Cashmeran

Cashmeran (trade name; also known as musk indanone or indomuscone; chemical name 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone or DPMI) is a chemical compound used in fragrances.

Cashmeran
Names
IUPAC name
(RS)-1,1,2,3,3-Pentamethyl-1,2,3,5,6,7-hexahydro-4H-inden-4-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.046.940
UNII
  • InChI=1S/C14H22O/c1-9-13(2,3)10-7-6-8-11(15)12(10)14(9,4)5/h9H,6-8H2,1-5H3
    Key: MIZGSAALSYARKU-UHFFFAOYSA-N
  • InChI=1/C14H22O/c1-9-13(2,3)10-7-6-8-11(15)12(10)14(9,4)5/h9H,6-8H2,1-5H3
    Key: MIZGSAALSYARKU-UHFFFAOYAK
  • CC1C(C2=C(C1(C)C)C(=O)CCC2)(C)C
Properties
C14H22O
Molar mass 206.329 g·mol−1
Appearance White solid
Melting point 27 °C (81 °F; 300 K)
Boiling point 256 °C (493 °F; 529 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Physical-chemical properties

Cashmeran is an alicyclic ketone with the molecular formula C14H22O and a molecular weight of 206 g/mol. At room temperature it occurs as a white solid but its melting point is 27 °C. Boiling point has been reported to be 256 °C, however in some tests decomposition of the material was noted at 220 °C.[1]

History

Cashmeran was discovered by International Flavors and Fragrances in the 1970s by John Hall.[2] Its invention came about researching inexpensive chemical transformations from ingredients from the pentamethyl indane and tetramethyl naphthalene structures. As a result, Cashmeran, an unsaturated ketone, was identified as an important new fragrance ingredient.

Odour

Although cashmeran has been described by some as a polycyclic musk, it is neither primarily a musk odour ingredient, nor does it belong to the polycyclic musk group as defined by the International Fragrance Association (IFRA). The IFRA definition defines a polycyclic musk as:

  • Being used primarily and uniquely for their musk odor
  • Having a molecular formula of C17H24O or C18H26O, and containing one central aromatic benzene ring.

Although there are woody-musky notes to Cashmeran, its odour is complex[3] with notes that are: rich spicy, fruity, chypre, balsamic and vanilla, overall intended to convey the soft sensuous feeling of cashmere (hence the trade name Cashmeran). As such, cashmeran is used to impart its own characteristic odour, which is completely different from regular musk ingredients. This is further reflected by its typical use level of around 2%[4] compared to for instance the polycyclic musk HHCB (galaxolide) with use levels in fragrances up to 30%. Cashmeran also lacks the aromatic benzene ring structure, which is present throughout the polycyclic musks. Cashmeran should therefore not be categorized as a polycyclic musk.

Environmental data

Cashmeran has a bio concentration factor (BCF) of 156 and an octanol-water partition coefficient (Log Kow) of 4.2, which makes that this material not a very persistent, very bioaccumulative (vPvB), nor a persistent bioaccumulating toxic (PBT) substance. Short term aquatic toxicity for cashmeran is >1 mg/kg for all species (Daphnia, algae and fish). Cashmeran has an environmental hazard classification (R51/53 according to the EU DSD[5] or H411 according to the EU CLP[6]). In this sense, Cashmeran's bio concentration and aquatic toxicity is even an order of magnitude more favourable than those substances considered as polycyclic musks, and therefore also does not meet those criteria for the materials considered to be included in that group.[7]

Environmental and human monitoring studies

Several monitoring studies[8][9][10][11][12][13][14][15][16] have been conducted in various environmental compartments and humans. In most studies, DPMI was not detected. Some studies have reported trace levels of DPMI, where the reported levels were below 1 ppm, and typically below 1 ppb. Considering the environmental fate studies, the likelihood of DPMI being present in environmental media is small, and if present, at extremely low levels (i.e. below ppm).

