Oxidized citrus oil (R-limonene): A frequent skin sensitizer in Europe

Matura, Mihály; Goossens, An; Bordalo, Olívia; García-Bravo, Begoñá; Magnussona, Kerstin; Wrangsjö, Karin; Karlberg, Ann‐Therése

doi:10.1067/mjd.2002.124817

Cited by 112 publications

(116 citation statements)

References 18 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(8), and pure geraniol shows a higher sensitizing potency in the LLNA compared to pure linalool (3) and pure limonene (unpublished results), which means that allergic reactions to geraniol could occur.…”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%

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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%

“…The primary oxidation products, the hydroperoxides, are strong contact allergens (2,4). Clinical studies have shown oxidized limonene and linalool to be frequent causes of contact allergy (5,6).…”

Section: Introductionmentioning

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.

Self Cite

123

200

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“…It has also been verified by Avalos-Peralta et al that there is an important association between work in the food industry (mostly of citrus fruits) and allergy to MP (4). Also, Matura et aI., in 2002 noticed in their study a high number of concomitant reactions to FM, balsam of Peru and colophonium in the patients with positive reactions to oxidized limonene compared with those who were negative (2).…”

Section: Discussionmentioning

confidence: 99%

“…Although the non-oxidized R-(+)-limonene itself is not allergic, it easily forms allergenic products (such as limonene oxide, limonene hydroperoxides, and R-(-)-carvone) due to autoxidation during handling and storage. Clinical aspects suggest that oxidized limonene is an ubiquitous allergen involved also in occupational allergic dermatitis (2).…”

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confidence: 99%

Contact Allergy to Limonene from a Home-Made Cosmetic

et al. 2012

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Contact allergy to fragrances is very common. It is the second sensitizer in contact allergic dermatitis, after nickel sulphate. The fragrance mix and Balsam of Peru affects about 50-80% of patients affected by fragrance allergy, but the study of recent literature highlights new markers implicated in the pathogenesis of this dermatitis. We report an unusual case of contact allergy to Iimonene in a young woman after daily Use of a self-made cosmetic product containing lemon juice and peel (rich in limonene), with a positive reaction to Balsam of Peru to patch test and a positive reaction to patch by patch performed with her cosmetic and lemon peel. This simultaneous sensitization has been previously described in literature.

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“…Allergenic activity could be due to oxidised derivatives, such as peroxides, as in case of limonene and linalool. On the contrary, phenols present in natural essential oils (lavender), have antioxidant properties and can protect from allergenic reactions [16][17][18][19][20][21][22][23][24]. Several publications have described the use of Gas Chromatography-Mass Spectrometry (GC-MS) technique in the qualitative and quantitative analysis of many compounds present in essential oils and perfumes [25][26][27][28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%