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Instrumental Analysis for Volatile Odorants and Flavours

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Analytical Chemistry".

Deadline for manuscript submissions: closed (31 May 2019) | Viewed by 55207

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Special Issue Editors

Prof. Dr. Michael C. Qian

E-Mail Website1 Website2
Guest Editor

Department of Food Science and Technology, Oregon State University, Corvallis, OR, USA
Interests: flavor chemistry; wine; volatile analysis; dairy science; GC-MS
Special Issues, Collections and Topics in MDPI journals

Dr. Yanping L. Qian

E-Mail Website
Guest Editor

Department of Crop and Soil Science, Oregon State University, Corvallis, OR, USA
Interests: volatile analysis; beer and hop aroma; liquor aroma; grape and wine aroma; grape and wine polyphenols; wine quality
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Odorants are volatile compounds that can be perceived sensorially by the human olfactory system. These compounds typically have a small molecular weight (<350 Dolton), are highly volatile, and, in many cases, not stable (sensitive to oxygen, heat). Odorant perception by the olfactometry system can be very sensitive and selective. For example, the coffee aroma contains over 800 volatile compounds, but only three dozen or so compounds have a considerable impact on the overall aroma of coffee. Some odor-active compounds can be perceived to the nanogram per liter and lower, whereas some other compounds, even presented at much higher concentrations, are odor-inactive.

This means that odor analysis should be focused on compounds with organoleptic significance, rather than simply identifying any volatile compound that may or may not contribute to a particular aroma. Therefore, accurate identification of each unique volatile compound that plays a role in contributing to the overall aroma of a particular food is the ultimate goal of odor analysis. This makes the volatile odorant analysis highly dynamic and challenging because the volatile composition of foods, beverages, perfumery and other natural products are frequently quite complex. Highly sophisticated techniques involved with the extraction and enrichment, separation and sensitive and selective detection are required for reliable determination of odorants in a biological system.

This Special Issue will cover a wide range of topics related to odor analysis in food and other biological system, including, but not limited to, advances in sample preparation (dynamic headspace sampling, solid phase micro-extraction, stir bar sorptive extraction, etc.), new development of column chemistry and separation science, multi-dimensional GC and GC-MS, mass spectrometry, and other detection techniques.

Prof. Michael Qian
Dr. Yanping L. Qian
Guest Editors

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Keywords

volatile compounds analysis
volatile odorant analysis
foods
beverages
perfumery
extraction and enrichment
separation and detection
multi-dimensional GC and GC-MS
mass spectrometry

Published Papers (13 papers)

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Research

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14 pages, 2519 KiB

Open AccessFeature PaperArticle

Removal of Volatile Phenols From Wine Using Crosslinked Cyclodextrin Polymers

by Chao Dang, Vladimir Jiranek, Dennis K. Taylor and Kerry L. Wilkinson

Molecules 2020, 25(4), 910; https://doi.org/10.3390/molecules25040910 - 18 Feb 2020

Cited by 17 | Viewed by 3016

Abstract

Volatile phenols have been implicated as contributors to off-odors associated with taints from bushfire smoke and microbial spoilage. Various methods for the amelioration of off-odors have been evaluated, but to date, they have not included cyclodextrin (CD) polymers. In the current study, two CD polymers were prepared from β- and γ-CD, using hexamethylene diisocyanate (HDI) as a crosslinking agent. Adsorption tests were performed with four volatile phenols (guaiacol, 4-methylguaiacol, 4-ethylguaiacol and 4-ethylphenol) at concentrations up to 1 mg/L. The removal of volatile phenols by CD polymers achieved equilibrium almost instantly, with isotherm tests suggesting an adsorption capacity of 20.7 µg of volatile phenol per gram of polymer. Langmuir and Freundlich models were subsequently used to fit the data. In batch adsorption tests, the CD polymers achieved 45 to 77% removal of volatile phenols. Polymer reusability was also evaluated and was found to be excellent. A comparison between volatile phenol adsorption by CDs vs. CD polymers, determined using a novel four-phase headspace solid-phase microextraction (HS-SPME) method for gas chromatography-mass spectrometry (GC-MS), suggests CD polymers offer several advantages for use by the wine industry. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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9 pages, 1332 KiB

