Institut für Lebensmittelchemie

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Analysis of acrylamide in vegetable chips after derivatization with 2-mercaptobenzoic acid by liquid chromatography–mass spectrometry
(2022) Oellig, Claudia; Gottstein, Eva; Granvogl, Michael
Since many years, acrylamide (AA) is a well-known toxicologically relevant processing contaminant (“food-borne toxicant”). However, only during the recent years, high levels of acrylamide have been reported in vegetable chips. In the present study, AA was quantitated via a modified derivatization procedure with 2-mercaptobenzoic acid based on stable isotope dilution analysis and liquid chromatography–mass spectrometry. Extraction with a modified QuEChERS (quick, easy, cheap, efficient, rugged, safe) method, defatting with n -hexane, and a solid phase extraction clean-up with strong cation-exchange material were performed prior to the derivatization step. Limits of detection and quantitation (LoD and LoQ) were 12 and 41 µg of AA/kg of vegetable chips (estimated via signal-to-noise ratios of 3:1 and 10:1, respectively), and thus below the LoQ of 50 µg/kg requested by the European Food Safety Authority. Recovery rates between 92 and 101% at four spiking levels with a good precision expressed as a relative standard deviation < 7% were determined. With this method at hand, a survey of the current AA amounts in 38 vegetable chips from the worldwide market was performed, showing a remarkable variability between the different vegetables, but also between different products of the same vegetable. Thereby, the AA amounts ranged between 77.3 and 3090 µg/kg, with an average of 954 µg/kg which was distinctly higher in comparison to commercially available potato chips also analyzed in the present study (12 samples, range: 117–832 µg/kg, average: 449 µg/kg). While for sweet potato and parsnip relatively low AA amounts were found, beetroot and carrot showed rather high contents.
Analysis of mono-, di-, triacylglycerols, and fatty acids in food emulsifiers by high-performance liquid chromatography–mass spectrometry
(2021) Schick, Dinah; Link, Katharina; Schwack, Wolfgang; Granvogl, Michael; Oellig, Claudia
Mono- and diacylglycerols (MG/DG) of fatty acids (FA), known as emulsifiers of the type E 471, are food additives used to adjust techno-functional properties of various foodstuffs. These emulsifiers, however, are not defined single compounds but comprise, in addition to MG and DG, other constituents such as FA, triacylglycerols (TG), and glycerol. Although the emulsifiers’ compositions affect techno-functional properties of the food, knowledge of the composition is scarcely available, and the emulsifiers and their dosage are generally chosen empirically. Thus, a simple and rather inexpensive method for the simultaneous determination of FA, 1-MG, 2-MG, 1,2-DG, 1,3-DG, and TG by high-performance liquid chromatography–mass spectrometry including a straightforward quantitation strategy has been developed. Reversed-phase chromatography with gradient elution offered adequate separation of 29 considered analytes within 21 peaks, while mass-selective detection provided their unequivocal identification. The quantitation strategy based on calibration just with the C16:0 representatives of each lipid class and a corresponding response factor system has proven to provide reliable results. The determined concentrations of different mixtures comprising varying compositions and concentrations of C16:0, C18:0, and C18:1 components of each lipid class deviated < 20% (n = 351) from the respective target concentrations. Limits of decision were determined to 0.3–0.8 mg/L and limits of quantitation to 0.8–1.7 mg/L, expressed as C16:0 representatives. Application of the method to various E 471 emulsifiers provided detailed data on their chemical compositions, and calculated FA compositions matched very well those determined by common methods such as gas chromatography with flame ionization detection.
