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PubMed1999

The significance of lichens and their metabolites.

Lichens, symbiontic organisms of fungi and algae, synthesize numerous metabolites, the "lichen substances," which comprise aliphatic, cycloaliphatic, aromatic, and terpenic compounds. Lichens and their metabolites have a manifold biological activity: antiviral, antibiotic, antitumor, allergenic, plant growth inhibitory, antiherbivore, and enzyme inhibitory. Usnic acid, a very active lichen substance is used in pharmaceutical preparations. Large amounts of Pseudevernia furfuracea and Evernia prunastri are processed in the perfume industry, and some lichens are sensitive reagents for the evaluation of air pollution.

Air Pollution↗
PubMed1986

Effect of odors in asthma.

Many patients complain that some odors worsen their asthma. Perfume and cologne are two of the most frequently mentioned offenders. Four patients with a history of worsening of asthma on exposure to cologne underwent challenge with a cologne, and their pulmonary function was tested before, during, and after the exposure. Forced expiratory volume in one second declined 18 to 58 percent below the baseline period during the 10-minute exposure and gradually increased in the next 20 minutes. Saline placebo pretreatment did not affect the response to subsequent challenge. Single-blind pretreatment with metaproterenol and atropine prevented decline in one-second forced expiratory volume in three of four patients and blunted the response in the other. Cromolyn sodium prevented decline in one of four, and occlusion of nostrils prevented decline in one of three. A survey of 60 asthmatic patients revealed a history of respiratory symptoms in 57 on exposure to one or more common odors. Odors are an important cause of worsening of asthma.

Adult↗
PubMed1984

Examination of some fragrance substances for mutagenic activity.

We tested 64 perfumes and aftershaves for mutagenicity in Salmonella typhimurium strains TA98 and TA100; most were tested both with and without metabolic activation. None of the test compounds gave a positive mutagenic response. The available amounts of some test samples were very small, however, and the possibility that larger samples might have produced positive results cannot be altogether discounted. Some tests indicated the presence of cytotoxic substances which require chemical analysis.

2-Acetylaminofluorene↗
PubMed1990

Phototumorigenesis studies of 5-methoxypsoralen in bergamot oil: evaluation and modification of risk of human use in an albino mouse skin model.

The skin of the female hairless albino mouse (Skh 1) was used to study the enhancement of solar simulated radiation (SSR) tumorigenesis by 5-methoxypsoralen (5-MOP) in model perfumes that contain bergamot oil. This work was done in association with yeast mutagenicity studies and human skin phototoxicity studies. Analyses of time-to-onset of tumour observation with 5-MOP at 0, 5, 15 and 50 ppm show a highly significant 5-MOP dose effect and the data indicate that 5-MOP has phototumorigenic potential even at 5 ppm. The addition of 0.5% UVB and 0.5% UVA sunscreens significantly reduces the tumorigenicity associated with the vehicle (i.e. 5-MOP at 0 ppm) and 5-MOP at all concentrations. Pairwise comparisons of 5-MOP (at 5 or 15 ppm) plus sunscreens with vehicle plus sunscreens show that the sunscreens afford total protection at the lower 5-MOP concentrations. Additional studies show that a 5-6 h delay between 5-MOP application and SSR exposure defers the time-to-onset of tumours as does intermittent 5-MOP and SSR treatment. A comparison of 5-MOP at 50 ppm in bergamot oil with 5-MOP at 50 ppm prepared from pure 5-MOP crystals shows identical results, indicating that the active phototumorigenic agent in bergamot oil is 5-MOP and not other related compounds, which may be present at greater concentrations. Analyses of tumour histology at death show, in general, similar patterns of malignancy for all groups. Thus although it is possible to delay tumorigenesis by various strategies, the tumours that eventually develop are just as likely to be malignant, if not more so, when compared with non-delayed groups.

5-Methoxypsoralen↗
PubMed2005

Headspace solid-phase microextraction gas chromatography-mass spectrometry method for the identification of cosmetic ingredients causing delamination of packagings.