Open AccessFeature PaperArticle

Effect of Ethanol on the Adsorption of Volatile Sulfur Compounds on Solid Phase Micro-Extraction Fiber Coatings and the Implication for Analysis in Wine

by Peter M. Davis and Michael C. Qian

Molecules 2019, 24(18), 3392; https://doi.org/10.3390/molecules24183392 - 18 Sep 2019

Cited by 8 | Viewed by 3165

Abstract

Complications in the analysis of volatile sulfur compounds (VSC) in wine using solid-phase microextraction (SPME) arise from sample variability. Constituents of the wine matrix, including ethanol, affect the volatility and adsorption of sulfur volatiles on SPME fiber coatings (Carboxen- polydimethylsiloxane(PDMS); DVB-Carboxen-PDMS and DVB-PDMS), which can impact sensitivity and accuracy. Here, several common wine sulfur volatiles, including hydrogen sulfide (H₂S), methanethiol (MeSH), dimethyl sulfide (DMS), dimethyl disulfide (DMDS), dimethyl trisulfide (DMTS), diethyl disulfide (DEDS), methyl thioacetate (MeSOAc), and ethyl thioacetate (EtSOAc) are analyzed, using SPME followed by gas chromatography (GC), using a system equipped with a pulsed-flame photometric detection (PFPD) system, at various ethanol concentrations in a synthetic wine matrix. Ethyl methyl sulfide (EMS), diethyl sulfide (DES), methyl isopropyl sulfide (MIS), ethyl isopropyl sulfide (EIS), and diisopropyl disulfide (DIDS) are evaluated as internal standards. The absorption of volatile compounds on the SPME fiber is greatly affected by ethanol. All compounds exhibit a stark decrease in detectability with the addition of ethanol, especially between 0.0 and 0.5% v/v. However, the ratio of interested sulfur compounds to the internal standard becomes more stable when the total alcohol concentration exceeds 2%. EMS was found to best resemble DMS. EIS and DES were found to best resemble DMDS, MeSOAc, and EtSOAc. DIDS was found to best resemble DEDS, DMTS, H₂S, and MeSH. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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14 pages, 2072 KiB

Open AccessArticle

Effect of Wine Matrix Composition on the Quantification of Volatile Sulfur Compounds by Headspace Solid-Phase Microextraction-Gas Chromatography-Pulsed Flame Photometric Detection

by Peter M. Davis and Michael C. Qian

Molecules 2019, 24(18), 3320; https://doi.org/10.3390/molecules24183320 - 12 Sep 2019

Cited by 11 | Viewed by 3067

Abstract

The analysis of volatile sulfur compounds using headspace solid-phase microextraction (HS-SPME) is heavily influenced by matrix effects. The effects of a wine matrix, both non-volatile and volatile components (other than ethanol) were studied on the analysis of several common sulfur volatiles found in wine, including hydrogen sulfide (H₂S), methanethiol (MeSH), dimethyl sulfide (DMS), dimethyl disulfide (DMDS), dimethyl trisulfide (DMTS), diethyl disulfide (DEDS), methyl thioacetate (MeSOAc), and ethyl thioacetate (EtSOAc). Varying levels of devolatilized wine and common wine volatiles (acids, esters, alcohols) were added to synthetic wine samples to act as matrices. Sulfur standards were added and analyzed using gas chromatography with pulsed-flame photometric detection (GC-PFPD). Five internal standards were used to find best representatives of each compound despite matrix effects. Sensitivity remained stable with the addition of devolatilized wine, while addition of volatile components decreased sensitivity. DMS was found to be best measured against EMS; DMDS and the thioacetates were best measured against DES; H₂S, MeSH, DEDS, and DMTS were best measured against DIDS. The method was used to quantitate the volatile sulfur compounds in 21 wines with various ethanol contents and volatile profiles. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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19 pages, 5763 KiB

