Experimental and theoretical investigations of the autoxidation of geranial: A dioxolane hydroperoxide identified as a skin sensitizer

Chemical Research in Toxicology

Volumn 24, Issue 9, 2011, Pages 1507-1515

  Hagvall, Lina ^a,b   Bäcktorp, Carina ^a   Norrby, Per Ola ^a   Karlberg, Ann Therese ^a   Börje, Anna ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

5 [2 (2,6 DIMETHYLHEPTA 1,5 DIENYL) 5,5 DIMETHYL 1,3 DIOXOLAN 4 YL] 3 METHYLPENT 2 ENAL; 5 [2 HYDROPEROXY 2 (2,6 DIMETHYLHEPTA 1,5 DIENYL) 5,5 DIMETHYL 1,3 DIOXOLAN 4 YL] 3 METHYLPENT 2 ENAL; 6,7 EPOXYGERANIAL; ACID; ALDEHYDE DERIVATIVE; CITRAL; DIOXOLAN HYDROPEROXIDE; GERANIC ACID; GERANIOL; GERANIOL HYDROPEROXIDE; HYDROPEROXIDE; LINALOOL; LINALOOL HYDROPEROXIDE; OXYGEN; PERACYL RADICAL; PEROXY RADICAL; RADICAL; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; AUTOOXIDATION; CATALYSIS; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DOSE RESPONSE; EPOXIDATION; EXPERIMENTAL STUDY; LYMPH NODE; MOLECULAR STABILITY; MOUSE; NONHUMAN; REACTION ANALYSIS; SKIN SENSITIZATION; THEORETICAL STUDY;

ALLERGENS; ANIMALS; DERMATITIS, ALLERGIC CONTACT; DIOXOLANES; HYDROGEN PEROXIDE; LOCAL LYMPH NODE ASSAY; MICE; MONOTERPENES; OXIDATION-REDUCTION; SKIN;

EID: 80053046796     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200120q     Document Type: Article

References (37)

