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Volumn 68, Issue 3, 2013, Pages 129-138

Cinnamyl alcohol oxidizes rapidly upon air exposure

Author keywords

autoxidation; bioactivation; cinnamal; cinnamyl alcohol; concomitant reactions; epoxides; fragrance; local lymph node assay (LLNA); mass spectrometry; prehapten; prohapten

Indexed keywords

CINNAMALDEHYDE; CINNAMIC ACID; CINNAMYL ALCOHOL;

EID: 84874268430     PISSN: 01051873     EISSN: 16000536     Source Type: Journal    
DOI: 10.1111/cod.12009     Document Type: Article
Times cited : (43)

References (36)
  • 1
    • 0034331402 scopus 로고    scopus 로고
    • Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol
    • Smith C K, Moore C A, Elahi E N et al., Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Toxicol Appl Pharmacol 2000: 168: 189-199.
    • (2000) Toxicol Appl Pharmacol , vol.168 , pp. 189-199
    • Smith, C.K.1    Moore, C.A.2    Elahi, E.N.3
  • 2
    • 35248880520 scopus 로고    scopus 로고
    • The epidemiology of contact allergy in the general population -prevalence and main findings
    • Thyssen J P, Linneberg A, Menné T et al., The epidemiology of contact allergy in the general population -prevalence and main findings. Contact Dermatitis 2007: 57: 287-299.
    • (2007) Contact Dermatitis , vol.57 , pp. 287-299
    • Thyssen, J.P.1    Linneberg, A.2    Menné, T.3
  • 3
    • 24744454354 scopus 로고    scopus 로고
    • The European standard series in 9 European countries, 2002/2003 -First results of the European Surveillance System on Contact Allergies
    • Uter W, Hegewald J, Aberer W et al., The European standard series in 9 European countries, 2002/2003 -First results of the European Surveillance System on Contact Allergies. Contact Dermatitis 2005: 53: 136-145.
    • (2005) Contact Dermatitis , vol.53 , pp. 136-145
    • Uter, W.1    Hegewald, J.2    Aberer, W.3
  • 5
    • 38949130710 scopus 로고    scopus 로고
    • Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitizers
    • Karlberg A T, Bergström M A, Börje A, Luthman K, Nilsson J L., Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitizers. Chem Res Toxicol 2008: 21: 53-69.
    • (2008) Chem Res Toxicol , vol.21 , pp. 53-69
    • Karlberg, A.T.1    Bergström, M.A.2    Börje, A.3    Luthman, K.4    Nilsson, J.L.5
  • 6
    • 16244403967 scopus 로고    scopus 로고
    • Fragrance material review on cinnamyl alcohol
    • Letizia C S, Cocchiara J, Lalko J et al., Fragrance material review on cinnamyl alcohol. Food Chem Toxicol 2005: 43: 837-866.
    • (2005) Food Chem Toxicol , vol.43 , pp. 837-866
    • Letizia, C.S.1    Cocchiara, J.2    Lalko, J.3
  • 7
    • 0026656575 scopus 로고
    • Skin sensitization to cinnamic alcohol -the role of skin metabolism
    • Basketter D A., Skin sensitization to cinnamic alcohol -the role of skin metabolism. Acta Derm Venereol 1992: 72: 264-265.
    • (1992) Acta Derm Venereol , vol.72 , pp. 264-265
    • Basketter, D.A.1
  • 8
    • 0037291918 scopus 로고    scopus 로고
    • Cinnamic compound metabolism in human skin and the role metabolism may play in determining relative sensitisation potency
    • Cheung C, Hotchkiss S A M, Pease C K S., Cinnamic compound metabolism in human skin and the role metabolism may play in determining relative sensitisation potency. Int J Dermatol Sci 2003: 31: 9-19.
    • (2003) Int J Dermatol Sci , vol.31 , pp. 9-19
    • Cheung, C.1    Hotchkiss, S.A.M.2    Pease, C.K.S.3
  • 9
    • 34247273019 scopus 로고    scopus 로고
