Cashmeran

Structural formula
1: 1 mixture of the ( R ) -form (left) and the ( S ) -form (right)
General
Surname	Cashmeran
other names	6,7-Dihydro-1,1,2,3,3-pentamethyl-4 (5 H ) -indanon DPMI 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4 H -inden-4-one
Molecular formula	C 14 H 22 O
Brief description	white solid
External identifiers / databases
CAS number 33704-61-9 (racemate) EC number 251-649-3 ECHA InfoCard 100.046.940 PubChem 92292 Wikidata Q1047397
properties
Molar mass	206.32 g mol −1
Physical state	firmly
density	0.969 g cm −3 (20 ° C)
Melting point	27 ° C ° C
boiling point	256 ° C
Vapor pressure	1.09 Pa (25 ° C)
solubility	112 mg l −1 in water (23 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-317-319-411 P: 261-272-273-280-302 + 352
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cashmeran is a synthetic fragrance from the group of cyclohexenones . As a racemate, it is often added to cleaning products as an odor-giving component.

Surname

The name was chosen in relation to the properties of cashmere wool . Cashmeran gives perfumes a soft, silky note. Cashmeran is the trade name given by International Flavors & Fragrances for the fragrance. The chemical name is 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5 H ) -indanone. The abbreviation - DPMI - is used synonymously in various publications.

history

Cashmeran was discovered by International Flavors and Fragrances in the 1970s by John Hall. The invention of Cashmeran came about as a result of research into inexpensive processes for the chemical transformation of substances with pentamethylindane and tetramethylnaphthalene structures. In this context, cashmeran, an unsaturated ketone, has been identified as an important new fragrance.

physical and chemical properties

Cashmeran is an alicyclic ketone . At room temperature it appears as a white solid, its melting point is 27 ° C. A temperature of 256 ° C was reported as the boiling point , but some tests showed that the material decomposed at 220 ° C.

odor

Although cashmeran has been described by some as a polycyclic musk compound, it is not primarily a musk fragrance, nor does it belong to the group of polycyclic musk compounds. The International Fragrance Association (IFRA) defines polycyclic musk compounds as compounds that:

• primarily and solely for their musky scent
• have a molecular formula of C ₁₇ H ₂₄ O or C ₁₈ H ₂₆ O, and contain a central aromatic benzene ring

Although Cashmeran has woody-musky scents , its smell is complex, characterized by spicy, fruity, balsamic , chypre and vanilla-like scents. Cashmeran is used because of its own characteristic smell, which is fundamentally different from conventional musk compounds. This is also reflected in its typical usage amount of around 2%, in comparison, for example, the usage amount of the polycyclic musk compound HHCB (Galaxolid) in fragrances is up to 30%. Cashmeran also lacks the aromatic benzene ring, which polycyclic musk compounds contain.

Environmental data

Cashmeran has a bioconcentration factor (BCF) of 157 for Cyprinus carpio and an octanol-water partition coefficient (log K _OW ) of 4.2 at 20 ° C. It follows from the BCF that this compound is not particularly bioaccumulating.

The short-term aquatic toxicity for Cashmeran is> 1 mg / L for aquatic species ( daphnia , algae and fish). Cashmeran has an environmental hazard classification H411 according to EU CLP .

In this sense, the bioconcentration and aquatic toxicity of cashmeran are rather uncritical at the concentrations found in the environment. Several surveillance studies have been carried out in different environmental areas and people. Some studies have shown traces of DPMI, the values ​​found were below 1 ppm , and sometimes even below 1 ppb .

toxicology

Cashmeran irritates the skin (H315) and causes serious eye irritation (H319). It can cause allergic reactions and have a sensitizing effect (H317). Cashmeran is classified as hazardous to health.

Individual evidence

1. ↑ ^{a b c d e f g h i j k} Registration dossier for 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-ones at the European Chemicals Agency (ECHA), accessed November 24, 2014.
2. ↑ ^{a b} Entry for CAS no. 33704-61-9 in the GESTIS substance database of the IFA , accessed on April 13, 2015(JavaScript required) .
3. ↑ L. Wang, SJ Kahn: Enantioselective analysis and fate of polycyclic musks in a water recycling plant in Sydney (Australia) , Water Science and Technology (2014), 69 (10) pp. 1996-2003, doi : 10.2166 / wst. 2014.095 .
4. ↑ Patent US3773836 : INDANONE DERIVATIVES AND PROCESSES FOR PRODUCING SAME. Published on November 20, 1973 , inventors J.
5. ^ Synthetics Compendium ( Memento from September 11, 2014 in the Internet Archive ). (PDF, 6.8 MB)
6. ↑ 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. Environmental science Damage research Z. Umweltchem Okotox., 7 (3), 131-138.
7. ↑ 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.
8. ^ 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.
9. ↑ 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.
10. ↑ 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.
11. ↑ 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.
12. ↑ Heberer Th., Jurgensen S., Fromme H. Synthetic musks in the aquatic 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.
13. ↑ 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.
14. ↑ Guo R., Lee I., Kim U., Oh J. Occurrence of synthetic musks in Korean sewage sludges. Science of the Total Environment 408, 1634-1639.
15. ↑ 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.
16. ↑ 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.
17. ↑ 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.