Iso E Super: Difference between revisions
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Revision as of 21:52, 3 February 2014
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| Names | |
|---|---|
| IUPAC name
1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)ethanone
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| Other names
1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one (INCI)
1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthalenone | |
| Identifiers | |
| ECHA InfoCard | 100.053.777 |
CompTox Dashboard (EPA)
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| Properties | |
| C16H26O | |
| Molar mass | 234.38 g/mol |
| Appearance | colorless to a pale yellow liquid |
| Boiling point | 134 °C |
Refractive index (nD)
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1.4975-1.500 |
| Hazards | |
| Flash point | > 100 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Iso E Super is a synthetic ketone used as an amber fragrance.[1]
Uses
Iso E Super is used as a perfume ingredient, providing a sandalwood-like and cedarwood-like fragrance, in soap, shampoo, perfumes, detergents, and malodor-reducing compounds, such as fabric freshening compounds, antiperspirants or deodorants, and air freshening compounds.[2]
It is used in tobacco products (at 200-2000 ppm) to improve the aroma and the flavor of tobacco and its smoke, giving them sweet, spicy, sandalwood-like and cedarwood-like notes.[3] It has also been used to control the hardness of a polyurethane foam, and as a precursor for the delivery of organoleptic and antimicrobial compounds.[2]
Production
Iso E Super is produced commercially by Diels–Alder reaction of Myrcene with 3-methyl-3-pentene-2-one in the presence of aluminum chloride to give a monocyclic intermediate that is cyclized in the presence of 85% phosphoric acid:[4]
Toxicity
Iso-E Super may cause allergic reactions detectable by patch tests in humans.[5] In a study with female mice, Iso E Super was positive in the local lymph node assay (LLNA) and irritancy assay (IRR), but negative in the mouse ear swelling test (MEST).[6]
No data were available regarding chemical disposition, metabolism, or toxicokinetics; acute, shortterm, subchronic, or chronic toxicity; synergistic or antagonistic activity; reproductive or teratological effects; carcinogenicity; genotoxicity; or immunotoxicity.[2]
List of products containing Iso E Super
- The fragrance Eternity by Calvin Klein contains 11.7 % Iso E Super in the fragrance portion of the formula.[2]
References
- ^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 45–46
{{citation}}: Explicit use of et al. in:|author=(help) - ^ a b c d Bonnie L. Carson (2001), 1-(1,2,3,4,5,6,7,8-Octahydro-2,3-8,8-tetramethyl-2-naphthalenyl) ethanone. Review of Toxicological Literature (PDF), National Institute of Environmental Health Sciences, Research Triangle Park, NC
- ^ Novel tobacco product comprising one or more isomers of an octahydrotetramethyl acetonaphthone, 1975
{{citation}}: Unknown parameter|country-code=ignored (help); Unknown parameter|inventor1-first=ignored (help); Unknown parameter|inventor1-last=ignored (help); Unknown parameter|inventor2-first=ignored (help); Unknown parameter|inventor2-last=ignored (help); Unknown parameter|patent-number=ignored (help) - ^ Perfume composition and perfume articles containing one isomer of an octahydrotetramethyl acetonaphthone, 1975
{{citation}}: Unknown parameter|country-code=ignored (help); Unknown parameter|inventor1-first=ignored (help); Unknown parameter|inventor1-last=ignored (help); Unknown parameter|inventor2-first=ignored (help); Unknown parameter|inventor2-last=ignored (help); Unknown parameter|patent-number=ignored (help) - ^ PJ Frosch; et al. (1995), "Patch testing with fragrances: results of a multicenter study of the European Environmental and Contact Dermatitis Research Group with 48 frequently used constituents of perfumes.", Contact Dermatitis, 33 (5): 333–42
{{citation}}: Explicit use of et al. in:|author=(help); Unknown parameter|month=ignored (help) - ^ NTP Report on the Assessment of Contact Hypersensitivity to Iso-E Super in Female BALB/c Mice (CASRN: 54464-57-2), National Institute of Environmental Health Sciences, 2010