    • A skin-like cytochrome P450 cocktail activates prohaptens to contact allergenic metabolites
    • Bergström M A, Ott H, Carlsson A et al., A skin-like cytochrome P450 cocktail activates prohaptens to contact allergenic metabolites. J Invest Dermatol 2007: 127: 1145-1153.
    • (2007) J Invest Dermatol , vol.127 , pp. 1145-1153
    • Bergström, M.A.1    Ott, H.2    Carlsson, A.3
  • 10
    • 77951520059 scopus 로고    scopus 로고
    • High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens
    • Ott H, Wiederholt T, Bergström M A et al., High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens. Skin Pharmacol Physiol 2010: 23: 213-224.
    • (2010) Skin Pharmacol Physiol , vol.23 , pp. 213-224
    • Ott, H.1    Wiederholt, T.2    Bergström, M.A.3
  • 11
    • 0036323117 scopus 로고    scopus 로고
    • Practical and environmentally friendly epoxidation of olefins using oxone
    • Hashimoto N, Kanda A., Practical and environmentally friendly epoxidation of olefins using oxone. Org Process Res Dev 2002: 6: 405-406.
    • (2002) Org Process Res Dev , vol.6 , pp. 405-406
    • Hashimoto, N.1    Kanda, A.2
  • 12
    • 34247871204 scopus 로고    scopus 로고
    • Highly efficient epoxidation of electron-deficient olefins with tetrabutylammonium peroxydisulfate
    • Yang S G, Hwang J P, Park M Y et al., Highly efficient epoxidation of electron-deficient olefins with tetrabutylammonium peroxydisulfate. Tetrahedron 2007: 63: 5184-5188.
    • (2007) Tetrahedron , vol.63 , pp. 5184-5188
    • Yang, S.G.1    Hwang, J.P.2    Park, M.Y.3
  • 13
    • 37249003424 scopus 로고    scopus 로고
    • Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens
    • Sköld M, Hagvall L, Karlberg A-T., Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens. Contact Dermatitis 2008: 58: 9-14.
    • (2008) Contact Dermatitis , vol.58 , pp. 9-14
    • Sköld, M.1    Hagvall, L.2    Karlberg, A.-T.3
  • 14
    • 33845195281 scopus 로고    scopus 로고
    • Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals
    • Gerberick G F, Ryan C A, Dearman R J et al., Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals. Methods 2007: 41: 54-60.
    • (2007) Methods , vol.41 , pp. 54-60
    • Gerberick, G.F.1    Ryan, C.A.2    Dearman, R.J.3
  • 15
    • 45549085219 scopus 로고    scopus 로고
    • Chemical reactivity measurement and the predictive identification of skin sensitizers
    • Gerberick F, Aleksic M, Basketter D et al., Chemical reactivity measurement and the predictive identification of skin sensitizers. Altern Lab Anim 2008: 36: 215-242.
    • (2008) Altern Lab Anim , vol.36 , pp. 215-242
    • Gerberick, F.1    Aleksic, M.2    Basketter, D.3
  • 16
    • 0141991332 scopus 로고    scopus 로고
    • Classification of contact allergens according to potency: Proposals
    • Kimber I, Basketter D A, Butler M et al., Classification of contact allergens according to potency: proposals. Food Chem Toxicol 2003: 41: 1799-1809.
    • (2003) Food Chem Toxicol , vol.41 , pp. 1799-1809
    • Kimber, I.1    Basketter, D.A.2    Butler, M.3
  • 17
    • 56249123225 scopus 로고    scopus 로고
    • Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens
    • Hagvall L, Baron J M, Börje A et al., Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens. Toxicol Appl Pharmacol 2008: 233: 308-313.
    • (2008) Toxicol Appl Pharmacol , vol.233 , pp. 308-313
    • Hagvall, L.1    Baron, J.M.2    Börje, A.3
  • 18
    • 34250765328 scopus 로고    scopus 로고
    • Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization
    • Hagvall L, Bäcktorp 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.
    • (2007) Chem Res Toxicol , vol.20 , pp. 807-814
    • Hagvall, L.1    Bäcktorp, C.2    Svensson, S.3
  • 19
    • 0036310812 scopus 로고    scopus 로고
    • Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide
    • Sköld M, Börje A, Matura M et al., Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide. Contact Dermatitis 2002: 46: 267-272.
    • (2002) Contact Dermatitis , vol.46 , pp. 267-272
    • Sköld, M.1    Börje, A.2    Matura, M.3
  • 20
    • 1642273144 scopus 로고    scopus 로고
    • Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds
    • Elahi E N, Wright Z, Hinselwood D et al., Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds. Chem Res Toxicol 2004: 17: 301-310.
    • (2004) Chem Res Toxicol , vol.17 , pp. 301-310
    • Elahi, E.N.1    Wright, Z.2    Hinselwood, D.3
  • 21
    • 0017360784 scopus 로고
    • Mechanism of cinnamaldehyde sensitization
    • Majeti V A, Suskind R R., Mechanism of cinnamaldehyde sensitization. Contact Dermatitis 1977: 3: 16-18.
    • (1977) Contact Dermatitis , vol.3 , pp. 16-18
    • Majeti, V.A.1    Suskind, R.R.2
  • 22
    • 33745290408 scopus 로고    scopus 로고
    • Conjugated dienes as prohaptens in contact allergy: In vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation
    • Bergström M A, Luthman K, Nilsson J L G et al., Conjugated dienes as prohaptens in contact allergy: in vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation. Chem Res Toxicol 2006: 19: 760-769.
    • (2006) Chem Res Toxicol , vol.19 , pp. 760-769
    • Bergström, M.A.1    Luthman, K.2    Nilsson, J.L.G.3
  • 23
    • 71049153638 scopus 로고    scopus 로고
    • Investigation of peptide reactivity of pro-hapten skin sensitizers using a peroxidase-peroxide oxidation system
    • Gerberick G F, Troutman J A, Foertsch L M et al., Investigation of peptide reactivity of pro-hapten skin sensitizers using a peroxidase-peroxide oxidation system. Toxicol Sci 2009: 112: 164-174.
    • (2009) Toxicol Sci , vol.112 , pp. 164-174
    • Gerberick, G.F.1    Troutman, J.A.2    Foertsch, L.M.3
  • 24
    • 80051687443 scopus 로고    scopus 로고
    • The incorporation of lysine into the peroxidase peptide reactivity assay for skin sensitization assessments
    • Troutman J A, Foertsch L M, Kern P S et al., The incorporation of lysine into the peroxidase peptide reactivity assay for skin sensitization assessments. Toxicol Sci 2011: 122: 422-436.
    • (2011) Toxicol Sci , vol.122 , pp. 422-436
    • Troutman, J.A.1    Foertsch, L.M.2    Kern, P.S.3
  • 25
    • 77955871452 scopus 로고    scopus 로고
    • Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds
    • Vandebriel R J, Pennings J L A, Baken K A et al., Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds. Toxicol Sci 2010: 117: 81-89.
    • (2010) Toxicol Sci , vol.117 , pp. 81-89
    • Vandebriel, R.J.1    Pennings, J.L.A.2    Baken, K.A.3
  • 26
    • 77952950728 scopus 로고    scopus 로고
    • Performance of a novel keratinocyte-based reporter cell line to screen skin sensitizers in vitro
    • Emter R, Ellis G, Natsch A., Performance of a novel keratinocyte-based reporter cell line to screen skin sensitizers in vitro. Toxicol Appl Pharmacol 2010: 245: 281-290.
    • (2010) Toxicol Appl Pharmacol , vol.245 , pp. 281-290
    • Emter, R.1    Ellis, G.2    Natsch, A.3
  • 27
    • 80053046796 scopus 로고    scopus 로고
