyright © 2009 Society of Chemical Industry     

Comparison of key aroma-active composition and aroma perception of cold-pressed and roasted peanut oils

The difference in the aroma composition of cold-pressed and roasted peanut oils was investigated. There were 28 and 75 odorants with flavour dilution (FD) factors between 1 and 512 in cold-pressed and roasted peanut oils, respectively. Fifty-nine odorants were newly identified in peanut oils. Ten key odorants with odour activity value (OAV) ≥ 1 were identified in cold-pressed peanut oil, of which hexanal (OAV = 1,288, green), (E,E)-2,4-decadienal (OAV = 370, earthy and fried fat) and α-pinene (OAV = 34, woody) were the most important contributors to the overall aroma of cold-pressed peanut oil. 2,3-Pentanedione (OAV = 5,054, buttery), 2-methoxy-4-vinylphenol (OAV = 326, smoky), 2,5-dimethylpyrazine (OAV = 160, roasted and nutty) and 2-methylpyrazine (OAV = 92, roasted and nutty) were the most important contributors among the 26 key odorants to the aroma of roasted peanut oil. Roasting peanut seeds induced apparent changes in the formation of aromatic heterocycles, loss of terpenes and increase in lipid oxidation odorants in peanut oil. This study would provide important practical applications in aroma regulation and process optimisation of peanut oil.     

Analysis of odour‐active compounds of black mangrove (Avicennia germinans L.) honey by solid‐phase microextraction combined with gas chromatography–mass spectrometry and gas chromatography–olfactometry

The volatile compounds of Cuban black mangrove (Avicennia germinans L.) honey were analysed by solid‐phase microextraction (SPME) followed by gas chromatography–mass spectrometry and gas chromatography–olfactometry. A total of 66 compounds were positively identified in this product for the first time. Application of the aroma extract dilution analysis in a novel approach, which consisted of carrying out successively dilutions of the honey sample with a synthetic honey before the SPME, revealed 17 odour‐active areas in the flavour dilution factor range of 32–1024. On the basis of the quantitative data and odour thresholds, odour activity values (OAV; ratio of concentration to odour threshold) were calculated. Sixteen compounds showed OAVs >1, among which dimethyl sulphide, 3‐methyl butanal, 2‐methylbutanal, heptanal, octanal, phenylacetaldehyde, (Z)‐linalool oxide, (E)‐linalool oxide, nonanal, hotrienol, isophorone, lilac aldehyde A, 1‐nonanol, decanal, 4‐vinyl‐2‐methoxyphenol and (E)‐β‐damascenone showed the highest values and should be considered as the most odour‐active compounds, particularly (E)‐β‐damascenone, nonanal and decanal.     

Key aroma volatile compounds of gulupa (Passiflora edulis Sims fo edulis) fruit

By application of the aroma extract dilution analysis of gulupa (Passiflora edulis Sims fo edulis), fruit pulp extract obtained by solvent-assisted flavour extraction, and also comparison of chromatographic, spectroscopic (mass spectrum), and odour properties with standards, β-ionone, γ-nonalactone, ethyl butanoate, and ethyl cinnamate were identified as volatiles exhibiting the highest flavour dilution (FD) factor. Among the nineteen odour-active compounds of gulupa, only those showing the highest FD factors were quantified by stable isotope dilution assay. After calculation of odour activity values (OAVs; ratio of concentration to odour threshold in water), ethyl butanoate, ethyl hexanoate, and β-ionone were identified as key aroma compounds in gulupa, responsible for the fruity and floral odour notes.     

