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== Production ==
== 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 et al. | contribution=Flavors and Fragrances | title=[[Ullmann's Encyclopedia of Industrial Chemistry]] | edition=7th | publisher=Wiley | year=2007 | pages=45–46}}</ref>
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]]
[[File:Iso E Super synthesis.svg|thumb|Synthesis]]
Line 42: Line 42:


== Safety ==
== Safety ==
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> 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 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>
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>

Revision as of 00:34, 27 December 2015

Iso E Super
Structure formula of Iso E Super
(2R,3R)- [54464-57-2]
(2S,3S)- [144651-56-9]
Names
IUPAC name
1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one
Other names
Amberonne; Ambralux; Boisvelone; Derambrene; Timbersilk; Methyl cyclomyrectone; 1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthalenone
Identifiers
3D model (JSmol)
ECHA InfoCard 100.053.777 Edit this at Wikidata
  • CC(=O)[C@]1(C)CC2=C(C[C@H]1C)CCCC2(C)C
Properties
C16H26O
Molar mass 234.38 g/mol
Appearance colorless to a pale yellow liquid
Odor amber, woody
Boiling point 134 °C (273 °F; 407 K)
1.4975–1.500 (at 20 °C)
Hazards
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.

Uses

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.[1]

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 cyclized in the presence of 85% phosphoric acid.[2]

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 diastereomers with the general structure depicted above, the predominant ones being (2R,3R) and (2S,3S).[3]

Safety

Iso E Super may cause allergic reactions detectable by patch tests in humans[4] and chronic exposure to Iso E Super from perfumes may result in permanent hypersensitivity.[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]

Iso E Super is toxic and bioaccumulative in aquatic organisms and the environment,[5][7] and is suspected to be bioaccumulative in humans.[8]

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.[1]

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.[1]
  • 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.

References

  1. ^ a b c 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
  2. ^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 45–46
  3. ^ Perfume composition and perfume articles containing one isomer of an octahydrotetramethyl acetonaphthone {{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 |issue-date= ignored (help); Unknown parameter |patent-number= ignored (help)
  4. ^ 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, doi:10.1111/j.1600-0536.1995.tb02048.x, PMID 8565489
  5. ^ a b Iso E Super Material Safety Data Sheet (PDF), Santa Cruz Biotechnology
  6. ^ 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
  7. ^ Predicting the Bioconcentration of Fragrance Ingredients by Rainbow Trout Using Measured Rates of in Vitro Intrinsic Clearance (PDF), ACS Publications, Environmental Science & Technology, 2014
  8. ^ Ranking of Concern from persistence, bioaccumulation and toxicity in the environmentof Pharmaceuticals and Personal Care Products (PDF)
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