Antifungal properties of bioactive compounds isolated from Fucus vesiculosus supercritical carbon dioxide extract
(2024) Tyśkiewicz, Katarzyna; Rüttler, Felix; Tyśkiewicz, Renata; Nowak, Artur; Gruba, Marcin; Wziątek, Anita; Dębczak, Agnieszka; Sandomierski, Michał; Vetter, Walter; Cacciola, Francesco
The exploration of natural antifungal substances from algal origins is significant due to the increasing resistance of pathogens to conventional antifungal agents and the growing consumer demand for natural products. This manuscript represents the inaugural investigation into the antifungal attributes of bioactive compounds extracted from Fucus vesiculosus via supercritical carbon dioxide (scCO2) extraction utilizing contemporary countercurrent chromatography (CCC). In aligning with the prospective utilization of this extract within the agricultural sector, this study also serves as the preliminary report demonstrating the capability of Fucus vesiculosus scCO2 extract to enhance the activity of plant resistance enzymes. The fractions obtained through CCC were subjected to evaluation for their efficacy in inhibiting the macrospores of Fusarium culmorum. The CCC methodology facilitated the successful separation of fatty acids (reaching up to 82.0 wt.% in a given fraction) and fucosterol (attaining up to 79.4 wt.% in another fraction). All CCC fractions at the concentration of 1.0% were found to inhibit 100% of Fusarium culmorum growth. Moreover, Fucus vesiculosus scCO2 extract was able to activate plant resistance enzymes (Catalase, Ascorbic Peroxidase, Guaiacol Peroxidase, Phenylalanine Ammonia-Lyase, and Phenylalanine Ammonia-Lyase Activity).
Characterization of the major odor-active compounds in fresh rhizomes and leaves of Houttuynia cordata by comparative aroma extract dilution analysis
(2025) Xu, Zhenli; Liu, Jing; Kreissl, Johanna; Oellig, Claudia; Vetter, Walter; Steinhaus, Martin; Frank, Stephanie; Rodov, Victor
Houttuynia cordata is a culinary herb from Asia. Its edible rhizomes and leaves have a fishy aroma, the molecular background of which was unknown. A comparative aroma extract dilution analysis applied to fresh rhizomes and leaves resulted in 44 and 41 odorants, respectively, 38 of which were present with FD factors ≥1 in both samples. The odorant with the highest FD factors, whether in the rhizomes or leaves, was identified as metallic, soapy, fishy smelling 3-oxododecanal. Toward clarifying its tautomeric composition, quantum calculations suggested a predominance of the enol forms in the plant. However, the form perceived at the sniffing port during GC–O remained unclear.
Chlorinated paraffins in hinges of kitchen appliances
(2021) Sprengel, Jannik; Vetter, Walter
Chlorinated paraffins (CPs) are anthropogenic pollutants of growing environmental concern. These highly complex mixtures of thousands of homologs and congeners are usually applied as additives in lubricants or as flame retardants and plasticizers in polymers and paints. Recent studies indicated the presence of high amounts of CPs in the kitchen environment whose sources could not be unequivocally identified. One option was the use of CPs as or in lubricants of hinges. To test this hypothesis, we performed wipe tests on lubricants on 29 hinges of different types of kitchen appliances (refrigerators, baking ovens, dishwashers, freezers, microwave oven, pasta machine, food processor, steam cooker) and analyzed them for short-chain CPs (SCCPs) and medium-chain CPs (MCCPs). CPs were detected in 21 samples (72%). Per wipe, SCCP concentrations ranged between 0.02 and 10 µg (median 0.23 µg), while MCCPs ranged from 0.09 to 750 µg (median 1.0 µg). Highest MCCP amounts (380 and 750 µg per wipe, respectively) were determined in new and unused appliances. A medium correlation between SCCP content and appliance age was observed, but no additional statistic correlation between SCCP/MCCP amount and appliance type or manufacturer could be observed. CPs released from hinges by volatilization, abrasion, and cleaning processes could enter the environment and come in contact with persons living in the corresponding households.