Characterisation of the key aroma compounds in a freshly reconstituted orange juice from concentrate

Application of an aroma extract dilution analysis on the entire volatile fraction isolated from an orange juice freshly reconstituted from concentrate revealed 40 odour-active constituents in the flavour dilution (FD) factor range of 4–2,048. Among them, ethyl butanoate and linalool showed the highest FD factor of 2,048, followed by octanal with an FD factor of 512. Thirty-six of the 40 odour-active compounds detected could be identified, all of which have previously been reported as volatile constituents of various orange juices. Quantification of 17 key odorants by stable isotope dilution assays followed by a calculation of odour activity values (OAVs) on the basis of odour thresholds in water or citrate buffer (pH 3.8), respectively, revealed the following most important odorants in the overall aroma of the freshly reconstituted juice: (R/S)-linalool, (R)-limonene and (S)-ethyl 2-methylbutanoate with the highest OAVs (>1,000) followed by octanal, (R)-α-pinene, ethyl butanoate, myrcene, acetaldehyde, decanal and (E)-β-damascenone with OAVs > 100. A model mixture containing all 14 aroma compounds with OAVs > 1 in their actual concentrations in the juice showed a good similarity with the aroma of the original orange juice under investigation, thus corroborating that the key odorants of a freshly reconstituted orange juice were characterised for the first time.     

Influence of yeast on the yield of fermentation and volatile profile of ‘Węgierka Zwykła’ plum distillates

The character of plum brandies depends on a unique aroma profile of the plum and the microbiota present on the surface of the fruits, as well as yeast used for fermentation. In this study, an evaluation of the effect of microorganisms applied for the fermentation of W?gierka Zwyk?a var. plum mashes and processing temperature (18 °C, 30 °C) on its efficiency and volatile profile, as well as taste and flavour of distillates obtained was performed. An estimation of the odour activity values (OAVs) of the volatile compounds was also conducted. Regardless of whether the fermentation was carried out using Saccharomyces bayanus wine yeast or by native microflora present on plums as well as raisins, the efficiency of this process was high and ranged between 91.7 and 96.7% of the theoretical efficiency. Especially rich in esters (among others ethyl acetate and isoamyl acetate) was the distillate derived after fermentation with the microflora of plums and raisins, at 18 °C. An evaluation of the individual aromatic effect of chemical compounds present in tested distillates, in terms of their OAVs, revealed that the highest OAVs were reached with isovaleraldehyde. Other compounds that showed aroma values >1 and possibly had an effect on the overall aroma of tested plum distillates were the following: hexanal, benzaldehyde, ethyl acetate, isoamyl acetate, ethyl benzoate, ethyl hexanoate, 1‐propanol, 2‐methyl‐1‐butanol, 3‐methyl‐1‐butanol and 1‐hexanol. The performed sensory ranking showed that the best rated distillate was the one obtained after fermentation with the indigenous microflora of plums and raisins, at 18 °C. Copyright © 2016 The Institute of Brewing & Distilling     

脂质对凡纳滨对虾热风干制品香气特性的影响

为研究脂质对凡纳滨对虾热风干制品香气特性的影响,通过有机试剂去除虾体中的甘油三酯或磷脂,采用气相色谱-质谱联用技术和感官评价分析脂质对虾干制品香气特性的影响,以气味活性值(odor activity value,OAV)为指标,筛选香气活性化合物,同时采用偏最小二乘回归法(partial least squares regression,PLSR)分析挥发性化合物与感官属性之间的相关性。结果表明:去除甘油三酯对虾干制品整体香气影响较小,烤香味、肉香味和腥味的感官评分稍有减弱,而去除磷脂对主要香气特征有很大影响,烤香味、肉香味、腥味、焦糖香和甜香味的感官评分均大幅度降低;虾干制品中鉴定出16种香气活性化合物,吡嗪类、胺类、杂环类、醛类是其主要成分,其中3-乙基-2,5-二甲基吡嗪、2,5-二甲基吡嗪、三甲胺、3-(甲硫基)丙醛是贡献最大的4种物质;去除甘油三酯和磷脂后,吡嗪类、胺类、杂环类、醛类的OAV值显著下降,而去除磷脂后下降幅度更大,且在去磷脂虾干制品中2-戊基呋喃和3-(甲硫基)丙醛未检出;PLSR结果表明,18种香气活性化合物与感官属性具有较好的相关性。综上所述,脂质对虾干制品整体香气有较大影响,而磷脂对香气特性的作用远大于甘油三酯。该研究为虾类特征香气的形成机制研究提供了理论参考。     

