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Fragrance Chemicals (fragrance + chemical)

Distribution by Scientific Domains

Medical Sciences	62%
Chemistry	37%

Selected Abstracts

Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens

CONTACT DERMATITIS, Issue 1 2008
Maria Sköld
Background:, Fragrances are among the most common causes of allergic contact dermatitis. We have in previous studies shown that linalool, present in lavender oil, autoxidizes on air exposure, forming allergenic oxidation products. Oxidized linalool was found to be a frequent cause of contact allergy in a patch test study on consecutive dermatitis patients. Linalyl acetate, the main component of lavender oil is commonly used as a fragrance chemical in scented products. Because of structural similarities, linalyl acetate should also be susceptible to oxidation on air exposure, forming similar oxidation products as linalool. Objective:, The aim of the present study was to investigate the autoxidation of linalyl acetate and the influence of oxidation on its sensitizing potency. Methods:, Analyses were performed using gas chromatography, nuclear magnetic resonance spectrometry and mass spectrometry. Sensitizing potencies of compounds were determined using the local lymph node assay (LLNA) in mice. Results:, Analyses showed that the content of linalyl acetate decreased over time on air exposure and other compounds were formed. Hydroperoxides, an epoxide and an alcohol were identified as oxidation products from linalyl acetate. In the LLNA, linalyl acetate of high purity showed a weak sensitizing potency (EC3 25%). Autoxidation increased the sensitizing potency of linalyl acetate, and a 10 weeks oxidized sample gave an EC3 value of 3.6%. As for linalool, the hydroperoxides were shown to be the oxidation products with the highest sensitizing potency. Conclusion:, It is concluded that autoxidation of the weakly allergenic linalyl acetate leads to formation of allergenic oxidation products. [source]

Skin sensitization potency of isoeugenol and its dimers evaluated by a non-radioisotopic modification of the local lymph node assay and guinea pig maximization test

JOURNAL OF APPLIED TOXICOLOGY, Issue 4 2008
Masahiro Takeyoshi
Abstract Allergic contact dermatitis is the serious unwanted effect arising from the use of consumer products such as cosmetics. Isoeugenol is a fragrance chemical with spicy, carnation-like scent, is used in many kinds of cosmetics and is a well-known moderate human sensitizer. It was previously reported that the dimerization of eugenol yielded two types of dimer possessing different sensitization potencies. This study reports the differences in skin sensitization potencies for isoeugenol and two types of dimer, , -O-4-dilignol and dehydrodiisoeugenol (DIEG), as evaluated by the non-radioisotopic local lymph node assay (non-RI LLNA) and guinea pig maximization test. In the guinea pig maximization test, isoeugenol, , -O-4-dilignol and DIEG were classified as extreme, weak and moderate sensitizers, respectively. As for the results of non-RI LLNA, the EC3 for isoeugenol, , -O-4-dilignol and DIEG were calculated as 12.7%, >30% and 9.4%, respectively. The two types of isoeugenol dimer showed different sensitizing activities similar to the case for eugenol dimers. A reduction of sensitization potency achieved by dimerization may lead to developing safer cosmetic ingredients. Isoeugenol dimers are not currently used for fragrance chemicals. However, the dimerization of isoeugenol may yield a promising candidate as a cosmetic ingredient with low sensitization risk. The data may also provide useful information for the structure-activity relationship (SAR) in skin sensitization. Copyright © 2007 John Wiley & Sons, Ltd. [source]

Cross-adaptation of a model human stress-related odour with fragrance chemicals and ethyl esters of axillary odorants: gender-specific effects

FLAVOUR AND FRAGRANCE JOURNAL, Issue 5 2009
Charles J. Wysocki
Abstract The human axillae have a characteristic odour that is comprised of or generated from a mixture of C6,C11 normal, branched, hydroxy- and unsaturated acids (and other compounds). We used ethyl esters of one of these acids and a palette of fragrance compounds (tested individually) to evaluate the effectiveness of these chemicals to reduce the overall olfactory impact of a model of human stress-related odour (SRO) by cross-adaptation (adaptation to one odorant can reduce sensitivity to other odorants). Sensory volunteers provided hedonic and intensity ratings of the SRO and of each of the potential cross-adapting agents prior to 2.5 min of induced olfactory adaptation to each agent. Across adaptation, possible cross-adaptation was evaluated by intermittent evaluations of the perceived intensity of the SRO. We determined that some potential cross-adapting agents did reduce the impact of the SRO; however, the same chemicals were not necessarily effective for male and female SRO. Indeed, the list of effective chemicals depended upon the gender of the donor of the SRO and the gender of the sensory volunteer, suggesting a gender-specific response to both the SRO-stimuli used and the fragrance chemicals used to cross-adapt it. Copyright © 2009 John Wiley & Sons, Ltd. [source]

