A toxicological and dermatological assessment of macrocyclic lactone and lactide derivatives when used as fragrance ingredients

Food and Chemical Toxicology

Volumn 49, Issue SUPPL. 2, 2011, Pages

  Belsito, D ^a   Bickers, D ^a   Bruze, M ^b   Calow, P ^c   Dagli, M L ^d   Fryer, A D ^e   Greim, H ^f   Miyachi, Y ^g   Saurat, J H ^h   Sipes, I G ⁱ  

^a NewYork Presbyterian Hospital   (United States)

^b LUND UNIVERSITY HOSPITAL   (Sweden)

^c ROSKILDE UNIVERSITY   (Denmark)

^d UNIVERSITY OF SÃO PAULO   (Brazil)

^e OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^f TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^g KYOTO UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^h UNIVERSITY OF GENEVA   (Switzerland)

ⁱ UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

Author keywords

Fragrance; Macrocylic lactide; Macrocylic lactone; Review; Safety

Indexed keywords

10 OXAHEXADECANOLIDE; 11 OXAHEXADECANOLIDE; 12 OXAHEXADECANOLIDE; 16 HYDROXY 7 HEXADECENOIC ACID LACTONE; ETHYLENE BRASSYLATE; ETHYLENE DODECANEDIOATE; FRAGRANCE; HEXADECANOLIDE; LACTIDE DERIVATIVE; LACTONE DERIVATIVE; OMEGA 6 HEXADECENLACTONE; OMEGA PENTADECALACTONE; OXACYCLOHEPTADEC 10 ENE 2 ONE; OXACYCLOHEXADECANE 2,13 DIONE; UNCLASSIFIED DRUG;

ACUTE TOXICITY; BIOCHEMISTRY; CHEMICAL STRUCTURE; DEVELOPMENTAL TOXICITY; DRUG EXPOSURE; GENOTOXICITY; HUMAN; METABOLISM; MUTAGENICITY; NONHUMAN; PHOTOSENSITIZATION; PHOTOTOXICITY; REPRODUCTIVE TOXICITY; REVIEW; SAFETY; SKIN IRRITATION;

ANIMALS; CONSUMER PRODUCT SAFETY; DIOXANES; DNA DAMAGE; HUMANS; IRRITANTS; LACTONES; ODORS; PERFUME; RISK ASSESSMENT; SKIN; SKIN DISEASES; TOXICITY TESTS;

ANIMALIA; MAMMALIA;

EID: 84155167319     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2011.07.052     Document Type: Review

References (165)

