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Related Esters and Alcohols of Cinnamic Acid and Cinnamyl Alcohol When Used As Fragrance Ingredients Q

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Related Esters and Alcohols of Cinnamic Acid and Cinnamyl Alcohol When Used As Fragrance Ingredients Q Available online at www.sciencedirect.com Food and Chemical Toxicology 45 (2007) S1–S23 www.elsevier.com/locate/foodchemtox Review A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol when used as fragrance ingredients q The RIFM Expert Panel D. Belsito a, D. Bickers b, M. Bruze c, P. Calow d, H. Greim e, J.M. Hanifin f, A.E. Rogers g, J.H. Saurat h, I.G. Sipes i, H. Tagami j a University of Missouri (Kansas City), Division of Dermatology, 6333 Long Avenue, Shawnee, KS 66216, USA b College of Physicians and Surgeons of Columbia University, Department of Dermatology, 161 Fort Washington Avenue, New York, NY 10032, USA c Lund University, Malmo University Hospital, Department of Occupational and Environmental Dermatology, Sodra Forstadsgatan 101 Malmo SE-20502, Sweden d Department of Environmental, Social and Spatial Change, Roskilde University, DK 4000, Denmark e Institute of Toxicology and Environmental Hygiene, Technical University of Munich, Hohenbachernstrasse 15-17, D-85354 Freising, Germany f Oregon Health Sciences University, Department of Dermatology L468, 3181 SW Sam Jackson Park Road, Portland, Oregon 97201-3098, USA g Boston University School of Medicine, Department of Pathology and Laboratory Medicine, 715 Albany Street, Boston, MA 02118-2394, USA h University Hospital Geneva, Department of Dermatology, CH-1211 Geneva 14, Switzerland i University of Arizona, Health Sciences Center, College of Pharmacy, 1703 East Mable Street, Tucson, AZ 85721, USA j Tohoku University School of Medicine, 1-1 Seiryo-machi, Aoba-ku Sendai 980, Japan Abstract An evaluation and review of a structurally related group of fragrance materials. Ó 2007 Elsevier Ltd. All rights reserved. Keywords: Safety; Review; Fragrance; Esters; Alcohols; Cinnamic Contents 1. Introduction . ........................................................................... S2 2. Chemical identity and exposure (Table 1) ......................................................... S2 2.1. Estimated consumer exposure. S6 3. Biological data . ........................................................................... S6 3.1. Absorption, distribution and metabolism. S6 3.1.1. Percutaneous absorption .............................................................. S6 3.1.2. Pharmacokinetics ................................................................... S6 3.1.3. Metabolism. ....................................................................... S6 4. Toxicological studies . ..................................................................... S9 4.1. Acute toxicity (Tables 2A–2C) ............................................................. S9 4.2. Subchronic toxicity (Table 3)............................................................. S10 q All correspondence should be addressed to: A.M. Api, 50 Tice Boulevard, Woodcliff Lake, NJ 07677, USA. Tel.: +1 201 689 8089; fax: +1 201 689 8090. E-mail address: [email protected] 0278-6915/$ - see front matter Ó 2007 Elsevier Ltd. All rights reserved. doi:10.1016/j.fct.2007.09.087 S2 D. Belsito et al. / Food and Chemical Toxicology 45 (2007) S1–S23 4.2.1. Dermal studies . S10 4.2.2. Oral studies . S10 4.3. Chronic toxicity . .............................................................. S11 4.4. Mutagenicity and genotoxicity . .............................................................. S11 4.4.1. Bacterial studies (Table 4)......................................................... S11 4.4.2. Insect studies (Table 5)........................................................... S12 4.4.3. Mammalian cell systems (Table 6) ................................................... S12 4.4.4. In vivo studies . S12 4.5. Carcinogenicity . .............................................................. S12 4.6. Reproductive and developmental toxicity . ................................................. S14 4.7. Skin irritation . .............................................................. S14 4.7.1. Human studies (Table 7).......................................................... S14 4.7.2. Animal studies (Table 8).......................................................... S14 4.8. Mucous membrane (eye) irritation (Table 9)..................................................... S14 4.9. Skin sensitization . .............................................................. S14 4.9.1. Human studies (Table 10)......................................................... S14 4.9.2. Animal studies (Table 11) ......................................................... S16 4.10. Phototoxicity and photoallergy. .............................................................. S16 4.10.1. Phototoxicity (Table 12) .......................................................... S16 4.11. Environmental data . .............................................................. S16 5. Summary . ................................................................................... S17 6. Conclusion ................................................................................... S19 Conflicts of interest statement . .............................................................. S20 References ................................................................................... S20 1. Introduction by the Food and Drug Administration (FDA) and 20 materials by the Flavor and Extract Manufacturers’ Asso- This report summarizes scientific data relevant to the ciation (FEMA, 1965) as Generally Recognized as Safe risk assessment of related esters and alcohols of cinnamic (GRAS) as flavor ingredients [Numbers 2022, 2063, 2064, acid and cinnamyl alcohol (see Table 1). These substances 2065, 2142, 2192, 2193, 2293, 2296, 2297, 2298, 2299, are all used as fragrance ingredients. This report uses data 2300, 2301, 2302, 2430, 2641, 2698, 2863, 2939]. Twenty from animals and humans by various routes of exposure, one of these materials were also included in the Council but emphasizes the risk assessment for the use of related of Europe’s list of substances [Numbers 79, 208, 216, esters and alcohols of cinnamic acid and cinnamyl alcohol 235, 279, 323, 325, 326, 327, 328, 329, 331, 332, 333, 335, as fragrance ingredients. The scientific evaluation focuses 336, 352, 414, 454, 496, 743] which may be used in food- on dermal exposure, which is considered to be the primary stuffs (Council of Europe, 2000). Finally, the International route for fragrance materials. Where relevant, toxicity, Joint FAO/WHO Expert Committee on Food Additives metabolism and biological fate data from other exposures (JECFA, 2000) has evaluated 19 of these materials and have been considered. This assessment, therefore, addresses found them to have no safety concerns based on current the use of the material as a fragrance ingredient. levels of intake as food flavors. The current format includes a group summary evaluation Seven of the 23 substances have been reported as com- paper and individual Fragrance Materials Reviews on dis- mon components of food occurring mainly in a wide vari- crete chemicals. The group summary is an evaluation of rel- ety of fruits, vegetables, herbs and spices in varying evant data selected from the large bibliography of studies concentrations. For example, concentrations of 2800– and reports on the individual chemicals. The selected data 51,000 ppm cinnamyl acetate in cinnamon (Cinnamomum were deemed to be relevant based on protocols that conform zeylanicum Blume and other Cinnamomum species), and with current guidelines, quality of the data, statistical signif- trace-278,000 ppm methyl cinnamate in basil (Ocimum icance and appropriate exposure. These are identified in tab- basilicum varieties) have been reported (TNO, 2006). ular form in the group summary. The Fragrance Material Quantitative natural occurrence data have been reported Reviews (available online at www.rifm.org) contain a com- for methyl cinnamate and ethyl cinnamate, and indicate prehensive summary of published and non-published that intake of these substances is predominately from food reports including complete bibliographies. (i.e., consumption ratio >1) (Stofberg and Grundschober, 1987). 2. Chemical identity and exposure (Table 1) Data from a survey conducted in the year 2004 indicate that the annual worldwide use of benzyl cinnamate, cin- In the United States, the regulatory status of these mate- namyl acetate and methyl cinnamate is between 10 and rials includes approval of 21 substances (21 CFR 172.515) 100 metric tons (see Table 1) and the annual worldwide Table 1 Material identification and summary of volume of use and dermal exposure Material Synonyms Structure Annual worldwide Dermal systemic exposure in Maximum skin (metric tons)a cosmetic products (mg/kg/day) Levelb Allyl cinnamate • Allyl b-phenylacrylate O <0.1 0.0127 0.10% CAS# 1866-31-5 • Allyl 3-phenyl-2-propenoate O Molecular weight: 188.23 • 2-Propenoic acid, 3-phenyl-, 2-propenyl ester Log Kow (calculated): 3.2 • Propenyl cinnamate • 2-Propen-1-yl 3-phenyl-2-propenoate • Vinyl carbinyl cinnamate Amyl cinnamate • Pentyl cinnamate <0.1 0.0127 0.10% CAS# 3487-99-8 • Pentyl 3-phenyl-2-propenoate o Molecular weight: 218.3 • 2-Propenoic acid, 3-phenyl-, pentyl ester o D. Belsito et al. / Food and Chemical Toxicology 45 (2007) S1–S23 Log Kow (calculated): 4.32 alpha-Amylcinnamyl • a-Amylcinnamic alcohol OH 0.1–1 0.0038 0.04% alcohol • 2-Amyl-3-phenyl-2-propen-1-ol CAS# 101-85-9 • 2-Benzylideneheptanol Molecular weight: 204.31 • 1-Heptanol, 2-(phenylmethylene)- Log Kow (calculated): 4.35 • a-Pentylcinnamyl alcohol Benzyl cinnamate
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