Vehicle effects on skin sensitizing potency of four chemicals: assessment using the local lymph node assay

INTERNATIONAL JOURNAL OF COSMETIC SCIENCE, Issue 2 2001
Z M Wright
Synopsis The murine local lymph node assay (LLNA) can be used to determine the relative skin sensitizing potency of chemicals via interpolation of the quantitative dose response data generated. Using this approach we have demonstrated previously that the vehicle matrix in which a chemical allergen is encountered on the skin can have a significant influence on sensitizing potency. Estimates of relative potency are calculated from LLNA dose responses as a function of the mathematically derived EC3 value, this being the concentration estimated to induce a stimulation index (SI) of 3. To investigate further the influence of application vehicle on sensitizing potency, the LLNA has been used to examine the activity of four recognized human contact allergens: isoeugenol and cinnamic aldehyde, two fragrance chemicals; 3-dimethylaminopropylamine (a sensitizing impurity of cocamidopropyl betaine, a surfactant used in shower gel) and dibromodicyanobutane (the sensitizing component of Euxyl K 400, a preservative used in cosmetics). The four chemicals were applied in each of seven different vehicles (acetone: olive oil [4 : 1]; dimethylsulphoxide; methylethylketone; dimethyl formamide; propylene glycol; and both 50 : 50 and 90 : 10 mixtures of ethanol and water). It was found that the vehicle in which a chemical is presented to the epidermis can have a marked effect on sensitizing activity. EC3 values ranged from 0.9 to 4.9% for isoeugenol, from 0.5 to 1.7% for cinnamic aldehyde, from 1.7 to > 10% for dimethylaminopropylamine and from 0.4 to 6.4% for dibromodicyanobutane. These data confirm that the vehicle in which a chemical is encountered on the skin has an important influence on the relative skin sensitizing potency of chemicals and may have a significant impact on the acquisition of allergic contact dermatitis. The data also demonstrate the utility of the LLNA as a method for the prediction of these effects and thus for the development of more accurate risk assessments. Résumé Le test local des ganglions lymphatiques murins (LLNA) peut être utilisé pour déterminer le potentiel relatif de sensibilisation de la peau de produits chimiques, par interpolation des données quantitatives de dose/réponse obtenues. En utilisant cette approche, nous avions démontré précédemment que la matrice vecteur par laquelle un allergène chimique est mis en contact avec la peau peut avoir une influence significative sur le potentiel de sensibilisation. Des estimations d'activité relative sont calculées à partir des doses/réponses de LLNA en fonction de la valeur EC3 dérivée mathématiquement, celle-ci étant la concentration estimée comme induisant un indice de stimulation (IS) de 3. Pour examiner plus avant l'influence du vecteur d'application sur l'activité de sensibilisation, on a utilisé le LLNA pour déterminer l'activité de quatre allergènes de contact humains reconnus: isoeugénol et aldéhyde cinnamique, deux substances chimiques de parfumerie; la 3-diméthylaminopropylamine (une impureté sensibilisante de la cocamidopropyl bétaïne, un tensioactif utilisé dans les gels douches) et le dibromodicyanobutane (le composant sensibilisant de Euxyl K 400, un conservateur utilisé dans les cosmétiques). Les quatre produits chimiques ont été appliqués dans chacun de sept vecteurs différents (acétone: huile d'olive [4: 1]; diméthylsulfoxyde; méthyléthylcétone; diméthylformamide; propy- lène glycol; et deux mélanges 50: 50 et 90: 10 d'éthanol et d'eau). On observe que le vecteur dans lequel le produit chimique est présentéà l'épiderme peut avoir un effet marqué sur l'activité sensibilisatrice. Les valeurs EC3 vont de 0,9 à 4,9 % pour l'isoeugénol, de 0,5 à 1,7 % pour l'aldéhyde cinnamique, de 1,7 à > 10 % pour la diméthylaminopropylamine et de 0,4 à 6,4 % pour le dibromodicyanobutane. Ces données confirment que le vecteur dans lequel un produit chimique est mis en contact avec la peau a une influence importante sur le potentiel relatif de sensibilisation de la peau des produits chimiques, et peut avoir un impact significatif sur l'apparition de dermatite allergique par contact. Les données démontrent aussi l'utilité du LLNA comme méthode de prévision de ces effets et donc pour le développement d'évaluations plus précises des risques. [source]

