Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide

Sköld, Maria; Börje, Anna; Matura, Mihály; Karlberg, Ann‐Therése

doi:10.1034/j.1600-0536.2002.460504.x

Cited by 129 publications

(130 citation statements)

References 22 publications

(25 reference statements)

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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: 99%

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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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Section: Discussionmentioning

confidence: 99%

“…In perfume products, d -limonene and linalool are unreactive molecules devoid of sensitizing properties. However, upon air exposure, d -limonene and linalool give rise to oxidation products which behave as contact sensitizers [24] and can induce ACD.…”

Section: Discussionmentioning

confidence: 99%

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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“…European legislators have become increasingly aware of the allergenic properties of many common essential oil constituents, and in 2003, the 7th Amendment to the European Cosmetic Directive required that cosmetic products containing any of 26 natural products, including linalool, be labeled as potentially allergenic [20]. While linalool itself may have limited allergenic properties, it can auto-oxidize upon air exposure into a hyperoxide species [21] which can lead to contact allergy responses in mice [22]. In a study of 1511 dermatitis patients, auto-oxidized linalool was shown to induce allergenic responses in 1.3 % of those tested, with 1.1 % of patients sensitive to the linalool hyperoxide fraction, using patch tests [23].…”

Section: Studies In Human Subjectsmentioning

confidence: 99%

Biosynthesis and Therapeutic Properties ofLavandulaEssential Oil Constituents

Woronuk

Demissie²,

Rheault³

et al. 2010

Planta Med

179

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“…Due to the high susceptibility of VO to photo and thermal oxidation, it is very common for appearance L. Bajerski, L. R. Michels, L. M. Colomé, E. A. Bender, R. J. Freddo, F. Bruxel, S. E. Haas 348 modification and allergic reactions to appear, caused under the skin by formulations with these compositions (Vigan, 2010;Hammer et al, 2006;Sköld et al, 2002;Neumann, Garcia, 1992). Therefore, the safety of the active elements and the use is limited to increase the concentration of these oils in the formulations.…”

Section: Introductionmentioning

confidence: 99%

The use of Brazilian vegetable oils in nanoemulsions: an update on preparation and biological applications

Bajerski

Michels

Colomé

et al. 2016

Braz. J. Pharm. Sci.

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Vegetable oils present important pharmacological properties, which gained ground in the pharmaceutical field. Its encapsulation in nanoemulsions is considered a promising strategy to facilitate the applicability of these natural compounds and to potentiate the actions. These formulations offer several advantages for topical and systemic delivery of cosmetic and pharmaceutical agents including controlled droplet size, protection of the vegetable oil to photo, thermal and volatilization instability and ability to dissolve and stabilize lipophilic drugs. For these reasons, the aim of this review is to report on some characteristics, preparation methods, applications and especially analyze recent research available in the literature concerning the use of vegetable oils with therapeutic characteristics as lipid core in nanoemulsions, specially from Brazilian flora, such as babassu (Orbignya oleifera), aroeira (Schinus molle L.), andiroba (Carapa guaianiensis), casca-de-anta (Drimys brasiliensis Miers), sucupira (Pterodon emarginatus Vogel) and carqueja doce (Stenachaenium megapotamicum) oils.Uniterms: Plant oils/nanoemulsions/preparation. Plant oils/biological applications. INTRODUCTIONThe use of submicrometric colloidal nanocarriers such as nanoparticles (NP) lipid and polymeric, nanoemulsions (NE), microemulsions (ME), liposomes, and polymeric micelles is considered a promising system in the pharmaceutical field, because they have numerous advantages over traditional formulations such as: sustained release of the active element; solubilization of lipophilic molecules; use for different routes of administration; protection from chemical and enzymatic degradation of labile molecules; reduction of vegetable oils (VO) volatilization, side effects and dose (Mäder, Mehnert, 2005;Mehnert, Mäder, 2001;Gref, Couvreour, 2006;Couvreur, Vauthier, 2006; Panyam, Labhasetwar, 2003;Soppimath et al., 2001;Ai et al., 2011; Contri et al., 2012;Contri et al., 2014;Dimer et al., 2014;Severino et al., 2015;Frank et al., 2015;Asbahani et al., 2015). However, all systems differ thermodynamic stability, structure, chemical composition, efficiency encapsulation and types of application (Mäder, Mehnert, 2005;Ai et al., 2011).The development of suitable nanocarriers for pharmaceutical or cosmetic application requires the adequate selection of their adjuvants such as polymers for nanocapsules (NC), surfactants, and oils (Schaffazick et al., 2003;Alvarez-Román et al., 2001;Bouchemal et al., 2004;Friedrich et al., 2008). Recently, special attention has been given to the type of oily phase used as the core in the preparation of NE. VO has been preferred not only due to the concept that it is safe and biocompatible, but mainly because of the diversity of benefits, and the complex composition of fatty acids can exercise under the skin, protecting it against dehydration, solar radiation, inflammation, insect attack, microorganisms, and viruses (Tadros, Kessell, 2004;Bloise, 2003;Oyedeji, Okeke, 2010;Bakkali et. al., 2008;Harris, 2002; Contri et al, ...

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Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide

Cited by 129 publications

References 22 publications

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

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

Biosynthesis and Therapeutic Properties ofLavandulaEssential Oil Constituents

The use of Brazilian vegetable oils in nanoemulsions: an update on preparation and biological applications

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