Abstract:Mass spectrometry (MS) has been intensively used in the field of flavor and fragrance since its beginning in the 1950s, and it remains an essential technique for current and future research in this field. After a short historical section on the introduction and development of MS at Firmenich, this work reviews the main applications of MS-based techniques published by Firmenich researchers over the past 5 years. It exemplifies the use of gas chromatography (GC)-MS for the discovery of new odorant - hence volati… Show more
“…It should be mediated by an enzyme, since only l-lactyl-l-amino acids were found in cheese [20]. In our work, the synthetic product Lac-Glu (8), synthesized from l-lactic acid and l-glutamic acid ester [19], contained a small amount of a minor diastereoisomer, likely d-Lac-l-Glu. We verified that this diastereoisomer was not present in soy sauce.…”
mentioning
confidence: 90%
“…The synthesis of Suc-Glu (6) and its spectral data were described by Frerot and Benzi [12]. The synthesis of l-Lac-Glu (8) and l-Lac-Leu (20), and their spectral data were described by Frerot and Escher [19].…”
Section: Experimental Partmentioning
confidence: 99%
“…The two products 1 and 5, as well as N-succinoylglutamic acid (6) [12], could not be identified by the first full-scan experiments using the ion-trap MS, but were detected by the TOF-MS. Their occurrence in soy sauce was firmly established by determining the MS transition ratios in the selected reaction monitoring mode (SRM), using the triple quadrupole mass spectrometer. The ratio of the peak area corresponding to two transitions was determined at different concentrations for the synthetic products.…”
mentioning
confidence: 99%
“…Chemically synthesized succinoyl amino acids such as N-succinyl glutamate were also found to be taste-active [12], but were never reported to occur in foods.…”
mentioning
confidence: 99%
“…g-Glutamyl dipeptides are ubiquitous compounds in foods [8] [9] [16] [17]. Lactoyl amino acids were first discovered by Firmenich during the analysis of Parmesan [18] and patented for their taste properties [19]. A thorough study of Parmesan and other Italian cheeses revealed that pyroglutamyl dipeptides, lactyl amino acids, and g-glutamyl dipeptides accumulated during ripening, probably because they could no longer be recognized by hydrolytic enzymes [20].…”
Glutamic acid is an abundant amino acid that lends a characteristic umami taste to foods. In fermented foods, glutamic acid can be found as a free amino acid formed by proteolysis or as a non-proteolytic derivative formed by microorganisms. The aim of the present study was to identify different structures of glutamic acid derivatives in a typical fermented protein-based food product, soy sauce. An acidic fraction was prepared with anion-exchange solid-phase extraction (SPE) and analyzed by UPLC/MS/MS and UPLC/TOF-MS. α-Glutamyl, γ-glutamyl, and pyroglutamyl dipeptides, as well as lactoyl amino acids, were identified in the acidic fraction of soy sauce. They were chemically synthesized for confirmation of their occurrence and quantified in the selected reaction monitoring (SRM) mode. Pyroglutamyl dipeptides accounted for 770 mg/kg of soy sauce, followed by lactoyl amino acids (135 mg/kg) and γ-glutamyl dipeptides (70 mg/kg). In addition, N-succinoylglutamic acid was identified for the first time in food as a minor compound in soy sauce (5 mg/kg).