1. Abramsson-Zetterberg L., Slanina P. Macrocyclic musk compounds - an absence of genotoxicity in the Ames test and the in vivo micronucleus assay. Toxicology Letters 2002, 135:155-163.
2. Aeschbacher H.U., Wolleb U., Loliger J., Spadone J.C., Liardon R. Contribution of coffee aroma constituents to the mutagenicity of coffee. Food and Chemical Toxicology 1989, 27(4):227-232.
3. An S., Lee A.Y., Lee C.H., Kim D.W., Hahm J.H., Kim K.J., Moon K.C., Won Y.H., Ro Y.S., Eun H.C. Fragrance contact dermatitis in Korea: a joint study. Contact Dermatitis 2005, 53(6):320-323.
4. Api A.M., Letizia C.S. Evaluation of the sensitization potential of hydroxycitronellal in an extended product use test. Society of Toxicology 2001, 60(1):61.
5. Bitsch N., Dudas C., Korner W., Failing K., Biselli S., Rimkus G., Brunn H. Estrogenic activity of musk fragrances detected by the E-screen assay using human MCF-7 cells. Archives of Environmental Contamination and Toxicology 2002, 43(3):257-264.
6. Cadby P.A., Troy W.R., Vey M.G.H. Consumer exposure to fragrance ingredients: providing estimates for safety evaluation. Regulatory Toxicology and Pharmacology 2002, 36(3):246-252.
7. EPA (Environmental Protection Agency), 2010. Estimation Programs Interface Suite™ for Microsoft® Windows, v 4.00. United States Environmental Protection Agency, Washington, DC, USA.
8. Flavoring Extract Manufacturing Association (FEMA), 1962. In Vitro Digestion of Four Lactones.
9. Forbes P.D., Urbach F., Davies R.E. Phototoxicity testing of fragrance raw materials. Food and Cosmetics Toxicology 1977, 15(1):55-60.
10. Ford R.A., Domeyer B., Easterday O., Maier K., Middleton J. Criteria for development of a database for safety evaluation of fragrance ingredients. Regulatory Toxicology and Pharmacology 2000, 31(2):166-181.
11. IFRA (international Fragrance Association), 2007. Volume of Use Survey, February 2007.
12. IFRA (International Fragrance Association), 2008. Use Level Survey, December 2008.
13. Ishihara M., Itoh M., Hosono K., Nishimura M. Some problems with patch tests using fragrance materials. Skin Research 1981, 23(6):808-817.
14. Itoh M., Ishihara M., Hosono K., Kantoh H., Kinoshita M., Yamada K., Nishimura M. Results of patch tests conducted between 1978 and 1985 using cosmetic ingredients. Skin Research 1986, 28(Suppl. 2):110-119.
15. Itoh M., Hosono K., Kantoh H., Kinoshita M., Yamada K., Kurosaka R., Nishimura M. Patch test results with cosmetic ingredients conducted between 1978 and 1986. Journal of Society Cosmetic Science 1988, 12(1):27-41.
16. Joint FAO/WHO Expert Committee on Food Additives (JECFA), 1998. Safety Evaluation of Certain Food Additives and Contaminates. WHO Additive Series 40, Aliphatic Lactones.
17. Joint FAO/WHO Expert Committee on Food Additives (JECFA), 2002. Safety Evaluation of Certain Food Additives and Contaminates. WHO Additive Series 44, Aliphatic Primary Alcohols, Aldehydes, Carboxylic Acids, Acetals and Esters Containing Additional Oxygenated Functional Groups.
18. Kimber I., Dearman R.J., Scholes E.W., Basketter D.A. The local lymph node assay: developments and applications. Toxicology 1994, 93(1):13-31.
19. Klecak, G., 1979. The open epicutaneous test (OET), a predictive test procedure in the guinea pig for estimation of allergenic properties of simple chemical compounds, their mixtures and of finished cosmetic preparations. International Federation Societies Cosmetic Chemists, 9/18/79.
20. Klecak G. The Freund's Complete Adjuvant Test and the Open Epicutaneous Test. Current Problems in Dermatology 1985, 14:152-171.
21. Kraft P., Bajgrowicz J.A., Denis C., Frater G. , Odds and trends: recent developments in the chemistry of odorants. Angewandte Chemie International Edition 2000, 39:2980-3010.
22. Larsen W.G. Allergic contact dermatitis to the perfume in Mycology cream. Journal of the American Academy of Dermatology 1979, 1(1):131-133.
23. Larsen W., Nakayama H., Fischer T., Elsner P., Frosch P., Burrows D., Jordan W., Shaw S., Wilkinson J., Marks J.J., Sugawara M., Nethercott M., Nethercott J. Fragrance contact dermatitis: a worldwide multicenter investigation (Part II). Contact Dermatitis 2001, 44(6):344-346.
24. Larsen W., Nakayama H., Fischer T., Elsner P., Frosch P., Burrows D., Jordan W., Shaw S., Wilkinson J., Marks J.J., Sugawara M., Nethercott M., Nethercott J. Fragrance contact dermatitis - a worldwide multicenter investigation (Part III). Contact Dermatitis 2002, 46(3):141-144.
25. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-a. Fragrance material review on ethylene brassylate. Food and Chemical Toxicology.
26. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-b. Fragrance material review on ethylene dodecanedioate. Food and Chemical Toxicology.
27. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-c. Fragrance material review on hexadecanolide. Food and Chemical Toxicology.
28. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-d. Fragrance material review on ω-6-hexadecenlactone. Food and Chemical Toxicology (Submitted to journal).
29. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-e. Fragrance material review on 16-hydroxy-7-hexadecenoic acid lactone. Food and Chemical Toxicology (Submitted to journal).
30. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-f. Fragrance material review on oxacycloheptadec-10-ene-2-one. Food and Chemical Toxicology.
31. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-g. Fragrance material review on oxacyclohexadecane-2,13-dione. Food and Chemical Toxicology.
32. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-h. Fragrance material review on (E) and (Z)-oxacyclohexadec-(12 or 13)-en-2-one. Food and Chemical Toxicology.
33. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-i. Fragrance material review on 10-oxahexadecanolide. Food and Chemical Toxicology.
34. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-j. Fragrance material review on 11-oxahexadecanolide. Food and Chemical Toxicology.
35. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-k. Fragrance material review on 12-oxahexadecanolide. Food and Chemical Toxicology.
36. McGinty, D.M., Letizia, C.S., Api, A.M., submitted for publication-l. Fragrance material review on ω-pentadecalactone. Food and Chemical Toxicology.
37. Nishimura M., Ishihara M., Itoh M., Hosono K., Kantoh H. Results of patch tests on cosmetic ingredients conducted between 1979 and 1982. Skin Research 1984, 26(4):945-954.
38. Ogoshi, K., Tanaka, N., Sekine, A., 1980. A study on the phototoxicity of musk type fragrances. Unpublished, A paper presented at S.C.C.J., Nov. 17, 1980, 1-7.
39. Ohkoshi K., Watanabe A., Tanaka N. Phototoxicity of musks in perfumery. Journal of Society Cosmetic Chemists Japan 1981, 15(3):207-213.
40. RIFM (Research Institute for Fragrance Materials, Inc.), 1963a. Eye irritation study with hexadecanolide in rabbits. Unpublished report from International Flavors and Fragrances, 13 November. Report number 51201 (RIFM, Woodcliff Lake, NJ, USA).
41. RIFM (Research Institute for Fragrance Materials, Inc.), 1963b. Eye irritation study of oxacycloheptadec-10-ene-2-one in rabbits. Unpublished report from International Flavors and Fragrances Incorporated, 30 September. Report number 47599 (RIFM, Woodcliff Lake, NJ, USA).
42. RIFM (Research Institute for Fragrance Materials, Inc.), 1964a. Repeated insult patch test with oxacycloheptadec-10-ene-2-one. Unpublished report from International Flavors and Fragrances Incorporated, 08 June. Report number 47598 (RIFM, Woodcliff Lake, NJ, USA).
43. RIFM (Research Institute for Fragrance Materials, Inc.), 1964b. Repeated insult patch test with hexadecanolide. Unpublished report from International Flavors and Fragrances, 08 June. Report number 51200 (RIFM, Woodcliff Lake, NJ, USA).
44. RIFM (Research Institute for Fragrance Materials, Inc.), 1971. Acute toxicological evaluations of alpha-angelica lactone in mice. Private communication to FEMA. Unpublished report from T.E. Shellenberger, 02 February. Report number 29980 (RIFM, Woodcliff Lake, NJ, USA).
45. RIFM (Research Institute for Fragrance Materials, Inc.), 1972a. Acute eye irritation study of hexadecanolide in rabbits. Unpublished report from Givaudan-Roure Corporation, 18 December. Report number 29830 (RIFM, Woodcliff Lake, NJ, USA).
46. RIFM (Research Institute for Fragrance Materials, Inc.), 1972b. Acute eye irritation study of omega-pentadecalactone in rabbits. Unpublished report from Givaudan-Roure Corporation, 18 December. Report number 29841 (RIFM, Woodcliff Lake, NJ, USA).
47. RIFM (Research Institute for Fragrance Materials, Inc.), 1972c. Sensitization and irritation studies of hexadecanolide and cyclopentadecanone in human subjects. Unpublished report from Givaudan-Roure Corporation, 10 January. Report number 29831 (RIFM, Woodcliff Lake, NJ, USA).
48. RIFM (Research Institute for Fragrance Materials, Inc.), 1972d. Sensitization and irritation studies of omega-pentadecalactone in human subjects. Unpublished report from Givaudan-Roure Corporation, 20 March. Report number 29842 (RIFM, Woodcliff Lake, NJ, USA).
49. RIFM (Research Institute for Fragrance Materials, Inc.), 1973a. Acute toxicity studies on rats and rabbits. RIFM report number 2021, May 14 (RIFM, Woodcliff Lake, NJ, USA).
50. RIFM (Research Institute for Fragrance Materials, Inc.), 1973b. Report on human maximization studies. RIFM report number 1802, July 13 (RIFM, Woodcliff Lake, NJ, USA).
51. RIFM (Research Institute for Fragrance Materials, Inc.), 1974a. Acute toxicity studies. RIFM report number 1778, August 26 (RIFM, Woodcliff Lake, NJ, USA).
52. RIFM (Research Institute for Fragrance Materials, Inc.), 1974b. Acute oral and dermal toxicity studies. RIFM report number 2028, April 02 (RIFM, Woodcliff Lake, NJ, USA).
53. RIFM (Research Institute for Fragrance Materials, Inc.), 1974c. Acute toxicity study in rats and rabbits. RIFM report number 2025, March 15 (RIFM, Woodcliff Lake, NJ, USA).
54. RIFM (Research Institute for Fragrance Materials, Inc.), 1974d. Twenty day percutaneous toxicity study of ethylene brassylate in rabbits. RIFM report number 2108, February 7 (RIFM, Woodcliff Lake, NJ, USA).
55. RIFM (Research Institute for Fragrance Materials, Inc.), 1974e. Report on human maximization studies. RIFM report number 1779, September 12 (RIFM, Woodcliff Lake, NJ, USA).
56. RIFM (Research Institute for Fragrance Materials, Inc.), 1974f. Report on human maximization studies. RIFM report number 1801, February 20 (RIFM, Woodcliff Lake, NJ, USA).
