Limonene and linalool hydroperoxides review: Pros and cons for routine patch testing.
allergic contact dermatitis
hydroperoxides
limonene
linalool
patch test
Journal
Contact dermatitis
ISSN: 1600-0536
Titre abrégé: Contact Dermatitis
Pays: England
ID NLM: 7604950
Informations de publication
Date de publication:
Jul 2022
Jul 2022
Historique:
revised:
29
01
2022
received:
14
11
2021
accepted:
02
02
2022
pubmed:
6
2
2022
medline:
15
6
2022
entrez:
5
2
2022
Statut:
ppublish
Résumé
Limonene and linalool are among the most common fragrance terpenes used in everyday products. They are pre-haptens, forming hydroperoxides (Lim-OOHs, Lin-OOHs) upon oxidation and inducing frequent positive patch test reactions in patients with dermatitis, and yet they are not routinely tested in Europe. This review evaluates current patch testing with Lim-OOHs and Lin-OOHs by asking whether hydroperoxide patch testing is warranted, examining the difficulties or challenges related to reading and interpreting hydroperoxide patch test results with currently available material, and assessing their relevance. Studies are increasingly pointing to high percentages of positive reactions in patients consecutively patch tested with these oxidized products. An association between a positive clinical history and a strong patch test reaction has been described, but problems with doubtful/irritant reactions have also been reported. Considering the high frequency of relevant positive reactions, the incorporation of Lim-OOHs 0.3% and Lin-OOHs 1% in the baseline series may be justified. Since exposure, sensitization, and elicitation limits of Lim-OOHs and Lin-OOHs in the products still need to be better determined, an assessment of previous exposure, possible sensitizations, and reactions may help to improve the clinical assessment.
Substances chimiques
Acyclic Monoterpenes
0
Allergens
0
Monoterpenes
0
Perfume
0
Terpenes
0
Limonene
9MC3I34447
Hydrogen Peroxide
BBX060AN9V
linalool
D81QY6I88E
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
1-12Informations de copyright
© 2022 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.
Références
Thyssen JP, Linneberg A, Menné T, Nielsen NH, Johansen JD. The prevalence and morbidity of sensitization to fragrance mix I in the general population. Br J Dermatol. 2009;161(1):95-101. doi:10.1111/j.1365-2133.2009.09157.x
Uter W, Johansen JD, Börje A, et al. Categorization of fragrance contact allergens for prioritization of preventive measures: clinical and experimental data and consideration of structure-activity relationships. Contact Dermatitis. 2013;69(4):196-230. doi:10.1111/cod.12117
Diepgen TL, Ofenloch R, Bruze M, et al. Prevalence of fragrance contact allergy in the general population of five European countries: a cross-sectional study. Br J Dermatol. 2015;173(6):1411-1419. doi:10.1111/bjd.14151
Marks JG, Belsito DV, DeLeo VA, et al. North American contact dermatitis group patch test results for the detection of delayed-type hypersensitivity to topical allergens. J Am Acad Dermatol. 1998;38(6):911-918. doi:10.1016/S0190-9622(98)70587-0
Nardelli A, Carbonez A, Ottoy W, Drieghe J, Goossens A. Frequency of and trends in fragrance allergy over a 15-year period. Contact Dermatitis. 2008;58(3):134-141. doi:10.1111/j.1600-0536.2007.01287.x