A headspace solid-phase microextraction gas chromatography-mass spectrometry (HS-SPME-GC-MS) method using a 75 microm Carboxen polydimethylsiloxane fibre was used to identify volatile compounds of cosmetic formulations responsible for causing loss of adhesion between layers of multilayer packagings. To obtain the sample, the sachet with the product was kept in an oven at 40 degrees C in order to favour the migration of the aggressive compounds to the inner layers. Then the sachet was manually delaminated and the aluminium/polyester and polyethylene layers were analysed. The cosmetic product was also analysed by HS-SPME-GC-MS. Several compounds used in the cosmetic industry such as perfumes or fixing agents were detected in the inner layers of the laminated material, showing the migration of them through the layer in contact with the product (polyethylene). Phenoxy ethanol, beta-linalool, menthol and p-propenylanisole are suspected to be responsible for the loss of adhesion. In order to provide a complete overview of the cause of the aforementioned phenomenon, the packaging material was exposed to the cosmetic products in order to measure the decrease of the adhesion strength with time. It was observed that the product with a higher phenoxy ethanol concentration caused a higher loss of adhesion strength. The results obtained showed that this method is suitable for identifying aggressive compounds in cosmetic products, as well as for giving prior information about which products may be problematic for packaging in sachets.

Absorption↗
PubMed1981

A case of contact dermatitis, erythema multiforme, and toxic epidermal necrolysis.

A young adult female patient, on prolonged corticosteroid therapy for nephrotic syndrome, developed erythema multiforme and toxic epidermal necrolysis following a double exposure to a locally applied perfume. We believe that this route of exposure should be re-emphasized. Toxic epidermal necrolysis, or the scalded skin syndrome, has become a well-recognized entity which may be divided into three distinct subgroups: the staphylococcal scalded skin syndrome, nonstaphylococcal or drug-induced scalded skin syndrome, and idiopathic. We present a patient who developed a dermatitis on her chest and abdomen after using a spray cologne, which resulted in the development of erythema multiforme with progression toxic epidermal necrolysis and, ultimately, her death.

Adrenal Cortex Hormones↗
PubMed1983

Sensitivity to alpha-amylcinnamic aldehyde and alpha-amylcinnamic alcohol.

Sensitivity to alpha-amylcinnamic aldehyde (alpha-AcAld) is apparently uncommon, but, like allergy to alpha-amylcinnamic alcohol (alpha-AcAlc), it often accompanies allergy to the perfume in Mycolog cream. Although alpha-AcAlc is a known ingredient, alpha-AcAld is not. However, gas-liquid chromatographic analysis shows alpha-AcAld to be present. Of fourteen persons sensitive to either chemical, ten reacted to both. Of these, one man and three women were markedly sensitive, and all three women had chronic recalcitrant vulvar eczema. That condition might have been the cause as well as the result of sensitization, but reexposure to a suspected product reproduced the eruption in both persons tested. Its use with other potent sensitizers, e.g., ethylenediamine, to treat irritations and chronic eczemas in an area of high absorption may partly explain development of allergy to a relatively weak sensitizer.

Alcohols↗
PubMed2000

Synthesis of ionones and carvone analogues: olfactory properties and preliminary toxicity assays.

Vilsmeier reagents react with alpha/beta-ionones and carvone to produce aldehydes 7-11 in a one-step procedure. The indene derivative 11, which came from the double iminoalkylation of carvone and ring closure with the elimination of dimethylamine, was practically odourless, while all the others had peculiar odours which were very different from the starting material. The cytotoxicity data of 9 and 10, which are the most promising potential perfume ingredients, are also reported.

Alkenes↗
PubMed2001

The in vivo dermal absorption and metabolism of [4-14C] coumarin by rats and by human volunteers under simulated conditions of use in fragrances.

The disposition and metabolic fate of [4-14C]coumarin in a 70% aqueous ethanol solution was studied in male Lister Hooded rats after occluded dermal application and in three male volunteers after an exposure designed to simulate that which may be encountered when using an alcohol-based perfumed product. In both cases, the 6-h exposure was 0.02 mg/cm(2) (rats 0.023 mg/kg and humans 0.77 mg/kg). In both, coumarin was quickly absorbed, distributed and excreted in urine and feces, although fecal excretion of coumarin in humans was only 1% of the applied dose as opposed to 21% in rats. Total absorption was 72% of the applied dose with rats and 60% with humans. Peak plasma radioactivity in both was at 1 h. The mean plasma half-life of coumarin and metabolites was approximately 1.7 h for humans and 5 h for rats. In humans, coumarin was primarily metabolized to and excreted in urine as 7-hydroxycoumarin glucuronide and 7-hydroxycoumarin sulfate. Small amounts of unconjugated 7-hydroxycoumarin and o-hydroxyphenylacetic acid (o-HPAA) were also excreted. In rats, about twenty metabolites were present, but only o-HPAA was identified. These studies show the rat is a very poor model for humans and toxicity in the rat cannot be extrapolated to humans.