57. RIFM (Research Institute for Fragrance Materials, Inc.), 1975a. Acute oral toxicity study of ethylene dodecanedioate in rats. Unpublished report from Dragoco Gerberding and Co. GmbH, 01 March. Report number 37766 (RIFM, Woodcliff Lake, NJ, USA).
58. RIFM (Research Institute for Fragrance Materials, Inc.), 1975b. Epicutaneous patch test of ethylene dodecanedioate in humans. Unpublished report from Dragoco Gerberding and Co. GmbH, 17 February. Report number 37762 (RIFM, Woodcliff Lake, NJ, USA).
59. RIFM (Research Institute for Fragrance Materials, Inc.), 1975c. Acute eye irritation study of ethylene dodecanedioate in rabbits. Unpublished report from Dragoco Gerberding and Co. GmbH, 01 May. Report number 37763 (RIFM, Woodcliff Lake, NJ, USA).
60. RIFM (Research Institute for Fragrance Materials, Inc.), 1975d. Acute eye irritation study of ethylene dodecanedioate in rabbits. Unpublished report from Dragoco Gerberding and Co. GmbH, 01 February. Report number 37764 (RIFM, Woodcliff Lake, NJ, USA).
61. RIFM (Research Institute for Fragrance Materials, Inc.), 1975e. Contact hypersensitivity test of ethylene dodecanedioate in guinea pigs. Unpublished report from Dragoco Gerberding and Co. GmbH, 01 March. Report number 37765 (RIFM, Woodcliff Lake, NJ, USA).
62. RIFM (Research Institute for Fragrance Materials, Inc.), 1976. An evaluation of the ability of various musk chemicals to produce the blue color phenomenon in female rats. Unpublished report from Avon Products Inc., 20 May. Report number 13599 (RIFM, Woodcliff Lake, NJ, USA).
63. RIFM (Research Institute for Fragrance Materials, Inc.), 1977a. Acute toxicity study in rats, rabbits and guinea pigs. RIFM report number 1695, September 29 (RIFM, Woodcliff Lake, NJ, USA).
64. RIFM (Research Institute for Fragrance Materials, Inc.), 1977b. Acute oral toxicity study of 12-oxahexadecanolide in mice. Unpublished report from Givaudan Roure Corporation, 21 November. Report number 29836 (RIFM, Woodcliff Lake, NJ, USA).
65. RIFM (Research Institute for Fragrance Materials, Inc.), 1977c. Report on human maximization studies. RIFM report number 1691, July 01 (RIFM, Woodcliff Lake, NJ, USA).
66. RIFM (Research Institute for Fragrance Materials, Inc.), 1977d. Report on human maximization studies. RIFM Report number 1702, February 2 (RIFM, Woodcliff Lake, NJ, USA).
67. RIFM (Research Institute for Fragrance Materials, Inc.), 1977e. Skin irritation and capacity of allergenic sensitization determined by the open epicutaneous test (OET) of 12-oxahexadecanolide on guinea pigs. Unpublished report from Givaudan-Roure Corporation, 14 September. Report number 29838 (RIFM, Woodcliff Lake, NJ, USA).
68. RIFM (Research Institute for Fragrance Materials, Inc.), 1977f. Irritation test of 12-oxahexadecanolide on the rabbit eye. Unpublished report from Givaudan-Roure Corporation, 12 July. Report number 29837 (RIFM, Woodcliff Lake, NJ, USA).
69. RIFM (Research Institute for Fragrance Materials, Inc.), 1977g. Skin irritation test of ethylene dodecanedionate in human subjects. Unpublished report from Takasago Inc., 06 December. Report number 7880 (RIFM, Woodcliff Lake, NJ, USA).
70. RIFM (Research Institute for Fragrance Materials, Inc.), 1978a. Acute dermal toxicity study with 12-oxahexadecanolide (musk 781) in rats. Unpublished report from International Flavors and Fragrances, 28 June. Report number 55045 (RIFM, Woodcliff Lake, NJ, USA).
71. RIFM (Research Institute for Fragrance Materials, Inc.), 1978b. Acute oral toxicity study with 12-oxahexadecanolide (musk 781) in rats. Unpublished report from International Flavors and Fragrances, 28 June. Report number 55044 (RIFM, Woodcliff Lake, NJ, USA).
72. RIFM (Research Institute for Fragrance Materials, Inc.), 1978c. Short term screen test with fragrance materials. Unpublished report from International Flavors and Fragrances, 17 October. Report number 55066 (RIFM, Woodcliff Lake, NJ, USA).
73. RIFM (Research Institute for Fragrance Materials, Inc.), 1978d. Testing for mutagenic activity of fragrance materials with Salmonella typhimurium. Unpublished report from Firmenich Incorporated, 01 August. Report number 29843 (RIFM, Woodcliff Lake, NJ, USA).
74. RIFM (Research Institute for Fragrance Materials, Inc.), 1978e. Report on human maximization studies. RIFM report number 1787, February 27 (RIFM, Woodcliff Lake, NJ, USA).
75. RIFM (Research Institute for Fragrance Materials, Inc.), 1978f. Report on human maximization studies. RIFM report number 1698, November 21 (RIFM, Woodcliff Lake, NJ, USA).
76. RIFM (Research Institute for Fragrance Materials, Inc.), 1978g. Phototoxicity of synthetic musks. Unpublished report from Shiseido Laboratories, 26 August. Report number 4415 (RIFM, Woodcliff Lake, NJ, USA).
77. RIFM (Research Institute for Fragrance Materials, Inc.), 1978h. Sensitization and irritation studies of 12-oxahexadecanolide in human subjects. Unpublished report from Givaudan-Roure Corporation, 27 April. Report number 29840 (RIFM, Woodcliff Lake, NJ, USA).
78. RIFM (Research Institute for Fragrance Materials, Inc.), 1979a. Acute toxicity studies in rats, rabbits and guinea pigs. RIFM report number 1696, March 23 (RIFM, Woodcliff Lake, NJ, USA).