de Groot AC, Schmidt E. Essential oils, part III: chemical composition. Dermatitis. 2016;27(4):161-169. doi:10.1097/DER.0000000000000193
Buckley DA. Fragrance ingredient labelling in products on sale in the U.K. Br J Dermatol. 2007;157(2):295-300. doi:10.1111/j.1365-2133.2007.08018.x
Rastogi SC, Heydorn S, Johansen JD, Basketter DA. Fragrance chemicals in domestic and occupational products. Contact Dermatitis. 2001;45(4):221-225. doi:10.1034/j.1600-0536.2001.450406.x
Rastogi SC, Menné T, Johansen JD. The composition of fine fragrances is changing. Contact Dermatitis. 2003;48(3):130-132. doi:10.1034/j.1600-0536.2003.00035.x
Bennike NH, Oturai NB, Müller S, et al. Fragrance contact allergens in 5588 cosmetic products identified through a novel smartphone application. J Eur Acad Dermatol Venereol. 2018;32(1):79-85. doi:10.1111/jdv.14513
Yazar K, Johnsson S, Lind ML, Boman A, Lidén C. Preservatives and fragrances in selected consumer-available cosmetics and detergents. Contact Dermatitis. 2010;64(5):265-272. doi:10.1111/j.1600-0536.2010.01828.x
Bråred Christensson J, Andersen KE, Bruze M, et al. Positive patch test reactions to oxidized limonene: exposure and relevance. Contact Dermatitis. 2014;71(5):264-272. doi:10.1111/cod.12285
Matura M, Goossens A, Bordalo O, et al. Oxidized citrus oil (R-limonene): A frequent skin sensitizer in Europe. J Am Acad Dermatol. 2002;47(5):709-714. doi:10.1067/mjd.2002.124817
Sköld M, Börje A, Matura M, Karlberg AT. Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide. Contact Dermatitis. 2002;46(5):267-272. doi:10.1034/j.1600-0536.2002.460504.x
Björkman YA, Hagvall L, Siwmark C, Niklasson B, Karlberg AT, Christensson JB. Air-oxidized linalool elicits eczema in allergic patients - a repeated open application test study. Contact Dermatitis. 2014;70(3):129-138. doi:10.1111/cod.12163
Bennike NH, Palangi L, Christensson JB, et al. Allergic contact dermatitis caused by hydroperoxides of limonene and dose-response relationship-A repeated open application test (ROAT) study. Contact Dermatitis. 2019;80(4):208-216. doi:10.1111/cod.13168
Wilkinson SM, Badulici S, Giménez-Arnau A, et al. The European baseline series: criteria for allergen inclusion with reference to formaldehyde releasers. Contact Dermatitis. 2021;85(2):125-128. doi:10.1111/cod.13836
Lepoittevin JP. Molecular aspects in allergic and irritant contact dermatitis. Contact Dermatitis. 5ft ed. New York: Springer-Verlag; 2011:91-110.
Kao D, Chaintreau A, Lepoittevin JP, Giménez-Arnau E. Synthesis of allylic hydroperoxides and EPR spin-trapping studies on the formation of radicals in iron systems as potential initiators of the sensitizing pathway. J Org Chem. 2011;76(15):6188-6200. doi:10.1021/jo200948x
Kao D, Chaintreau A, Lepoittevin JP, Giménez-Arnau E. Mechanistic studies on the reactivity of sensitizing allylic hydroperoxides: investigation of the covalent modification of amino acids by carbon-radical intermediates. Toxicol Res. 2014;3(4):278-289. doi:10.1039/C3TX50109D
Lauricella R, Tuccio B. Detection and characterization of free radicals after spin trapping. Electron Paramagnetic Resonance Spectroscopy. Cham: Springer; 2020:51-82.