Administration, Topical↗
PubMed2002

Macrocyclic musk compounds--an absence of genotoxicity in the Ames test and the in vivo Micronucleus assay.

Three synthetic macrocyclic musks, ethylene dodecanedioate, ethylene brassylate, and cyclopentadecanolide, which are widely used as ingredients of perfume fragrances, were tested for genotoxicity. In this report we present results from two different studies, the flow-cytometer-based micronucleus assay in peripheral blood of mice and the Salmonella/microsome test with TA 97, TA 98, and TA 100. Female NMRI and male CD 1 mice were intraperitoneally injected with one of the three macrocyclic musk compounds. Three different doses (0.1-1.6 g/kg bw) of each of the compounds were tested. Blood samples were collected on two occasions from each mouse and the frequency of micronucleated polychromatic erythrocytes (fMPCE) was determined. Neither of the compounds caused a significant difference from the control fMPCE. No mutagenic effect with and without S9 mix in the tested Salmonella strains was observed. The presence of S9 mix reduced the killing effect of high doses.

Alkanes↗
PubMed1999

Polycyclic musk fragrances in the aquatic environment.

The polycyclic musk fragrances, mainly 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta(g)-2-ben zopyrane (HHCB) and 7-acetyl-1,1,3,4,4,6-hexamethyltetrahydronaphthalene (AHTN) are synthetic musk fragrances which are used in almost all scented consumer products, such as perfumes, cosmetics and laundry detergents. Concerning their chemical structures the polycyclic musks are indane and tetraline derivatives highly substituted mainly by methyl groups. Their production has been increased continuously during the last years with a world-wide production volume today of about 6000 t/year. After their application in private households they are dumped via the sewage treatment plants into the aquatic environment. In this review the analysis of polycyclic musk compounds in environmental samples is shortly presented and all published data of polycyclic musk compounds in water, sediment, suspended particulate matter (SPM), sewage sludge, and biota are summarized and discussed. The highest HHCB and AHTN concentrations were analysed in water (maximum concentrations: 6 microg HHCB/l, 4.4 microg AHTN/1) and sludge (maximum concentrations: 63 mg HHCB/kg dry matter, 34 mg AHTN/kg dry matter) from sewage plants, and in fish (maximum concentrations: 159 mg HHCB/kg lipid, 58 mg AHTN/kg lipid) from sewage ponds. In all other samples from different aquatic ecosystems these chemicals were unequivocally detected in varying concentrations dependent on the distance to sewage treatment plants. Even in marine water samples from the German Bight HHCB and AHTN could be quantified at the lower ng/l level. Very often HHCB and AHTN formed the major organic contaminants, in all samples their concentrations exceeded those of musk xylene and musk ketone. Also several by-products and impurities of the commercial polycyclic musks were analysed in river and waste water samples in not negligible amounts. The apparently ubiquitous distribution of polycyclic musks in the aquatic environment demonstrates the persistence and lipophilicity of these pollutants. The high log K(ow) values of HHCB and AHTN (5.7-5.9) do not directly correlate with their relatively low bioconcentration factors (BCFs) derived from fish experiments, this discrepancy may be explained by a particular metabolism in fish. There are indications of a possible species dependent metabolisation. For a general risk assessment of this new group of environmental pollutants besides the missing toxicological data, further studies on the distribution of the polycyclic musk fragrances including their by-products in the aquatic environment, on possible degradation processes in sediment/sludge as well as on the metabolism in fish are urgently needed.

Animals↗
PubMed2004

In vitro and in vivo antiestrogenic effects of polycyclic musks in zebrafish.

