Molar mass 234.38 g/mol | ||
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Appearance colorless to a pale yellow liquid | ||
Adventures in iso e super
Iso E Super is a synthetic ketone fragrance.
Contents
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.
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.
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).
Safety
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).
Iso E Super is toxic and bioaccumulative in aquatic organisms and the environment, and is suspected to be bioaccumulative in humans.
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.