Determination of mono- and diacylglycerols from E 471 food emulsifiers in aerosol whipping cream by high-performance thin-layer chromatography–fluorescence detection
(2020) Oellig, Claudia; Blankart, Max; Hinrichs, Jörg; Schwack, Wolfgang; Granvogl, Michael
Mono- and diacylglycerol (MAG and DAG) emulsifiers (E 471) are widely applied to regulate techno-functional properties in different food categories, for example, in dairy products. A method for the determination of MAG and DAG in aerosol whipping cream by high-performance thin-layer chromatography with fluorescence detection (HPTLC–FLD) after derivatization with primuline was developed. For sample preparation, aerosol whipping cream was mixed with ethanol, followed by the addition of water and liquid-liquid extraction with tert-butyl methyl ether. The sample extracts were analyzed by HPTLC–FLD on silica gel LiChrospher plates with n-pentane/n-hexane/diethyl ether (22.5:22.5:55, v/v/v) as mobile phase, when interfering matrix like cholesterol and triacylglycerols were successfully separated from the E 471 food additives. For quantitation, an emulsifier with known composition was used as calibration standard and the fluorescent MAG and DAG were scanned at 366/> 400 nm. Limits of detection and quantitation of 4 and 11 mg/100 g aerosol whipping cream were obtained for both monostearin and 1,2-distearin, respectively, and allowed the reliable quantitation of MAG and DAG from E 471 far below commonly applied emulsifier amounts. Recoveries from model aerosol whipping cream with 400 mg E 471/100 g were determined in a calibration range of 200–600 mg E 471/100 g sample and ranged between 86 and 105% with relative standard deviations below 7%. In aerosol whipping creams from the German market, E 471 amounts ranged between 384 and 610 mg/100 g.
Effect of relative humidity on the thin-layer chromatographic separation of E 472 emulsifiers
(2023) Schuster, Katharina; Oellig, Claudia
E 472 emulsifiers are organic acid esters of mono- and diacylglycerides. These emulsifiers are categorized into six subgroups (E 472a-f) based on the specific acid component, e.g., acetic acid, lactic acid, citric acid, tartaric acid, or mixtures of tartaric and acetic acid. The present study investigated the effect of relative humidity (RH) on the thin-layer chromatographic separation of four E 472 emulsifier subgroups, addressing practical concerns due to RH variations between seasons and within laboratories. Three RH-setting techniques affecting plate activity and chamber climate were assessed using saturated salt and aqueous sulfuric acid solutions. Aqueous sulfuric acid solutions for RH adjustment resulted in decreased hRF values, while no trends in hRF value changes were observed for saturated salt solutions. Unlike RH itself, the RH setting technique led to substantial changes in the chromatographic fingerprint. Thus, the choice of the RH setting method should be tailored to the specific analyte and analysis goal. Despite variations in chromatographic fingerprints between the three RH setting techniques, the fingerprint remained consistent within the same technique across the tested RH range.
Enzymatically formed fatty acid hydroperoxides determined through GC‐MS analysis of enantiomeric excess of hydroxy fatty acids after reduction and ibuprofen derivatization
(2025) Hotz, Lisa; Zartmann, Anne; Noack, Isabelle; Drees, Luca J.; Kuschow, Meret K.; Heinrich, Markus R.; Janssen, Hans‐Gerd; Hammann, Simon
Unsaturated fatty acids are susceptible to lipid oxidation through autoxidation, photooxygenation or enzymatical oxidation. A characteristic feature of enzyme‐catalyzed oxidation is the high regio‐ and stereospecificity of the formed fatty acid hydroperoxides. In this study, we present a method to quantify enzymatic lipid oxidation through reducing hydroperoxy fatty acid methyl esters to hydroxy fatty acid methyl esters and derivatizing them with enantiopure (S)‐ibuprofen, allowing the resolution of the enantiomer pairs as diastereomers via achiral GC‐MS. After application to enantiopure reference fatty acids, the approach was applied to autoxidation products of linoleic acid, and the expected racemic mixtures of the 9‐ and 13‐hydroperoxide derived hydroxy fatty acids were detected. On the other hand, when linoleic acid was oxidized using soybean lipoxygenase, clear enantiomeric excess of the (13S) enantiomer could be detected, proving the applicability of this method to detect enzymatic oxidation through enantiomeric excess.
