Iso E Super: Difference between revisions

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Tetramethyl acetyloctahydronaphthalenes

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+#REDIRECT [[Tetramethyl acetyloctahydronaphthalenes]] {{R from merge}}
-{{merge|Tetramethyl_acetyloctahydronaphthalenes|discuss=Talk:Tetramethyl_acetyloctahydronaphthalenes|date=March 2016}}
-{{Chembox
-| ImageFile = Iso E Super structure.svg
-| ImageSize =
-| ImageAlt = Structure formula of Iso E Super
-| ImageFileL1 = (2R,3R)-Iso E Super structure.svg
-| ImageCaptionL1 = (2R,3R)- [54464-57-2]
-| ImageFileR1 = (2S,3S)-Iso E Super structure.svg
-| ImageCaptionR1 = (2S,3S)- [144651-56-9]
-| IUPACName = 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one
-| OtherNames = Amberonne; Ambralux; Boisvelone; Derambrene; Timbersilk; Methyl cyclomyrectone; 1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthalenone; OTNE
-|Section1={{Chembox Identifiers
-| CASNo = 54464-57-2
-| PubChem =
-| SMILES = CC(=O)[C@]1(C)CC2=C(C[C@H]1C)CCCC2(C)C }}
-|Section2={{Chembox Properties
-| C=16 | H=26 | O=1
-| MolarMass = 234.38 g/mol
-| Appearance = colorless to a pale yellow liquid
-| Density =
-| MeltingPt =
-| BoilingPtC = 134
-| RefractIndex = 1.4975–1.500 (at 20 °C)
-| Odor = amber, woody
-| Solubility = }}
-|Section3={{Chembox Hazards
-| MainHazards =
-| FlashPt = > 100 °C (closed cup)
-| AutoignitionPt = }}
-}}
-'''Iso E Super''' is a synthetic [[ketone]] fragrance.
-== Uses ==
-Iso E Super is a very common perfume ingredient, providing a [[sandalwood]]-like and [[cedarwood]]-like fragrance, in [[soap]], [[shampoo]], [[perfumes]], [[detergents]], [[fabric freshener]]s, [[antiperspirant]]s or [[deodorant]]s, and [[air freshener]]s. 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.<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>
-== Production ==
-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="flav">{{citation | author=Karl-Georg Fahlbusch | contribution=Flavors and Fragrances | title=[[Ullmann's Encyclopedia of Industrial Chemistry]] | edition=7th | publisher=Wiley | year=2007 | pages=45–46|display-authors=etal}}</ref>
-[[File:Iso E Super synthesis.svg|thumb|Synthesis]]
-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 [[diastereomer]]s with the general structure depicted above, the predominant ones being (2R,3R) and (2S,3S).<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>
-== Safety ==
-Iso E Super may cause allergic reactions detectable by [[patch test]]s in humans<ref name="derm">{{citation | author=PJ Frosch | 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|display-authors=etal}}</ref> and chronic exposure to Iso E Super from perfumes may result in permanent [[hypersensitivity]].<ref name="aqua1"/> 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>
-Iso E Super is [[toxic]] and [[bioaccumulative]] in aquatic organisms and the environment,<ref name="aqua1">{{citation | title=Iso E Super Material Safety Data Sheet | publisher=Santa Cruz Biotechnology | url=http://datasheets.scbt.com/sc-211663.pdf}}</ref><ref name="aqua2">{{citation | title=Predicting the Bioconcentration of Fragrance Ingredients by Rainbow Trout Using Measured Rates of in Vitro Intrinsic Clearance | publisher=ACS Publications, Environmental Science & Technology | year=2014 | url=http://www.d.umn.edu/biology/documents/Nichols1.pdf}}</ref> and is suspected to be bioaccumulative in humans.<ref name="bioacc">{{citation | title=Ranking of Concern from persistence, bioaccumulation and toxicity in the environmentof Pharmaceuticals and Personal Care Products | url=http://www.researchgate.net/profile/R_Irusta/publication/266516858_Ranking_of_Concern_from_persistence_bioaccumulation_and_toxicity_in_the_environment_of_Pharmaceuticals_and_Personal_Care_Products/links/5433d2780cf2bf1f1f263502.pdf}}</ref>
-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" />
-== 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 (perfume)|Eternity]] by [[Calvin Klein]] (1988) contained 11.7% Iso E Super in the fragrance portion of the formula.<ref name="tox" />
-* The fragrance '''''"Paper "''''' by [https://www.commoditygoods.com Commodity], lists Iso E Super in the fragrance description on the website.
-* The male fragrance [[Fahrenheit (perfume)|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.
-== References ==
-{{reflist|2}}
-[[Category:Perfume ingredients]]
-[[Category:Flavors]]
-[[Category:Ketones]]