1. Thyssen, J. P., Linneberg, A., Menne, T., and Johansen., J. D. (2007) The epidemiology of contact allergy in the general population: prevalence and main findings Contact Dermatitis. 57 (5) 287-299 (Pubitemid 47568789)
2. Hagvall, L., Backtorp, C., Svensson, S., Nyman, G., Borje, A., and Karlberg., A. T. (2007) Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization Chem. Res. Toxicol. 20 (5) 807-814 (Pubitemid 46953688)
3. Karlberg, A. T., Shao, L. P., Nilsson, U., Gafvert, E., and Nilsson., J. L. (1994) Hydroperoxides in oxidized d-limonene identified as potent contact allergens Arch. Dermatol. Res. 286 (2) 97-103 (Pubitemid 24025575)
4. Skold, M., Borje, A., Harambasic, E., and Karlberg., A. T. (2004) Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization Chem. Res. Toxicol. 17 (12) 1697-1705 (Pubitemid 39665563)
5. Gafvert, E., Shao, L. P., Karlberg, A. T., Nilsson, U., and Nilsson., J. L. (1994) Contact allergy to resin acid hydroperoxides. Hapten binding via free radicals and epoxides Chem. Res. Toxicol. 7 (2) 260-266 (Pubitemid 24105359)
6. Redeby, T., Nilsson, U., Altamore, T. M., Ilag, L., Ambrosi, A., Broo, K., Borje, A., and Karlberg., A. T. (2010) Specific adducts formed through a radical reaction between peptides and contact allergenic hydroperoxides Chem. Res. Toxicol. 23 (1) 203-210
7. Karlberg, A. T., Bergstrom, M. A., Borje, A., Luthman, K., and Nilsson., J. L. G. (2008) Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitizers Chem. Res. Toxicol. 21 (1) 53-69 (Pubitemid 351219708)
8. Bodin, A., Linnerborg, M., Nilsson, J. L., and Karlberg., A. T. (2003) Structure elucidation, synthesis, and contact allergenic activity of a major hydroperoxide formed at autoxidation of the ethoxylated surfactant C12E5 Chem. Res. Toxicol. 16 (5) 575-582 (Pubitemid 36613090)
9. Bäcktorp, C., Wass, J. R., Panas, I., Sköld, M., Börje, A., and Nyman., G. (2006) Theoretical investigation of linalool oxidation J. Phys. Chem. A 110 (44) 12204-12212 (Pubitemid 44806863)
10. Bäcktorp, C., Hagvall, L., Borje, A., Karlberg, A. T., Norrby, P. O., and Nyman., G. (2008) Mechanism of air oxidation of the fragrance terpene geraniol J. Chem. Theory Comput. 4 (1) 101-106
11. Lalko, J. and Api., A. M. (2006) Investigation of the dermal sensitization potential of various essential oils in the local lymph node assay Food Chem. Toxicol. 44 (5) 739-746
12. Lota, M. L., de Rocca Serra, D., Tomi, F., Jacquemond, C., and Casanova., J. (2002) Volatile components of peel and leaf oils of lemon and lime species J. Agric. Food Chem. 50 (4) 796-805 (Pubitemid 34163625)
13. Rastogi, S. C., Heydorn, S., Johansen, J. D., and Basketter., D. A. (2001) Fragrance chemicals in domestic and occupational products Contact Dermatitis 45 (4) 221-225 (Pubitemid 32958567)
14. Rauber Cda, S., Guterres, S. S., and Schapoval., E. E. (2005) LC determination of citral in Cymbopogon citratus volatile oil J. Pharm. Biomed. Anal. 37 (3) 597-601 (Pubitemid 40312307)
15. Liang, C. P., Wang, M. F., Simon, J. E., and Ho., C. T. (2004) Antioxidant activity of plant extracts on the inhibition of citral off-odor formation Mol. Nutr. Food Res. 48 (4) 308-317 (Pubitemid 39592263)
16. Ueno, T., Masuda, H., and Ho., C. T. (2004) Formation mechanism of p-methylacetophenone from citral via a tert-alkoxy radical intermediate J. Agric. Food Chem. 52 (18) 5677-5684
17. Kimura, K., Nishimura, H., Iwata, I., and Mizutani., J. (1983) Deterioration mechanism of lemon flavor 0.2. Formation mechanism of off-odor substances arising from citral J. Agric. Food Chem. 31 (4) 801-804
18. Bäcktorp, C., Borje, A., Nilsson, J. L. G., Karlberg, A. T., Norrby, P. O., and Nyman., G. (2008) Mechanisms of air oxidation of ethoxylated surfactants: Computational estimations of energies and reaction behaviors Chem.- Eur. J. 14 (31) 9549-9554
19. Skold, M., Hagvall, L., and Karlberg., A. T. (2008) Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens Contact Dermatitis 58 (1) 9-14 (Pubitemid 350264762)
20. Hagvall, L., Baron, J. M., Borje, A., Weidolf, L., Merk, H. F., and Karlberg., A. T. (2008) Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens Toxicol. Appl. Pharmacol. 233 (2) 308-313 (Pubitemid 50295777)
21. Vyvyan, J. R., Meyer, J. A., and Meyer., K. D. (2003) Conversion of epoxides to 1,3-dioxolanes catalyzed by tin(II) chloride J. Org. Chem. 68 (23) 9144-9147 (Pubitemid 37409575)
22. OECD (2002) Guideline for the Testing of Chemicals, in Guideline No. 429. Skin Sensitization: Local Lymph Node Assay.
23. Basketter, D. A., Lea, L. J., Dickens, A., Briggs, D., Pate, I., Dearman, R. J., and Kimber., I. (1999) A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose responses J. Appl. Toxicol. 19 (4) 261-266 (Pubitemid 29360983)
24. Kimber, I., Basketter, D. A., Butler, M., Gamer, A., Garrigue, J. L., Gerberick, G. F., Newsome, C., Steiling, W., and Vohr., H. W. (2003) Classification of contact allergens according to potency: proposals Food Chem. Toxicol. 41 (12) 1799-1809 (Pubitemid 37249347)
25. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. (2004) Gaussian 03, revision C.02, Gaussian, Inc., Wallingford, CT.
26. Becke, A. D. (1993) Density-functional thermochemistry 0.3. The role of exact exchange J. Chem. Phys. 98 (7) 5648-5652
27. Lee, C. T., Yang, W. T., and Parr., R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density Phys. Rev. B 37 (2) 785-789
28. Ikeda, C. K., Braun, R. A., and Sorenson., B. E. (1964) Autoxidation of 2-alkenyldioxolanes + 2-alkenyl1-1,3-dioxanes J. Org. Chem. 29 (2) 286-290
29. Adams, R. D., Barnard, T. S., and Brosius., K. (1999) Synthesis of 1,3-dioxolanes by the addition of ketones to epoxides by using [Cp*Ir(NCMe)32+ as catalyst J. Organomet. Chem. 582, 358-361 (Pubitemid 129596011)
30. Benfatti, F., Cardillo, G., Gentilucci, L., Tolomelli, A., Monari, M., and Piccinelli., F. (2007) A microwave-enhanced, Lewis acid-catalyzed synthesis of 1,3-dioxolanes and oxazolines from epoxides Adv. Synth. Catal. 349 (7) 1256-1264
31. Gerberick, G. F., Vassallo, J. D., Foertsch, L. M., Price, B. B., Chaney, J. G., and Lepoittevin., J. P. (2007) Quantification of chemical peptide reactivity for screening contact allergens: a classification tree model approach Toxicol. Sci. 97 (2) 417-27 (Pubitemid 47073857)
32. Karlsson, I., Hillerstrom, L., Stenfeldt, A. L., Martensson, J., and Borje., A. (2009) Photodegradation of dibenzoylmethanes: potential cause of photocontact allergy to sunscreens Chem. Res. Toxicol. 22 (11) 1881-1892
33. Murahashi, S. I., Naota, T., and Hirai., N. (1993) Aerobic oxidation of alcohols with ruthenium-cobalt bimetallic catalyst in the presence of aldehydes J. Org. Chem. 58 (26) 7318-7319 (Pubitemid 24066133)
34. Raja, R. and Thomas., J. M. (2005) Producing hazardous reagents in situ using single-site heterogeneous catalysts Z. Anorg. Allg. Chem. 631 (13-14) 2942-2946 (Pubitemid 41578467)
35. Shi, H. C., Zhang, Z. G., and Wang., Y. L. (2005) Mechanism on epoxidation of alkenes by peracids: A protonation-promoted pathway and its quantum chemical elucidation J. Mol. Catal A: Chem. 238 (1-2) 13-25
36. Hsiue, G. H., Perng, T. L., and Yang., J. M. (1991) New peracid-type polymeric initiator for radical polymerization J. Appl. Polym. Sci. 42 (7) 1899-1904
37. Zimerson, E. and Bruze., M. (2002) Sensitizing capacity of some trimers in p-tert-butylphenol-formaldehyde resin Contact Dermatitis 47 (1) 40-46