Scent Production Research Articles

Isomerization of α-pinene oxide using Fe-supported catalysts: Selective synthesis of campholenic aldehyde

α-Pinene oxide, an oxygenated derivative of α-pinene, can be converted into various valuable substances useful as flavour, fragrance and pharmaceutical compounds. Campholenic aldehyde is one of the most desired products of α-pinene oxide isomerization being a valuable intermediate for the production of sandalwood-like fragrances. Iron modified zeolites Beta-75 and ZSM-5, mesoporous material MCM-41, silica and alumina were prepared by two methods (impregnation and solid-state ion exchange) and tested for selective preparation of campholenic aldehyde by isomerization of α-pinene oxide. The characterization of tested catalyst was carried out using scanning electron microscope analysis, nitrogen adsorption measurements, pyridine adsorption–desorption with FTIR, X-ray absorption spectroscopy measurements, XPS-analysis, 29Si MAS NMR and 27Al MAS NMR and X-ray diffraction. The isomerization of α-pinene oxide was carried out in toluene as a solvent at 70°C. The main properties influencing the activity and the selectivity are the acidic and structural properties of the tested catalysts. The highest selectivity of 66% was achieved at complete conversion of α-pinene oxide with Fe-MCM-41.

Coupled exposure to ingredients of cosmetic products: I. Fragrances

The use of cosmetics exposes consumers to mixtures of ingredients, many of which are contact allergens. Fragrances in particular are mostly used in combination; combinations of fragrances have been shown to enhance sensitization and elicitation. To examine the pattern of co-exposure to fragrances in different categories of cosmetics, addressing the 26 fragrances that need to be identified on the label according to the Cosmetics Directive 76/768/EEC amended by 2003/15/EC. A survey of products marketed in Germany, conducted in 2006-2009 by the Chemical and Veterinary Investigation Office in Karlsruhe, identified 4991 products with information on the presence of fragrances. The products were categorized according to Annex I to the Cosmetics Directive. The occurrence and co-occurrence of fragrances were analysed in tabular form and as social network diagrams. The median number of fragrances in products varied greatly between categories, ranging up to nine in perfumes. Limonene and linalool were the most commonly identified fragrances, often used together, but also with other fragrances. Thirty per cent of all products were not declared to contain any fragrances. For the first time, the pattern of co-exposure to fragrance ingredients in important categories of cosmetic products has been described. The observations illustrate and quantify the 'cocktail' of fragrance allergens that may facilitate sensitization.

Demographic Subgroups Report Differential Use of Fragranced Products.

Demographic Subgroups Report Differential Use of Fragranced Products.

Fragrance materials in asthma: a pilot study using a surrogate aerosol product

Objective: Many household products contain fragrances. Little is known about exposure to fragrances on human health, particularly within the airways. This study aimed to evaluate how common household fragrance products (i.e. air fresheners, cleaning products) affect people with asthma, who frequently report sensitivity to these products. Many of these products have volatile organic compounds or semi-volatile organic compounds. This study evaluated nine fragrance materials in an aerosol formulation to assess effects on airway physiology, airway inflammation and symptom perception in normal controls and those with asthma. Methods: The effects of fragrances were evaluated in people without asthma, people with mild asthma and people with moderate asthma in a four-way crossover placebo-controlled study. Subjects were exposed twice to a fragranced aerosol and twice to a placebo aerosol (15 and 30 min each). Subjects completed a questionnaire for 29 symptoms during and up to 3 h after each exposure scenario. Spirometry was performed prior to and 3 h post-exposure; sputum induction was conducted 3 h post-exposure. Results: Nasal symptoms showed the greatest frequency of response in all three subject groups, and moderate asthmatics reported the greatest symptom severity and symptom types. No significant differences were noted in physiology or cellular inflammation. Conclusion: A trend for increased symptoms was noted in moderate asthmatics, suggesting that asthma severity may play a factor in fragrance sensitivity.

