메뉴 건너뛰기




Volumn 16, Issue 5, 2003, Pages 575-582

Structure elucidation, synthesis, and contact allergenic activity of a major hydroperoxide formed at autoxidation of the ethoxylated surfactant C12E5

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYPEROXY 3,6,9,12,15 PENTAOXAHEPTACOSAN 1 OL; 16 HYDROPEROXY 3,6,9,12,15 PENTAOXAHEPTACOSAN 1 OL; ALLERGEN; DIETHYLENEGLYCOL ETHYL ETHER; ETHYLENE DERIVATIVE; FORMALDEHYDE; HYDROPEROXIDE; HYDROPEROXIDE DERIVATIVE; HYDROXYALDEHYDE; IRRITANT AGENT; PENTAETHYLENE GLYCOL N DODECYL ETHER; PEROXIDE; POLY(ETHYLENE GLYCOL) ALDEHYDE; POLY(ETHYLENE GLYCOL) FORMATE; SURFACTANT; UNCLASSIFIED DRUG;

EID: 0037568107     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025609n     Document Type: Article
Times cited : (35)

References (39)
  • 2
    • 0001950575 scopus 로고
    • Surfactants and percutaneous absorption
    • (Scott, R. C., Guy, R. H., and Hadgraft, J., Eds.) IBC Technical Services, London
    • Walters, K. A. (1990) Surfactants and percutaneous absorption. In Prediction of Percutaneous Penetration (Scott, R. C., Guy, R. H., and Hadgraft, J., Eds.) pp 148-162, IBC Technical Services, London.
    • (1990) Prediction of Percutaneous Penetration , pp. 148-162
    • Walters, K.A.1
  • 3
    • 0029117477 scopus 로고
    • Surfactants and experimental irritant contact dermatitis
    • Effendy, I., and Maibach, H. I. (1995) Surfactants and experimental irritant contact dermatitis. Contact Dermatitis 33, 217-225.
    • (1995) Contact Dermatitis , vol.33 , pp. 217-225
    • Effendy, I.1    Maibach, H.I.2
  • 5
    • 15144358594 scopus 로고    scopus 로고
    • Contact allergens from surfactants. Atmospheric oxidation of polyoxyethylene alcohols, formation of ethoxylated aldehydes, and their allergenic activity
    • Bergh, M., Shao, L. P., Hagelthorn, G., Gäfvert, E., Nilsson, J. L. G., and Karlberg, A.-T. (1998) Contact allergens from surfactants. Atmospheric oxidation of polyoxyethylene alcohols, formation of ethoxylated aldehydes, and their allergenic activity. J. Pharm. Sci. 87, 276-282.
    • (1998) J. Pharm. Sci. , vol.87 , pp. 276-282
    • Bergh, M.1    Shao, L.P.2    Hagelthorn, G.3    Gäfvert, E.4    Nilsson, J.L.G.5    Karlberg, A.-T.6
  • 6
    • 0035080367 scopus 로고    scopus 로고
    • Identification and allergenic activity of hydroxyaldehydes - A new type of oxidation products from an ethoxylated nonionic surfactant
    • Bodin, A., Shao, L. P., Nilsson, J. L. G., and Karlberg, A.-T. (2001) Identification and allergenic activity of hydroxyaldehydes - a new type of oxidation products from an ethoxylated nonionic surfactant. Contact Dermatitis 44, 207-212.
    • (2001) Contact Dermatitis , vol.44 , pp. 207-212
    • Bodin, A.1    Shao, L.P.2    Nilsson, J.L.G.3    Karlberg, A.-T.4
  • 7
    • 0002667968 scopus 로고
    • Stability of the polyoxyethylene chain
    • (Schick, M. J., Ed) Surfactant Science Series, New York
    • Donbrow, M. (1987) Stability of the polyoxyethylene chain. In Nonionic Surfactants: Physical Chemistry (Schick, M. J., Ed) pp 1011-1067, Surfactant Science Series Volume 23, New York.