Human health

Cashmeran is a slight skin irritant and an eye irritant (R36/38 according to EU DSD, H315-319 according to EU CLP) and a weak sensitiser (R43/H317) with an EC3 of 33%. Cashmeran is not classified as toxic nor is it a CMR substance[17][18][19][20]

References
  1. All data from the Cashmeran REACH dossier Archived September 11, 2014, at the Wayback Machine
  2. US Patent 3,773,836 Nov 20, 1973
  3. "What is Cashmeran - Definition of the Perfume Ingredient Cashmeran". Archived from the original on 2014-09-11. Retrieved 2014-09-11.
  4. Cashmeran in: "Archived copy" (PDF). Archived from the original (PDF) on 2014-09-11. Retrieved 2014-09-11.{{cite web}}: CS1 maint: archived copy as title (link)
  5. "The directive on dangerous substances - Environment - European Commission".
  6. "CLP Legislation - ECHA".
  7. All data from the Cashmeran REACH dossier http://apps.echa.europa.eu/registered/data/dossiers/DISS-dffb4072-e4bf-47ae-e044-00144f67d031/AGGR-bb75495d-97b9-4633-be1c-cf3c830d975b_DISS-dffb4072-e4bf-47ae-e044-00144f67d031.html#AGGR-bb75495d-97b9-4633-be1c-cf3c830d975b} Archived September 11, 2014, at the Wayback Machine
  8. Eschke H.-D. , Dibowski H.-J. and Traud J. Studies on the occurrence of polycyclic musk flavors in different environmental compartments. Second communication: Findings in surface waters, waste waters, and fish as well as in detergents and cosmetics. Umweltwiss. Schadst.-Forsch. Z. Umweltchem Okotox., 7(3), 131-138.
  9. Eschke H.-D. , Dibowski H.-J. and Traud J. Detection and quantitative analysis of musk fragrances by means of ion-trap GC/MS/MS in human fat and breast milk. Deutsche Lebensmittel-Rundschau, 91(12), 375-379.
  10. Zehringer M. and Herrmann A. Analysis of polychlorinated biphenyls, pyrethroid insecticides and fragrances in human milk using a laminar cup liner in the GC injector. European Food Research and Technology, 212(2), 247-251
  11. Hutter H.-P. , Wallner P. , Moshammer H. , Hartl W. , Sattelberger R. , Lorbeer G. and Kundi M. Blood concentrations of polycyclic musks in healthy young adults. Chemosphere, 59(4), 487-492
  12. Ricking M. , Schwarzbauer J. , Hellou J. , Svenson A. and Zitko V. Polycyclic aromatic musk compounds in sewage treatment plant effluents of Canada and Sweden--first results. Marine Pollution Bulletin, 46(4), 410-417
  13. Zhang S., DiFrancesco, A., Chiu, P., Allen, H. and Salvito, D. Removal mechanisms for fragrance materials in sludge-amended soils. American Chemical Society 228th National Meeting, Philadelphia, PA. 25 August 2004
  14. Heberer Th., Jurgensen S., Fromme H. Synthetic musks in theaquatic system of Berlin as an example for urban ecosystems. In: Rimkus GH (ed.), Synthetic Musk Fragrances in the Environment. The Handbook of Environmental Chemistry. Springer Verlag, Berlin, Germany, pp. 123-150
  15. Schlumpf, M., Kypke, K., Wittassek, M., Angerer, J., Mascher, H., Mascher, D., Vokt, C., Birchler, M., and Lichtensteiger, W. Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: Correlation of UV filters with use of cosmetics. Chemosphere 81, 1171-1183
  16. Guo R., Lee I., Kim U., Oh J. Occurrence of synthetic musks in Korean sewage sludges. Science of the Total Environment 408, 1634-1639.
  17. http://apps.echa.europa.eu/registered/data/dossiers/DISS-dffb4072-e4bf-47ae-e044-00144f67d031/AGGR-bb75495d-97b9-4633-be1c-cf3c830d975b_DISS-dffb4072-e4bf-47ae-e044-00144f67d031.html#AGGR-bb75495d-97b9-4633-be1c-cf3c830d975b} Archived September 11, 2014, at the Wayback Machine
  18. Kevekordes S. , Mersch-Sundermann V. , Diez M. and Dunkelberg H. In vitro genotoxicity of polycyclic musk fragrances in the micronucleus test. Mutation Research, 395(2-3), 145-150.
  19. Kevekordes S. , Mersch-Sundermann V. , Diez M. , Bolten C. and Dunkelberg H. Genotoxicity of polycyclic musk fragrances in the sister-chromatid exchange test. Anticancer Research, 18(1A), 449-452.
  20. Mersch-Sundermann V. , Kevekordes S. and Jenter C. Lack of mutagenicity of polycyclic musk fragrances in Salmonella typhimurium. Toxicology in Vitro, 12(4), 389-393.
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