Virus-induced gene silencing unravels multiple transcription factors involved in floral growth and development in Phalaenopsis orchids

Orchidaceae, one of the largest angiosperm families, has significant commercial value. Isolation of genes involved in orchid floral development and morphogenesis, scent production, and colouration will advance knowledge of orchid flower formation and facilitate breeding new varieties to increase the commercial value. With high-throughput virus-induced gene silencing (VIGS), this study identified five transcription factors involved in various aspects of flower morphogenesis in the orchid Phalaenopsis equestris. These genes are PeMADS1, PeMADS7, PeHB, PebHLH, and PeZIP. Silencing PeMADS1 and PebHLH resulted in reduced flower size together with a pelaloid column containing petal-like epidermal cells and alterations of epidermal cell arrangement in lip lateral lobes, respectively. Silencing PeMADS7, PeHB, and PeZIP alone resulted in abortion of the first three fully developed flower buds of an inflorescence, which indicates the roles of the genes in late flower development. Furthermore, double silencing PeMADS1 and PeMADS6, C- and B-class MADS-box genes, respectively, produced a combinatorial phenotype with two genes cloned in separate vectors. Both PeMADS1 and PeMADS6 are required to ensure the normal development of the lip and column as well as the cuticle formation on the floral epidermal cell surface. Thus, VIGS allows for unravelling the interaction between two classes of MADS transcription factors for dictating orchid floral morphogenesis.

Synthesis of 9‐Oxononanoic Acid, a Precursor for Biopolymers

Polymers based on renewable resources have become increasingly important. The natural functionalization of fats and oils enables an easy access to interesting monomeric building blocks, which in turn transform the derivative biopolymers into high-performance materials. Unfortunately, interesting building blocks of medium-chain length are difficult to obtain by traditional chemical means. Herein, a biotechnological pathway is established that could provide an environmentally suitable and sustainable alternative. A multiple enzyme two-step one-pot process efficiently catalyzed by a coupled 9S-lipoxygenase (St-LOX1, Solanum tuberosum) and 9/13-hydroperoxide lyase (Cm-9/13HPL, Cucumis melo) cascade reaction is proposed as a potential route for the conversion of linoleic acid into 9-oxononanoic acid, which is a precursor for biopolymers. Lipoxygenase catalyzes the insertion of oxygen into linoleic acid through a radical mechanism to give 9S-hydroperoxy-octadecadienoic acid (9S-HPODE) as a cascade intermediate, which is subsequently cleaved by the action of Cm-9/13HPL. This one-pot process afforded a yield of 73 % combined with high selectivity. The best reaction performance was achieved when lipoxygenase and hydroperoxide lyase were applied in a successive rather than a simultaneous manner. Green leaf volatiles, which are desired flavor and fragrance products, are formed as by-products in this reaction cascade. Furthermore, we have investigated the enantioselectivity of 9/13-HPLs, which exhibited a strong preference for 9S-HPODE over 9R-HPODE.

Lung function in fragrance industry employees

Production employees in the UK fragrance industry are exposed to large numbers of chemical substances and mixtures. There is a lack of published literature describing the effects of occupational respiratory exposure in this industry. To investigate whether occupational respiratory exposure to chemicals in the UK fragrance industry is linked to a statistically significant change in lung function as measured using spirometry. A multi-site cross-sectional study in which five UK companies took part, comprising an exposed group (fragrance production and associated functions) and a control group (non-exposed industry employees, e.g. office staff). Spirometric measurements (forced expiratory volume in 1 second, forced vital capacity and peak expiratory flow) were taken pre- and post-shift. Participants provided information on potential confounding factors (smoking, history of respiratory problems and body mass index). Post-shift measurements were compared between groups, using analysis of covariance to adjust for the baseline pre-shift measurements. A total of 112 subjects participated: 60 in the exposed group and 52 in control group (response rate 33 and 24%, respectively). Adjusted mean differences in post-shift spirometric measurements between exposed and control groups were not statistically significant. No significant effects were observed on the spirometric performance of the study population. This work is the first step in a novel area of research, and the industry would benefit from further such research.

Production of Flavours and Fragrances via Bioreduction of (4R)-(-)-Carvone and (1R)-(-)-Myrtenal by Non-Conventional Yeast Whole-Cells

As part of a program aiming at the selection of yeast strains which might be of interest as sources of natural flavours and fragrances, the bioreduction of (4R)-(−)-carvone and (1R)-(−)-myrtenal by whole-cells of non-conventional yeasts (NCYs) belonging to the genera Candida, Cryptococcus, Debaryomyces, Hanseniaspora, Kazachstania, Kluyveromyces, Lindnera, Nakaseomyces, Vanderwaltozyma and Wickerhamomyces was studied. Volatiles produced were sampled by means of headspace solid-phase microextraction (SPME) and the compounds were analysed and identified by gas chromatography–mass spectroscopy (GC-MS). Yields (expressed as % of biotransformation) varied in dependence of the strain. The reduction of both (4R)-(−)-carvone and (1R)-(−)-myrtenal were catalyzed by some ene-reductases (ERs) and/or carbonyl reductases (CRs), which determined the formation of (1R,4R)-dihydrocarvone and (1R)-myrtenol respectively, as main flavouring products. The potential of NCYs as novel whole-cell biocatalysts for selective biotransformation of electron-poor alkenes for producing flavours and fragrances of industrial interest is discussed.