Open AccessArticle

Changes in the Volatile Components of Candied Kumquats in Different Processing Methodologies with Headspace–Gas Chromatography–Ion Mobility Spectrometry

by Xiao Hu, Rongrong Wang, Jiajing Guo, Keda Ge, Gaoyang Li, Fuhua Fu, Shenghua Ding and Yang Shan

Molecules 2019, 24(17), 3053; https://doi.org/10.3390/molecules24173053 - 22 Aug 2019

Cited by 36 | Viewed by 3575

Abstract

The effects of two different processing methods on the volatile components of candied kumquats were investigated via headspace–gas chromatography–ion mobility spectrometry (HS–GC–IMS). The characteristic volatile fingerprints of fresh kumquats (FKs), vacuum sugaring osmosis combined with hot-air drying kumquats (VS-ADKs), and atmospheric pressure sugaring osmosis combined with hot-air drying kumquats (AS-ADKs) were established using 3D topographic plots. From the fingerprints, 40 signal peaks for 22 compounds were confirmed and quantified in all types of kumquats, namely, two terpenes, four esters, seven aldehydes, three ketones, and six alcohols. 3-Pentanone was identified as the major component of FKs; followed by 1-hexanol and the Z-3-hexen-1-ol dimer. The hexanal dimer, 2-hexen-1-ol, and the ethyl acetate dimer were the major markers of VS-ADKs. Benzaldehyde and furfurol were the prominent constituent parts of AS-ADKs. Compared with that in FKs, the pentanal and dimethyl ketone contents of VS-ADKs and AS-ADKs exhibited a dramatic increase (p < 0.05). By contrast, the change in ethanol dimer tended to decrease (p < 0.05). Principal component analysis (PCA) clearly showed that the samples, which were distributed in a separate space could be well-distinguished. Furthermore, the similarity of different processed kumquats and their corresponding volatile components was demonstrated via heat map clustering analysis. The results confirmed the potential of HS–GC–IMS-based approaches to evaluate processed kumquats with various volatile profiles. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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16 pages, 822 KiB

Open AccessArticle

Harvesting at the Right Time: Maturity and its Effects on the Aromatic Characteristics of Cabernet Sauvignon Wine

by Ting Zhao, Jiaying Wu, Jiangfei Meng, Pengbao Shi, Yulin Fang, Zhenwen Zhang and Xiangyu Sun

Molecules 2019, 24(15), 2777; https://doi.org/10.3390/molecules24152777 - 30 Jul 2019

Cited by 16 | Viewed by 2816

Abstract

The aim of this paper was to investigate how maturity affects the aroma characteristics of Cabernet Sauvignon wine. A series of four Vitis vinifera cv. Cabernet Sauvignon wines were produced from grapes of different harvest dates. The berries of sequential harvest treatments showed an increase in total soluble solids and anthocyanin and a decrease in titratable acidity. Berry shriveling was observed as berry weight decreased. In the wines, anthocyanin, dry extract, alcoholic strength, and pH were enhanced with the sequential harvest, whereas polyphenol and tannin were decreased. The concentrations of volatile compounds in sequential harvests were found to be at higher levels. Isopentanol, phenylethyl alcohol, ethyl acetate, ethyl lactate, benzaldehyde, citronellol, and linalool significantly increased when harvest was delayed by one or two weeks. Through a principal component analysis, the volatile compounds and phenols characterizing each harvest date were clearly differentiated. These results suggest that sequential harvest may be an optional strategy for winemakers to produce high-quality wine. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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11 pages, 604 KiB

