Iso E Super: Difference between revisions
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Merge to Tetramethyl acetyloctahydronaphthalenes following unopposed 2016 proposal; see Talk:Tetramethyl acetyloctahydronaphthalenes#Merge? Tag: New redirect |
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#REDIRECT [[Tetramethyl acetyloctahydronaphthalenes]] {{R from merge}} |
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{{Chembox |
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| ImageFile = Iso E Super structure.svg |
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| ImageSize = |
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| ImageAlt = Structure formula of Iso E Super |
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| IUPACName = 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)ethanone |
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| OtherNames = 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one ([[INCI]])<br />1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthalenone<br />Ethanone, 1-(1,2,3,4,5,6,7,8-Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-<br /><br />Amberonne<br />Ambralux<br />Boisvelone<br />Derambrene<br />Iso-E Super<br />Methyl cyclomyrectone |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 54464-57-2 |
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| PubChem = |
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| SMILES = CC(=O)[C@]1(C)CC2=C(C[C@H]1C)CCCC2(C)C }} |
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| Section2 = {{Chembox Properties |
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| C = 16 |
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| H = 26 |
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| O = 1 |
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| MolarMass = 234.38 g/mol |
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| Appearance = colorless to a pale yellow liquid |
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| Density = |
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| MeltingPt = |
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| BoilingPt = 134 °C |
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| RefractIndex = 1.4975-1.500 (at 20 °C) |
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| Odor = amber, woody |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = > 100 °C (closed cup) |
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| Autoignition = }} |
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}} |
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'''Iso E Super''' is a polycyclic synthetic [[musk]] [[ketone]], which is used as an [[ambergris]] fragrance.<ref name="flav">{{citation | author=Karl-Georg Fahlbusch et al. | contribution=Flavors and Fragrances | title=[[Ullmann's Encyclopedia of Industrial Chemistry]] | edition=7th | publisher=Wiley | year=2007 | pages=45-46}}</ref> |
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== Uses == |
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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 freshener|fabric freshening compounds]], [[antiperspirant]]s or [[deodorant]]s, and [[air freshener|air freshening compounds]].<ref name="tox">{{citation | author=Bonnie L. Carson | title=1-(1,2,3,4,5,6,7,8-Octahydro-2,3-8,8-tetramethyl-2-naphthalenyl) ethanone. Review of Toxicological Literature | publisher=[[National Institute of Environmental Health Sciences]] | year=2001 | url=http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPDF/IsoESuper_508.pdf}}</ref> |
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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.<ref name="tp">{{citation | inventor1-last=Hall | inventor1-first=John B. | inventor2-last=Sanders | inventor2-first=James Milton | title=Novel tobacco product comprising one or more isomers of an octahydrotetramethyl acetonaphthone | country-code=US | patent-number=3907321 | issue-date=1975}}</ref> |
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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.<ref name="tox" /> |
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== Production == |
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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 [[cyclization|cyclized]] in the presence of 85 % [[phosphoric acid]]:<ref name="pp">{{citation | inventor1-last=Hall | inventor1-first=John B. | inventor2-last=Sanders | inventor2-first=James Milton | title=Perfume composition and perfume articles containing one isomer of an octahydrotetramethyl acetonaphthone | country-code=US | patent-number=3929677 | issue-date=1975}}</ref> |
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[[File:Iso E Super synthesis.svg|center]] |
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Carrying out the initial Diels-Alder reaction using a [[Lewis acid]] [[catalyst]] 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.<ref name="pp" /> The second cyclization reaction yields a mixture of [[diastereomer]]s with the general structure depicted above, the predominant ones being (2R,3R)- and (2S,3S)-:<ref name="tox" /> |
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[[Image:(2R,3R)-Iso E Super structure.svg|thumb|(2R,3R)- [54464-57-2]]] |
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[[Image:(2S,3S)-Iso E Super structure.svg|thumb|(2S,3S)- [144651-56-9]]] |
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== Toxicity == |
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Iso-E Super may cause allergic reactions detectable by [[patch test]]s in humans.<ref name="derm">{{citation | author=PJ Frosch et al. | title=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. | journal=Contact Dermatitis | volume=33 | issue=5 |date=Nov 1995 | pages=333–42 | pmid=8565489 | doi=10.1111/j.1600-0536.1995.tb02048.x}}</ref> 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).<ref name="mice">{{citation | title=NTP Report on the Assessment of Contact Hypersensitivity to Iso-E Super in Female BALB/c Mice (CASRN: 54464-57-2) | publisher=National Institute of Environmental Health Sciences | year=2010 | url=http://ntp.niehs.nih.gov/?objectid=FD21FC74-C672-AC9C-5395E19CB7EB1F04}}</ref> |
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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.<ref name="tox" /> |
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== List of products containing Iso E Super == |
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* The fragrance [[Eternity (perfume)|Eternity]] by [[Calvin Klein]] contains 11.7 % Iso E Super in the fragrance portion of the formula.<ref name="tox" /> |
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* The fragrance "Paper" by [https://www.commoditygoods.com Commodity], lists Iso E Super in the fragrance description on the website. |
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* The male fragrance [[Fahrenheit (perfume)|Fahrenheit]] (Dior, 1988) is 25% Iso E Super. |
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* While Lalique's Eau de Parfum '''''Perles de Lalique''''' (Lalique, 2007) is a whopping 80% Iso E Super. |
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== References == |
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{{reflist|2}} |
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[[Category:Perfume ingredients]] |
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[[Category:Flavors]] |
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[[Category:Ketones]] |
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Latest revision as of 21:02, 17 January 2018
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