    • (1987) Nonionic Surfactants: Physical Chemistry , vol.23 , pp. 1011-1067
    • Donbrow, M.1
  • 8
    • 0345471456 scopus 로고    scopus 로고
    • Atmospheric oxidation of polyoxyethylene alcohols. Identification of ethoxylated formats as oxidation products and study of their contact allergenic activity
    • Bergh, M., Shao, L. P., Magnusson, K., Gäfvert, E., Nilsson, J. L. G., and Karlberg, A.-T. (1999) Atmospheric oxidation of polyoxyethylene alcohols. Identification of ethoxylated formats as oxidation products and study of their contact allergenic activity. J. Pharm. Sci. 88, 483-488.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 483-488
    • Bergh, M.1    Shao, L.P.2    Magnusson, K.3    Gäfvert, E.4    Nilsson, J.L.G.5    Karlberg, A.-T.6
  • 11
    • 0036241146 scopus 로고    scopus 로고
    • Novel hydroperoxides as primary oxidation products of a model ethoxylated surfactant
    • Bodin, A., Linnerborg, M., Nilsson, J. L. G., and Karlberg, A.-T. (2002) Novel hydroperoxides as primary oxidation products of a model ethoxylated surfactant. J. Surfactants Deterg. 5, 107-110.
    • (2002) J. Surfactants Deterg. , vol.5 , pp. 107-110
    • Bodin, A.1    Linnerborg, M.2    Nilsson, J.L.G.3    Karlberg, A.-T.4
  • 12
    • 0021042504 scopus 로고
    • Novel synthetic route to the key intermediate for hirsutic acid
    • Yamazaki, M., Shibasaki, M., and Ikegami, S. (1983) Novel synthetic route to the key intermediate for hirsutic acid. J. Org. Chem. 48, 4402-4404.
    • (1983) J. Org. Chem. , vol.48 , pp. 4402-4404
    • Yamazaki, M.1    Shibasaki, M.2    Ikegami, S.3
  • 13
    • 0030031320 scopus 로고    scopus 로고
    • Synthesis of 1,2-dioxanes, 1,2,4-trioxanes and 1,2,4-trioxepanes via cyclization of unsaturated hydroperoxyacetals
    • Dussault, P. H., and Davies, D. R. (1996) Synthesis of 1,2-dioxanes, 1,2,4-trioxanes and 1,2,4-trioxepanes via cyclization of unsaturated hydroperoxyacetals. Tetrahedron Lett. 37, 463-466.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 463-466
    • Dussault, P.H.1    Davies, D.R.2
  • 14
    • 12444337721 scopus 로고
    • Modified regioselectivity of abietic acid esters towards epoxidating agents
    • Lopez, J. C., Rabanal, R. M., and Valverde, S. (1986) Modified regioselectivity of abietic acid esters towards epoxidating agents. An. Quim. Ser. C 82, 245-249.
    • (1986) An. Quim. Ser. C , vol.82 , pp. 245-249
    • Lopez, J.C.1    Rabanal, R.M.2    Valverde, S.3
  • 15
    • 0033032928 scopus 로고    scopus 로고
    • Sensitizing potential of acetaldehyde and formaldehyde using a modified cumulative contact enhancement test (CCET)
    • Bergh, M., and Karlberg, A.-T. (1999) Sensitizing potential of acetaldehyde and formaldehyde using a modified cumulative contact enhancement test (CCET). Contact Dermatitis 40, 139-145.
    • (1999) Contact Dermatitis , vol.40 , pp. 139-145
    • Bergh, M.1    Karlberg, A.-T.2
  • 16
    • 0022293547 scopus 로고
    • The cumulative contact enhancement test
    • (Andersen, K. E., and Maibach, H. I., Eds.) Karger, Basel
    • Tsuchyia, S., Kondo, M., Okamoto, K., and Takase, Y. (1985) The cumulative contact enhancement test. In Contact Allergy Test in Guinea Pigs (Andersen, K. E., and Maibach, H. I., Eds.) pp 208-219, Karger, Basel.