79. RIFM (Research Institute for Fragrance Materials, Inc.), 1979b. Evaluation of 11-oxahexadecanolide in the Salmonella/microsome mutagenicity test. Unpublished report from Quest International, 01 November. Report number 29829 (RIFM, Woodcliff Lake, NJ, USA).
80. RIFM (Research Institute for Fragrance Materials, Inc.), 1980a. Primary skin irritation, eye irritation and phototoxicity tests with 11-oxahexadecanolide in albino rabbits. Unpublished report from Quest International, 01 November. Report number 29826 (RIFM, Woodcliff Lake, NJ, USA).
81. RIFM (Research Institute for Fragrance Materials, Inc.), 1980b. Photosensitization test with 11-oxahexadecanolide in guinea pigs. Unpublished report from Quest International, 01 May. Report number 29827 (RIFM, Woodcliff Lake, NJ, USA).
82. RIFM (Research Institute for Fragrance Materials, Inc.), 1980c. Maximization test with 11-oxahexadecanolide in guinea pigs. Unpublished report from Quest International, 01 April. Report number 29828 (RIFM, Woodcliff Lake, NJ, USA).
83. RIFM (Research Institute for Fragrance Materials, Inc.), 1982a. Acute dermal toxicity of oxacyclohexadecane-2,13-dione in albino rabbits. Unpublished report from Firmenich Incorporated, 21 July. Report number 38903 (RIFM, Woodcliff Lake, NJ, USA).
84. RIFM (Research Institute for Fragrance Materials, Inc.), 1982b. Single dose oral toxicity/LD50 of oxacyclohexadecane-2,13-dione in rats. Unpublished report from Firmenich Incorporated, 21 July. Report number 38902 (RIFM, Woodcliff Lake, NJ, USA).
85. RIFM (Research Institute for Fragrance Materials, Inc.), 1982c. Repeated insult patch test/photosensitization study of oxacyclohexadecane-2,13-dione in human subjects. Unpublished report from Firmenich Incorporated, 21 May. Report number 38906 (RIFM, Woodcliff Lake, NJ, USA).
86. RIFM (Research Institute for Fragrance Materials, Inc.), 1982d. Skin irritation study of oxacyclohexadecane-2,13-dione in rabbits. Unpublished report from Firmenich Incorporated, 30 April. Report number 38904 (RIFM, Woodcliff Lake, NJ, USA).
87. RIFM (Research Institute for Fragrance Materials, Inc.), 1982e. Eye irritation study of oxacyclohexadecane-2,13-dione in rabbits. Unpublished report from Firmenich Incorporated, 21 July. Report number 38905. (RIFM, Woodcliff Lake, NJ, USA).
88. RIFM (Research Institute for Fragrance Materials, Inc.), 1982f. Delayed contact hypersensitivity study in guinea pigs of 10-oxahexadecanolide. Unpublished report from Takasago International Corporation, 10 November. Report number 32632 (RIFM, Woodcliff Lake, NJ, USA).
89. RIFM (Research Institute for Fragrance Materials, Inc.), 1983a. Determination of phototoxicity of ethylene brassylate in guinea pigs. Unpublished report from Givaudan-Roure Corporation, 01 March. Report number 33518 (RIFM, Woodcliff Lake, NJ, USA).
90. RIFM (Research Institute for Fragrance Materials, Inc.), 1983b. Determination of phototoxicity of 12-oxahexadecanolide in guinea pigs. Unpublished report from Givaudan-Roure Corporation, 01 March. Report number 29839 (RIFM, Woodcliff Lake, NJ, USA).
91. RIFM (Research Institute for Fragrance Materials, Inc.), 1985. Ames metabolic activation test to assess the potential mutagenic effect of oxacyclohexadecane-2,13-dione. Unpublished report from Firmenich Incorporated, 18 February. Report number 38907 (RIFM, Woodcliff Lake, NJ, USA).
92. RIFM (Research Institute for Fragrance Materials, Inc.), 1987. Report on human repeated insult patch test. RIFM report number 7973, July 20 (RIFM, Woodcliff Lake, NJ, USA).
93. RIFM (Research Institute for Fragrance Materials, Inc.), 1988a. Repeat insult patch test of ethylene brassylate in human subjects. RIFM report number 8517, December 07 (RIFM, Woodcliff Lake, NJ, USA).
94. RIFM (Research Institute for Fragrance Materials, Inc.), 1988b. Repeated insult patch test in human subjects. RIFM report number 27675, March 17 (RIFM, Woodcliff Lake, NJ, USA).
95. RIFM (Research Institute for Fragrance Materials, Inc.), 1988c. Repeated insult patch test in human subjects. RIFM report number 27674, October 2 (RIFM, Woodcliff Lake, NJ, USA).
96. RIFM (Research Institute for Fragrance Materials, Inc.), 1988d. Repeated insult patch test in human subjects. RIFM report number 27673, February 8 (RIFM, Woodcliff Lake, NJ, USA).
97. RIFM (Research Institute for Fragrance Materials, Inc.), 1988e. Repeated insult patch test in human subjects. RIFM report number 8881, December 16 (RIFM, Woodcliff Lake, NJ, USA).
98. RIFM (Research Institute for Fragrance Materials, Inc.), 1988f. Repeat insult patch test of ethylene brassylate, methyl 2-nonynoate, 6,7-dihydrogeraniol and cyclohexyl methyl pentanone in humans. RIFM report number 6063, December 13 (RIFM, Woodcliff Lake, NJ, USA).
99. RIFM (Research Institute for Fragrance Materials, Inc.), 1989a. Human repeated insult patch test of ethylene brassylate. RIFM report number 12366, November 16 (RIFM, Woodcliff Lake, NJ, USA).
100. RIFM (Research Institute for Fragrance Materials, Inc.), 1989b. Human repeated insult patch test of ethylene brassylate. RIFM report number 12359, October 31 (RIFM, Woodcliff Lake, NJ, USA).