GC/EI-MS method for the determination of phytosterols in vegetable oils
(2021) Schlag, Sarah; Huang, Yining; Vetter, Walter
Sterols are a highly complex group of lipophilic compounds present in the unsaponifiable matter of virtually all living organisms. In this study, we developed a novel gas chromatography with mass spectrometry selected ion monitoring (GC/MS-SIM) method for the comprehensive analysis of sterols after saponification and silylation. A new referencing system was introduced by means of a series of saturated fatty acid pyrrolidides (FAPs) as internal standards. Linked with retention time locking (RTL), the resulting FAP retention indices (RIFAP) of the sterols could be determined with high precision. The GC/MS-SIM method was based on the parallel measurement of 17 SIM ions in four time windows. This set included eight molecular ions and seven diagnostic fragment ions of silylated sterols as well as two abundant ions of FAPs. Altogether, twenty molecular ions of C27- to C31-sterols with 0–3 double bonds were included in the final method. Screening of four common vegetable oils (sunflower oil, hemp oil, rapeseed oil, and corn oil) enabled the detection of 30 different sterols and triterpenes most of which could be identified.
High-performance thin-layer chromatography for the detection of compositional changes in LACTEM emulsifiers during storage
(2025) Schuster, Katharina; Blankart, Max; Hinrichs, Jörg; Oellig, Claudia
Quality control of food emulsifiers, such as lactic acid esters of mono- and diacylglycerols (LACTEM), is crucial in the reproducible production of food products. The current study investigated compositional changes of LACTEM emulsifiers using high-performance thin-layer chromatography (HPTLC) during storage at 60 °C for 8 weeks. Ultraviolet (UV) and fluorescence images of the HPTLC silica gel F254s plates after primuline derivatization and densitometric data were analyzed to assess changes in the composition. Significant changes were observed for minor LACTEM components (< 10% relative intensity), specifically a decrease in higher-lactylated monoacylglycerols and an increase in triacylglycerols. Techno-functional properties, such as particle size distribution, apparent viscosity, overrun, foam firmness, drainage, and residual cream of aerosol whipping cream (0.8 g 100 g−1 LACTEM) were investigated. While emulsion stability was not affected, the foam firmness increased significantly, corresponding to a visibly more brittle foam. On the basis of these results, monitoring compositional changes in the food-manufacturing process is necessary to maintain constant food quality.
Hydroxylated transformation products obtained after UV irradiation of the current-use brominated flame retardants hexabromobenzene, pentabromotoluene, and pentabromoethylbenzene
(2023) Klimm, Alexandra; Vetter, Walter
Hexabromobenzene (HBB), pentabromotoluene (PBT), and pentabromoethylbenzene (PBEB) are current-use brominated flame retardants (cuBFRs) which have been repeatedly detected in environmental samples. Since information on hydroxylated transformation products (OH-TPs) was scarcely available, the three polybrominated compounds were UV irradiated for 10 min in benzotrifluoride. Fractionation on silica gel enabled the separate collection and identification of OH-TPs. For more insights, aliquots of the separated OH-TPs were UV irradiated for another 50 min (60 min total UV irradiation time). The present investigation of polar UV irradiation products of HBB, PBT, and PBEB was successful in each case. Altogether, eight bromophenols were detected in the case of HBB (three Br3-, four Br4-, and one Br5-isomer), and nine OH-TPs were observed in the case of PBT/PBEB (six Br3- and three Br4-congeners). In either case, Br➔OH exchange was more relevant than H➔OH exchange. Also, such exchange was most relevant in meta- and ortho-positions. As a further point, and in agreement with other studies, the transformation rate decreased with decreasing degree of bromination. UV irradiation of HBB additionally resulted in the formation of tri- and tetrabrominated dihydroxylated compounds (brominated diphenols) that were subsequently identified. These dihydroxylated transformation products were found to be more stable than OH-TPs.