    • Experimental and theoretical investigations of the autoxidation of geranial: A dioxolane hydroperoxide identified as a skin sensitizer
    • Hagvall L, Bäcktorp C, Norrby P-O et al., Experimental and theoretical investigations of the autoxidation of geranial: a dioxolane hydroperoxide identified as a skin sensitizer. Chem Res Toxicol 2011: 24: 1507-1515.
    • (2011) Chem Res Toxicol , vol.24 , pp. 1507-1515
    • Hagvall, L.1    Bäcktorp, C.2    Norrby, P.-O.3
  • 29
    • 33745924673 scopus 로고    scopus 로고
    • Cross-reactions in patch testing with ketoprofen, fragrance mix and cinnamic derivatives
    • Girardin P, Vigan M, Humbert P et al., Cross-reactions in patch testing with ketoprofen, fragrance mix and cinnamic derivatives. Contact Dermatitis 2006: 55: 126-128.
    • (2006) Contact Dermatitis , vol.55 , pp. 126-128
    • Girardin, P.1    Vigan, M.2    Humbert, P.3
  • 30
    • 34250629329 scopus 로고    scopus 로고
    • Sensitization to 26 fragrances to be labelled according to current European regulation -results of the IVDK and review of the literature
    • Schnuch A, Uter W, Geier J et al., 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: 1-10.
    • (2007) Contact Dermatitis , vol.57 , pp. 1-10
    • Schnuch, A.1    Uter, W.2    Geier, J.3
  • 31
    • 0030888041 scopus 로고    scopus 로고
    • Reaktionen auf Zimtalkohol und Zimtaldehyd
    • Geier J, Schnuch A., Reaktionen auf Zimtalkohol und Zimtaldehyd. Dermatosen 1997: 45: 29-30.
    • (1997) Dermatosen , vol.45 , pp. 29-30
    • Geier, J.1    Schnuch, A.2
  • 32
    • 0030949496 scopus 로고    scopus 로고
    • Contact allergy to oxidized d-limonene among dermatitis patients
    • Karlberg A T, DoomsGoossens A., Contact allergy to oxidized d-limonene among dermatitis patients. Contact Dermatitis 1997: 36: 201-206.
    • (1997) Contact Dermatitis , vol.36 , pp. 201-206
    • Karlberg, A.T.1    Doomsgoossens, A.2
  • 33
    • 0036828127 scopus 로고    scopus 로고
    • Oxidized citrus oil (R-limonene): A frequent skin sensitizer in Europe
    • 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: 709-714.
    • (2002) J Am Acad Dermatol , vol.47 , pp. 709-714
    • Matura, M.1    Goossens, A.2    Bordalo, O.3
  • 34
    • 20544478198 scopus 로고    scopus 로고
    • Selected oxidized fragrance terpenes are common contact allergens
    • Matura M, Sköld M, Börje A et al., Selected oxidized fragrance terpenes are common contact allergens. Contact Dermatitis 2005: 52: 320-328.
    • (2005) Contact Dermatitis , vol.52 , pp. 320-328
    • Matura, M.1    Sköld, M.2    Börje, A.3
  • 35
    • 33749581267 scopus 로고    scopus 로고
    • Not only oxidized R-(+)- but also S-(-)-limonene is a common cause of contact allergy in dermatitis patients in Europe
    • Matura M, Sköld M, Börje A et al., Not only oxidized R-(+)- but also S-(-)-limonene is a common cause of contact allergy in dermatitis patients in Europe. Contact Dermatitis 2006: 55: 274-279.
    • (2006) Contact Dermatitis , vol.55 , pp. 274-279
    • Matura, M.1    Sköld, M.2    Börje, A.3
  • 36
    • 74949115964 scopus 로고    scopus 로고
    • Linalool -a significant contact sensitizer after air exposure
    • Christensson J B, Matura M, Gruvberger B et al., Linalool -a significant contact sensitizer after air exposure. Contact Dermatitis 2010: 62: 32-41.
    • (2010) Contact Dermatitis , vol.62 , pp. 32-41
    • Christensson, J.B.1    Matura, M.2    Gruvberger, B.3


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