Contact allergy to capryloyl salicylic acid: a mechanistic chemistry and structure-activity perspective
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Published in | Contact dermatitis Vol. 72; no. 5; pp. 347 - 351 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
Oxford, UK
Blackwell Publishing Ltd
01.05.2015
Wiley Subscription Services, Inc |
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Online Access | Get full text |
ISSN | 0105-1873 1600-0536 1600-0536 |
DOI | 10.1111/cod.12368 |
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Author | Aptula, Aynur O. Roberts, David W. |
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Cites_doi | 10.1002/jat.1289 10.1021/jo01016a060 10.1111/cod.12239 10.1021/tx060102o 10.1007/978-94-009-5883-8 10.1021/tx300278t 10.1016/j.tox.2012.05.002 10.1021/tx060121y 10.1021/jo01212a011 |
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Copyright | 2015 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd |
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References | Landsteiner K, Jacobs J. Studies on the sensitization of animals with simple chemical compounds. J Exp Med 1936: 64: 643-655. Roberts D W, Aptula A O, Patlewicz G. Mechanistic applicability domains for non-animal based prediction of toxicological endpoints. QSAR analysis of the Schiff base applicability domain for skin sensitization. Chem Res Toxicol 2006: 19: 1228-1233. de Groot A, Rustemeyer T, Hissink D, Bakker M. Contact allergy to capryloyl salicylic acid. Contact Dermatitis 2014: 71: 176-190. Roberts D W, Aptula A O, Patlewicz G. Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published dataset of 106 chemicals tested in the mouse local lymph node assay. Chem Res Toxicol 2007: 20: 44-60. Perrin D D, Dempsey B, Serjeant E P. pKa Prediction for Organic Acids and Bases: London, Chapman and Hall, 1981. Ralston A W, McCorkle M R, Bauer S T. Orientation in the acylation of phenol and in the rearrangement of phenolic esters. J Org Chem 1940: 05: 645-649. Roberts D W, Aptula A O. Determinants of skin sensitization potential. J Appl Toxicol 2008: 28: 377-387. Ezendam J, Vermeulen J P, Klerk A, Jong W H, Loveren H. A quantitative approach to assess the potency of skin sensitizers in the elicitation phase. Toxicology 2012: 299: 20-24. Natsch A, Gfeller H, Haupt T, Brunner G. Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything? Chem Res Toxicol 2012: 2: 2203-2215. Kovacic P, Hillier J J Jr. The ortho/para ratio in electrophilic aromatic substitution. Mercuration and alkylation of chlorobenzene and anisole. Evidence for a coordination effect. J Org Chem 1965: 30: 1581-1588. Isaacs N. Physical Organic Chemistry, 2nd edition: Harlow, Longman, 1995. 1965; 30 2012; 2 2012; 299 2008; 28 2006; 19 1995 2015 1936; 64 1981 1940; 05 2007; 20 2014; 71 1988 e_1_2_2_4_1 e_1_2_2_14_1 e_1_2_2_5_1 e_1_2_2_13_1 e_1_2_2_6_1 e_1_2_2_7_1 e_1_2_2_11_1 e_1_2_2_10_1 e_1_2_2_2_1 Isaacs N (e_1_2_2_12_1) 1995 e_1_2_2_9_1 e_1_2_2_8_1 Landsteiner K (e_1_2_2_3_1) 1936; 64 25155078 - Contact Dermatitis. 2014 Sep;71(3):185-7 |
References_xml | – reference: Natsch A, Gfeller H, Haupt T, Brunner G. Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything? Chem Res Toxicol 2012: 2: 2203-2215. – reference: de Groot A, Rustemeyer T, Hissink D, Bakker M. Contact allergy to capryloyl salicylic acid. Contact Dermatitis 2014: 71: 176-190. – reference: Roberts D W, Aptula A O, Patlewicz G. Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published dataset of 106 chemicals tested in the mouse local lymph node assay. Chem Res Toxicol 2007: 20: 44-60. – reference: Isaacs N. Physical Organic Chemistry, 2nd edition: Harlow, Longman, 1995. – reference: Landsteiner K, Jacobs J. Studies on the sensitization of animals with simple chemical compounds. J Exp Med 1936: 64: 643-655. – reference: Roberts D W, Aptula A O. Determinants of skin sensitization potential. J Appl Toxicol 2008: 28: 377-387. – reference: Perrin D D, Dempsey B, Serjeant E P. pKa Prediction for Organic Acids and Bases: London, Chapman and Hall, 1981. – reference: Ralston A W, McCorkle M R, Bauer S T. Orientation in the acylation of phenol and in the rearrangement of phenolic esters. J Org Chem 1940: 05: 645-649. – reference: Kovacic P, Hillier J J Jr. The ortho/para ratio in electrophilic aromatic substitution. Mercuration and alkylation of chlorobenzene and anisole. Evidence for a coordination effect. J Org Chem 1965: 30: 1581-1588. – reference: Roberts D W, Aptula A O, Patlewicz G. Mechanistic applicability domains for non-animal based prediction of toxicological endpoints. QSAR analysis of the Schiff base applicability domain for skin sensitization. Chem Res Toxicol 2006: 19: 1228-1233. – reference: Ezendam J, Vermeulen J P, Klerk A, Jong W H, Loveren H. A quantitative approach to assess the potency of skin sensitizers in the elicitation phase. Toxicology 2012: 299: 20-24. – volume: 20 start-page: 44 year: 2007 end-page: 60 article-title: Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published dataset of 106 chemicals tested in the mouse local lymph node assay publication-title: Chem Res Toxicol – volume: 05 start-page: 645 year: 1940 end-page: 649 article-title: Orientation in the acylation of phenol and in the rearrangement of phenolic esters publication-title: J Org Chem – volume: 2 start-page: 2203 year: 2012 end-page: 2215 article-title: Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything? publication-title: Chem Res Toxicol – year: 1981 – volume: 19 start-page: 1228 year: 2006 end-page: 1233 article-title: Mechanistic applicability domains for non‐animal based prediction of toxicological endpoints. QSAR analysis of the Schiff base applicability domain for skin sensitization publication-title: Chem Res Toxicol – volume: 30 start-page: 1581 year: 1965 end-page: 1588 article-title: The ortho/para ratio in electrophilic aromatic substitution. Mercuration and alkylation of chlorobenzene and anisole. Evidence for a coordination effect publication-title: J Org Chem – year: 1988 – volume: 28 start-page: 377 year: 2008 end-page: 387 article-title: Determinants of skin sensitization potential publication-title: J Appl Toxicol – volume: 299 start-page: 20 year: 2012 end-page: 24 article-title: A quantitative approach to assess the potency of skin sensitizers in the elicitation phase publication-title: Toxicology – year: 1995 – volume: 64 start-page: 643 year: 1936 end-page: 655 article-title: Studies on the sensitization of animals with simple chemical compounds publication-title: J Exp Med – year: 2015 – volume: 71 start-page: 176 year: 2014 end-page: 190 article-title: Contact allergy to capryloyl salicylic acid publication-title: Contact Dermatitis – ident: e_1_2_2_6_1 doi: 10.1002/jat.1289 – ident: e_1_2_2_11_1 – ident: e_1_2_2_13_1 doi: 10.1021/jo01016a060 – ident: e_1_2_2_2_1 doi: 10.1111/cod.12239 – ident: e_1_2_2_4_1 doi: 10.1021/tx060102o – ident: e_1_2_2_8_1 doi: 10.1007/978-94-009-5883-8 – volume-title: Physical Organic Chemistry year: 1995 ident: e_1_2_2_12_1 – ident: e_1_2_2_7_1 doi: 10.1021/tx300278t – ident: e_1_2_2_10_1 doi: 10.1016/j.tox.2012.05.002 – ident: e_1_2_2_5_1 doi: 10.1021/tx060121y – ident: e_1_2_2_9_1 – ident: e_1_2_2_14_1 doi: 10.1021/jo01212a011 – volume: 64 start-page: 643 year: 1936 ident: e_1_2_2_3_1 article-title: Studies on the sensitization of animals with simple chemical compounds publication-title: J Exp Med – reference: 25155078 - Contact Dermatitis. 2014 Sep;71(3):185-7 |
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SubjectTerms | Cosmetics - adverse effects Dermatitis, Allergic Contact - etiology Facial Dermatoses - chemically induced Female Humans Salicylates - adverse effects |
Title | Contact allergy to capryloyl salicylic acid: a mechanistic chemistry and structure-activity perspective |
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