Monitoring a coffee roasting process based on near‐infrared and raman spectroscopy coupled with chemometrics
(2025) Munyendo, Leah; Schuster, Katharina; Armbruster, Wolfgang; Babor, Majharulislam; Njoroge, Daniel; Zhang, Yanyan; von Wrochem, Almut; Schaum, Alexander; Hitzmann, Bernd
Roasting is a fundamental step in coffee processing, where complex reactions form chemical compounds related to the coffee flavor and its health‐beneficial effects. These reactions occur on various time scales depending on the roasting conditions. To monitor the process and ensure reproducibility, the study proposes simple and fast techniques based on spectroscopy. This work uses analytical tools based on near‐infrared (NIR) and Raman spectroscopy to monitor the coffee roasting process by predicting chemical changes in coffee beans during roasting. Green coffee beans of Robusta and Arabica species were roasted at 240°C for different roasting times. The spectra of the samples were taken using the spectrometers and modeled by the k‐nearest neighbor regression (KNR), partial least squares regression (PLSR), and multiple linear regression (MLR) to predict concentrations from the spectral data sets. For NIR spectra, all the models provided satisfactory results for the prediction of chlorogenic acid, trigonelline, and DPPH radical scavenging activity with low relative root mean square error of prediction (pRMSEP < 9.649%) and high coefficient of determination ( R 2 > 0.915). The predictions for ABTS radical scavenging activity were reasonably good. On the contrary, the models poorly predicted the caffeine and total phenolic content (TPC). Similarly, all the models based on the Raman spectra provided good prediction accuracies for monitoring the dynamics of chlorogenic acid, trigonelline, and DPPH radical scavenging activity (pRMSEP < 7.849% and R 2 > 0.944). The results for ABTS radical scavenging activity, caffeine, and TPC were similar to those of NIR spectra. These findings demonstrate the potential of Raman and NIR spectroscopy methods in tracking chemical changes in coffee during roasting. By doing so, it may be possible to control the quality of coffee in terms of its aroma, flavor, and roast level.
Monodopsis subterranea is a source of α‐tocomonoenol, and its concentration, in contrast to α‐tocopherol, is not affected by nitrogen depletion
(2024) Montoya‐Arroyo, Alexander; Muñoz‐González, Alejandra; Lehnert, Katja; Frick, Konstantin; Schmid‐Staiger, Ulrike; Vetter, Walter; Frank, Jan
α-Tomonoenols (αT1) are tocochromanols structurally related to tocopherols (T) and tocotrienols (T3), the bioactive members of the vitamin E family. However, limited evidence exists regarding the sources and biosynthesis of tocomonoenols. Nitrogen depletion increases the content of α-tocopherol (αT), the main vitamin E congener, in microalgae, but little is known regarding its effect on other tocochromanols, such as tocomonoenols and tocotrienols. We therefore quantified the concentrations of T, T1, and T3, in freeze-dried biomass from nitrogen-sufficient, and nitrogen-depleted Monodopsis subterranea (Eustigmatophyceae). The identities of isomers of αT1 were confirmed by LC–MS and GC–MS. αT was the predominant tocochromanol (82% of total tocochromanols). αT1 was present in higher quantities than the sum of all T3 (6% vs. 1% of total tocochromanols). 11′-αT1 was the main αT1 isomer. Nitrogen depletion increased αT, but not αT1 or T3 in M. subterranea. In conclusion, nitrogen depletion increased the content of αT, the biologically most active form of vitamin E, in M. subterranea without affecting αT1 and T3 and could potentially be used as a strategy to enhance its nutritional value but not to increase αT1 content, indicating that αT1 accumulation is independent of that of αT in microalgae.
