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#REDIRECT [[Tetramethyl acetyloctahydronaphthalenes]] {{R from merge}}
{{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; Methyl cyclomyrectone; 1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthalenone
| 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)
| Autoignition = }}
}}

'''Iso E Super''', first synthesised in 1975, is a synthetic polycyclic musk [[ketone]] molecule/compound, with smooth, 'velvety', dry woody / peppery / amber scent tonalities, often used in ambergris-like accords etc, in fragrance, cosmetic and fine perfume production. <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> It is an odd and relatively larger molecule, size-wise, which tends to smell differently to different people, some perceiving it as more 'woody' whilst others more 'musky', and others still might not be able to smell it at all (i.e. are anosmic to it).
The compound is used to impart fullness and subtle strength to fragrances. It's also known as a superb 'floraliser', helping to heighten a floral effect ; an effective 'harmoniser' (has excellent blending power) ; plus useful for achieving various other maximising 'magic tricks' for the perfumer.

Essentially it attempts to replicate/achieve some of what authentic whale ambergris is so good at, and so revered for, in perfume composition. (Though that's a very tall order!)

== Synonyms ==
'''Iso E Super''' is also known by various other names, such as : Amber Fleur , Iso Amber Super , Ambergris Ketone , Amberix Super , Amberlan , Amberonne , Ambroise Super , Anthamber , Boisvelone , Iso Cyclemone E , Dimethyl Myrcetone , Hamber , Methyl Cyclo Myrcetone , Methyl Cyclomyrcetone , Orbitone , Patchouli Ethanone , Tetramethyl Acetyl Octahydronaphthalenes,
Timbersilk , Timbrone Supra , Iso Velvetone ... (amongst others, depending on manufacturer)

== 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 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>

It is used in [[tobacco]] products (at 200-2000 ppm) to improve both 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>
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" />

== 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&nbsp;% [[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>

[[File:Iso E Super synthesis.svg|400px]]

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" />

== Toxicity ==
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>

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 100% Iso E Super. - It's partner fragrance '''''Escentric 01''''' comprises of 65% IES.
* The fragrance [[Eternity (perfume)|Eternity]] by [[Calvin Klein]] (1988) contained 11.7&nbsp;% 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.
* While Lalique's Eau de Parfum '''''Perles de Lalique''''' (Lalique, 2007) is apparently a whopping 80% Iso E Super.
* The fragrance '''''Poivre Samarcande''''' (Hermes, 2004) contains 71% Iso E Super.
* The very popular '''''Terre D'Hermes''''' (Hermes, 2006) contains 55% Iso E Super.

== References ==
{{reflist|2}}

[[Category:Perfume ingredients]]
[[Category:Flavors]]
[[Category:Ketones]]

Latest revision as of 21:02, 17 January 2018

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