Open AccessArticle

Comparison of the Aroma Profiles of Intermediate Wheatgrass and Wheat Bread Crusts

by Laurianne Paravisini, Kelsey A. Sneddon and Devin G. Peterson

Molecules 2019, 24(13), 2484; https://doi.org/10.3390/molecules24132484 - 06 Jul 2019

Cited by 8 | Viewed by 3162

Abstract

The aroma profiles of bread crusts made from intermediate wheatgrass (Thinopyrum intermedium) and whole wheat (Triticum aestivum) flours were compared. Based on gas chromatography/mass spectrometry/olfactometry analysis, twenty-four odorants were identified and further quantified. The concentrations of seventeen compounds were significantly different between intermediate wheatgrass and whole wheat bread crusts, of which sixteen compounds were higher in the whole wheat sample. The aroma profiles of the bread samples were subsequently characterized using sensory descriptive analysis (DA) and indicated that the roasted attribute was perceived at a significantly higher intensity in the whole wheat sample due to a greater amount of Maillard reaction compounds. Alternatively, bran and green notes were perceived at higher intensities in the intermediate wheatgrass sample, however they were not attributed to the presence of specific compounds but rather to a change in the aroma composition. Aroma recombination DA of the whole wheat and intermediate wheatgrass aroma models was similar to the original aroma profiles of the bread samples, demonstrating the sensory relevance of the identified odorants. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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14 pages, 576 KiB

Open AccessArticle

An HS-SPME-GC-MS Method for Profiling Volatile Compounds as Related to Technology Used in Cider Production

by Jakub Nešpor, Marcel Karabín, Kateřina Štulíková and Pavel Dostálek

Molecules 2019, 24(11), 2117; https://doi.org/10.3390/molecules24112117 - 04 Jun 2019

Cited by 17 | Viewed by 3718

Abstract

Volatile aromatic compounds have a major impact on the final organoleptic properties of cider, and their profiles are influenced by a number of parameters that are closely related to production technologies, especially with regard to the raw material, the microorganism used and the fermentation process. In this work, the profiles of volatile compounds (4 fatty acids, 6 higher alcohols and 12 esters) from 34 European ciders were studied using HS-SPME-GC-MS. Volatiles were isolated by HS-SPME using a CAR/PDMS fiber. Analytical data were statistically evaluated using principal component analysis, and differences in composition of volatiles between cider produced using “intensified” technologies and that of ciders produced by traditional production processes were demonstrated. This difference was mainly due to varying contents of some higher alcohols (2-methylpropanol, isoamyl alcohols, hexanol, and butane-2,3-diol) and esters (ethyl 2-methylbutanoate, butylacetate, and hexyl acetate). Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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16 pages, 1241 KiB

Open AccessArticle

Comparison of Four Extraction Techniques for the Evaluation of Volatile Compounds in Spray-Dried New Zealand Sheep Milk

by Ryan High, Phil Bremer, Biniam Kebede and Graham T. Eyres

Molecules 2019, 24(10), 1917; https://doi.org/10.3390/molecules24101917 - 18 May 2019

Cited by 22 | Viewed by 3802

Abstract

Recent growth and diversification of sheep milk products means more sophisticated methods are required to ensure their flavour quality. The objective of this study was to compare four extraction techniques for the analysis of volatile compounds in sheep milk by gas chromatography-mass spectrometry (GC-MS). Solvent Assisted Flavour Evaporation (SAFE), Solid Phase Microextraction (SPME), Headspace Sorptive Extraction (HSSE) and Stir Bar Sorptive Extraction (SBSE) were evaluated for their sensitivity, selectivity, reproducibility, and overall efficiency. A total of 48 volatile compounds from nine compound classes were identified in the spray-dried sheep milk. Alcohols, aldehydes, alkanes, carboxylic acids, ketones, lactones, sulphur compounds, nitrogen compounds, and terpenes were all present, but the differences between the methods were most apparent for lactones. SBSE extracted eight lactones, SAFE extracted four lactones and HSSE and SPME only detected trace levels of two lactones. Six of the lactones—δ-hexa-lactone, δ-octalactone, γ-decalactone, γ-dodecalactone, δ-tetradecalactone, and δ-hexadeca-lactone—were identified for the first time in spray-dried sheep milk. The present work demonstrated that SBSE is an effective tool for the extraction and analysis of volatiles, especially lactones, in sheep milk and dairy products in general. A discussion of the benefits and limitations of each method is included. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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15 pages, 664 KiB

