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At least 667 records · Page 37Linked to original sources
PubMed2005

The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization.

Fragrances are common causes of allergic contact dermatitis. beta-Caryophyllene is a sesquiterpene that is used as a fragrance chemical. Analogous to the monoterpenes R-limonene and linalool, it can be expected to autoxidize when air exposed. The aim of the present study was to investigate the autoxidation of beta-caryophyllene and to evaluate the effect on the contact allergenic activity. beta-Caryophyllene started to oxidize immediately when air exposed and after 5 weeks almost 50% of the original compound was consumed. Caryophyllene oxide was found to be the major oxidation product. Hydroperoxides of beta-caryophyllene could not be detected in the oxidation mixture. Caryophyllene oxide was shown to be an allergen of moderate strength and beta-caryophyllene air exposed for 10 weeks showed a weak sensitizing capacity in the local lymph node assay. The study reveals that the allergenic activity of beta-caryophyllene is affected by autoxidation, but to a lesser extent when compared to R-limonene and linalool. The present findings support our results in clinical studies showing oxidized beta-caryophyllene to be a rather rare sensitizer compared to oxidized R-limonene and linalool.

Air↗
PubMed2005

Investigation of the dermal sensitization potential of various essential oils in the local lymph node assay.

Essential oils are commonly used fragrance ingredients. The oils themselves are complex mixtures, which may contain naturally occurring contact sensitizers. The local lymph node assay was used to evaluate the dermal sensitization potential of basil, citronella, clove leaf, geranium, litsea cubeba, lemongrass, and palmarosa oils. Three of the major components--citral, eugenol, and geraniol--were included to investigate any difference in sensitization potential arising from their exposure in a mixture. Each fragrance material was tested at five concentration ranging from 2.5% to 50% w/v in 1:3 ethanol:diethyl phthalate. The stimulation index (SI) values were calculated for each dose level, an SI > or = 3 was considered a positive response. The estimated concentration (EC3) required to elicit a positive was calculated and taken as a measure of relative potency. The EC3 values and potency classification for basil, clove leaf, litsea cubeba, lemongrass and palmarosa oils were calculated to be <2.5% (> or = moderate), 7.1% (weak), 8.4% (weak), 6.5% (weak) and 9.6% (weak), respectively. Citronella and geranium oils were negative. The individual components citral, eugenol and geraniol resulted in EC3 values of 6.3%, 5.4% and 11.4%, respectively. In general, the potency of each essential oil did not differ significantly from that observed for its main individual component.

Acyclic Monoterpenes↗
PubMed2006

Phylogenetic fragrance patterns in Nicotiana sections Alatae and Suaveolentes.

We analyzed floral volatiles from eight tobacco species (Nicotiana; Solanaceae) including newly discovered Brazilian taxa (Nicotiana mutabilis and "Rastroensis") in section Alatae. Eighty-four compounds were found, including mono- and sesquiterpenoids, nitrogenous compounds, benzenoid and aliphatic alcohols, aldehydes and esters. Floral scent from recent accessions of Nicotiana alata, Nicotiana bonariensis and Nicotiana langsdorffii differed from previously published data, suggesting intraspecific variation in scent composition at the level of biosynthetic class. Newly discovered taxa in Alatae, like their relatives, emit large amounts of 1,8-cineole and smaller amounts of monoterpenes on a nocturnal rhythm, constituting a chemical synapomorphy for this lineage. Fragrance data from three species of Nicotiana sect. Suaveolentes, the sister group of Alatae, (two Australian species: N. cavicola, N. ingulba; one African species: N. africana), were compared to previously reported data from their close relative, N. suaveolens. Like N. suaveolens, N. cavicola and N. ingulba emit fragrances dominated by benzenoids and phenylpropanoids, whereas the flowers of N. africana lacked a distinct floral scent and instead emitted only small amounts of an aliphatic methyl ester from foliage. Interestingly, this ester also is emitted from foliage of N. longiflora and N. plumbaginifolia (both in section Alatae s.l.), which share a common ancestor with N. africana. This result, combined with the synapomorphic pattern of 1,8 cineole emission in Alatae s.s., suggests that phylogenetic signal explains a major component of fragrance composition among tobacco species in sections Alatae and Suaveolentes. At the intraspecific level, interpopulational scent variation is widespread in sect. Alatae, and may reflect edaphic specialization, introgression, local pollinator shifts, genetic drift or artificial selection in cultivation. Further studies with genetically and geographically well-defined populations are needed to distinguish between these possibilities.

Cyclohexanols↗
PubMed2005

Fate of synthetic musks in a domestic wastewater treatment plant and in an agricultural field amended with biosolids.

