Contact allergy to oxidized <i>d</i>‐limonene among dermatitis patients

Karlberg, Ann‐Therése; Dooms‐Goossens, A.

doi:10.1111/j.1600-0536.1997.tb00270.x

Cited by 155 publications

(136 citation statements)

References 24 publications

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“…Clinical studies with oxidized linalool and limonene show a high frequency of positive reactions among eczema patients (5,6,37), whereas the pure substances give very few reactions (38,39). Geraniol gives a higher frequency of positive reactions compared to limonene and linalool (8), and pure geraniol shows a higher sensitizing potency in the LLNA compared to pure linalool (3) and pure limonene (unpublished results), which means that allergic reactions to geraniol could occur.…”

Section: Resultsmentioning

confidence: 99%

Fragrance Compound Geraniol Forms Contact Allergens on Air Exposure. Identification and Quantification of Oxidation Products and Effect on Skin Sensitization

Hagvall

Bäcktorp

Svensson

et al. 2007

Chem. Res. Toxicol.

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Fragrances are common causes of contact allergy. Geraniol (trans-3,7-dimethyl-2,6-octadiene-1-ol) is an important fragrance terpene. It is considered a weak contact allergen and is used for fragrance allergy screening among consecutive dermatitis patients. Analogous to other monoterpenes studied, such as limonene and linalool, geraniol has the potential to autoxidize on air exposure and form highly allergenic compounds. The aim of the present study was to investigate and propose a mechanism for the autoxidation of geraniol at room temperature. To investigate whether allergenic compounds are formed, the sensitizing potency of geraniol itself, air-exposed geraniol, and its oxidation products was determined using the local lymph node assay in mice. The results obtained show that the allylic alcohol geraniol follows an oxidation pattern different from those of linalool and limonene, which autoxidize forming hydroperoxides as the only primary oxidation products. The autoxidation of geraniol follows two paths, originating from allylic hydrogen abstraction near the two double bonds. From geraniol, hydrogen peroxide is primarily formed together with aldehydes geranial and neral from a hydroxyhydroperoxide. In addition, small amounts of a hydroperoxide are formed, analogous to the formation of the major linalool hydroperoxide. The autoxidation of geraniol greatly influenced the sensitizing effect of geraniol. The oxidized samples had moderate sensitizing capacity, quite different from that of pure geraniol. The hydroperoxide formed is believed to be the major contributor to allergenic activity, together with the aldehydes geranial and neral. On the basis of the present study and previous experience, we recommend that the possibility of autoxidation and the subsequent formation of contact allergenic oxidation products are considered in risk assessments performed on fragrance terpenes.

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Section: Resultsmentioning

confidence: 99%

Fragrance Compound Geraniol Forms Contact Allergens on Air Exposure. Identification and Quantification of Oxidation Products and Effect on Skin Sensitization

Hagvall

Bäcktorp

Svensson

et al. 2007

Chem. Res. Toxicol.

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128

200

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“…The observation that contaminants or degradation products, but not the parent compound, are responsible for skin allergenicity has already been reported for other families of chemicals [8,23,24,25]. In perfume products, d -limonene and linalool are unreactive molecules devoid of sensitizing properties.…”

Section: Discussionmentioning

confidence: 98%

The Skin Allergenic Properties of Chemicals May Depend on Contaminants – Evidence from Studies on Coumarin

Vocanson

Goujon

Chabeau

et al. 2006

Int Arch Allergy Immunol

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Background/Aims: Positive patch tests are considered representative of a contact allergy to the tested chemical. However, contaminants and derivatives rather than the suspected chemical itself could be responsible for the allergic skin reactions. Here, we tested the importance of contaminants in the sensitizing and allergenic properties of coumarin in mice and humans. Coumarin, an ingredient in cosmetics and fragrances, was chosen as the reference chemical since conflicting results have been obtained regarding its ability to induce contact allergy. In some chemical preparations, this could be explained by the presence of coumarin derivatives endowed with allergenic properties. Methods: In mice, three different coumarin preparations were tested in the local lymph node assay. In humans, we assessed the irritant and allergenic properties of highly pure coumarin in nonallergic and fragrance-allergic patients. Results: Pure coumarin did not exhibit irritant or sensitizing properties in the local lymph node assay. In contrast, two other commercially available coumarins and three contaminants that were detected in these coumarin preparations were identified as weak and moderate sensitizers, respectively. In humans, pure coumarin was extremely well tolerated since only 1 out of 512 patients exhibited a positive patch test to the chemical. Conclusions: These results indicate that coumarin cannot be considered as a common contact allergen and further emphasize that purity of chemicals is mandatory for the assessment of their allergenicity.

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“…In this way, patients reacting to oxidized d-limonene can have different allergies. Testing with isolated haptens will not detect all cases of contact allergy caused by oxidized d-limonene (19).…”

Section: Classification Of Limonenementioning

confidence: 99%

Regulatory classification of substances oxidized to skin sensitizers on exposure to air

et al. 1999

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Regulatory classification of substances in the European Union (EU) is intended to identify their hazardous toxicological properties in a formal and harmonized manner. In the regulatory work, a specific chemical with its molecular structure is classified as a skin sensitizer. This implies that the compound is stable throughout its lifetime. The purpose of the present paper is to discuss the problem of skin sensitizing oxidation/degradation products formed by air exposure of various materials or substances with very low allergenic activity. In regulatory classification work on skin sensitizers, the intrinsic suspectibility of a chemical to air oxidation (autoxidation) should be taken into consideration. We give examples of natural terpenoid materials, but the concept of allergens formed by air oxidation can apply to other materials widely used in industrial products. If a positive classification is made for a substance with a known chemical structure, a note should indicate that the primary chemical structure of the notified substance is not a skin sensitizer, but that (some of) its oxidation products are. Complex mixtures which inevitably contain sensitizing oxidation products should (on the basis of sufficient evidence) be classified as skin sensitizing.

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Contact allergy to oxidized d‐limonene among dermatitis patients

Cited by 155 publications

References 24 publications

Fragrance Compound Geraniol Forms Contact Allergens on Air Exposure. Identification and Quantification of Oxidation Products and Effect on Skin Sensitization

Fragrance Compound Geraniol Forms Contact Allergens on Air Exposure. Identification and Quantification of Oxidation Products and Effect on Skin Sensitization

The Skin Allergenic Properties of Chemicals May Depend on Contaminants – Evidence from Studies on Coumarin

Regulatory classification of substances oxidized to skin sensitizers on exposure to air

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