Odour‐active compounds in pineapple (Ananas comosus [L.] Merril cv. Red Spanish)

Application of solid‐phase microextraction, simultaneous distillation–extraction and liquid–liquid extraction combined with GC‐FID, GC‐MS, aroma extract dilution analysis, and odour activity value was used to analyse volatile compounds from pineapple (Ananas comosus [L.] Merril cv. Red Spanish) and to estimate the most odour‐active compounds. The analyses led to the identification of ninety‐four compounds, seventy‐two of them were positively identified. Twenty odorants were considered as odour‐active compounds, from which ethyl 2‐methylbutanoate, 2,5‐dimethyl‐4‐hydroxy‐3(2H)‐furanone, 1‐(E,Z,Z)‐3,5,8‐undecatetraene, ethyl 3‐(methylthio)propanoate, 1‐(E,Z)‐3,5‐undecatriene, ethyl hexanoate and methyl hexanoate were the most odour contributors and contribute to the typical pineapple aroma, while the others are responsible for fruity and sweet odour notes.     

Volatile composition and sensory quality of Spanish pomegranates (Punica granatum L.)

BACKGROUND: Pomegranate is highly valued for its health‐promoting effects. Fruits of nine pomegranate cultivars were analysed for volatile compounds, antioxidant activity and quality parameters, including maturity index and CIEL*a*b* colour. Volatile compounds were isolated from fresh juices using hydrodistillation; extracts were analysed using gas chromatography/mass spectrometry. Fruit colour was influenced by cultivar and grouping of cultivars according to their taste (sweet, sour‐sweet or sour), with sweet fruits having more intense red colour and higher lightness values. RESULTS: A total of 18 compounds were found in pomegranate aroma profiles, including monoterpenes, aldehydes, alcohols, monoterpenoids and linear hydrocarbons. The most abundant compound were trans‐2‐hexenal, 3‐carene, α‐terpinene and α‐terpineol. The total concentration of volatiles ranged from 1.7 to 10.9 g kg^?1. Overall consumer liking of pomegranate juices was associated with the presence of monoterpenes such as α‐pinene, β‐pinene, β‐myrcene, limonene and γ‐terpinene. The presence of aldehydes such as hexanol, hexanal and cis‐3‐hexenol was correlated with poor overall consumer liking. CONCLUSION: Fruits from the cultivar Mollar de Elche 2 were those most suited for juice processing because they had the highest total concentration of volatiles, which was related to high overall consumer liking, intense and acceptable fresh pomegranate odour and flavour (high scores of satisfaction degree), medium intensity of red colour and low sourness. Copyright © 2010 Society of Chemical Industry     

Characteristic aroma compounds of cooked and fermented soybean (Chungkook‐Jang) inoculated with various Bacilli

BACKGROUND: For selecting Chungkook‐jang products with a less undesirable odour, the volatile compounds that affect the overall consumer acceptance of Chungkook‐jang products were analysed. The volatile compounds of Chungkook‐jang were extracted by using solid phase microextraction and direct solvent extraction and were detected by using gas chromatography‐olfactometry. The results were represented as the mean of the log₃ flavour dilution factors; principal component analysis was used to determine the effective components. RESULTS: Fifteen and 14 volatile compounds were detected in the extracts using solid phase microextraction and direct solvent extraction, respectively. The Bacillus species 2‐M1L, which has the most overall acceptance, might have a nutty initial top note and nutty and cheesy long‐lasting note aromas. In correlation analysis between the characteristic aromas and the overall acceptance, trimethyl pyrazine (nutty, pungent), butanoic acid (cheesy, butyric), and methyl pyrazine (burnt, roasted) were positively correlated with overall acceptance. In contrast, 3‐hydroxy‐2‐butanone (buttery, fatty) and 2,3‐butanediol (chemical, fatty) were negatively correlated with overall acceptance. CONCLUSION: Consumers might prefer Chungkook‐jang that has a more nutty and cheesy flavour and a less fatty one. Copyright © 2012 Society of Chemical Industry     

Free and Bound Volatile Chemicals in Mulberry (Morus atropurpurea Roxb.)