Structure of the Osmophore and Labellum Micromorphology in the Sexually Deceptive Orchids Ophrys Bombyliflora and Ophrys tenthredinifera (Orchidaceae)

Premise of research. The insect-like flowers of the Ophrys orchids are adapted to sexually deceptive pollination through pseudocopulation, providing chemical, visual, and tactile stimuli for male insects. Although the chemical composition of the odor bouquet of several species has long been identified, the precise site of fragrance production in the labellum remains unknown for most species, and little attention has been given to the visual and tactile signals provided by the labellum for pollinators. Here, the occurrence of an osmophore is investigated and the labellum micromorphology is characterized in detail for Ophrys bombyliflora and Ophrys tenthredinifera, two closely related species pollinated by Eucera bees.Methodology. Labella of flowers before and at anthesis were studied with scanning electron microscopy, light microscopy, and histochemistry.Pivotal results. The labellum of O. bombyliflora presents a distinctive hidden apical appendix that forms a concavity with a multicellular protuberance an...

Floral biology and histochemical analysis of Vanilla edwallii Hoehne (Orchidaceae: Vanilloideae): an orchid pollinated by Epicharis (Apidae: Centridini)

AbstractThe genus Vanilla is the most diverse in Vanilloideae, with ca 90 species distributed among tropical regions. Despite their economic importance, studies on pollination of Vanilla are very scarce and data on pollinators of species endemic to Brazil are lacking. Based on fieldwork and laboratory investigations, the floral biology of V. edwallii was studied. The pollinators and pollination process were recorded at the Serra do Japi reserve, state of São Paulo, southeastern Brazil, and the presence of floral reward was also investigated. Vanilla edwallii blooms in summer. The lateral inflorescences produce up to four pale green flowers. The white labellum is united to the base of the column forming a mentum. In the studied population V. edwallii is pollinated by Epicharis (Hoplepicharis) affinis, where the males exhibit a territorial behavior, defending flowers from other possible flower visitors. The pollen is deposited on the scutellum of bees when they abandon the flower. The mentum region is dry, suggesting no nectar production. The only secretory structures are osmophores dispersed on the inner surface of the lip responsible for production of a sweet fragrance, which together with color and morphology of flowers is related to bee attraction. The labellum is rich in mucilaginous cells, while the mucilaginous substance is retained inside the cells. The histochemical analysis also detected the presence of phenolic compounds and starch concentrated mainly at the adaxial surface of the lip and around the vascular bundles.

Tight Genetic Linkage of Prezygotic Barrier Loci Creates a Multifunctional Speciation Island in Petunia

Most flowering plants depend on animal vectors for pollination and seed dispersal. Differential pollinator preferences lead to premating isolation and thus reduced gene flow between interbreeding plant populations. Sets of floral traits, adapted to attract specific pollinator guilds, are called pollination syndromes. Shifts in pollination syndromes have occurred surprisingly frequently, considering that they must involve coordinated changes in multiple genes affecting multiple floral traits. Although the identification of individual genes specifying single pollination syndrome traits is in progress in many species, little is known about the genetic architecture of coadapted pollination syndrome traits and how they are embedded within the genome. Here we describe the tight genetic linkage of loci specifying five major pollination syndrome traits in the genus Petunia: visible color, UV absorption, floral scent production, pistil length, and stamen length. Comparison with other Solanaceae indicates that, in P. exserta and P. axillaris, loci specifying these floral traits have specifically become clustered into a multifunctional "speciation island". Such an arrangement promotes linkage disequilibrium and avoids the dissolution of pollination syndromes by recombination. We suggest that tight genetic linkage provides a mechanism for rapid switches between distinct pollination syndromes in response to changes in pollinator availabilities.