101. RIFM (Research Institute for Fragrance Materials, Inc.), 1989c. Repeated insult patch test of t-2-hexenal in human subjects. RIFM report number 27821, May 22 (RIFM, Woodcliff Lake, NJ, USA).
102. RIFM (Research Institute for Fragrance Materials, Inc.), 1989d. Repeated insult patch test of methyl octine carbonate in human subjects. RIFM report number 27820, May 22 (RIFM, Woodcliff Lake, NJ, USA).
103. RIFM (Research Institute for Fragrance Materials, Inc.), 1989e. Repeated insult patch test in human subjects. RIFM report number 9433, June 07 (RIFM, Woodcliff Lake, NJ, USA).
104. RIFM (Research Institute for Fragrance Materials, Inc.), 1990a. Human repeated insult patch test on ethylene brassylate. RIFM report number 14121, November 26 (RIFM, Woodcliff Lake, NJ, USA).
105. RIFM (Research Institute for Fragrance Materials, Inc.), 1990b. Human repeated insult patch test on ethylene brassylate. RIFM report number 14119, November 26 (RIFM, Woodcliff Lake, NJ, USA).
106. RIFM (Research Institute for Fragrance Materials, Inc.), 1990c. Repeat insult patch test on ethylene brassylate in human subjects. RIFM report number 12457, April 27 (RIFM, Woodcliff Lake, NJ, USA).
107. RIFM (Research Institute for Fragrance Materials, Inc.), 1990d. Repeat insult patch test of ethylene brassylate in human subjects. RIFM report number 12455, April 27 (RIFM, Woodcliff Lake, NJ, USA).
108. RIFM (Research Institute for Fragrance Materials, Inc.), 1990e. Repeat insult patch test of ethylene brassylate in human subjects. RIFM report number 12453, April 27 (RIFM, Woodcliff Lake, NJ, USA).
109. RIFM (Research Institute for Fragrance Materials, Inc.), 1990f. Human repeat insult patch test of ethylene brassylate. RIFM report number 12381, March 01 (RIFM, Woodcliff Lake, NJ, USA).
110. RIFM (Research Institute for Fragrance Materials, Inc.), 1990g. Repeated insult patch test of methyl octine carbonate and t-2-hexenal in human subjects. RIFM report number 27822, January 09 (RIFM, Woodcliff Lake, NJ, USA).
111. RIFM (Research Institute for Fragrance Materials, Inc.), 1991. Repeated insult patch test of fragrance materials in human subjects. RIFM report number 33718, November 25 (RIFM, Woodcliff Lake, NJ, USA).
112. RIFM (Research Institute for Fragrance Materials, Inc.), 1992a. Acute dermal toxicity study of oxacyclohexadecen-2-one in the rat. Unpublished report from Firmenich Incorporated, 06 May. Report number 31506 (RIFM, Woodcliff Lake, NJ, USA).
113. RIFM (Research Institute for Fragrance Materials, Inc.), 1992b. Acute oral toxicity study of oxacyclohexadecen-2-one in the rat. Unpublished report from Firmenich Incorporated, 06 May. Report number 31505 (RIFM, Woodcliff Lake, NJ, USA).
114. RIFM (Research Institute for Fragrance Materials, Inc.), 1992c. Bacterial reverse mutation assay of oxacyclohexadecen-2-one. Unpublished report from Firmenich Incorporated, 30 July. Report number 31513 (RIFM, Woodcliff Lake, NJ, USA).
115. RIFM (Research Institute for Fragrance Materials, Inc.), 1992d. Acute dermal irritation/corrosion study of oxacyclohexadecen-2-one in the rabbit. Unpublished report from Firmenich Incorporated, 06 May. Report number 31507 (RIFM, Woodcliff Lake, NJ, USA).
116. RIFM (Research Institute for Fragrance Materials, Inc.), 1992e. Acute eye irritation study of oxacyclohexadecen-2-one in the rabbit. Unpublished report from Firmenich Incorporated, 06 May. Report number 31508 (RIFM, Woodcliff Lake, NJ, USA).
117. RIFM (Research Institute for Fragrance Materials, Inc.), 1992f. Skin sensitization study of oxacyclohexadecen-2-one in the guinea pig - Magnusson & Kligman maximization. Unpublished report from Firmenich Incorporated, 02 April. Report number 31509 (RIFM, Woodcliff Lake, NJ, USA).
118. RIFM (Research Institute for Fragrance Materials, Inc.), 1993. Repeated insult patch test of ethylene brassylate on human subjects. RIFM report number 25756, November 12 (RIFM, Woodcliff Lake, NJ, USA).
119. RIFM (Research Institute for Fragrance Materials, Inc.), 1994a. Repeated insult patch test on ethylene brassylate in humans. RIFM report number 26501, July 29 (RIFM, Woodcliff Lake, NJ, USA).
120. RIFM (Research Institute for Fragrance Materials, Inc.), 1994b. Repeated insult patch test on ethylene brassylate in humans. RIFM report number 26499, July 29 (RIFM, Woodcliff Lake, NJ, USA).
121. RIFM (Research Institute for Fragrance Materials, Inc.), 1994c. Repeated insult patch test of ethylene brassylate in human subjects. RIFM report number 25752, July 25 (RIFM, Woodcliff Lake, NJ, USA).
122. RIFM (Research Institute for Fragrance Materials, Inc.), 1994d. Primary skin irritation study of ethylene brassylate in the rabbit. Unpublished report from Haarmann & Reimer GmbH, Report number 35548 (RIFM, Woodcliff Lake, NJ, USA).
123. RIFM (Research Institute for Fragrance Materials, Inc.), 1995a. 7-Day oral (gavage) dose rangefinding study of oxacyclohexadecen-2-one in the rat. Unpublished report from Firmenich Incorporated, 07 September. Report number 31511 (RIFM, Woodcliff Lake, NJ, USA).
124. RIFM (Research Institute for Fragrance Materials, Inc.), 1995b. Bacterial reverse mutation test with omega-pentadecalactone. Unpublished report from Soda Aromatic Company Ltd., 26 December. Report number 31967 (RIFM, Woodcliff Lake, NJ, USA).