The polycyclic musks 6-acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN) and 1,2,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran (HHCB) are used as fragrance ingredients in perfumes, soaps, and household cleaning products. They are known to be ubiquitously present in the aquatic environment, and because of their lipophilic nature, they tend to bioaccumulate in aquatic biota. In surface waters, concentrations between 1 ng/L and 5 microg/L have been found, depending mainly on the proportion of sewage effluents in the water. In fish, under normal environmental conditions, concentrations in the microgram per kilogram fresh weight (fw) range are found. In a previous study we showed that AHTN and HHCB exert mainly antiestrogenic effects on the human estrogen receptor alpha (ERalpha) and ERbeta in an in vitro reporter gene assay. In the current study, we assessed the in vitro antiestrogenic effects of both musks on zebrafish ERs. Antagonism was observed on zfERbeta, and more pronounced on the newly cloned zfERgamma. Using a transgenic zebrafish assay, we studied antiestrogenicity of the musks in vivo. Dose-dependent antagonistic effects were observed at concentrations of 0.1 and 1 microM AHTN and HHCB. GC-MS analysis showed that the musks bioaccumulated in the fish, with internal concentrations (15-150 mg/kg fw) which were roughly 600 times higher than the nominal test doses. To our knowledge, this is the first time that environmental contaminants are shown to be antiestrogenic in an in vivo fish assay that focuses solely on ER-mediated effects. This makes the transgenic zebrafish assay a promising tool for the rapid detection of both estrogenic and antiestrogenic effects of chemicals in fish.

Animals↗
PubMed2007

GC-MS quantification of suspected volatile allergens in fragrances. 2. Data treatment strategies and method performances.

The performances of the GC-MS determination of suspected allergens in fragrance concentrates have been investigated. The limit of quantification was experimentally determined (10 mg/L), and the variability was investigated for three different data treatment strategies: (1) two columns and three quantification ions; (2) two columns and one quantification ion; and (3) one column and three quantification ions. The first strategy best minimizes the risk of determination bias due to coelutions. This risk was evaluated by calculating the probability of coeluting a suspected allergen with perfume constituents exhibiting ions in common. For hydroxycitronellal, when using a two-column strategy, this may statistically occur more than once every 36 analyses for one ion or once every 144 analyses for three ions in common.

Allergens↗
PubMed2002

Oak moss extracts in the diagnosis of fragrance contact allergy.

Oak moss absolute is one of the eight ingredients of the fragrance mix (FM) used for diagnosing perfume allergy. Oak moss absolute is an extract prepared from the lichen Evernia prunastri growing on oak trees. It has been shown that the oak moss patch test material from one producer contained resin acids which are ingredients of another lichen, tree moss. Resin acids, e.g. abietic acid and dehydroabietic acid, are also the main allergens in colophonium. The aim of the study was to assess whether the contamination of oak moss absolute and thus the FM with resin acids had affected their diagnostic value so that they, instead of indicating fragrance allergy, had become indicators of allergy to resin acids and thus colophonium. Two studies were undertaken. First the relationship between patch test reactions to FM, oak moss absolute, both with contents of resin acids, and colophonium were assessed in 885 consecutive patients. A significant relationship between reactions to colophonium and FM was seen (p < 0.001) as well as a significant relationship between oak moss absolute and colophonium (p < 0.001). The relationship between colophonium and FM was still significant when all reactions to oak moss absolute were disregarded (p < 0.001), showing a relationship also between colophonium and fragrance ingredients other than oak moss absolute. Second, 119 consecutive patients were tested with an old and a new version of oak moss absolute containing resin acid (0.05%) and no measurable resin acid, respectively, and with the corresponding FM. No overall difference in reactivity to the old and new version of oak moss absolute/FM was seen. It is concluded the diagnostic value of oak moss absolute as indicator fragrance contact allergy has been and is unaffected by the resin acid contamination.

Dermatitis, Allergic Contact↗
PubMed2002

Further important sensitizers in patients sensitive to fragrances.

In order to find sensitizers additional to the current fragrance mix (FM) a series of fragrance materials (series II) was evaluated in 6 dermatological centres in Europe. 11 of the test materials were essential oils, the remaining 7 being either mixtures of isomers or simple chemicals of frequent usage in the perfume industry. 1606 patients were consecutively tested with series II and 8% FM. Each patient was classified regarding a history of adverse reactions to scented products: certain, probable, questionable, none. Reactions to FM occurred most frequently in 11.4% of the subjects. The 6 materials with the highest reactivity after the FM were ylang-ylang oil (YY) I (2.6%), YY II (2.5%), lemongrass oil (1.6%), narcissus absolute (1.3%), jasmine absolute (1.2%) and sandalwood oil (0.9%). 48 (3.0%) of the patients reacted only to materials of series II and not to FM. 6.0% of 1606 patients gave a history of adverse reactions to fragrances which was classified as certain. This group reacted to FM only in 22.9%, to series II and FM in 15.6% and to series II only in 5.2%. 63.5% of the patients reacting to both FM and 1 of the materials of series II had some type of positive fragrance history, which was higher in comparison to those with isolated reactions to FM (46.2% of 121) or to series II, respectively, (45.8% of 48). However, this difference was not statistically significant. In conclusion, the materials of series II identified a further subset of patients with a fragrance problem, which would have been missed by the current FM as the single screening tool for patch testing.