Kuresepi S, Vileno B, Lepoittevin JP, Giménez-Arnau E. Mechanistic insights on skin sensitization to linalool hydroperoxides: EPR evidence on radical intermediates formation in reconstructed human epidermis and 13C NMR reactivity studies with thiol residues. Chem Res Toxicol. 2020;33(7):1922-1932. doi:10.1021/acs.chemrestox.0c00125
Kuresepi S, Vileno B, Turek P, Lepoittevin JP, Giménez-Arnau E. Potential of EPR spin-trapping to investigate in situ free radicals generation from skin allergens in reconstructed human epidermis: cumene hydroperoxide as proof of concept. Free Radic Res. 2018;52(2):171-179. doi:10.1080/10715762.2017.1420906
Sahli F, Sousa MSE, Vileno B, et al. Understanding the skin sensitization capacity of ascaridole: a combined study of chemical reactivity and activation of the innate immune system (dendritic cells) in the epidermal environment. Arch Toxicol. 2019;93(5):1337-1347. doi:10.1007/s00204-019-02444-3
Test No. 439. In Vitro Skin Irritation: Reconstructed Human Epidermis Test Method. https://www.oecd-ilibrary.org/environment/test-no-439-in-vitro-skin-irritation-reconstructed-human-epidermis-test-method_9789264242845-en
Lichter J, Silva E, Sousa M, Peter N, et al. Skin sensitization to fragrance hydroperoxides: interplay between dendritic cells, keratinocytes and free radicals. Br J Dermatol. 2020;18(6):1143-1152. doi:10.1111/bjd.19685
Sahli F, Godard A, Vileno B, Lepoittevin JP, Giménez-Arnau E. Formation of methyl radicals derived from cumene hydroperoxide in reconstructed human epidermis: an EPR spin trapping confirmation by using 13C-substitution. Free Radic Res. 2019;53(7):737-747. doi:10.1080/10715762.2019.1624741
Karlberg AT, Dooms-Goossens A. Contact allergy to oxidized d-limonene among dermatitis patients. Contact Dermatitis. 1997;36(4):201-206. doi:10.1111/j.1600-0536.1997.tb00270.x
Matura M, Sköld M, Börje A, et al. Selected oxidized fragrance terpenes are common contact allergens. Contact Dermatitis. 2005;52(6):320-328. doi:10.1111/j.0105-1873.2005.00605.x
Bråred Christensson J, Matura M, Gruvberger B, Bruze M, Karlberg AT. Linalool - a significant contact sensitizer after air exposure. Contact Dermatitis. 2010;62(1):32-41. doi:10.1111/j.1600-0536.2009.01657.x
Bråred Christensson J, Andersen KE, Bruze M, et al. Air-oxidized linalool: a frequent cause of fragrance contact allergy. Contact Dermatitis. 2012;67(5):247-259. doi:10.1111/j.1600-0536.2012.02134.x
Bråred Christensson J, Andersen KE, Bruze M, et al. An international multicentre study on the allergenic activity of air-oxidized R-limonene. Contact Dermatitis. 2013;68(4):214-223. doi:10.1111/cod.12036
Deza G, García-Bravo B, Silvestre JF, et al. Contact sensitization to limonene and linalool hydroperoxides in Spain: a GEIDAC* prospective study. Contact Dermatitis. 2017;76(2):74-80. doi:10.1111/cod.12714
Wlodek C, Penfold CM, Bourke JF, et al. Recommendation to test limonene hydroperoxides 0·3% and linalool hydroperoxides 1·0% in the British baseline patch test series. Br J Dermatol. 2017;177(6):1708-1715. doi:10.1111/bjd.15648
Sukakul T, Bruze M, Mowitz M, et al. Contact allergy to oxidized linalool and oxidized limonene: patch testing in consecutive patients with dermatitis. Contact Dermatitis. 2021;86(1):15-24. doi:10.1111/cod.13980
Bruusgaard-Mouritsen MA, Garvey LH, Johansen JD. Facial contact dermatitis caused by cosmetic-relevant allergens. Contact Dermatitis. 2021;85(6):650-659. doi:10.1111/cod.13966
Noë E, Huygens S, Morren MA, Garmyn M, Goossens A, Gilissen L. Contact allergy in a paediatric population observed in a tertiary referral Centre in Belgium. Contact Dermatitis. 2022;86(1):3-8. doi:10.1111/cod.13975