NMR and GC/MS analysis of industrial chloroparaffin mixtures
(2020) Sprengel, Jannik; Vetter, Walter
Chlorinated paraffins (CPs) are high-volume chemicals used worldwide in various industries as plasticizers, lubricants, and flame retardants. CPs are produced by chlorination of alkane mixtures which leads to complex products of thousands of homologs and congeners. Classic mass spectrometric analyses of CPs allow determining carbon chain lengths and degrees of chlorination while information on the substitution patterns cannot be derived. Therefore, we performed different one- and two-dimensional nuclear magnetic resonance spectroscopy (NMR) experiments, elemental analysis (EA), and gas chromatography coupled with electron capture negative ion mass spectrometry (GC/ECNI-MS) for the analysis of ten technical CP products with 42%, 52%, and 70% chlorine content from four producers. Slight differences in chlorine content but varying chain length compositions were observed for similarly labeled products from different manufacturers. Two-dimensional heteronuclear spectral quantum coherence (HSQC) measurements helped to evaluate ten structural elements in the products and confirmed the presence of geminal chlorine atoms in primary and secondary carbons in products with 70% chlorine. The variation of signal groups increased with increasing chlorine content of the products. Two-dimensional heteronuclear multiple bond coherence (HMBC) analysis of one sample and GC/ECNI-MS measurements indicated the presence of impurities (e.g., C9-CPs, iso-alkanes) in different technical CP products. These methods could in future allow for better distinction of CP mixtures, and an improved trace-back of environmental CPs to the source, based on specific structural features. Additionally, further structural characterization could help in the development of more accurate analysis processes.
Pesticide residues in daily bee pollen samples (April–July) from an intensive agricultural region in Southern Germany
(2021) Friedle, Carolin; Wallner, Klaus; Rosenkranz, Peter; Martens, Dieter; Vetter, Walter
Insect-pollinated plants are essential for honey bees to feed their brood. In agricultural landscapes, honey bees and other pollinators are often exposed to pesticides used for cultivation. In order to gain more insight into the fluctuation of pesticide loads, 102 daily pollen samples were collected between April and July 2018 in a fruit-growing area in Southern Germany. Samples were analyzed with respect to more than 260 pesticides using a multi-residue pesticide analysis method. Almost 90% of the analyzed pollen samples featured between one and thirteen different pesticides. In total, 29 pesticides were detected at maximum concentrations of up to 4500 ng/g pollen. Maximum residual concentrations of most pesticides were observed during April and the first half of May, as well as during the second half of June. In most cases, serial data of pesticide residuals were detected for approximately 10 subsequent days with two or three maximum values, which were several folds higher than concentrations on the days before and thereafter. The pollen hazard quotient (PHQ) was calculated to estimate the risk of the detected pesticides to honey bees and wild pollinators.
Potentially beneficial effects on healthy aging by supplementation of the EPA-rich microalgae phaeodactylum tricornutum or its supernatant - a randomized controlled pilot trial in elderly individuals
(2022) Stiefvatter, Lena; Frick, Konstantin; Lehnert, Katja; Vetter, Walter; Montoya-Arroyo, Alexander; Frank, Jan; Schmid-Staiger, Ulrike; Bischoff, Stephan C.