    • (1985) Contact Allergy Test in Guinea Pigs , pp. 208-219
    • Tsuchyia, S.1    Kondo, M.2    Okamoto, K.3    Takase, Y.4
  • 17
    • 0002700897 scopus 로고
    • Peroxides in poly(ethylene glycol)s and poly-(ethylene glycol) derivatives
    • Rieger, M. M. (1975) Peroxides in poly(ethylene glycol)s and poly-(ethylene glycol) derivatives. Cosmet. Perfum. 90, 13-16.
    • (1975) Cosmet. Perfum. , vol.90 , pp. 13-16
    • Rieger, M.M.1
  • 18
    • 0027225375 scopus 로고
    • Quantitation of hydroperoxides in the aqueous solutions of nonionic surfactants using polysorbate 80 as the model surfactant
    • Ding, S. (1993) Quantitation of hydroperoxides in the aqueous solutions of nonionic surfactants using polysorbate 80 as the model surfactant. J. Pharm. Biomed. Anal. 2, 95-101.
    • (1993) J. Pharm. Biomed. Anal. , vol.2 , pp. 95-101
    • Ding, S.1
  • 19
    • 0031823605 scopus 로고    scopus 로고
    • Formation of formaldehyde and peroxides by air oxidation of high purity polyoxyethylene surfactants
    • Bergh, M., Magnusson, K., Nilsson, J. L. G., and Karlberg, A.-T. (1998) Formation of formaldehyde and peroxides by air oxidation of high purity polyoxyethylene surfactants. Contact Dermatitis 39, 14-20.
    • (1998) Contact Dermatitis , vol.39 , pp. 14-20
    • Bergh, M.1    Magnusson, K.2    Nilsson, J.L.G.3    Karlberg, A.-T.4
  • 21
    • 0033257840 scopus 로고    scopus 로고
    • Allergenic oxidation products in ethoxylated nonionic surfactants
    • Bergh, M. (1999) Allergenic oxidation products in ethoxylated nonionic surfactants. Acta Derm. Venerol. 79 (Suppl.), 1.
    • (1999) Acta Derm. Venerol. , vol.79 , Issue.SUPPL. , pp. 1
    • Bergh, M.1
  • 22
    • 0017668715 scopus 로고
    • Peroxides in detergents as interfacing factors in biochemical analysis
    • Lever, M. (1977) Peroxides in detergents as interfacing factors in biochemical analysis. Anal. Biochem. 83, 274-284.
    • (1977) Anal. Biochem. , vol.83 , pp. 274-284
    • Lever, M.1
  • 23
    • 0013297474 scopus 로고    scopus 로고
    • Allergens from the standard series
    • (Rycroft, R. J. G., Menné, T., Frosch, P. J., and Lepoittevin, J.-P., Eds.) Springer-Verlag, Berlin-Heidelberg
    • Andersen, K. E., White, I. R., and Goossens, A. (2001) Allergens from the standard series. In Textbook of Contact Dermatitis (Rycroft, R. J. G., Menné, T., Frosch, P. J., and Lepoittevin, J.-P., Eds.) pp 605-658, Springer-Verlag, Berlin-Heidelberg.
    • (2001) Textbook of Contact Dermatitis , pp. 605-658
    • Andersen, K.E.1    White, I.R.2    Goossens, A.3
  • 24
    • 0002093068 scopus 로고    scopus 로고
    • Hapten-protein interaction
    • (Lepoittevin, J.-P., Basketter, D. A., Goosens, A., and Karlberg, A.-T., Eds.) Springer-Verlag, Berlin
    • Roberts, D. W., and Lepoittevin, J.-P. (1998) Hapten-protein interaction. In Allergic Contact Dermatitis (Lepoittevin, J.-P., Basketter, D. A., Goosens, A., and Karlberg, A.-T., Eds.) pp 81-111, Springer-Verlag, Berlin.