Scent glands in legume flowers

Scent glands, or osmophores, are predominantly floral secretory structures that secrete volatile substances during anthesis, and therefore act in interactions with pollinators. The Leguminosae family, despite being the third largest angiosperm family, with a wide geographical distribution and diversity of habits, morphology and pollinators, has been ignored with respect to these glands. Thus, we localised and characterised the sites of fragrance production and release in flowers of legumes, in which scent plays an important role in pollination, and also tested whether there are relationships between the structure of the scent gland and the pollinator habit: diurnal or nocturnal. Flowers in pre-anthesis and anthesis of 12 legume species were collected and analysed using immersion in neutral red, olfactory tests and anatomical studies (light and scanning electron microscopy). The main production site of floral scent is the perianth, especially the petals. The scent glands are distributed in a restricted way in Caesalpinia pulcherrima, Anadenanthera peregrina, Inga edulis and Parkia pendula, constituting mesophilic osmophores, and in a diffuse way in Bauhinia rufa, Hymenaea courbaril, Erythrostemon gilliesii, Poincianella pluviosa, Pterodon pubescens, Platycyamus regnellii, Mucuna urens and Tipuana tipu. The glands are comprised of cells of the epidermis and mesophyll that secrete mainly terpenes, nitrogen compounds and phenols. Relationships between the presence of osmophores and type of anthesis (diurnal and nocturnal) and the pollinator were not found. Our data on scent glands in Leguminosae are original and detail the type of diffuse release, which has been very poorly studied.

Metabolome profiling of floral scent production in Petunia axillaris

Emission of floral scent benzenoid/phenylpropanoid compounds in Petunia axillaris increases significantly at night, a change that is primarily determined by the endogenous concentration of these compounds in the corolla. Among wild type P. axillaris plants, there are lines that emit different amounts of scent. To understand how the nocturnal rhythm of floral scent concentrations is controlled, the concentration profiles of metabolites in the scent biosynthetic pathway in two lines of P. axillaris, a strongly scented line and a weakly scented line, are reported. In the strongly scented line, the concentration of a series of compounds from glucose-6-phosphate (G6P) to the scent compounds changed synchronously. In the weakly scented lines, the concentrations of some metabolites including 6-phosphogluconate (6PG) and downstream metabolites of shikimic acid were remarkably lower, suggesting a reduction in metabolism of G6P to 6PG and the metabolism of shikimic acid in the weakly scented line. Nocturnal increases in the concentrations of sucrose, fructose, and glucose were not found in strongly scented line. Nocturnal increases in concentrations of S-adenosylhomocysteine (SAH) and methionine and reductions in the concentrations of S-adenosylmethionine (SAM), a methylation donor to benzenoid-skeletons, were observed only in strongly scented line. It is concluded that the biosynthetic regulation of each step from G6P to the volatile scent benzenoids is performed by, at least in part, concentrations of substrates, and the regulation also affects concentrations of SAM cycle compounds.

Bacterial biotransformation of phenylpropanoid compounds for producing flavor and fragrance compounds

Phenylpropanoids are common aromatic compounds synthesized by plants that are often used as starting compounds for the production of various flavor and fragrance compounds. The use of bacterial metabolism as a means to produce valueadded compounds from natural resources has been given much attention as an alternative method to replace conventional chemical syntheses. This review describes bacterial metabolisms of the phenylpropanoid compounds trans-anethole, isoeugenol, and isosafrole to better understand efficient production of natural fragrance and other value-added compounds.

ChemInform Abstract: Palladium‐Catalysed Coupling Reactions

AbstractReview: 116 refs.

Standardization of Gyrinops Walla Gaertn. (Thymalaeaceae): Newly Discovered, Fragrant Industrial Potential, Endemic Plant from Sri Lanka

