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Macrocyclic Ketones When Used As Fragrance Ingredients Q the RIFM Expert Panel

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Macrocyclic Ketones When Used As Fragrance Ingredients Q the RIFM Expert Panel Food and Chemical Toxicology 49 (2011) S126–S141 Contents lists available at ScienceDirect Food and Chemical Toxicology journal homepage: www.elsevier.com/locate/foodchemtox Review A toxicological and dermatological assessment of macrocyclic ketones when used as fragrance ingredients q The RIFM Expert Panel D. Belsito a, D. Bickers b, M. Bruze c, P. Calow d, M.L. Dagli e, A.D. Fryer f, H. Greim g, Y. Miyachi h, J.H. Saurat i, I.G. Sipes j a Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Avenue, New York, NY 10032, USA b Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Ave., New York, NY 10032, USA c Malmo University Hospital, Department of Occupational & Environmental Dermatology, Sodra Forstadsgatan 101, Entrance 47, Malmo SE-20502, Sweden d Science and Public Policy, Office of Research and Economic Development, 230 Whittier Research Center, Lincoln NE 68583-0857, USA e University of Sao Paulo, School of Veterinary Medicine and Animal Science, Department of Pathology, Av. Prof. dr. Orlando Marques de Paiva, 87, Sao Paulo CEP 05508-900, Brazil f Oregon Health Science University, 3181 SW Sam Jackson Park Rd., Portland, OR 97239, USA g Technical University of Munich, Institute for Toxicology & Environmental Hygiene, Hohenbachernstrasse 15-17, Freising-Weihenstephan D-85354, Germany h Department of Dermatology, Kyoto University Graduate School of Medicine, 54 Kawahara-cho, Shogoin, Sakyo-ku, Kyoto 606-8507, Japan i Swiss Centre for Human Applied Toxicology, University Medical Center, University of Geneva, Rue Michel Servat, 1211 Geneve 4 CH, Switzerland j Department of Pharmacology, University of Arizona, College of Medicine, 1501 North Campbell Avenue, P.O. Box 245050, Tucson, AZ 85724-5050, USA article info abstract Article history: The macrocyclic ketone (MK) group of fragrance ingredients was evaluated for safety following a com- Available online 23 July 2011 plete literature search. For high end users, calculated maximum dermal exposures vary from 0.13% to 1.10%; systemic exposures vary from 0.0005 to 0.0441 mg/kg/day. The MKs had low acute toxicity and Keywords: no significant repeat dose toxicity. Liver weight and blood biochemistry effects were reversible after Safety 2 weeks. No genotoxicity in bacteria and mammalian cell lines was observed. Reproductive toxicity Review was not observed for 3-methylcyclopentadecenone in an OECD compliant study. In humans, MKs are gen- Fragrance erally not irritating after one application. Animal studies showed irritation for some materials at concen- Macrocyclic ketone trations higher than current consumer exposure. At rates consistent with current human exposure, phototoxicity and photosensitization were not observed. In animals, some MKs are sensitizers only at concentrations of 20%, 30%, or 100%, which are higher than current consumer exposure. No evidence of sensitization was observed in human tests. In patients with fragrance allergy, reactions were seen with cyclopentadecanone (3/178). Based on these findings, the Panel is of the opinion that there are no safety concerns for the MKs at reported levels of use and exposure as fragrance ingredients. Ó 2011 Published by Elsevier Ltd. Contents 1. Introduction ........................................................................................................ S127 2. Chemical identity, regulatory status, and exposure . ..................................................................... S127 2.1. Rationale for grouping macrocyclic ketones . ........................................................... S127 2.2. Occurrence and use. ........................................................................... S130 2.3. Estimated consumer exposure . ........................................................................... S130 3. Metabolism. ........................................................................................................ S131 4. Toxicokinetics. ........................................................................................ S131 5. Toxicological studies . ........................................................................................ S131 5.1. Acute toxicity . .............................................................................................. S131 5.2. Repeat-dose studies . ........................................................................... S132 5.2.1. Oral studies. ................................................................................ S132 q All correspondence should be addressed to A.M. Api, Research Institute for Fragrance Materials Inc., 50 Tice Boulevard, Woodcliff Lake, NJ 07677, USA. E-mail address: [email protected] (A.M. Api). 0278-6915/$ - see front matter Ó 2011 Published by Elsevier Ltd. doi:10.1016/j.fct.2011.07.040 D. Belsito et al. / Food and Chemical Toxicology 49 (2011) S126–S141 S127 5.2.2. Dermal studies . ............................................................................. S134 5.2.3. Inhalation studies . ............................................................................. S134 6. Genotoxicity studies. .................................................................................. S134 6.1. Bacteria . ........................................................................................ S134 6.2. Mammalian cell lines . ........................................................................................ S134 7. Carcinogenicity. ..................................................................................................... S134 8. Reproductive toxicity . .................................................................................. S134 9. Irritation . ..................................................................................................... S135 9.1. Human studies . ........................................................................................ S135 9.2. Animal studies. ........................................................................................ S135 9.2.1. Skin irritation . ............................................................................. S135 9.2.2. Mucous membrane (eye) irritation in rabbits. .......................................................... S135 10. Skin sensitization . .................................................................................. S135 10.1. Human studies. ........................................................................................ S135 10.1.1. Induction of human sensitization . .......................................................... S135 10.1.2. Diagnostic patch-tests . ............................................................................. S136 10.2. Animal studies. ........................................................................................ S136 11. Phototoxicity and photosensitization . .................................................................................. S137 11.1. Phototoxicity . ........................................................................................ S138 11.2. Photosensitization . ........................................................................................ S138 12. Conclusions . ..................................................................................................... S139 Conflict of Interest . .................................................................................. S139 Acknowledgements . .................................................................................. S139 References. ..................................................................................................... S139 1. Introduction for flavoring and concluded that they do not present a safety con- cern at current levels of intake when used as a flavoring agent. The In 2010 complete literature searches were conducted on the Flavor and Extract Manufacturers Association (FEMA) companies macrocyclic ketones (MK) group of fragrance ingredients. This doc- have designated 3-methyl-1-cylopentadecanone (CAS RN 541-91-3) ument provides a risk assessment of these materials as fragrance and cycloheptadeca-9-en-1-one (CAS RN 542-46-1) as Generally ingredients. These fragrance ingredients are blended with other Recognized as Safe (GRAS) for use as flavor ingredients. fragrance ingredients that may or may not be MK for use in deco- Table 1 provides a list of the MK fragrance ingredients that are rative cosmetics, fine perfumes, personal care products such as evaluated in this report along with their Chemical Abstract Service shampoos, soaps, and in household products such as cleaners, air registration numbers (CAS RN), synonyms, structural formulas, and fresheners and detergents. The scientific evaluation focuses on der- some physiochemical properties (e.g., calculated log Kow, vapor mal exposure, which is considered to be the primary route for fra- pressure, and water solubility), annual worldwide production, grance materials. Where relevant; toxicity, metabolism, and and estimated dermal systemic exposure data for these com- biological fate data from other exposures have been considered. pounds. Tables 2–10 summarize the available MK toxicology data. The current format includes a group summary evaluation paper Two structurally related compounds, 3-methylcyclotridecan-1-one and individual Fragrance Material Reviews on discrete chemicals. (CAS RN 61415-11-0) and cyclotetradecan-1-one (CAS RN 3603- The group summary is an evaluation of relevant data selected from 99-4) are listed in the RIFM database but not
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