125. RIFM (Research Institute for Fragrance Materials, Inc.), 1995c. Chromosome aberration test of oxacyclohexadecen-2-one in human lymphocytes in vitro. Unpublished report from Firmenich Incorporated, 06 October. Report number 31514 (RIFM, Woodcliff Lake, NJ, USA).
126. RIFM (Research Institute for Fragrance Materials, Inc.), 1995d. Repeated insult patch test of ethylene brassylate. RIFM report number 41232, December 22 (RIFM, Woodcliff Lake, NJ, USA).
127. RIFM (Research Institute for Fragrance Materials, Inc.), 1995e. Repeated insult patch test of ethylene brassylate in human subjects. RIFM report number 25754, June 20 (RIFM, Woodcliff Lake, NJ, USA).
128. RIFM (Research Institute for Fragrance Materials, Inc.), 1995f. Repeated insult patch test of ethylene brassylate in human subjects. RIFM report number 25750, June 21 (RIFM, Woodcliff Lake, NJ, USA).
129. RIFM (Research Institute for Fragrance Materials, Inc.), 1995g. Magnusson & Kligman maximisation study of ethylene brassylate in the guinea pig. Unpublished report from Haarmann & Reimer GmbH, 24 January. Report number 35549 (RIFM, Woodcliff Lake, NJ, USA).
130. RIFM (Research Institute for Fragrance Materials, Inc.), 1995h. Primary skin irritation study of w-pentadecalactone in the rabbit. Unpublished report from Symrise, 14 February. Report number 54975 (RIFM, Woodcliff Lake, NJ, USA).
131. RIFM (Research Institute for Fragrance Materials, Inc.), 1995i. Guinea pig maximisation study with w-pentadecalactone. Unpublished report from Symrise, 24 January. Report number 54976 (RIFM, Woodcliff Lake, NJ, USA).
132. RIFM (Research Institute for Fragrance Materials, Inc.), 1996. 4-Week oral (gavage) toxicity study of oxacyclohexadecen-2-one in the rat followed by a 2 week treatment-free period. Unpublished report from Firmenich Incorporated, 06 June. Report number 31512 (RIFM, Woodcliff Lake, NJ, USA).
133. RIFM (Research Institute for Fragrance Materials, Inc.), 1997a. Cutaneous test - patch test on ethylene brassylate. Unpublished report from Haarmann & Reimer GmbH, 01 July. Report number 35551 (RIFM, Woodcliff Lake, NJ, USA).
134. RIFM (Research Institute for Fragrance Materials, Inc.), 1997b. Human patch test of ethylene dodecanedioate (musk C-14). Unpublished report from Takasago International Corporation, 10 November. Report number 32954 (RIFM, Woodcliff Lake, NJ, USA).
135. RIFM (Research Institute for Fragrance Materials, Inc.), 1997c. Repeated insult patch study of oxacyclohexadecen-2-one. Unpublished report from Firmenich Incorporated, 21 August. Report number 31510 (RIFM, Woodcliff Lake, NJ, USA).
136. RIFM (Research Institute for Fragrance Materials, Inc.), 1997d. Cutaneous patch test with w-pentadecalactone. Unpublished report from Symrise, 01 July. Report number 54977 (RIFM, Woodcliff Lake, NJ, USA).
137. RIFM (Research Institute for Fragrance Materials, Inc.), 1997e. Primary skin irritation study and phototoxicity study in guinea pigs of ethylene brassylate. Unpublished report from Takasago International Corporation, 10 November. Report number 32581 (RIFM, Woodcliff Lake, NJ, USA).
138. RIFM (Research Institute for Fragrance Materials, Inc.), 1997f. Primary skin irritation study and phototoxicity study in guinea pigs of musk C-14. Unpublished report from Takasago International Corporation, 10 November. Report number 32953 (RIFM, Woodcliff Lake, NJ, USA).
139. RIFM (Research Institute for Fragrance Materials, Inc.), 1997g. Primary skin irritation study and phototoxicity study in guinea pigs of 10-oxahexadecanolide. Unpublished report from Takasago International Corporation, 10 November. Report number 32633 (RIFM, Woodcliff Lake, NJ, USA).
140. RIFM (Research Institute for Fragrance Materials, Inc.), 1997h. Delayed contact hypersensitivity study of guinea pigs of ethylene dodecanedioate (musk C-14). Unpublished report from Takasago International Corporation, 10 November. Report number 32952 (RIFM, Woodcliff Lake, NJ, USA).
141. RIFM (Research Institute for Fragrance Materials, Inc.), 1997i. Test for delayed contact hypersensitivity of w-pentadecalactone using the guinea pig maximization test. Unpublished report from Symrise, Report number 54978 (RIFM, Woodcliff Lake, NJ, USA).
142. RIFM (Research Institute for Fragrance Materials, Inc.), 1997j. Ethylene brassylate - local lymph node assay. Unpublished report from Haarmann & Reimer GmbH, 24 April. Report number 35550 (RIFM, Woodcliff Lake, NJ, USA).
143. RIFM (Research Institute for Fragrance Materials, Inc.), 1998a. 90-Day oral (gavage) toxicity study of oxacyclohexadecen-2-one in the rat. [Addendum Attached]. Unpublished report from Firmenich Incorporated, 13 March. Report number 32224 (RIFM, Woodcliff Lake, NJ, USA).
144. RIFM (Research Institute for Fragrance Materials, Inc.), 1998b. Repetetive cutaneous patch test with w-pentadecalactone. Unpublished report from Symrise, 02 February. Report number 54979 (RIFM, Woodcliff Lake, NJ, USA).
145. RIFM (Research Institute for Fragrance Materials, Inc.), 1999a. Ethylene dodecanedioate: Seven-day preliminary oral toxicity study in the rat. Unpublished report from International Flavors and Fragrances Incorporated, 22 March. Report number 47322 (RIFM, Woodcliff Lake, NJ, USA).