Gyrinops walla Gaertner. (Thymelaeaceae), is an endemic resinous plant used in traditional medicine, perfume production, incenses, aroma therapy and cosmetic industry. Due to the high economic value, large-scale smuggling of G. walla from Sri Lanka has been practiced for a long time. Therefore, present study was undertaken to study the phytochemical and volatile oil components of G. walla. Phytochemical analysis of leaf, bark and stems were performed according to the methods described in WHO guidelines. Aerial parts were hydro-distilled in a Clevenger-type apparatus for 8 h. Oil was analyzed using GC-MS and identification of components of volatile oils was carried out based on retention indices and fragmentation patterns of the mass spectra. Phytochemical screening of leaf, stem and bark crude extracts of G. walla revealed the presence of tannins, saponins, steroid glycosides, flavonoids and alkaloids in all three parts tested. Thin layer chromatographic profiles observed under UV light at 366 nm exhibited higher number of spots in CH2Cl2 extracts for all three parts followed by hexane and methanol fractions, respectively. Sky blue spot present in all three fractions [hexane (Rf = 0.83), dichloromethane (Rf = 0.66) and methanol (Rf = 0.77)] of stem extracts was characteristic to the stem extract. The yield of the essential oils obtained from stem parts of G. walla was 0.20 ± 0.01%. Major constituents, which exist more than 1% in heartwood of G. walla oil, were gamma-selinene (72.49%), 3-Phenyl-2-butanone (2.04%), 3-pentanone (2.02%), beta-patchoulene (1.37%) respectively. Present study reports the presence of preliminary phytochemicals, TLC finger prints and GC-MS analysis of essential oil of G.walla for the first time in Sri Lanka. Presence of high content of γ-selinene and β-patchoulene (73.86%) indicates potential for commercial production of world class perfume and other scented products.

Tipo de explante e diferentes concentrações de sais em meio de cultura MS no estabelecimento in vitro de Aniba canelilla

The peel - precious ( Aniba canelilla ) is a plant species native to the Amazon region , with economic potential in silvicultural terms , the production of perfumes and cosmetics . However , one limitation to the domestication of the species is the absence of propagation methods . The objective of this study was to evaluate the effect of explant type and different salt concentrations of MS medium in their establishment in vitro . Shoot tips ( 1.5 cm ) and nodal segments were used with two gems, isolated from bark - precious seedlings maintained in the greenhouse . The treatments consisted of two types of explants and six concentrations of salts in MS medium plus 15 or 30 g L- 1 sucrose and disinfectants . It was found that the nodal segment is less sensitive to treatments performed disinfestation and decontamination showed higher successful in survival and in vitro establishment of shell - precious.

Screening of a selection of commercially available homogeneous Ru-catalysts in valuable olefin metathesis transformations

A library of thirteen different commercially available Ru-based catalysts was evaluated in valuable metathesis reactions for the production of fragrance and bioactive molecule precursors. Rigorous library screening clearly illustrated the different catalytic behaviour of the catalyst selection and highlighted its significant advantage to provide efficiency in specific metathesis applications. Interestingly, this strategy offered substantial improvement over the state of the art, with the efficient synthesis of the macrocyclic Exaltolide 2 at low catalyst loading and dilution conditions.

The R2R3-MYB-like regulatory factor EOBI, acting downstream of EOBII, regulates scent production by activating ODO1 and structural scent-related genes in petunia.

Flower scent is a highly dynamic trait, under developmental, spatial, and diurnal regulation. The mechanism governing scent production is only beginning to be unraveled. In petunia (Petunia hybrida), EMISSION OF BENZENOIDS II (EOBII) controls transcription of both the shikimate pathway-regulating MYB factor ODORANT1 (ODO1) and phenylpropanoid scent-related structural genes. A promoter-activation screen identified an R2R3-MYB-like regulatory factor of phenylpropanoid volatile biosynthesis acting downstream of EOBII, designated EOBI. EOBI silencing led to downregulation of ODO1 and numerous structural scent-related genes from both the shikimate and phenylpropanoid pathways. The ability of EOBI to directly activate ODO1, as revealed by electrophoretic mobility shift assay and yeast one-hybrid analysis, place EOBI upstream of ODO1 in regulating substrate availability for volatile biosynthesis. Interestingly, ODO1-silenced transgenic petunia flowers accumulated higher EOBI transcript levels than controls, suggesting a complex feedback loop between these regulatory factors. The accumulation pattern of EOBI transcript relative to EOBII and ODO1, and the effect of up/downregulation of EOBII on transcript levels of EOBI and ODO1, further support these factors' hierarchical relationships. The dependence of scent production on EOBI expression and its direct interaction with both regulatory and structural genes provide evidence for EOBI's wide-ranging involvement in the production of floral volatiles.

A Study on tons of advertising expressions in perfume products -Sex appeal of Vogue magazine advertising-

A Study on tons of advertising expressions in perfume products -Sex appeal of Vogue magazine advertising-