Contact allergy to citral and its constituents geranial and neral, coupled with reactions to the prehapten and prohapten geraniol.
RRID:SCR_001905
allergic contact dermatitis
autoxidation
citral
fragrance mix I
fragrance mix II
geranial
geraniol
neral
oxidized geraniol
patch testing
Journal
Contact dermatitis
ISSN: 1600-0536
Titre abrégé: Contact Dermatitis
Pays: England
ID NLM: 7604950
Informations de publication
Date de publication:
Jan 2020
Jan 2020
Historique:
received:
06
09
2019
revised:
20
09
2019
accepted:
22
09
2019
pubmed:
1
10
2019
medline:
30
5
2020
entrez:
1
10
2019
Statut:
ppublish
Résumé
Citral is commonly used as a fragrance and flavor material and consists of the aldehydes geranial and neral. Citral is included in fragrance mix (FM) II. Geranial and neral have also been identified in autoxidation of geraniol, a fragrance compound present in FM I. To study contact allergy to citral, geranial, and neral, and concomitant reactivity to oxidized geraniol and fragrance markers of the baseline series. A total of 1476 dermatitis patients with suspected allergic contact dermatitis were patch tested using geranial, neral, and citral, all 3.5% petrolatum (pet.) as well as geraniol 6.0% and oxidized geraniol 11% pet. in addition to the Swedish baseline series. Frequencies of positive reactions to citral, geranial, and neral were 2.9%, 3.4% and 1.9%, respectively. Together, citral and geranial gave 4.2% positive patch test reactions in consecutive dermatitis patients. In patients with positive reactions to citral or its components, 25% to 34% reacted to FM II and 61% reacted to oxidized geraniol. Patch testing with citral, its components, or oxidized geraniol detects contact allergic reactions not detected using the baseline series. Patch testing with pure geraniol was shown to be of little value. Geranial and neral, although closely chemically related, are concluded to be separate haptens.
Sections du résumé
BACKGROUND
BACKGROUND
Citral is commonly used as a fragrance and flavor material and consists of the aldehydes geranial and neral. Citral is included in fragrance mix (FM) II. Geranial and neral have also been identified in autoxidation of geraniol, a fragrance compound present in FM I.
OBJECTIVES
OBJECTIVE
To study contact allergy to citral, geranial, and neral, and concomitant reactivity to oxidized geraniol and fragrance markers of the baseline series.
METHODS
METHODS
A total of 1476 dermatitis patients with suspected allergic contact dermatitis were patch tested using geranial, neral, and citral, all 3.5% petrolatum (pet.) as well as geraniol 6.0% and oxidized geraniol 11% pet. in addition to the Swedish baseline series.
RESULTS
RESULTS
Frequencies of positive reactions to citral, geranial, and neral were 2.9%, 3.4% and 1.9%, respectively. Together, citral and geranial gave 4.2% positive patch test reactions in consecutive dermatitis patients. In patients with positive reactions to citral or its components, 25% to 34% reacted to FM II and 61% reacted to oxidized geraniol.
CONCLUSIONS
CONCLUSIONS
Patch testing with citral, its components, or oxidized geraniol detects contact allergic reactions not detected using the baseline series. Patch testing with pure geraniol was shown to be of little value. Geranial and neral, although closely chemically related, are concluded to be separate haptens.
Substances chimiques
Acyclic Monoterpenes
0
geraniol
L837108USY
citral
T7EU0O9VPP
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
31-38Subventions
Organisme : Edvard Welanders Stiftelse
Informations de copyright
© 2019 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.
Références
European Union. Directive 2003/15/EC of the European Parliament and of the Council of 27 February 2003 amending Council Directive 76/768/EEC in the approximation of the laws of the Member States relating to cosmetic products. Off J Eur Union. 2003;L66:26-35.
Buckley DA. Fragrance ingredient labelling in products on sale in the U.K. Br J Dermatol. 2007;157:295-300.
Rastogi SC, Heydorn S, Johansen JD, et al. Fragrance chemicals in domestic and occupational products. Contact Dermatitis. 2001;45:221-225.
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;32:79-85.
Lalko J, Api AM. Investigation of the dermal sensitization potential of various essential oils in the local lymph node assay. Food Chem Toxicol. 2006;44:739-746.
Lota ML, De Rocca Serra D, Tomi F, et al. Volatile components of peel and leaf oils of lemon and lime species. J Agric Food Chem. 2002;50:796-805.
Opdyke DLJ. Citral. Monographs on fragrance raw materials. Food Chem Toxicol. 1979;17:259-266.
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;77:270-279.
Mowitz M, Svedman C, Zimerson E, et al. Simultaneous patch testing with fragrance mix I, fragrance mix II and their ingredients in southern Sweden between 2009 and 2015. Contact Dermatitis. 2017;77:280-287.
Ung CY, White JML, White IR, et al. Patch testing with the European baseline series fragrance markers: a 2016 update. Br J Dermatol. 2018;178:776-780.