Mulberry (Morus atropurpurea Roxb.) is a popular and desirable fruit that is widely cultivated in China. Despite its popularity, the free volatile chemicals and glycosidically bound volatiles (GBVs) of mulberry have been minimally studied. To this end, we have investigated these compounds in 4 mulberry cultivars via solid phase extraction (SPE) and headspace solid phase microextraction with gas chromatography–mass spectrometry (HS‐SPME‐GC‐MS). A total of 55 free volatile chemicals and 57 GBVs were identified and quantified. In 3 of the cultivars (“YFS,” “T10,” and “D10”), the GBVs were found in higher amounts than their free counterparts, corresponding to a ratio of 1.2 to 1.8. The characteristic aromas were determined by their odor activity values (OAVs) and by generating an aroma series (AS). A total of 20 volatile compounds had OAVs ≥ 1.0. In particular, ethyl butanoate, hexanal, (Z)‐3‐hexenal (E)‐2‐hexenal, (E)‐2‐nonenal, and eugenol had relatively high OAVs and were considered to be the key aromas contributing to the mulberry flavor. Consequently, mulberry was characterized by a variety of herbaceous scents having a background of sweet, spicy, fruity, and floral notes. The free volatiles exhibited strong herbaceous notes, whereas the GBVs were responsible for the sweet and spicy qualities of the fruit. Based on our results, 2 cultivars (“YFS” and “D10”) are proposed to be good candidates suitable for the further development of mulberry‐based food products due to their complex and desirable aromas.     

Impact of starter cultures and fermentation techniques on the volatile aroma and sensory profile of chocolate

The sensory quality of chocolate is widely determined by the qualitative and quantitative composition of volatile compounds resulting from microbial metabolism during fermentation, and Maillard reactions taking place during drying, roasting and conching. The influence of applying mixed starter cultures on the formation of flavour precursors, composition of volatile aroma compounds and sensory profile was investigated in cocoa inoculated with cultures encompassing a highly aromatic strain of Pichia kluyveri or a pectinolytic strain of Kluyveromyces marxianus, and compared to commercially fermented heap and tray cocoa. Although only minor differences in the concentration of free amino acids and reducing sugars was measured, identification and quantification by dynamic headspace gas chromatography–mass spectrometry (HS/GC–MS) revealed pronounced differences in the composition of volatiles in roasted cocoa liquors and finished chocolates. 19 of the 56 volatile compounds identified in the chocolates were found in significantly higher amounts in the tray fermented sample, whilst significantly higher amounts of 2-methoxyphenol was measured in the two inoculated chocolates. The P. kluyveri inoculated chocolate was characterized by a significantly higher concentration of phenylacetaldehyde and the K. marxianus inoculated chocolate by significantly higher amounts of benzyl alcohol, phenethyl alcohol, benzyl acetate and phenethyl acetate compared to a spontaneously fermented control. Sensory profiling described the heap and tray fermented chocolates as sweet with cocoa and caramel flavours, whilst the inoculated chocolates were characterized as fruity, acid and bitter with berry, yoghurt and balsamic flavours. The choice of fermentation technique had the greatest overall impact on the volatile aroma and sensory profile, but whilst the application of starter cultures did affect the volatile aroma profile, differences were too small to significantly change consumer perception of the chocolates as compared to a spontaneously fermented control.     