“…It should be mediated by an enzyme, since only l-lactyl-l-amino acids were found in cheese [20]. In our work, the synthetic product Lac-Glu (8), synthesized from l-lactic acid and l-glutamic acid ester [19], contained a small amount of a minor diastereoisomer, likely d-Lac-l-Glu. We verified that this diastereoisomer was not present in soy sauce.…”
mentioning
confidence: 90%
“…The synthesis of Suc-Glu (6) and its spectral data were described by Frerot and Benzi [12]. The synthesis of l-Lac-Glu (8) and l-Lac-Leu (20), and their spectral data were described by Frerot and Escher [19].…”
Section: Experimental Partmentioning
confidence: 99%
“…The two products 1 and 5, as well as N-succinoylglutamic acid (6) [12], could not be identified by the first full-scan experiments using the ion-trap MS, but were detected by the TOF-MS. Their occurrence in soy sauce was firmly established by determining the MS transition ratios in the selected reaction monitoring mode (SRM), using the triple quadrupole mass spectrometer. The ratio of the peak area corresponding to two transitions was determined at different concentrations for the synthetic products.…”
mentioning
confidence: 99%
“…Chemically synthesized succinoyl amino acids such as N-succinyl glutamate were also found to be taste-active [12], but were never reported to occur in foods.…”
mentioning
confidence: 99%
“…g-Glutamyl dipeptides are ubiquitous compounds in foods [8] [9] [16] [17]. Lactoyl amino acids were first discovered by Firmenich during the analysis of Parmesan [18] and patented for their taste properties [19]. A thorough study of Parmesan and other Italian cheeses revealed that pyroglutamyl dipeptides, lactyl amino acids, and g-glutamyl dipeptides accumulated during ripening, probably because they could no longer be recognized by hydrolytic enzymes [20].…”
Glutamic acid is an abundant amino acid that lends a characteristic umami taste to foods. In fermented foods, glutamic acid can be found as a free amino acid formed by proteolysis or as a non-proteolytic derivative formed by microorganisms. The aim of the present study was to identify different structures of glutamic acid derivatives in a typical fermented protein-based food product, soy sauce. An acidic fraction was prepared with anion-exchange solid-phase extraction (SPE) and analyzed by UPLC/MS/MS and UPLC/TOF-MS. α-Glutamyl, γ-glutamyl, and pyroglutamyl dipeptides, as well as lactoyl amino acids, were identified in the acidic fraction of soy sauce. They were chemically synthesized for confirmation of their occurrence and quantified in the selected reaction monitoring (SRM) mode. Pyroglutamyl dipeptides accounted for 770 mg/kg of soy sauce, followed by lactoyl amino acids (135 mg/kg) and γ-glutamyl dipeptides (70 mg/kg). In addition, N-succinoylglutamic acid was identified for the first time in food as a minor compound in soy sauce (5 mg/kg).
Perfumery has evolved from a handcraft activity, marking supreme aristocratic luxury in the Renaissance, to a global industry powering scent experiences for present‐day consumers through the use of a myriad of consumer packaged goods. This contribution reviews major breakthroughs in the field, including landmark fragrance ingredients, technological advances in scent delivery, and key innovations in consumer products which created the demand for scientific and technological advancements in the scent domain. These innovations are presented chronologically, relying solely on information drawn from public written sources, spanning a time period of 150 years (1870‐2020). We hope with this contribution to generate interest in the readership for this fascinating field, while celebrating 150 years of innovation for scented mass‐market products..
This study aims to resolve one of the longest-standing problems in mass spectrometry, which is how to accurately identify an organic substance from its mass spectrum when a spectrum of the suspected substance has not been analyzed contemporaneously on the same instrument. Part one of this two-part report describes how Rice−Ramsperger−Kassel−Marcus (RRKM) theory predicts that many branching ratios in replicate electron−ionization mass spectra will provide approximately linear correlations when analysis conditions change within or between instruments. Here, proof-of-concept general linear modeling is based on the 20 most abundant fragments in a database of 128 training spectra of cocaine collected over 6 months in an operational crime laboratory. The statistical validity of the approach is confirmed through both analysis of variance (ANOVA) of the regression models and assessment of the distributions of the residuals of the models. General linear modeling models typically explain more than 90% of the variance in normalized abundances. When the linear models from the training set are applied to 175 additional known positive cocaine spectra from more than 20 different laboratories, the linear models enabled ion abundances to be predicted with an accuracy of <2% relative to the base peak, even though the measured abundances vary by more than 30%. The same models were also applied to 716 known negative spectra, including the diastereomers of cocaine: allococaine, pseudococaine, and pseudoallococaine, and the residual errors were larger for the known negatives than for known positives. The second part of the manuscript describes how general linear regression modeling can serve as the basis for binary classification and reliable identification of cocaine from its diastereomers and all other known negatives.
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