Flavour and Fragrance Journal最新文献

A novel automated flow-cell coupled dynamic solid-phase microextraction (SPME) method was developed to study the emission of volatile fragrance compounds from fabric samples in a microchamber. Calibration curves were developed with the liquid-inner tube diffusion-film-emission (LIFE) vial technique to quantify the gas-phase concentration of nine significant volatile fragrance compounds. The linearity range for the various volatile fragrance compounds ranged from 0.001 to 37.9 mg/m³. The limit of quantitation (LOQ) for each fragrance compound was determined as ~3.6–12.1 μg/m³. Using this method, we obtained comprehensive emission curves of target volatiles to quantify the volatile emission profiles of fabric samples. Compared with traditional chamber test method procedures, this work provides a novel and automated method to allow the online monitoring of the emission of various volatiles from multiple samples in one experiment. The repeatability and sensitivity of the method are comparable to or better than existing offline techniques.

Studies have shown that olfactory experience during breastfeeding plays an important role in the later development of certain food preferences in life. Thus, the aim of this study was to predict partitioning of odorous terpenes and terpenoids into breast milk from a predictive QSAR model for drug transfer. A large heterogenous data set based on drugs and their active metabolites that were used to build a QSAR was collected from the literature. Due to the vast structural diversity of these compounds and possibly different mechanisms involved in M/P partitioning, a non-linear artificial neural network (ANN) model was used to develop a predictive QSAR model. The value of the correlation coefficient of predicted versus experimentally measured M/P values for the final model (14-2-1) was high (R = .82). The descriptors selected in the final model (14-2-1) belong to 3 main categories: (a) solubility/permeability descriptors (dipole moment, polar surface area, aromatic ring count and hydroxyl group count), (b) reactivity descriptors (i.e. HOMO energy) and (c) shape descriptors (different ring size counts, counts of methyl groups and molecular depth). Results of this study predict that many volatile terpenes from the essential oils are transferred into breast milk selectively. The highest M/P values (>3.5) were predicted for β-caryophyllene, aromadendrene, alloaromadendrene, and 1,4- and 1,8-cineole, high values for carvacrol (M/P = 3.2), eugenol (M/P = 3.0) and thymol (M/P = 3.6), and moderate values for α-pinene (M/P = 2.3) and low values (M/P = 0.4) for phellandrene and limonene. Our model helps to explain and expand on the current knowledge of volatile compounds in breast milk by predicting that a variety of volatile terpenoids can be found in breast milk.

This research aimed to evaluate the combined effects of chemical, biological and organic fertilizers on several features of Satureja khuzistanica. As an aromatic plant with medicinal properties, endemic to Iran, S. khuzistanica was studied for essential oil (EO%) and composition. Spanning for two growing seasons (2017–2019), the experiments involved 13 nutritional treatments, ie, (a) control (C), (b) nitrogen, phosphorus and potassium (NPK; 50-25-25 Kg ha⁻¹), (c) cattle manure (CM₃₀; 30 ton ha⁻¹), (d) CM₆₀ (60 ton ha⁻¹), (e) CM₃₀ + NPK, (f) CM₆₀ + NPK, (g) vermicompost (V₅, 5 ton ha⁻¹), (h) V₅ + NPK, (i) Glomus mosseae (GM), (j) Glomus Intra (GI), (k) sulphur (S₀; 0 Kg ha⁻¹) + thiobacillus (T), (l) S₂₅₀ + T (sulphur: 250 Kg ha⁻¹, ) and (m) V₅ + T. At full flowering stage, samples were taken from aerial segments of plants in all treatment groups. After shade-drying, the samples were hydro-distillated to obtain essential oil (EO) and were then evaluated by gas chromatography–mass spectrometry (GC–MS). The interaction between year and fertilizer, as two treatments, had a significant effect (P ≤ 0.01) on the oil percentage, oil constituents and essential oil yield (EO.Y) of S. khuzistanica. GM and S₀ + T caused the highest oil percentage in the first (3.7%) and second year (3.9%), respectively. V₅ + NPK and V₅ + T resulted in a substantial rise in EO.Y in the first (30.4 kg ha⁻¹) and second year (64.3 kg ha⁻¹), respectively. Carvacrol was highest in the first (92.1%) and second year (95.2%), as a result of using V₅ + T and NPK treatments, respectively. Biological and vermicompost fertilizers not only improved the amount of EO but also enhanced its quality and aroma, as reflected in the constituents of the EO. The GI treatment and the V₅ + NPK treatment led to high amounts of K in the branches. Meanwhile, high S contents were measured in the branches in response to the V₅ and the S₂₅₀ + T treatments. These findings suggested that biofertilizers and organic fertilizers can benefit the cultivation of S. khuzistanica because, when combined together, they can enhance the percentage and phenolic compounds in the EO.