Common aroma‐active components of propolis from 23 regions of China

BACKGROUND: The study of propolis odorants by gas chromatography–olfactometry–mass spectrometry has rarely been put into practice until now. This study aimed to investigate the common odorants of 23 samples of Chinese propolis and analyse the relationship between the principal components and the regions where the samples had been obtained. RESULTS: By using dynamic headspace sampling, gas chromatography–olfactometry–mass spectrometry and two internal standards, the principal aroma‐active components of 23 propolis samples were analysed qualitatively and quantitatively. The common aroma‐active components were compared with each other by principal component analysis from concentration, odour activity value (OAV) and sensory evaluation score. The components with high OAVs were acetic acid, 2‐phenylethyl acetate, and naphthalene, in decreasing order, which approximated the sensory evaluation scores. On the discrete‐point map the first three principal components seemed to be grouped into three patterns, while four samples were outliers. CONCLUSION: The concentrations of aroma‐active components were closely related to the regions from a discrete‐point map by the first three principal components. It was confirmed that components with high concentrations did not always play important roles in odour contribution, for odour level was linked with their threshold. OAVs could reflect the level of odour exactly according to the approximate result from the comparison between OAVs and sensory evaluation scores. Copyright © 2010 Society of Chemical Industry     

Characterization and discrimination of premium‐quality,waxy, and black‐pigmented rice based on odor‐active compounds

BACKGROUND: Odor‐active compounds have been studied in cooked aromatic rice, but not in specialty rice types that have distinctly different flavors. We analyzed the odor‐active compounds emanating from three different types of specialty rice (premium‐quality, waxy and black‐pigmented) and identified the differences in odor‐active compounds among them. RESULTS: Twenty‐one, 21 and 23 odorants were detected using GC‐O for cooked samples of premium‐quality, waxy and black‐pigmented rice cultivars, respectively. Hexanal was the main odorant in premium‐quality and waxy cultivars; however, waxy cultivars had 16 times higher hexanal odor activity values (OAVs) than premium‐quality cultivars, indicating premium‐quality rice had a less pronounced overall aroma. 2‐Acetyl‐1‐pyrroline was the main contributor to overall aroma in black‐pigmented rice, followed by guaiacol. The three types of specialty rice were clearly discriminated based on the OAVs of their odor‐active compounds using multivariate analyses. Six odor‐active compounds [2‐acetyl‐1‐pyrroline, guaiacol, hexanal, (E)‐2‐nonenal, octanal and heptanal] contributed the most in discriminating the three types of specialty rice. Six very similar superior cultivars of premium rice could likewise be readily separated using aroma chemistry. CONCLUSION: The ability to discriminate the aroma among rice types using the OAVs of the principal odor‐active compounds facilitates our understanding of the aroma chemistry of specialty rice. Copyright © 2010 Society of Chemical Industry     

Characterisation of odour-active compounds in aged rum

The volatiles of rum matured in oak casks were carefully isolated by solvent extraction followed by solvent-assisted flavour evaporation. Among the 116 volatile compounds identified by GC-MS, seven of them were found for the first time in rum. Application of the aroma extract dilution analysis (AEDA) on the volatile fraction revealed 18 odour-active areas in the flavour dilution factor range of 32-1024. On the basis of the quantitative data and odour thresholds in 35% ethanol (v/v), the odour activity values (OAV; ratio of concentration to odour threshold) were calculated. Nineteen aroma compounds showed OAVs >1, among which ethanol, (E)-β-damascenone, ethyl butanoate, ethyl hexanoate, vanillin, (Z)-oak lactone, ethyl 2-methylpropanoate, 1,1-diethoxyethane, ethyl 2-methylbutanoate, 3-methylbutyl acetate, ethyl octanoate, ethyl decanoate, 2-phenylethyl acetate, 2-phenylethanol, 2-methoxyphenol, 4-ethyl-2-methoxyphenol, 4-propyl-2-methoxyphenol, γ-nonalactone, and eugenol showed the highest values and should be considered as the most odour-active compounds.     