Synthetic musks are widely used as fragrance ingredients in personal care products, and they enter domestic wastewater treatment plants (WWTPs) through discharges into municipal sewage systems. Samples of aqueous sewage and biosolids collected from the Peterborough Wastewater Treatment Plant (WWTP), Ontario, Canada were analyzed for 11 synthetic musk compounds using GC/MS. The results showed that 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta[g]-2-benzopyrane (HHCB, 173.1+/-43.4 ng/L) and 7-acetyl-1,1,3,4,4,6-hexamethyl-tetrahydronaphthalene (AHTN, 41.6+/-15.8 ng/L) were the dominant fragrances in sewage, but other polycyclic musks and nitro musks were present at lower concentrations. The concentrations of HHCB and AHTN in the aqueous phase of the sewage were highly correlated with both BOD5 and TOC. The overall removal efficiency of synthetic musks from the aqueous sewage in the WWTP ranged from 43.3% to 56.9%, but removal occurred mainly by partitioning into the biosolids. Based on a mass balance model, the daily input and output of HHCB and AHTN in the Peterborough WWTP were 47 g and 46 g, respectively. In an agricultural field amended with biosolids from the Peterborough WWTP, HHCB and AHTN were detected in soil immediately after application at mean concentrations of 1.0 and 1.3 mug/kg, respectively, but concentrations declined relatively rapidly over the next 6 weeks, post-application.

Agriculture↗
PubMed2005

Assessment of the phototoxic hazard of some essential oils using modified 3T3 neutral red uptake assay.

When substances are developed in the aim to be a constituent of personal care products, and to be applied on the skin, it is necessary to carry out an assessment of potential phototoxic hazard. Phototoxicity is skin reaction caused by concurrent topical or systemic exposure to specific molecule and ultraviolet radiation. Most phototoxic compounds absorb energy particularly from UVA light leading to the generation of activated derivatives which can induce cellular damage. This type of adverse cutaneous response can be reproduced in vitro using different models of phototoxicity such as the validated 3T3 Neutral Red Uptake (NRU) phototoxicity assay. In the present study we utilised two different cell lines (the murine fibroblastic cell line 3T3 and the rabbit cornea derived cell line SIRC) to compare the photo-irritation potential of a strong phototoxic compound, chlorpromazine, to a weaker composite, such as 8-methoxypsoralen and Bergamot oil. After comparison of the different systems, five other essential oils were tested with both cell lines. Cellular damage was evaluated by the NRU cytotoxicity test or by MTT conversion test.

Animals↗
PubMed2006

In-vitro human skin penetration of the fragrance material geranyl nitrile.

In-vitro human skin permeation and distribution of geranyl nitrile (GN) was determined using epidermal membranes following application (5 microl/cm(2)) in 70% ethanol, under non-occlusive conditions, at maximum in-use concentration (1%). Permeation was measured (12 time-points over 24 h) using 6% (w/v) Oleth-20 in pH 7.4 phosphate buffered saline as receptor. Permeation of reference benzoic acid was assessed using the same skin donors. Overall recovery of GN at 24 h was low (14.1+/-0.4%) due to evaporation. Evaporative loss of GN from polytetrafluoroethylene (PTFE) sheet, under the same conditions was rapid (93% over 24h) although this overestimated loss during permeation where evaporation competed with uptake. At 24 h, 1.89+/-0.15 microg/cm(2) GN, (3.74+/-0.30% of applied dose) (mean+/-standard error, SE, n=12), had permeated. Following rapid initial permeation, the absorption plateaued due to depletion. Levels of GN in the epidermis (plus any remaining stratum corneum after tape stripping), filter paper membrane support and receptor fluid were combined (as per SCCNFP guidelines) to produce a total absorbed dose value of 4.72+/-0.32%. Systemic exposure resulting from the use of GN as a fragrance ingredient, under unoccluded conditions, would be low based on the currently reported use levels.

Benzoic Acid↗
PubMed2005

Examination of the in vitro (anti)estrogenic, (anti)androgenic and (anti)dioxin-like activities of tetralin, indane and isochroman derivatives using receptor-specific bioassays.

Molecules derived from tetralin, indane and isochroman are often used in the synthesis of fragrance materials. The two polycyclic musk fragrances AHTN (6-acetyl-1,1,2,4,4,7-hexamethyltetralin), HHCB (1,2,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran) and ADBI (4-acetyl-1,1-dimethyl-6-tert-butylindane) are derived from tetralin, isochroman and indane, respectively. In previous studies, AHTN and HHCB have been shown to antagonize estrogen receptors (ERs), both in vitro and in vivo. Here, we used two newly developed reporter gene assays, to examine the agonistic and antagonistic properties of several indane, tetralin and isochroman derivatives towards the human androgen receptor (AR) and aryl hydrocarbon receptor (AhR). Additionally, we also assessed (anti)estrogenicity of these compounds. A number of compounds showed weak estrogenic activity towards the human ER alpha. Several compounds showed (anti)estrogenic effects, starting at a concentration of 0.1 microM. Surprisingly, almost all compounds were found to be AR antagonists, starting at 0.1 microM. None of the compounds tested, showed either agonism or antagonism towards the AhR. Non-specific effects via crosstalk of the AhR and the ER or AR can therefore be ruled out. As far as we are aware, molecules derived from indane, tetralin and isochroman showing direct interaction with the ER and AR have not been reported previously.

