atranol and chloroatranol

Oak moss absolute, an extract from the lichen Evernia prunastri, is a valued perfume ingredient but contains extreme allergens.. To compare the elicitation properties of two preparations of oak moss absolute: 'classic oak moss', the historically used preparation, and 'new oak moss', with reduced contents of the major allergens atranol and chloroatranol.. The two preparations were compared in randomized double-blinded repeated open application tests and serial dilution patch tests in 30 oak moss-sensitive volunteers and 30 non-allergic control subjects.. In both test models, new oak moss elicited significantly less allergic contact dermatitis in oak moss-sensitive subjects than classic oak moss. The control subjects did not react to either of the preparations.. New oak moss is still a fragrance allergen, but elicits less allergic contact dermatitis in previously oak moss-sensitized individuals, suggesting that new oak moss is less allergenic to non-sensitized individuals.

Topics: Allergens; Benzaldehydes; Dermatitis, Allergic Contact; Dose-Response Relationship, Drug; Double-Blind Method; Female; Humans; Male; Middle Aged; Patch Tests; Perfume; Resins, Plant; Risk Assessment; Terpenes

Oak moss absolute (Evernia prunastri extract) contains a large number of substances, among them the potent allergens atranol and chloroatranol. Since 2008, their content in oak moss absolute has been restricted by the International Fragrance Association to a maximum level of 100 ppm each.. To compare the elicitation capacities of a traditional (sample A) and a treated (sample B) oak moss absolute containing, in total, 27 000 and 66 ppm of atranol and chloroatranol, respectively, and to investigate reactions to components of oak moss absolute separated by thin-layer chromatography (TLC).. Fifteen oak moss-allergic subjects were patch tested with serial dilutions and TLC strips of samples A and B.. Fifteen subjects reacted to sample A at concentrations ≤ 2.0%, and 2 subjects reacted to sample B at 2.0% but not to lower concentrations. Among 13 subjects reacting to the TLC strip of sample A, 11 reacted to spots with retardation factor values corresponding to those of atranol and/or chloroatranol, and 11 reacted to other areas on the TLC strip. Only one subject reacted to the TLC strip of sample B.. The patch test reactivity of sample B was significantly lower than that of sample A. The TLC patch tests indicate the presence of sensitizers other than atranol and chloroatranol in oak moss absolute.

Topics: Adult; Aged; Allergens; Benzaldehydes; Chromatography, Thin Layer; Dermatitis, Allergic Contact; Dose-Response Relationship, Drug; Female; Humans; Male; Middle Aged; Patch Tests; Resins, Plant; Solutions; Terpenes

Atranol and chloroatranol are strong contact allergens in oak moss absolute, a lichen extract used in perfumery. Fifteen subjects with contact allergy to oak moss absolute underwent a repeated open application test (ROAT) using solutions of an untreated oak moss absolute (sample A) and an oak moss absolute with reduced content of atranol and chloroatranol (sample B). All subjects were in addition patch-tested with serial dilutions of samples A and B. Statistically significantly more subjects reacted to sample A than to sample B in the patch tests. No corresponding difference was observed in the ROAT, though there was a significant difference in the time required to elicit a positive reaction. Still, the ROAT indicates that the use of a cosmetic product containing oak moss absolute with reduced levels of atranol and chloroatranol is capable of eliciting an allergic reaction in previously sensitised individuals.

Topics: Administration, Cutaneous; Adult; Aged; Allergens; Benzaldehydes; Dermatitis, Allergic Contact; Double-Blind Method; Female; Humans; Male; Middle Aged; Patch Tests; Predictive Value of Tests; Resins, Plant; Skin; Skin Tests; Terpenes; Time Factors

Atranol and chloroatranol are the main allergens of oakmoss absolute. However, the immune responses induced by these substances are poorly characterized.. To characterize immune responses induced by atranol, chloroatranol and oakmoss absolute in mice.. Mice were sensitized and challenged with various concentrations of atranol, chloroatranol, and oakmoss absolute. The immune responses were analysed as B cell infiltration, T cell proliferation in the draining lymph nodes, and expression of interleukin (IL)-18, IL-1β and tumour necrosis factor-α in skin. The cytotoxicity of atranol and chloroatranol against keratinocytes was determined.. Sensitization experiments showed that atranol, chloroatranol and oakmoss induced sensitization when applied in high concentrations. Challenge experiments showed that even low concentrations of atranol and chloroatranol induced sensitization. In parallel, atranol and chloroatranol elicited challenge reactions following sensitization with oakmoss. The magnitude of the immune response to the three allergens increased in the following order: atranol, chloroatranol, and oakmoss. The expression of proinflammatory cytokines was induced by chloroatranol and oakmoss, but not by atranol. Chloroatranol was found to be more cytotoxic than atranol against keratinocytes.. Atranol and chloroatranol can elicit both sensitization and challenge reactions, but the mixture of allergens in oakmoss absolute is more potent than atranol and chloroatranol alone.