    • (1998) Allergic Contact Dermatitis , pp. 81-111
    • Roberts, D.W.1    Lepoittevin, J.-P.2
  • 25
    • 0033787944 scopus 로고    scopus 로고
    • Synthesis and allergenic potential of a 15-hydroxyabietic acid-like model: Trapping of radical intermediates
    • Mutterer, V., Giménez Arnau, E., Karlberg, A.-T., and Lepoittevin, J.-P. (2000) Synthesis and allergenic potential of a 15-hydroxyabietic acid-like model: trapping of radical intermediates. Chem. Res. Toxicol. 13, 1028-1036.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 1028-1036
    • Mutterer, V.1    Giménez Arnau, E.2    Karlberg, A.-T.3    Lepoittevin, J.-P.4
  • 26
    • 0030869279 scopus 로고    scopus 로고
    • Skin sensitization to linalyl hydroperoxide: Support for radical intermediates
    • Bezard, M., Karlberg, A.-T., Montelius, J., and Lepoittevin, J.-P. (1997) Skin sensitization to linalyl hydroperoxide: support for radical intermediates. Chem. Res. Toxicol. 10, 987-993.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 987-993
    • Bezard, M.1    Karlberg, A.-T.2    Montelius, J.3    Lepoittevin, J.-P.4
  • 27
    • 0036240007 scopus 로고    scopus 로고
    • Free radicals in antigen formation: Reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants
    • Gäfvert, E., Nilsson, J. L. G., Hagelthorn, G., and Karlberg, A.-T. (2002) Free radicals in antigen formation: reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants. Brit. J. Dermatol. 146, 649-656.
    • (2002) Brit. J. Dermatol. , vol.146 , pp. 649-656
    • Gäfvert, E.1    Nilsson, J.L.G.2    Hagelthorn, G.3    Karlberg, A.-T.4
  • 28
    • 0028326973 scopus 로고
    • Interactions of allergenic hydroperoxides with proteins: A radical mechanism?
    • Lepoittevin, J.-P., and Karlberg, A.-T. (1994) Interactions of allergenic hydroperoxides with proteins: a radical mechanism? Chem. Res. Toxicol. 7, 130-133.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 130-133
    • Lepoittevin, J.-P.1    Karlberg, A.-T.2
  • 29
    • 0028258366 scopus 로고
    • Contact allergy to resin acid hydroperoxides. Hapten binding via free radicals and epoxides
    • Gäfvert, E., Shao, L. P., Karlberg, A.-T., Nilsson, U., and Nilsson, J. L. G. (1994) Contact allergy to resin acid hydroperoxides. Hapten binding via free radicals and epoxides. Chem. Res. Toxicol. 7, 260-266.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 260-266
    • Gäfvert, E.1    Shao, L.P.2    Karlberg, A.-T.3    Nilsson, U.4    Nilsson, J.L.G.5
  • 30
    • 0028414136 scopus 로고
    • Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene
    • Karlberg, A.-T., Magnusson, K., and Nilsson, U. (1994) Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene. Ann. Occup. Hyg. 38, 199-207.
    • (1994) Ann. Occup. Hyg. , vol.38 , pp. 199-207
    • Karlberg, A.-T.1    Magnusson, K.2    Nilsson, U.3
  • 31
    • 0036310812 scopus 로고    scopus 로고
    • Studies on the autoxidation and sensitising capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide
    • Sköld, M., Börje, A., Matura, M., and Karlberg, A.-T. (2002) Studies on the autoxidation and sensitising capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide. Contact Dermatitis 46, 267-272.
