Muscon

Structural formula
General
Surname	Muscon
other names	( R ) -3-methylcyclopentadecanone
Molecular formula	C 16 H 30 O
Brief description	colorless oil with a characteristic odor
External identifiers / databases
CAS number 541-91-3 EC number 208-795-8 ECHA InfoCard 100.007.997 PubChem 10947 Wikidata Q416022
properties
Molar mass	238.40 g · mol -1
Physical state	liquid
density	0.9221 g cm −3
boiling point	329 ° C
solubility	soluble in acetone , diethyl ether and ethanol
Refractive index	1.4802 (at 17 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Muscon (from late Latin muscus = musk) is an organic-chemical compound from the group of cyclic ketones and occurs naturally as the main component of musk .

Occurrence

With a share of 0.5 to 2%, muscone is the most important fragrance of natural musk .

Siberian musk deer ( Moschus moschiferus )

The German chemist Heinrich Walbaum (1864–1946) was able to isolate the main component of musk in the form of white crystals in 1906 . He named the connection Muscon, the structure was clarified by Lavoslav Ružicka in 1926 .

Natural muscon is made from musk that has been used as a perfume for centuries. Nowadays it is produced synthetically for animal welfare reasons.

Chemical properties

As a macrocycle, muscon belongs to the group of alicyclic compounds and ketones . It consists of a 15-membered ketone ring with a methyl substituent in the 3-position. Muscone is an oily liquid found in nature as the enantiomer ( R ) - (-) - 3-methylcyclopentadecanone. Synthetically produced muscon is a racemate , i.e. it consists of a 1: 1 mixture of ( R ) - (-) - 3-methylcyclopentadecanone and ( S ) - (+) - 3-methylcyclopentadecanone.

Extraction and presentation

Muscone can be produced by methylating ( E ) -2-cyclopentadecenone.

use

Muscon is used as a fragrance in cosmetic products , perfumes , soaps , shampoos , detergents and cleaning agents.

See also

• Civetone

Individual evidence

1. ↑ Enius: Muscon .
2. ↑ ^{a b c} David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 89th edition. (Internet version: 2009), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-346.
3. ↑ Entry on Muscon in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on October 24, 2017.
4. ↑ There is not yet a harmonized classification for this substance . A labeling of 3-methylcyclopentadecan-1-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on October 24, 2017, is reproduced from a self-classification by the distributor .
5. ↑ Bernd Schäfer: Natural substances in the chemical industry , Spectrum Akademischer Verlag, 2007, pp. 118–119, ISBN 978-3-8274-1614-8 .
6. ^ H. Walbaum: The natural musk aroma. In: Journal for Practical Chemistry . Volume 73, 1906, pp. 488-493, doi: 10.1002 / prac.19060730132 .
7. ↑ chemgapedia.de
8. ↑ Sonja Lüthje: Dynamic-combinatorial synthesis of macrocycles . Kiel 2006, DNB  980868084 , urn : nbn: de: gbv: 8-diss-18018 (dissertation, University of Kiel).