Topics: Animals; Antigens, CD19; B-Lymphocytes; Benzaldehydes; CD4-Positive T-Lymphocytes; CD8-Positive T-Lymphocytes; Cell Line; Cell Proliferation; Dermatitis, Allergic Contact; Interleukin-18; Interleukin-1beta; Keratinocytes; Mice; Mice, Inbred CBA; Patch Tests; Resins, Plant; Terpenes; Tumor Necrosis Factor-alpha

A new analytical method based on simultaneous derivatization and dispersive liquid-liquid microextraction (DLLME) followed by gas chromatography-mass spectrometry (GC-MS), for the determination of the allergenic compounds atranol and chloroatranol in perfumes, is presented. Derivatization of the target analytes by means of acetylation with anhydride acetic in carbonate buffer was carried out. Thereby volatility and detectability were increased for improved GC-MS sensitivity. In addition, extractability by DLLME was also enhanced due to a less polar character of the solutes. A liquid-liquid extraction was performed before DLLME to clean up the sample and to obtain an aqueous sample solution, free of the low polar matrix from the essential oils, as donor phase. Different parameters, such as the nature and volume of both the extraction and disperser solvents, the ionic strength of the aqueous donor phase or the effect of the derivatization reagent volume, were optimized. Under the selected conditions (injection of a mixture of 750μL of acetone as disperser solvent, 100μL of chloroform as extraction solvent and 100μL of anhydride acetic as derivatization reagent) the figures of merit of the proposed method were evaluated. Limits of detection in the low ngmL(-1) range were obtained. Matrix effect was observed in real perfume samples and thus, standard addition calibration is recommended.

Topics: Benzaldehydes; Gas Chromatography-Mass Spectrometry; Hydrogen-Ion Concentration; Liquid Phase Microextraction; Molecular Structure; Osmolar Concentration; Perfume; Solvents; Time Factors

Chloroatranol and atranol are degradation products of chloroatranorin and atranorin, respectively, and have been identified as important contact allergens in oak moss absolute (Evernia prunastri).. To investigate whether chemically modified extracts of oak moss produce positive patch test reactions in previously sensitized subjects.. A sample of oak moss was treated by a polymer-based method to reduce the content of the two main allergens, namely atranol and chloroatranol, from 3.4% to less than 75 p.p.m. and from 1.8% to less than 25 p.p.m., respectively. Fourteen subjects with positive reactions to oak moss from Trolab and/or Chemotechnique were patch tested to this sample, diluted 1% in petrolatum.. The chemically modified sample reacted negatively in six but gave still positive reactions in eight subjects, with the same intensity as the commercially available oak moss patch test materials.. Polymer-based treatment of oak moss extract reduces the allergenic elicitation potential in previously sensitized individuals only to a minor extent. The residual concentrations of atranol and chloroatranol being less than 75 p.p.m. and 25 p.p.m., respectively, are unsafe for the consumer.

Topics: Adult; Allergens; Benzaldehydes; Dermatitis, Allergic Contact; Dose-Response Relationship, Drug; Drug Combinations; Female; Humans; Male; Middle Aged; Patch Tests; Plant Extracts

Contact allergy to fragrance ingredients is frequent. Recommendations and regulations of some of the most frequent and potent fragrance allergens have recently been introduced. To investigate current exposures to 4 important fragrance allergens in hydroalcoholic cosmetic products. 25 popular perfume products of Danish as well as international brands were purchased from the Danish retail market. Contents of 4 important fragrance allergens, isoeugenol, hydroxy-iso-hexyl 3-cyclohexene carboxaldehyde (HICC, Lyral), were determined by gas chromatography-mass spectrometry, and atranol and chloro-atranol were determined by liquid chromatography-tandem mass spectrometry. Isoeugenol was found in 56%, HICC in 72%, atranol in 59%, and chloro-atranol in 36% of the 22 eau de toilette/eau de parfum products. The concentrations of isoeugenol were, in all products, below the recommended maximum concentration of 0.02%. HICC reached a maximum of 0.2%, which is 10-fold higher than maximum tolerable concentration considered safe by the EU Scientific Committee. The median concentrations of atranol and chloro-atranol in the investigated products were similar to those found in similar products in 2003. A significant decrease in the frequency of presence of chloro-atranol in the products was observed. There is still a wide-spread exposure to potent fragrance allergens in perfumes.