Androgen Receptor Antagonists↗
PubMed2005

Removal of pharmaceuticals and fragrances in biological wastewater treatment.

The removal of seven pharmaceuticals and two fragrances in the biological units of various full-scale municipal wastewater treatment plants was studied. The observed removal of pharmaceuticals was mainly due to biological transformation and varied from insignificant (<10%, carbamazepine) to>90% (ibuprofen). However, no quantitative relationship between structure and activity can be set up for the biological transformation. Overall, it can be concluded that for compounds showing a sorption coefficient (K(d)) of below 300 L kg(-1), sorption onto secondary sludge is not relevant and their transformation can consequently be assessed simply by comparing influent and effluent concentrations. The two fragrances (HHCB, AHTN) studied were mainly removed by sorption onto sludge. For the compounds studied, comparable transformation and sorption was seen for different reactor types (conventional activated sludge, membrane bioreactor and fixed bed reactor) as well as for sludge ages between 10 and 60-80 days and temperatures between 12 degrees C and 21 degrees C. However, some significant variations in the observed removal currently lack an explanation. The observed incoming daily load of iopromide and roxithromycin in medium-sized municipal wastewater treatment plants (up to 80,000 population equivalents) is generated by only a small number of patients: the consequences for representative 24h composite sampling are discussed. Generally, the paper presents a method for setting up mass balances for micropollutants over entire wastewater treatment plants, including an estimation of the accuracy of the quantified fate (i.e. removal by sorption and biological transformation).

Adsorption↗
PubMed2005

Removal of selected pharmaceuticals, fragrances and endocrine disrupting compounds in a membrane bioreactor and conventional wastewater treatment plants.

Eight pharmaceuticals, two polycyclic musk fragrances and nine endocrine disrupting chemicals were analysed in several waste water treatment plants (WWTPs). A membrane bioreactor in pilot scale was operated at different solid retention times (SRTs) and the results obtained are compared to conventional activated sludge plants (CASP) operated at different SRTs. The SRT is an important design parameter and its impact on achievable treatment efficiencies was evaluated. Different behaviours were observed for the different investigated compounds. Some compounds as the antiepileptic drug carbamazepine were not removed in any of the sampled treatment facilities and effluent concentrations in the range of influent concentrations were measured. Other compounds as bisphenol-A, the analgesic ibuprofen or the lipid regulator bezafibrate were nearly completely removed (removal rates >90%). The operation of WWTPs with SRTs suitable for nitrogen removal (SRT>10 days at 10 degrees C) also increases the removal potential regarding selected micropollutants. No differences in treatment efficiencies were detected between the two treatment techniques. As in conventional WWTP also the removal potential of MBRs depends on the SRT. Ultrafiltration membranes do not allow any additional detention of the investigated substances due to size exclusion. However, MBRs achieve a high SRT within a compact reactor. Nonylphenolpolyehtoxylates were removed in higher extend in very low-loaded conventional WWTPs, due to variations of redox conditions, necessary for the degradation of those compounds.

Biodegradation, Environmental↗
PubMedDate not supplied

[Sensitization to Lyral].

INTRODUCTION: Lyral is a fragrance that is present in many cosmetic products. It has turned into an emergent allergen during the last years. In studies carried out in other European countries, the prevalence of sensitization to Lyral has been found to be 1.9-2.7 %, but it is unknown the prevalence in Spain, as well as the need to include it or not in the standard series of the Spanish Group of Contact Dermatitis (GEIDC). METHODS: We have patch-tested to Lyral all patients with suspicion of contact dermatitis of any origin who attended our Service between April and May-2005. RESULTS: From a total of 170 patients included in our study, 2 of them had a sensitization to Lyral (1.2 %). One of these two patients had an axillae contact dermatitis caused by a deodorant containing Lyral. The other patient was a masseur-woman with a contact dermatitis on both hands, with periods of dissemination to upper extremities and trunk, and who used several cosmetics products for private reasons and during her job. CONCLUSION: Although the sample of this study is quite small, we think that the results allow to suspect that Lyral is one of the main allergens, or even the most important, in causing allergic contact dermatitis to fragrances in our environment. Therefore, we believe that we must raise the inclusion of Lyral in the standard series of GEIDC, either as independent allergen, or including it in a new mixture of fragrances.

Adult↗
PubMed1998

Fragrance compounds and amphiphilic association structures.

Fragrance formulations have traditionally been based on alcohol as the solvent, but the recent legal restrictions on volatile organic solvents have prompted the industry to change to aqueous solubilized systems. The article reviews the fundamental factors in the application of such systems evaluating the influence by different amphiphilic association structures on the vapor pressure of fragrance compounds. This information is subsequently used to estimate the variation of fragrance compound vapor pressures during evaporation. The results reveal that the vapor pressure versus time variation is improved compared to solvent-based formulations.

Micelles↗