Dermatitis, Allergic Contact↗
PubMed2002

Principles and methodology for identification of fragrance allergens in consumer products.

Fragrances contain several hundreds of different chemicals, a few major and many minor, which are responsible for the complexity of the odour. Fragrances are a major cause of allergic contact dermatitis. As a diagnostic tool, the current fragrance mix is very useful though not ideal. A 50-year-old woman presented with a pruriginous, erythematous eruption, characterized by papules, vesicles, exudation and crusting over the neck and chest. With the suspicion of fragrance allergy, patch testing was performed. Initially, the only positive reaction observed was with her own eau de toilette named Woman. The TRUE Test fragrance mix patch test was negative. Chemical fractionation of Woman perfume concentrate was combined with a sequenced patch testing procedure and with structure-activity relationship studies. Ingredients supplied by the manufacturer were also included in the study. Benzophenone-2, Lyral, alpha-hexyl cinnamic aldehyde and alpha-damascone were found to be responsible for the patient's contact allergy to the commercial product. These substances contain chemical structural alerts giving them antigenic ability. The common use of new chemicals to manufacture fragrances, and the increased number of patients sensitive to them but with negative fragrance mix reactions, makes it necessary to identify new potential fragrance sensitizers in commercial products.

Allergens↗
PubMed1998

Allergens in combination have a synergistic effect on the elicitation response: a study of fragrance-sensitized individuals.

Perfume ingredients were chosen as model substances to study the effect of allergens in combination on the elicitation response. Two groups of eczema patients were studied. One consisted of 18 subjects with a contact allergy to two fragrance substances and the other was a control group of 15 subjects allergic to only one of the same two fragrance substances. The test and matched control subject were patch tested in exactly the same way with two allergens applied in serial dilution in separate chambers on one side and combined in one chamber on the other side of the upper back. The assessment of reactions was carried out on day 3 by clinical grading and laser Doppler flowmetry, and the extent of the reaction was measured in millimetres. The data were analysed by logistic dose-response models. It was found that the combination of two allergens in individuals allergic to both substances had a synergistic effect on the elicitation response evaluated by all three methods. The 1 : 1 mixtures of the two allergens elicited responses as if the doses were three to four times higher than those actually used, which is significantly more than expected if an additive effect had been present. In the control group, no increased response was seen to the combined allergens compared with the allergens tested separately. The synergistic effect demonstrated is likely to apply to other contact allergens as well and should be taken into account in designing diagnostic tests and performing safety assessments.

Allergens↗
PubMed1999

Lyral is an important sensitizer in patients sensitive to fragrances.

Contact allergy to fragrances is a common problem world-wide. The currently used fragrance mix (FM) for patch testing has only eight constituents and does not identify all fragrance-allergic patients. As perfumes may contain 100 or more substances, the search for markers for allergy continues. The synthetic fragrance 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene carboxaldehyde (Lyral) was tested together with the FM and 11 other fragrance substances on consecutive patients in six European departments of dermatology. All patients were carefully questioned regarding a history of reactions to scented products in the past and were grouped into four categories: 'certain', 'probable', 'questionable' and 'none'. Lyral (5% in petrolatum) gave a positive reaction in 2.7% of 1855 patients (range 1.2-17%) and ranked next to 11.3% with FM allergy. Twenty-four patients reacted to both Lyral and FM, but 21 (1.1%) reacted positively only to Lyral. Of 124 patients with a 'certain' history, 53.2% reacted to the FM and a further 7.2% to Lyral only. If any kind of history of fragrance intolerance was given, 80% (40 of 50) of Lyral positive patients had a 'positive' history while only 58.6% (123 of 210) of FM positive patients had such a history; this difference was significant at P < 0.01. Lyral was identified by gas chromatography-mass spectrometry in some products which had caused an allergic contact dermatitis in four typical patients who showed a patch test positive to Lyral and negative or doubtful to FM. In conclusion, we recommend the testing of 5% Lyral (in petrolatum) in patients suspected of contact dermatitis.

Adult↗