Hagvall L, Bråred Christensson J. Cross-reactivity between citral and geraniol - can it be attributed to oxidized geraniol? Contact Dermatitis. 2014;71:280-288.
Bruze M, Conde-Salazar L, Goossens A, et al. Thoughts on sensitizers in a standard patch test series. The European Society of Contact Dermatitis. Contact Dermatitis. 1999;41:241-250.
Uter W, Yazar K, Kratz EM, et al. Coupled exposure to ingredients of cosmetic products: I. Fragrances. Contact Dermatitis. 2013;69:335-341.
Nardelli A, Carbonez A, Drieghe J, et al. Results of patch testing with fragrance mix 1, fragrance mix 2, and their ingredients, and Myroxylon pereirae and Colophonium, over a 21-year period. Contact Dermatitis. 2013;68:307-313.
Hagvall L, Backtorp C, Svensson S, et al. Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization. Chem Res Toxicol. 2007;20:807-814.
Hagvall L, Baron JM, Börje A, et al. Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens. Toxicol Appl Pharmacol. 2008;233:308-313.
Hagvall L, Karlberg AT, Bråred Christensson J. Contact allergy to air-exposed geraniol: clinical observations and report of 14 cases. Contact Dermatitis. 2012;67:20-27.
Hagvall L, Karlberg AT, Bråred Christensson J. Finding the optimal patch test material and test concentration to detect contact allergy to geraniol. Contact Dermatitis. 2013;68:224-231.
Hagvall L, Bruze M, Engfeldt M, et al. Contact allergy to oxidized geraniol among Swedish dermatitis patients-A multicentre study by the Swedish Contact Dermatitis Research Group. Contact Dermatitis. 2018;79:232-238.
Nilsson U, Magnusson K, Karlberg O, et al. Are contact allergens stable in patch test preparations? Investigation of the degradation of d-limonene hydroperoxides in petrolatum. Contact Dermatitis. 1999;40:127-132.
Fregert S. Manual of Contact Dermatitis. 2nd ed. Copenhagen: Munksgaard; 1981.
Johansen JD, Aalto-Korte K, Agner T, et al. European Society of Contact Dermatitis guideline for diagnostic patch testing - recommendations on best practice. Contact Dermatitis. 2015;73:195-221.
Bruze M. Thoughts on how to improve the quality of multicentre patch test studies. Contact Dermatitis. 2016;74:168-174.
Micallef L, Rodgers P. eulerAPE: drawing area-proportional 3-Venn diagrams using ellipses. PLoS One. 2014;e101717:9.
Wolken WA, ten Have R, van der Werf MJ. Amino acid-catalyzed conversion of citral: cis-trans isomerization and its conversion into 6-methyl-5-hepten-2-one and acetaldehyde. J Agric Food Chem. 2000;48:5401-5405.
Nilsson AM, Gäfvert E, Salvador L, et al. Mechanism of the antigen formation of carvone and related alpha, beta-unsaturated ketones. Contact Dermatitis. 2001;44:347-356.
Rao PV, Mangala A, Towers GH, et al. Immunological activity of parthenin and its diasteriomer in persons sensitized by Parthenium hysterophorus L. Contact Dermatitis. 1978;4:199-203.
Wahlberg JE, Boman A. Contact sensitivity to quinidine sulfate from occupational exposure. Contact Dermatitis. 1981;7:27-31.
Lang M, Giménez-Arnau E, Lepoittevin JP. Is it possible to assess the allergenicity of mixtures based on in chemico methods? Preliminary results on common fragrance aldehydes. Flavour Frag J. 2017;32:63-71.
Raffalli C, Clouet E, Kuresepi S, et al. Fragrance allergens linalool and limonene allylic hydroperoxides in skin allergy: mechanisms of action focusing on transcription factor Nrf2. Toxicol Sci. 2018;161:139-148.
Bråred Christensson J, Andersen K, Bruze M, et al. Air-oxidized linalool - a frequent cause of fragrance allergy. Contact Dermatitis. 2012;67:247-259.
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;68:214-223.
Hagvall L, Berglund V, Bråred Christensson J. Air-oxidized linalyl acetate - an emerging fragrance allergen? Contact Dermatitis. 2015;72:216-223.
Audrain H, Kenward C, Lovell CR, et al. Allergy to oxidized limonene and linalool is frequent in the U.K. Br J Dermatol. 2014;171:292-297.
Bråred Christensson J, Andersen KE, Bruze M, et al. Positive patch test reactions to oxidized limonene: exposure and relevance. Contact Dermatitis. 2014;71:264-272.
Hagvall L, Niklasson IB, Luthman K, et al. Can the epoxides of cinnamyl alcohol and cinnamal show new cases of contact allergy? Contact Dermatitis. 2018;78:399-405.
Heisterberg MV, Menné T, Johansen JD. Contact allergy to the 26 specific fragrance ingredients to be declared on cosmetic products in accordance with the EU cosmetics directive. Contact Dermatitis. 2011;65:266-275.