Bråred Christensson J, Forsström P, Wennberg AM, Karlberg AT, Matura M. Air oxidation increases skin irritation from fragrance terpenes. Contact Dermatitis. 2009;60(1):32-40. doi:10.1111/j.1600-0536.2008.01471.x
Bråred Christensson J, Karlberg AT, Andersen KE, et al. Oxidized limonene and oxidized linalool - concomitant contact allergy to common fragrance terpenes. Contact Dermatitis. 2016;74(5):273-280. doi:10.1111/cod.12545
Audrain H, Kenward C, Lovell CR, et al. Allergy to oxidized limonene and linalool is frequent in the U.K. Br J Dermatol. 2014;171(2):292-297. doi:10.1111/bjd.13037
Uter W, Yazar K, Kratz EM, Mildau G, Lidén C. Coupled exposure to ingredients of cosmetic products: I. Fragrances. Contact Dermatitis. 2013;69(6):335-341. doi:10.1111/cod.12125
Bråred Christensson J, Johansson S, Hagvall L, Jonsson C, Börje A, Karlberg AT. Limonene hydroperoxide analogues differ in allergenic activity. Contact Dermatitis. 2008;59(6):344-352. doi:10.1111/j.1600-0536.2008.01442.x
Dittmar D, Schuttelaar MLA. Contact sensitization to hydroperoxides of limonene and linalool: results of consecutive patch testing and clinical relevance. Contact Dermatitis. 2019;80(2):101-109. doi:10.1111/cod.13137
LexUriServ.pdf; 2021. Accessed February 25, 2021. https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2003:066:0026:0035:EN:PDF
Bennike NH, Zachariae C, Johansen JD. Non-mix fragrances are top sensitizers in consecutive dermatitis patients -a cross-sectional study of the 26 EU-labelled fragrance allergens. Contact Dermatitis. 2017;77(5):270-279. doi:10.1111/cod.12822
Dendooven E, Foubert K, Goossens A, et al. Concomitant positive patch test reactions in FreeStyle-allergic patients sensitized to isobornyl acrylate. Contact Dermatitis. 2021;84(3):166-174. doi:10.1111/cod.13706
Mowitz M, Fornander L, Hosseiny S, Ryberg K, Bruze M. Patch testing with Isobornyl acrylate in 16 Swedish patients with contact dermatitis from glucose sensors and/or insulin pumps. Acta Derm Venereol. 2019;99(13):1286-1287. doi:10.2340/00015555-3256
Thomas AF, Bessière Y. Limonene. Nat Prod Rep. 1989;6(3):291-309. doi:10.1039/NP9890600291
Nanyan P. Fragrance allergens in hair removal cosmetic products. Dermatitis. 2019;30(4):268-271. doi:10.1097/DER.0000000000000491
Hagvall L, Sköld M, Bråredhristensson J, Börje A, Karlberg AT. Lavender oil lacks natural protection against autoxidation, forming strong contact allergens on air exposure. Contact Dermatitis. 2008;59(3):143-150. doi:10.1111/j.1600-0536.2008.01402.x
Sköld M, Hagvall L, Karlberg AT. Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens. Contact Dermatitis. 2008;58(1):9-14. doi:10.1111/j.1600-0536.2007.01262.x
Foti C, Zambonin CG, Conserva A, Casulli C, D'Accolti L, Angelini G. Occupational contact dermatitis to a limonene-based solvent in a histopathology technician. Contact Dermatitis. 2007;56(2):109-112. doi:10.1111/j.1600-0536.2007.00995.x
Gatica-Ortega ME, Pastor-Nieto MA, Schoendorff-Ortega C, Mollejo-Villanueva M, Giménez-Arnau A. Lymphomatoid contact dermatitis caused by limonene hydroperoxides confirmed by an exposure provocation test with the involved personal hygiene products. Contact Dermatitis. 2018;78(3):230-233. doi:10.1111/cod.12908
Elliott JF, Ramzy A, Nilsson U, Moffat W, Suzuki K. Severe intractable eyelid dermatitis probably caused by exposure to hydroperoxides of linalool in a heavily fragranced shampoo. Contact Dermatitis. 2017;76(2):114-115. doi:10.1111/cod.12738
Isaksson M, Karlberg AT, Nilsson U. Allergic contact dermatitis caused by oxidized linalool in a deodorant. Contact Dermatitis. 2019;81(3):213-214. doi:10.1111/cod.13276