    • (2002) Contact Dermatitis , vol.46 , pp. 267-272
    • Sköld, M.1    Börje, A.2    Matura, M.3    Karlberg, A.-T.4
  • 32
    • 0029104640 scopus 로고
    • 15-Hydroperoxy dehydroabietic acid - A contact allergen in colophony from pinus species
    • Shao, L. P., Gäfvert, E., Nilsson, U., Karlberg, A.-T., and Nilsson, J. L. G. (1995) 15-Hydroperoxy dehydroabietic acid - a contact allergen in colophony from pinus species. Phytochemistry 4, 853-857.
    • (1995) Phytochemistry , vol.4 , pp. 853-857
    • Shao, L.P.1    Gäfvert, E.2    Nilsson, U.3    Karlberg, A.-T.4    Nilsson, J.L.G.5
  • 33
    • 0029952865 scopus 로고    scopus 로고
    • Isolated rosin (colophony) allergens as screening substances for contact allergy
    • Karlberg, A.-T., and Gäfvert, E. (1996) Isolated rosin (colophony) allergens as screening substances for contact allergy. Contact Dermatitis 35, 201-207.
    • (1996) Contact Dermatitis , vol.35 , pp. 201-207
    • Karlberg, A.-T.1    Gäfvert, E.2
  • 34
    • 0030949496 scopus 로고    scopus 로고
    • Contact allergy to oxidized d-limonene among dermatitis patients
    • Karlberg, A.-T., and Dooms-Goossens, A. (1997) Contact allergy to oxidized d-limonene among dermatitis patients. Contact Dermatitis 36, 201-206.
    • (1997) Contact Dermatitis , vol.36 , pp. 201-206
    • Karlberg, A.-T.1    Dooms-Goossens, A.2
  • 35
    • 0036828127 scopus 로고    scopus 로고
    • Oxidized citrus oil (R-limonene): A frequent skin sensitizer in Europe
    • Matura, M., Goossens, A., Bordalo, O., and et al. (2002) Oxidized citrus oil (R-limonene): a frequent skin sensitizer in Europe. J. Am. Acad. Dermatol. 47, 709-714.
    • (2002) J. Am. Acad. Dermatol. , vol.47 , pp. 709-714
    • Matura, M.1    Goossens, A.2    Bordalo, O.3
  • 37
    • 0023762270 scopus 로고
    • Contact allergy to dehydroabietic acid derivatives isolated from Portuguese colophony
    • Karlberg, A.-T., Boman, A., Hacksell, U., Jacobsson, S., and Nilsson, J. L. G. (1988) Contact allergy to dehydroabietic acid derivatives isolated from Portuguese colophony. Contact Dermatitis 19, 166-174.
    • (1988) Contact Dermatitis , vol.19 , pp. 166-174
    • Karlberg, A.-T.1    Boman, A.2    Hacksell, U.3    Jacobsson, S.4    Nilsson, J.L.G.5
  • 38
    • 0032989342 scopus 로고    scopus 로고
    • Are contact allergens stable in patch test preparations? Investigation of the degradation of d-limonene hydroperoxides in petrolatum
    • Nilsson, U., Magnusson, K., Karlberg, O., and Karlberg, A.-T. (1999) Are contact allergens stable in patch test preparations? Investigation of the degradation of d-limonene hydroperoxides in petrolatum. Contact Dermatitis 40, 127-132.
    • (1999) Contact Dermatitis , vol.40 , pp. 127-132
    • Nilsson, U.1    Magnusson, K.2    Karlberg, O.3    Karlberg, A.-T.4
  • 39
    • 0025776246 scopus 로고
    • Irritants increase the response to an allergen in allergic contact dermatitis
    • McLelland, J., Shuster, S., and Matthews, J. N. S. (1991) Irritants increase the response to an allergen in allergic contact dermatitis. Arch. Dermatol. 127, 1016-1019.
    • (1991) Arch. Dermatol. , vol.127 , pp. 1016-1019
    • McLelland, J.1    Shuster, S.2    Matthews, J.N.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.