The effect of lipid level and reaction temperature and time on the heated cysteine-xylose reaction to form meaty flavours was investigated. The presence of 1% or 2% methyl linoleate inhibited the formation of volatile sulfur-containing compounds and heterocyclic compounds via the Maillard reaction, that is Maillard compounds. However, the former was better because of the moderate inhibition and more compounds generated from the lipid-Maillard interaction, that is lipid-Maillard compounds. Partial least squares-discriminant analysis suggested the lipid-Maillard compounds were the main markers during varying dosage of methyl linoleate, reaction temperature (100–140°C) and reaction time (30–180 min). Lower temperatures increased formation of the Maillard compounds (eg, 2-furfurylthiol) or lipid-Maillard compounds (eg, 2-pentylpyridine) with reaction time. However, high temperatures caused their amounts changed in a curve or irregularly due to the complications from the Maillard and lipid oxidization reactions. By comparing time-courses of the levels of cysteine and Cys-Amadori compounds, and 294 and 420 nm UV absorbance values in the reaction systems under 120°C with or without 2% methyl linoleate, it was revealed that the underlying lipid effect mechanism was to initially inhibit and later attend the Maillard reaction, leading to less formation of the Maillard compounds and generation of the lipid-Maillard compounds.

The study aims to develop wash-resistant antibacterial cotton fabrics without using synthetic chemicals. Therefore, natural active agents of thyme, thymol and carvacrol were selected. The inclusion complexes were formed with β-cyclodextrin using kneading method which is a simple and reproducible method for the encapsulation with high production yield. Differential scanning calorimeter analysis showed that 1:1 and 1:2 β-CD: Guest Molecule (M:M) for thymol and carvacrol from different ratios studied has the highest complexation degree as 50% and 100%, respectively. It is also revealed that the volatile agents are retained and showed better thermal stability as a result of complexation. Carvacrol inclusion complexes were found relatively more stable (Zeta potential: −28.2 mV) than thymol complexes with smaller particle sizes (204.9 nm). Chemical structures of the inclusion complexes were revealed with Fourier transform-infrared spectroscopy and nuclear magnetic resonance analyses. The optimum formulations for each active agent were applied to cotton fabrics as per the impregnation method and the capsule treated fabrics were washed 1, 10 and 20 times. The images exhibited the presence of inclusion complexes on the fabrics after 20 washing cycles. Although the antibacterial efficacy of fabrics decreased with increasing washing, the fabrics showed the antibacterial effect after 20 washes against Klebsiella pneumoniae and Staphylococcus aureus. This study showed that the developed products can be an alternative to the other products in the market as the long-lasting fragrant natural antibacterial.

(−)-Menthol is one of the most popular aroma compounds worldwide. While in the past mostly extracted from mint plants, today (−)-menthol synthesis from other raw materials is becoming more relevant. Common starting materials for menthol synthesis are m-cresol, citral and myrcene, but also substrates like menthone, mono- and bicyclic terpenes and terpenoids have been used for this purpose in the past. As for many applications (−)-menthol of high purity is required, asymmetric syntheses and enantiomeric resolution of obtained raw products are applied for menthol production. This review gives an overview on the most important synthetic menthol production processes of the companies Symrise, Takasago and BASF and relevant literature in the field of menthol synthesis with a focus on the last 20 years.

Lipoxygenases (LOX) catalyse allylic oxidations and epoxidations of a co-substrate in the presence of an unsaturated fatty acid containing a 1,4-pentadiene moiety. One- and two-step enzyme assays were established to verify the role or involvement of LOX in such co-oxidations. It was shown that LOX is only involved in the formation of reactive hydroperoxides, but not in the oxidation of a co-substrate, assuming a mechanism involving free peroxy radicals for the latter. Ten mono- and sesquiterpenes were used as co-substrates and the resulting products were analysed by mass spectrometry. A semi-preparative approach was developed using (+)-valencene as an example, and the resulting products were isolated by preparative GC and their structures elucidated by NMR spectroscopy.

