Contact allergy to capryloyl salicylic acid: a mechanistic chemistry and structure-activity perspective

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Published inContact dermatitis Vol. 72; no. 5; pp. 347 - 351
Main Authors Roberts, David W., Aptula, Aynur O.
Format Journal Article
LanguageEnglish
Published Oxford, UK Blackwell Publishing Ltd 01.05.2015
Wiley Subscription Services, Inc
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ISSN0105-1873
1600-0536
1600-0536
DOI10.1111/cod.12368

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Author Aptula, Aynur O.
Roberts, David W.
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CitedBy_id crossref_primary_10_1111_cod_14573
crossref_primary_10_1016_j_ad_2016_02_012
crossref_primary_10_1002_jat_3354
crossref_primary_10_1177_10915818241237794
crossref_primary_10_1016_j_adengl_2016_07_008
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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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.
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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
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  doi: 10.1021/tx060102o
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  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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