146. RIFM (Research Institute for Fragrance Materials, Inc.), 1999b. Ethylene dodecanedioate: Bacterial mutation assay. Unpublished report from International Flavors and Fragrances Incorporated, 10 September. Report number 47321 (RIFM, Woodcliff Lake, NJ, USA).
147. RIFM (Research Institute for Fragrance Materials, Inc.), 1999c. Hexadecanolide: Summary report of bacterial mutation assay. Unpublished report from International Flavors and Fragrances Incorporated, 02 February. Report number 54400 (RIFM, Woodcliff Lake, NJ, USA).
148. RIFM (Research Institute for Fragrance Materials, Inc.), 1999d. Hexadecanolide: Bacterial mutation assay. Unpublished report from International Flavors and Fragrances Incorporated, 02 February. Report number 54401 (RIFM, Woodcliff Lake, NJ, USA).
149. RIFM (Research Institute for Fragrance Materials, Inc.), 1999e. Ethylene dodecanedioate: In vitro mammalian chromosome aberration test in human lymphocytes. Unpublished report from International Flavors and Fragrances Incorporated, 06 August. Report number 47320 (RIFM, Woodcliff Lake, NJ, USA).
150. RIFM (Research Institute for Fragrance Materials, Inc.), 1999f. Hexadecanolide: In vitro mammalian chromosome aberration test in human lymphocytes. Unpublished report from International Flavors and Fragrances Incorporated, 06 August. Report number 54402 (RIFM, Woodcliff Lake, NJ, USA).
151. RIFM (Research Institute for Fragrance Materials, Inc.), 2000a. Ethylene dodecanedioate: Toxicity study by oral administration to CD rats for 4 weeks followed by a 2 week recovery period. Unpublished report from International Flavors and Fragrances Incorporated, 26 June. Report number 47323 (RIFM, Woodcliff Lake, NJ, USA).
152. RIFM (Research Institute for Fragrance Materials, Inc.), 2000b. Repeat insult patch test with ethylene dodecanedioate. Unpublished report from International Flavors and Fragrances Incorporated, 29 February. Report number 47317 (RIFM, Woodcliff Lake, NJ, USA).
153. RIFM (Research Institute for Fragrance Materials, Inc.), 2001a. Mutagenicity study of w-pentadecalactone in the Salmonella typhimurium/mammalian microsome reverse mutation assay. Unpublished report from Symrise, 09 April. Report number 54980 (RIFM, Woodcliff Lake, NJ, USA).
154. RIFM (Research Institute for Fragrance Materials, Inc.), 2001b. Oxacyclohexadecen-2-one: L5178Y TK +/- Mouse lymphoma assay. Unpublished report from Firmenich Incorporated, 13 November. Report number 40992 (RIFM, Woodcliff Lake, NJ, USA).
155. RIFM (Research Institute for Fragrance Materials, Inc.), 2003a. Salmonella typhimurium reverse mutation assay with oxacycloheptadec-10-ene-2-one. Unpublished report from Givaudan, 03 January. Report number 42054 (RIFM, Woodcliff Lake, NJ, USA).
156. RIFM (Research Institute for Fragrance Materials, Inc.), 2003b. Oxacyclohexadecen-2-one: Oral gavage one generation reproduction study in the rat. Unpublished report from Firmenich Incorporated, 14 July. Report number 44313 (RIFM, Woodcliff Lake, NJ, USA).
157. RIFM (Research Institute for Fragrance Materials, Inc.), 2003c. Oxacyclohexadecen-2-one: Oral gavage teratology study in the rat. Unpublished report from Firmenich Incorporated, 14 July. Report number 44314 (RIFM, Woodcliff Lake, NJ, USA).
158. RIFM (Research Institute for Fragrance Materials, Inc.), 2005a. E- and Z-Oxacyclohexadec-12(+13)-en-2-one (habanolide): reverse mutation assay " Ames Test" using Salmonella typhimurium and Escherichia coli. Unpublished report from Firmenich Incorporated, 3 August. Report number 58644 (RIFM, Woodcliff Lake, NJ, USA).
159. RIFM (Research Institute for Fragrance Materials, Inc.), 2005b. Ethylene brassylate: skin sensitization guinea pig maximization test. Unpublished report from Takasago International Corporation, 14 February. Report number 47396 (RIFM, Woodcliff Lake, NJ, USA).
160. RIFM (Research Institute for Fragrance Materials, Inc.), 2006. Repeated insult patch test with w-pentadecalactone. Unpublished report from Symrise, 15 December. Report number 54981 (RIFM, Woodcliff Lake, NJ, USA).
161. Rout P.K., Rao Y.R., Jena K.S., Sahoo D., Mishra B.C. A novel process for the extraction of fragrance components from Ambrette (Hibiscus abelmoschus L.) seeds. Organic Process Research and Development 2002, 6(4):401-404.
162. Salvito, D., Lapczynski, A., Calow, P., Greim, H., Escher, B., Sachse-Vasquez, C., McIntosh, C., submitted for publication. Macrocyclic fragrance materials- a screening level environmental assessment using chemical categorization. Journal of Ecotoxicology and Environmental Safety.
163. Sommer, C., 2004. The role of musk and musk compounds in the fragrance industry. In: Rimkus, G.G. (Ed.), The Handbook of Environmental Chemistry, Vol. 3, Part X. Springer-Verlag, Berlin, pp. 1-16.
164. vonOettingen W.F., Garcia F. The toxicology and vermicidal properties of the dilactone of acetone diacetic acid and beta angelica lactone in cats. Dilactone and beta angelica lactone as anthelmintics. The Journal of Pharmacology and Experimental Therapeutics 1929, 36:355-362.
165. Wild D., King M.T., Gocke E., Eckhardt K. Study of artificial flavouring substances for mutagenicity in the Salmonella/microsome, basc and micronucleus tests. Food and Chemical Toxicology 1983, 21(6):707-719.