Open AccessArticle

Comparison of Volatile and Nonvolatile Compounds in Rice Fermented by Different Lactic Acid Bacteria

by Sang Mi Lee, Young Rim Hwang, Moon Seok Kim, Myung Sub Chung and Young-Suk Kim

Molecules 2019, 24(6), 1183; https://doi.org/10.3390/molecules24061183 - 26 Mar 2019

Cited by 21 | Viewed by 4718

Abstract

The production of rice-based beverages fermented by lactic acid bacteria (LAB) can increase the consumption of rice in the form of a dairy replacement. This study investigated volatile and nonvolatile components in rice fermented by 12 different LABs. Volatile compounds of fermented rice samples were analyzed using gas chromatography-mass spectrometry (GC-MS) combined with solid-phase microextraction (SPME), while nonvolatile compounds were determined using gas chromatography-time-of-flight/mass spectrometry (GC-TOF/MS) after derivatization. The 47 identified volatile compounds included acids, aldehydes, esters, furan derivatives, ketones, alcohols, benzene and benzene derivatives, hydrocarbons, and terpenes, while the 37 identified nonvolatile components included amino acids, organic acids, and carbohydrates. The profiles of volatile and nonvolatile components generally differed significantly between obligatorily homofermentative/facultatively heterofermentative LAB and obligatorily heterofermentative LAB. The rice sample fermented by Lactobacillus sakei (RTCL16) was clearly differentiated from the other samples on principal component analysis (PCA) plots. The results of PCA revealed that the rice samples fermented by LABs could be distinguished according to microbial strains. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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23 pages, 3948 KiB

Open AccessArticle

Olfactory Impact of Terpene Alcohol on Terpenes Aroma Expression in Chrysanthemum Essential Oils

by Yunwei Niu, Xiaoxin Sun, Zuobing Xiao, Pinpin Wang and Ruolin Wang

Molecules 2018, 23(11), 2803; https://doi.org/10.3390/molecules23112803 - 29 Oct 2018

Cited by 9 | Viewed by 3383

Abstract

The key point of our work was evaluating the impact of terpene alcohols on the aroma expression of terpenes recombination in Chrysanthemum essential oils. Using pure commercial products, various aromatic recombinations were prepared, consisting of terpenes recombination and six terpene alcohols, all the concentrations found in Chrysanthemum essential oils. There were five groups of terpene alcohols mixtures performed very interesting with the addition or omission tests. The “olfactory threshold” of the terpenes recombination had a notable decrease when adding isoborneol, d-Fenchyl alcohol respectively through the Feller’s additive model analysis. Furthermore, the descriptive test indicated that the addition of terpene alcohols mixture had the different effect on fruity, floral, woody, green, and herbal aroma intensity. Specifically, when isoborneol was added to the terpenes recombination in squalane solution, it was revealed that isoborneol had a synergy impact on herbal and green notes of the terpenes recombination and masked the fruity note. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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12 pages, 2384 KiB

Open AccessFeature PaperArticle

HS-SPME-GC-MS Analyses of Volatiles in Plant Populations—Quantitating Compound × Individual Matrix Effects

by Elizabeth A. Burzynski-Chang, Imelda Ryona, Bruce I. Reisch, Itay Gonda, Majid R. Foolad, James J. Giovannoni and Gavin L. Sacks

Molecules 2018, 23(10), 2436; https://doi.org/10.3390/molecules23102436 - 23 Sep 2018