Ocimum tenuiflorum has a characteristic spicy, sweet and green aroma and has been used as a medicinal herb for various diseases in Ayurveda systems. This study aimed to investigate the aroma-impact components and antioxidant activity of the essential oil from O. tenuiflorum leaves, grown in Sri Lanka, which was obtained by hydrodistillation. The volatile compounds in the essential oil were measured by gas chromatograph–mass spectrometry. The major components were caryophyllene oxide (23.8%), β-caryophyllene (18.2%), germacrene D (14.6%), α-copaene (14.4%) and eugenol (10.0%). The characteristics of aroma components of the essential oil were determined by gas chromatography–olfactometry and aroma extract dilution analysis. Eleven compounds, including eugenol, rotundone, β-damascenone, linalool and geraniol, were identified as aroma-impact components of the essential oil. Among them, the dominant components were identified as eugenol, rotundone, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, coumarin and vanillin, which were quite different from the results of chemical analysis. The antioxidant activity of the essential oil was evaluated by 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity, 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) radical cation scavenging activity and β-carotene bleaching assays. All results showed that the essential oil exhibited strong antioxidant activity, and antioxidant-active components were proved to be eugenol by column chromatography. Furthermore, the presence of new antioxidant compounds other than eugenol, which had previously been reported, was also revealed. Therefore, the essential oil from O. tenuiflorum leaves has great potential as a resource in the cosmetics and food industries.

Jben is a highly popular soft white cheese consumed in Morocco for its nutritional and health benefits. The aroma and aroma-active compounds of salted and unsalted Jben were investigated in this study. Aroma compounds were isolated by the purge and trap extraction (PTE) method and analysed by aroma extract dilution analysis (AEDA) and gas chromatography–mass spectrometry-olfactometry (GC–MS-O). A total of 36 aroma compounds were characterized Jben samples, among them 30 and 32 compounds were detected in the salted Jben (260.88 mg/kg) and unsalted Jben (230.04 mg/kg) samples respectively. The alcohols, followed by acids and esters, were the most dominant aroma compounds in both samples. A total of 22 (salted Jben) and 25 (unsalted Jben) aroma-active compounds were detected in the samples using GC–MS-O. Based on the flavour dilution (FD) factor, the most potent aroma-active compounds were ethyl caproate (FD = 2048, OAV = 2306, overripe fruit and pineapple odours), isoamyl acetate (FD = 2048, OAV = 2491, apple odour), hexyl acetate (FD = 1024, OAV = 1355, green odour), and isoamyl butyrate (FD = 1024, OAV = 932, green-fruity odour) for the salted Jben sample and ethyl caproate (FD = 2048, OAV = 2388) and isoamyl acetate (FD = 1024, OAV = 880) for the unsalted Jben sample. The odour activity values (OAVs) ranged from 1 to 2491. The lowest OAVs represent the low aromatic active compounds (FD ≤ 32). The GC–MS-O results were also consistent with the results of sensory analysis of the Jben samples.

Carvol and carvone are oxidation products from the natural product limonene. They are important raw materials for the flavours and fragrances industry and also act as pharmaceutical active ingredients. Orange waste peels possibly represent an attractive source for limonene, but studies on valorizing orange peel wastes are rare. In this study, we report a new enzymatic cascade system for the in-situ conversion of limonene from orange peel into valued-added carvol and carvone. The use of deep eutectic solvents (DES) allows for efficient in-situ extraction of limonene from waste orange peels. We propose a dual function use of DES as solvent for the extraction and the biocatalytic oxidation of limonene as well as cosubstrate to promote the oxidation reaction. Using ChCl-Pro-H₂O DES for the extraction of limonene from waste orange peels, approximately 17 milligrams of limonene per gram of orange peel was achieved at 40°C for 24 h. Then, with ChCl-Pro-H₂O DES as the extractant and reaction medium, a cascade reaction system of choline oxidase (ChOx) and unspecific peroxygenase (UPO) was established to catalyse the conversion of limonene into carvol and carvone. The concentration of the final products was up to about 1.6 mmol L⁻¹. This study showed a biocatalytic transformation pathway and provides technical support for the high-value utilization of waste in orange peel.