Dietary supplements that promote healthy aging are mostly warranted in an aging society. Because of age-related risks, anti-inflammatory and anti-oxidative agents such as microalgae are potential candidates for intervention. In a randomized controlled trial, we tested Phaeodactylum tricornutum (PT), a microalgae rich in eicosapentaenoic acid (EPA), carotenoids, vitamins, and β-glucans, cultured in bioreactors. In this pilot trial, 19 healthy elderly received supplements for two weeks based on either the whole PT (A), the β-1,3-glucan-rich PT supernatant (SupB), the combination thereof (A+SupB), or a Comparator product (Comp). The primary outcome variable plasma interleukin-6 was reduced after treatment with A+SupB compared to the Comp group (p = 0.04). The mobility parameters 5 s sit-to-stand test (p = 0.04 in the A group) and by trend gait speed (p = 0.08 in the A+SupB diet) were improved compared to Comp. No treatment effects were observed for fatty acids, compared to Comp but omega-6 to -3 fatty acid ratio (p = 0.006) and arachidonic acid/EPA ratio (p = 0.006) were reduced within group A+SupB. Further, the SupB study product reduced faecal zonulin (p = 0.03) compared to the Comp. The data revealed an anti-inflammatory and potentially anti-oxidative effect of particular PT preparations, suggesting that they might be suitable for effects in healthy elderly.
Stable isotope analysis confirms substantial changes in the fatty acid composition of bacteria treated with antimicrobial random peptide mixtures (RPMs)
(2022) Wiedmaier-Czerny, Nina; Schroth, Dorothee; Krauß, Stephanie; Topman-Rakover, Shiri; Brill, Aya; Burdman, Saul; Hayouka, Zvi; Vetter, Walter
Resistance of plant-pathogenic bacteria to classic antibiotics has prompted the search for suitable alternative antimicrobial substances. One promising strategy could be the use of purposely synthesized random peptide mixtures (RPMs). Six plant-pathogenic bacteria were cultivated and treated with two RPMs previously found to show antimicrobial activity mainly by bacterial membrane disruption. Here, we show that bacteria treated with RPMs showed partly remarkable changes in the fatty acid pattern while those unaffected did not. Quantitative changes could be verified by compound specific isotope analysis of δ 13 C values (‰). This technique was employed due to the characteristic feature of stronger bonds between heavier isotopes in (bio)chemical reactions. As a proof of concept, the increase in abundance of a fatty acid group after RPM treatment was accompanied with a decrease in the 13 C content and vice versa. We propose that our findings will help designing and synthesizing more selective antimicrobial peptides.
Valuable furan fatty acids in soybeans and soy products
(2020) Müller, Franziska; Hogg, Melanie; Vetter, Walter
Furan fatty acids (FuFAs) are valuable minor compounds in our food with excellent antioxidant properties. Naturally occurring FuFAs are characterised by a central furan moiety with one or two methyl groups in β-/β’-position of the heterocycle (monomethyl- or M-FuFAs and dimethyl- or D-FuFAs). Comparably high concentrations of D-/M-FuFAs were reported in soybeans, but soy is often consumed as a processed product, such as full-fat soy flour and flakes, soy drink, tofu and texturised soy protein (TSP). Due to the chemical lability of D-/M-FuFAs, e.g. in the presence of light or oxygen, a degradation during the processing is possible. For this purpose, freshly harvested soybeans (n = 4) and differently processed soybean products (n = 22) were analysed on FuFAs. Three FuFAs, i.e. 11-(3,4-dimethyl-5-pentylfuran-2-yl)-undecanoic acid (11D5), 9-(3,4-dimethyl-5-pentylfuran-2-yl)-nonanoic acid (9D5), and 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5), were identified and quantified in all fresh soybeans and most of the processed soy products (n = 20). A trend towards lower D-/M-FuFA contents in higher processed products was observable. Lower FuFA concentrations were usually accompanied with a decrease of the share of the less stable D-FuFAs (9D5, 11D5) in favour of the M-FuFA 9M5. Furthermore, one or two 3,4-nonmethylated furan fatty acids (N-FuFAs), i.e. 8-(5-hexylfuran-2-yl)-octanoic acid (8F6) and partly 7-(5-heptylfuran-2-yl)-heptanoic acid (7F7), were detected in all processed products, but not in the freshly harvested soybeans. Our results indicate that D-/M-/N-FuFAs may serve as suitable markers for both, careful manufacturing processes and adequate storage conditions of soy products.

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