Iso E Super
||It has been suggested that this article be merged with Tetramethyl_acetyloctahydronaphthalenes. (Discuss) Proposed since March 2016.|
Amberonne; Ambralux; Boisvelone; Derambrene; Timbersilk; Methyl cyclomyrectone; 1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthalenone; OTNE
3D model (JSmol)
|Molar mass||234.38 g/mol|
|Appearance||colorless to a pale yellow liquid|
|Boiling point||134 °C (273 °F; 407 K)|
Refractive index (nD)
|1.4975–1.500 (at 20 °C)|
|Flash point||> 100 °C (closed cup)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Iso E Super is a synthetic ketone fragrance.
Iso E Super is a very common perfume ingredient, providing a sandalwood-like and cedarwood-like fragrance, in soap, shampoo, perfumes, detergents, fabric fresheners, antiperspirants or deodorants, and air fresheners. It is also used as a tobacco flavoring (at 200–2000 ppm), as a plasticizer and as a precursor for the delivery of organoleptic and antimicrobial compounds.
Iso E Super is produced commercially by Diels–Alder reaction of Myrcene with 3-Methyl-3-penten-2-one in the presence of aluminum chloride to give a monocyclic intermediate that is cyclized in the presence of 85% phosphoric acid.
Carrying out the initial Diels-Alder reaction using a Lewis acid catalyst such as aluminum chloride appears to ensure that the acetyl group is at position 2 of the resulting cyclohexene adduct, which distinguished Iso E Super from other (previously patented) fragrances based on tetramethyl-acetyl-octaline. The second cyclization reaction yields a mixture of diastereomers with the general structure depicted above, the predominant ones being (2R,3R) and (2S,3S).
Iso E Super may cause allergic reactions detectable by patch tests in humans and chronic exposure to Iso E Super from perfumes may result in permanent hypersensitivity. 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).
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.
List of products containing Iso E Super
- The fragrance Molecule 01 (Escentric Molecules, 2005) is essentially just Iso E Super note. Its partner fragrance Escentric 01 contains Iso E Super but also ambroxan, pink pepper, green lime with balsamic notes like benzoin mastic and incense.
- The fragrance Eternity by Calvin Klein (1988) contained 11.7% Iso E Super in the fragrance portion of the formula.
- The fragrance "Paper " by Commodity, lists Iso E Super in the fragrance description on the website.
- The male fragrance Fahrenheit (Dior, 1988) is 25% Iso E Super. (of the fragrance compound).
- While Lalique's Eau de Parfum Perles de Lalique (Lalique, 2007) is apparently a whopping 80% Iso E Super (of the perfume compound).
- The men's fragrance Encre Noire (Lalique, 2006) is 45% of the fragrance compound, Iso E Super.
- The fragrance Poivre Samarcande (Hermes, 2004) contains 71% Iso E Super (of the perfume compound).
- The very popular Terre D'Hermes (Hermes, 2006) contains 55% Iso E Super (of the perfume compound).
- Kenzo Air (Kenzo, 2003) is 48% of the fragrance compound Iso E Super.
- The men's fragrance Fierce Cologne (Abercrombie & Fitch, 2002) is 48% Iso E Super.
- Home fragance "Under a fig tree" from Rituals brand.
- Creed's Aventus (2010) contains 18% Iso E Super in its fragrance compound.
- 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
- Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 45–46
- US 3929677, Hall, John B. & James Milton Sanders, "Perfume composition and perfume articles containing one isomer of an octahydrotetramethyl acetonaphthone", issued 1975
- PJ Frosch; et al. (Nov 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, PMID 8565489, doi:10.1111/j.1600-0536.1995.tb02048.x
- Iso E Super Material Safety Data Sheet (PDF), Santa Cruz Biotechnology
- 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
- Predicting the Bioconcentration of Fragrance Ingredients by Rainbow Trout Using Measured Rates of in Vitro Intrinsic Clearance (PDF), ACS Publications, Environmental Science & Technology, 2014
- Ranking of Concern from persistence, bioaccumulation and toxicity in the environmentof Pharmaceuticals and Personal Care Products (PDF)
- "Stagnant water, charcoal, semen... 10 smells that changed the perfume industry". The Telegraph. Retrieved 2017-06-21.