Skin sensitization potency of isoeugenol and its dimers evaluated by a non-radioisotopic modification of the local lymph node assay and guinea pig maximization test

Simultaneous sensitivity to fragrances

BRITISH JOURNAL OF DERMATOLOGY, Issue 5 2006
D.A. Buckley
Summary Background, Cinnamal/cinnamic alcohol and isoeugenol/eugenol are pairs of related fragrance chemicals found in Fragrance Mix I (FM I), and thus are routinely tested in combination with other fragrances in the European standard patch test series. Their close structural similarity makes the occurrence of simultaneous sensitivity within these chemical pairs likely, although at present there are no robust data to support this hypothesis. Objectives, To establish the frequency of simultaneous reactions to these fragrance chemicals in patients with suspected fragrance allergy attending a contact dermatitis clinic; to provide evidence in support of proposed metabolic pathways; and to determine whether including all four separately in FM I is necessary to avoid missing a diagnosis of fragrance allergy. Methods, We analysed retrospectively the records of patients patch tested to the European standard series during the 15-year period 1984,98 for positive reactions to FM I. In a subset of patients tested to the constituents of FM I, positive reactions to cinnamal, cinnamic alcohol, isoeugenol and eugenol were sought. Data were analysed using 2 × 2 contingency tables (Fisher's exact test). Results, During this period, 23 660 patients were tested to the European standard series, of whom 1811 (7·7%) had positive reactions to FM I. Of the 1112 patients tested to the constituents of FM I, 934 had positive reactions to at least one constituent (total 1324 positive reactions to constituents). Of these 934, 826 also had positive reactions to FM I itself; 108 were negative to FM I but reacted to one or more of its constituents. One hundred and seventy-eight patients did not react to any of the breakdown constituents of FM I; 34 of these had positive reactions to FM I itself. Of 139 patients allergic to cinnamic alcohol, 87 were also allergic to cinnamal (63%), compared with 108 (11·1%) of 973 cinnamic alcohol-negative patients (P < 0·00001). Of 231 patients allergic to isoeugenol, 50 were also allergic to eugenol (22%), vs. 109 (12·4%) of 881 isoeugenol-negative patients (P = 0·0002). Conclusions, These data support in vitro experiments indicating that cinnamal and cinnamic alcohol may generate a common hapten and are consistent with the view that simultaneous sensitization to isoeugenol and eugenol occurs to a limited extent, despite their being metabolized via different pathways. In view of the substantial number of isolated reactions to each of these fragrance chemicals, all four should continue to be included separately as constituents of FM I. [source]

The frequency of fragrance allergy in patch-tested patients increases with their age

BRITISH JOURNAL OF DERMATOLOGY, Issue 5 2003
D.A. Buckley
Summary Background The most likely age of sensitization to fragrance chemicals is unknown. Objectives To investigate the frequency of allergy to the 8% fragrance mix (FM) in each decade of life in patients undergoing patch testing for the investigation of skin symptoms. Methods Patients (n = 23 846; 14 104 female and 9742 male) underwent patch testing to a standard series between 1 January 1984 and 31 December 1998. All data were recorded on a computerized database. Results We found that 8·4% of females and 6·4% of males were allergic to the FM. The frequency of fragrance allergy was low in the first two decades of life (2·5,3·4%). It gradually increased in females after the age of 20 years to peak in the 60s at 14·4% of those tested, with a decline to 11·6% in the 80s. The prevalence in males rose more slowly and peaked at 13·7% in the 70s, declining to 10·8% in the 80s. The youngest patients sensitized were aged 2 years. Conclusions These findings support the hypothesis that allergy to fragrance results from a combination of repeated environmental exposure and age-related susceptibility factors. [source]