The Contribution of 4‐Hydroxyfuranone Derivatives to the Aroma of Commercial Beers and Malts

Analysis of hot water extracts from a range of commercial malts showed that 2,5‐dimethyl‐4‐hydroxy‐3(2H)furanone (DMHF) varied from undetectable (lager malt) to 4.2 mg/litre (crystal malt), a concentration twenty‐six times the flavour threshold in water. 5‐Methyl‐4‐hydroxy‐3 (2H)furanone (MHF) was detected in all samples except one but was always well under its flavour threshold value. 2(or 5)‐Ethyl‐5(or 2)‐methyl‐4‐hydroxy‐3(2H)furanone (EMHF) was not detected in any of the samples. Fermentation of lager, ale and crystal malt extracts with an ale strain of yeast led to the appearance of EMHF in all cases as well as additional DMHF. The greatest increases in both compounds was with the ale malt. Both increases and decreases occurred in MHF concentration as a result of fermentation but final levels were always well below the flavour threshold value. Analysis of ten commercial beers found DMHF in all the samples and in five cases levels exceeded twice the flavour threshold value in beer with flavour units from 2.4 to 9.1. A flavour panel noted that in four of these cases the beer had a distinctly sweet/caramel aroma which is typical of DMHF. EMHF was undetectable in six samples, detectable, but unquantifiable, in three cases but at about 80% of the flavour threshold value in the remaining sample. MHF was found in all samples but at insignificant levels. The results show that DMHF is an important flavour compound in British ales and EMHF may make a contribution in a limited number of situations. The contribution of malt type, brewery processing and yeast strain in determining the concentration of the two 4‐hydroxyfuranones in beer remains uncertain.     

Important odorants of sweet bell pepper powder (Capsicum annuum cv. annuum): differences between samples of Hungarian and Morrocan origin

 By application of gas chromatography–olfactometry on aroma extracts prepared from Hungarian sweet bell pepper powder (HBP) and Moroccan sweet bell pepper powder (MBP), 35 and 42 odour-active compounds were detected in the HBP and the MBP, respectively. The identification experiments, in combination with the flavour dilution (FD) factors obtained by application of aroma extract dilution analysis, revealed that β-ionone (violet-like), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol; caramel-like), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (Sotolon; seasoning-like) and 2- and 3-methylbutanoic acids had the highest odour activities (FD factors of 8192 to 32768) among the 33 odorants that could be identified in the HBP. All odorants identified in the HBP were also characterized as odour-active volatiles in the MBP. The overall different aroma of the Moroccan sample could, however, be attributed to the lower FD factors of the five key odorants mentioned above and, in addition, to the higher FD factors of 10 odorants not present among the aroma compounds of the HBP, e.g. (Z)-1,5-octadien-3-one. In total, 20 odour-active volatiles are reported here for the first time as volatile bell pepper constituents. Received: 30 July 1999 / Revised version: 11 October 1999     

The impact of maturation on concentrations of key odour active compounds which determine the aroma of tequila

Samples of non‐mature and añejo (matured) tequila of the same brand/provenance were analysed using GC–MS and gas chromatography olfactometry (GC‐O)/aroma extract dilution analysis (AEDA) to provide quantitative data on the most odour active compounds that contribute to the aroma of these spirits. Extracts of non‐mature tequila were characterized by 26 odour‐active regions, which included ethyl hexanoate, ethyl octanoate, 2‐phenylethyl acetate, β‐damascenone, isoamyl alcohol and octanoic acid as the most odour‐active compounds (flavour dilution, FD, factor ≥ 6561). In contrast, extracts of the mature spirit showed 36 odour‐active zones, where the compounds with the highest FD factors (6561) were ethyl hexanoate, ethyl octanoate, 2‐phenylethyl acetate, isoamyl alcohol, phenethyl alcohol, guaiacol, 4‐ethyl guaiacol, vanillin, cis/trans whisky lactones, β‐damascenone and octanoic acid. The aromagram of mature tequila was thus differentiated from that of the non‐mature spirit owing to the presence of cask‐extractive compounds and the increased FD factors of certain terpenes, higher alcohols and acetals. This study provides a comprehensive and quantitative understanding of changes in key odourants of tequila as a result of the maturation process and also reveals a further characterization of the likely impact of each compound on overall spirit flavour, in terms of odour activity values. Copyright © 2016 The Institute of Brewing & Distilling