Topics: Aldehydes; Allergens; Benzaldehydes; Chromatography, Liquid; Cyclohexenes; Denmark; Dermatitis, Allergic Contact; Eugenol; Gas Chromatography-Mass Spectrometry; Humans; Perfume

Chloroatranol and atranol are degradation products of chloroatranorin and atranorin, respectively, and have recently been identified as important contact allergens in the natural fragrance extract, oak moss absolute. Oak moss absolute is widely used in perfumery and is the cause of many cases of fragrance allergic contact dermatitis. Chloroatranol elicits reactions at very low levels of exposure. In oak moss absolute, chloroatranol and atranol are present together and both may contribute to the allergenicity and eliciting capacity of the natural extract. In this study, 10 eczema patients with known sensitization to chloroatranol and oak moss absolute were tested simultaneously to a serial dilution of chloroatranol and atranol in ethanol, in equimolar concentrations (0.0034-1072 microM). Dose-response curves were estimated and analysed by logistic regression. The estimated difference in elicitation potency of chloroatranol relative to atranol based on testing with equimolar concentrations was 217% (95% confidence interval 116-409%). Both substances elicited reactions at very low levels of exposure. It is concluded that the differences in elicitation capacity between the 2 substances are counterbalanced by exposure being greater to atranol than to chloroatranol and that both substances contribute to the clinical problems seen in oak moss absolute-sensitized individuals.

Topics: Adult; Aged; Allergens; Benzaldehydes; Dermatitis, Allergic Contact; Dose-Response Relationship, Drug; Drug Combinations; Eczema; Female; Humans; Logistic Models; Male; Middle Aged; Patch Tests

Several recent (1999 onward) publications on skin sensitization to aldehydes and ketones, which can sensitize by covalent binding to skin protein via Schiff base formation, present QSARs based on the Taft sigma parameter to model reactivity and log P to model hydrophobicity. Here, all of the data are reanalyzed together in a stepwise self-consistent way using the parameters log P (octanol/water) and Sigmasigma, the latter being the sum of Taft sigma values for the two groups R and R' in RCOR'. A QSAR is derived: pEC3 = 1.12(+/-0.07) Sigmasigma + 0.42(+/-0.04) log P - 0.62(+/-0.13); n = 16 R(2) = 0.952 R(2)(adj) = 0.945 s = 0.12 F = 129.6, based on mouse local lymph node assay (LLNA) data for 11 aliphatic aldehydes, 1 alpha-ketoester and 4 alpha,beta-diketones. In developing this QSAR, an initial regression equation for a training set of 10 aldehydes was found to predict a test set consisting of the other 6 compounds. The QSAR is found to be well predictive for LLNA data on a series of alpha,gamma-diketones and also correctly predicts the nonsensitizing properties of simple dialkylketones. It is shown to meet all of the criteria of the OECD principles for applicability within regulatory practice. In view of the structural diversity within the sets of compounds considered here, the present findings confirm the view that within the mechanistic applicability domain the differences in sensitization potential are dependent solely on differences in chemical reactivity and partitioning.

Topics: Benzaldehydes; Formaldehyde; Glutaral; Ketones; Quantitative Structure-Activity Relationship; Schiff Bases; Skin; Toxicity Tests

Chloroatranol and atranol have been identified as the main allergens in the fragrance material of botanical origin, oak moss absolute. A previous study has shown that nearly all individuals sensitized to chloroatranol will elicit to 5 microg/ml. in a repeated open application test and that 50% will get a reaction to 0.15 micro g/ml under patch test conditions. Thus, chloroatranol is known as a potent allergen. The aim of the current investigation was to quantify exposure to chloroatranol and the chemically related substance atranol in some popular perfumes, eaux de parfum and eaux de toilette available on the European market. In total, 31 products were analysed by liquid chromatography-electrospray ionization-tandemmass spectrometry (LC-ESI-MS-MS) for their contents of atranol and chloroatranol. The 2 substances were found in 87% (n = 27) of the products. The median concentration of atranol in perfumes was 0.502 micro g/ml and 0.012 micro g/ml in eaux de toilette, and 0.235 micro g/ml and 0.006 micro g/ml for chloroatranol, respectively, in perfumes and eaux de toilette. Chloroatranol was found at a maximum concentration of 53 micro g/ml and atranol at one of 190 micro g/ml. The wide exposure to oak moss allergens, together with significant amounts of these potent allergens in at least half of perfumes and some eaux de toilettes explains the high frequencies of oak moss absolute allergy. It is suggested that regulations should be introduced aimed directly at these substances, and not just at oak moss absolute.

Topics: Allergens; Benzaldehydes; Chromatography, Liquid; Perfume; Resins, Plant; Spectrometry, Mass, Electrospray Ionization; Terpenes