Cited by 17 | Viewed by 7412

Abstract

Headspace solid-phase microextraction (HS-SPME) coupled to gas chromatography–mass spectrometry (GC-MS) is widely employed for volatile analyses of plants, including mapping populations used in plant breeding research. Studies often employ a single internal surrogate standard, even when multiple analytes are measured, with the assumption that any relative changes in matrix effects among individuals would be similar for all compounds, i.e., matrix effects do not show Compound × Individual interactions. We tested this assumption using individuals from two plant populations: an interspecific grape (Vitis spp.) mapping population (n = 140) and a tomato (Solanum spp.) recombinant inbred line (RIL) population (n = 148). Individual plants from the two populations were spiked with a cocktail of internal standards (n = 6, 9, respectively) prior to HS-SPME-GC-MS. Variation in the relative responses of internal standards indicated that Compound × Individual interactions exist but were different between the two populations. For the grape population, relative responses among pairs of internal standards varied considerably among individuals, with a maximum of 249% relative standard deviation (RSD) for the pair of [U¹³C]hexanal and [U¹³C]hexanol. However, in the tomato population, relative responses of internal standard pairs varied much less, with pairwise RSDs ranging from 8% to 56%. The approach described in this paper could be used to evaluate the suitability of using surrogate standards for HS-SPME-GC-MS studies in other plant populations. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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Review

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24 pages, 1554 KiB

Open AccessFeature PaperReview

Analysis of Potent Odour-Active Volatile Thiols in Foods and Beverages with a Focus on Wine

by Liang Chen, Dimitra L. Capone and David W. Jeffery

Molecules 2019, 24(13), 2472; https://doi.org/10.3390/molecules24132472 - 05 Jul 2019

Cited by 30 | Viewed by 6988

Abstract

Certain volatile thiols are some of the most potent odour-active molecules that are found in nature. Thiols play significant roles in the aroma qualities of a range of foods and beverages, including wine, with extremely low odour detection thresholds (nanogram per litre range). A fundamental understanding of their formation, fate, and impact essentially depends on the development of suitable analytical methods. The analysis of volatile thiols in foods and beverages is a challenging task when considering (1) the complexity of food and beverage matrices and (2) that thiols are highly reactive, low molecular-weight volatiles that are generally present at trace to ultra-trace concentrations. For the past three decades, the analytical evaluation of volatile thiols has been intensively performed in various foods and beverages, and many novel techniques related to derivatisation, isolation, separation, and detection have been developed, particularly by wine researchers. This review aims to provide an up-to-date overview of the major analytical methodologies that are proposed for potent volatile thiol analysis in wine, foods, and other beverages. The analytical challenges for thiol analysis in foods and beverages are outlined, and the main analytical methods and recent advances in methodology are summarised and evaluated for their strengths and limitations. The key analytical aspects reviewed include derivatisation and sample preparation techniques, chromatographic separation, mass spectrometric detection, matrix effects, and quantitative analysis. In addition, future perspectives on volatile thiol research are also suggested. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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30 pages, 2357 KiB

Open AccessReview

The Blossoming of Technology for the Analysis of Complex Aroma Bouquets—A Review on Flavour and Odorant Multidimensional and Comprehensive Gas Chromatography Applications

by Michelle S.S. Amaral and Philip J. Marriott

Molecules 2019, 24(11), 2080; https://doi.org/10.3390/molecules24112080 - 31 May 2019

Cited by 23 | Viewed by 5652

Abstract

Multidimensional approaches in gas chromatography have been established as potent tools to (almost) attain fully resolved analyses. Flavours and odours are important application fields for these techniques since they include complex matrices, and are of interest for both scientific study and to consumers. This article is a review of the main research studies in the above theme, discussing the achievements and challenges that demonstrate a maturing of analytical separation technology. Full article

(This article belongs to the Special Issue Instrumental Analysis for Volatile Odorants and Flavours)

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