Cashmeran

Chemistry and properties

Cashmeran is an alicyclic ketone with the molecular formula C14H22O and a molecular weight of 206 g/mol. Its IUPAC name is 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one.

At room temperature it is a white solid, and its melting point is 27 °C. Its boiling point has been reported as 256 °C, but in some tests the material decomposed at 220 °C.

Some describe cashmeran as a polycyclic musk, but it does not belong to the polycyclic musk group as defined by the International Fragrance Association. It also lacks the aromatic benzene ring structure that is present throughout the polycyclic musks.

The patent describes four indanone derivatives, one of them an epoxy compound, and notes that they can exist in several stereoisomeric forms. The compound is a racemic mixture, written (±)-Cashmeran. Reported Kovats retention indices are 1503.2 and 1512.7.

History

Cashmeran's invention came about through research into inexpensive chemical transformations of ingredients with pentamethyl indane and tetramethyl naphthalene structures. US Patent 3,773,836 for indanone derivatives was filed on 18 August 1969 and granted on 20 November 1973. The patent starts from a continuing need for fragrance materials with persistent musk-woody odours of satisfactory quality. Cashmeran, an unsaturated ketone, was identified as an important new fragrance ingredient.

Environment and health

Cashmeran has a bioconcentration factor of 156 and an octanol-water partition coefficient (Log Kow) of 4.2. In most monitoring studies, DPMI was not detected; where DPMI was found, the levels were below 1 ppm and typically below 1 ppb. It is a slight skin irritant and an eye irritant, and a weak sensitiser. Its skin and eye irritation classification is H315 and H319, and its sensitiser classification is H317, with an EC3 of 33%. It is not classified as toxic, nor is it a CMR substance. Its short-term aquatic toxicity is above 1 mg/kg for all species tested (Daphnia, algae and fish). With these figures it is neither a very persistent, very bioaccumulative substance nor a persistent, bioaccumulating, toxic one. It does carry an environmental hazard classification, H411 under EU CLP.

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