Natsch A, Nägelin M, Leijs H, et al. Exposure source for skin sensitizing hydroperoxides of limonene and linalool remains elusive: an analytical market surveillance. Food Chem Toxicol. 2019;127:156-162. doi:10.1016/j.fct.2019.03.028
Kern S, Dkhil H, Hendarsa P, Ellis G, Natsch A. Detection of potentially skin sensitizing hydroperoxides of linalool in fragranced products. Anal Bioanal Chem. 2014;406(25):6165-6178. doi:10.1007/s00216-014-8066-3
Ramzi A, Ahmadi H, Sadiktsis I, Nilsson U. A two-dimensional non-comprehensive reversed/normal phase high-performance liquid chromatography/tandem mass spectrometry system for determination of limonene and linalool hydroperoxides. J Chromatogr A. 2018;1566:102-110. doi:10.1016/j.chroma.2018.06.056
Rudbäck J, Islam MN, Börje A, Nilsson U, Karlberg AT. Essential oils can contain allergenic hydroperoxides at eliciting levels, regardless of handling and storage. Contact Dermatitis. 2015;73(4):253-254. doi:10.1111/cod.12427
Karlberg AT, Magnusson K, Nilsson U. Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene. Ann Occup Hyg. 1994;38(2):199-207. doi:10.1093/annhyg/38.2.199
Johansen JD, Andersen KE, Menné T. Quantitative aspects of isoeugenol contact allergy assessed by use and patch tests. Contact Dermatitis. 1996;34(6):414-418. doi:10.1111/j.1600-0536.1996.tb02244.x
Karlberg AT, Börje A, Duus Johansen J, et al. Activation of non-sensitizing or low-sensitizing fragrance substances into potent sensitizers - prehaptens and prohaptens. Contact Dermatitis. 2013;69(6):323-334. doi:10.1111/cod.12127
Schnuch A, Uter W, Geier J, Lessmann H, Frosch PJ. Sensitization to 26 fragrances to be labelled according to current European regulation. Results of the IVDK and review of the literature. Contact Dermatitis. 2007;57(1):1-10. doi:10.1111/j.1600-0536.2007.01088.x
van Oosten EJ, Schuttelaar MLA, Coenraads PJ. Clinical relevance of positive patch test reactions to the 26 EU-labelled fragrances. Contact Dermatitis. 2009;61(4):217-223. doi:10.1111/j.1600-0536.2009.01605.x
Uter W, Geier J, Frosch P, Schnuch A. Contact allergy to fragrances: current patch test results (2005-2008) from the information network of departments of dermatology. Contact Dermatitis. 2010;63(5):254-261. doi:10.1111/j.1600-0536.2010.01759.x
Santucci B, Cristaudo A, Cannistraci C, Picardo M. Contact dermatitis to fragrances. Contact Dermatitis. 1987;16(2):93-95. doi:10.1111/j.1600-0536.1987.tb01386.x
de Groot AC, Liem DH, Nater JP, van Ketel WG. Patch tests with fragrance materials and preservatives. Contact Dermatitis. 1985;12(2):87-92. doi:10.1111/j.1600-0536.1985.tb01059.x
de Groot AC, Coenraads PJ, Bruynzeel DP, et al. Routine patch testing with fragrance chemicals in The Netherlands. Contact Dermatitis. 2000;42(3):184-185.
Ung CY, White JML, White IR, Banerjee P, McFadden JP. Patch testing with the European baseline series fragrance markers: a 2016 update. Br J Dermatol. 2018;178(3):776-780. doi:10.1111/bjd.15949
Nath NS, Liu B, Green C, Atwater AR. Contact allergy to Hydroperoxides of linalool and d-limonene in a US population. Dermatitis. 2017;28(5):313-316. doi:10.1097/DER.0000000000000318
Bennike NH, Lepoittevin JP, Johansen JD. Can contact allergy to p-phenylenediamine explain the high rates of terpene hydroperoxide allergy? - an epidemiological study based on consecutive patch test results. Contact Dermatitis. 2017;76(2):67-73. doi:10.1111/cod.12618
Sabroe RA, Holden CR, Gawkrodger DJ. Contact allergy to essential oils cannot always be predicted from allergy to fragrance markers in the baseline series. Contact Dermatitis. 2016;74(4):236-241. doi:10.1111/cod.12528
Christensson JB, Hellsén S, Börje A, Karlberg AT. Limonene hydroperoxide analogues show specific patch test reactions. Contact Dermatitis. 2014;70(5):291-299. doi:10.1111/cod.12195