Muscone

Muscone
Formula di struttura del muscone
Nome IUPAC
(3R)-3-Metilciclopentadecan-1-one
Caratteristiche generali
Formula bruta o molecolare	C₁₆H₃₀O
Massa molecolare (u)	238,40
Aspetto	liquido oleoso^[1]
Numero CAS	541-91-3
Numero EINECS	208-795-8
PubChem	10947
SMILES	`CC1CCCCCCCCCCCCC(=O)C1`
Proprietà chimico-fisiche
Densità (g/cm³, in c.s.)	0.9221 a 17 °C^[1]
Indice di rifrazione	1,4802 a 17 °C^[1]
Temperatura di ebollizione	329 °C (602 K)^[1]
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

Il muscone è un chetone macrociclico, un composto organico dal caratteristico odore muschiato. Il muscone naturale si ottiene dal muschio, una secrezione ghiandolare del Moschus, utilizzata da migliaia di anni in profumeria e in medicina. Per ottenere il muschio naturale veniva ucciso l'animale. Dal 1979 il commercio di muschio naturale è stato regolamentato per proteggere la specie, e oggi il muscone utilizzato in profumeria e prodotti di consumo è quasi tutto sintetico.[1]

Struttura e sintesi chimica

Il chimico tedesco Heinrich Walbaum isolò per primo nel 1906 il componente principale del muschio naturale e lo chiamò muscone.^[2] La struttura macrociclica del muscone fu determinata solo nel 1926 da Leopold Ruzicka.^[3] Il muscone è un chetone ciclico a 15 membri con un metile in posizione 3. È un liquido oleoso che in natura è presente come enantiomero (−)-(R)-3-metilciclopentadecanone. Il composto è solubile in acetone, etere dietilico, etanolo.^[1] Si può sintetizzare sia l'enantiomero (−) puro o il racemo. Una sintesi asimmetrica del (−)-muscone è illustrata nella figura seguente. Il composto di partenza (+)-citronellale è disponibile in commercio; la chiusura dell'anello a 15 membri avviene per metatesi olefinica.^[4]

Sintesi del muscone via metatesi olefinica

Un'altra sintesi di (−)-muscone tramite condensazione aldolica intramolecolare di un macrociclo dichetonico facilmente disponibile è schematizzata nella figura seguente.^[5]

Bibliografia

(EN) V. P. Kamat, H. Hagiwara, T. Katsumi, T. Hoshi e at al., Ring Closing Metathesis Directed Synthesis of (R)-(−)-Muscone from (+)-Citronellal, in Tetrahedron, vol. 56, n. 26, 2000, pp. 4397-4403, DOI:10.1016/S0040-4020(00)00333-1.
(EN) O. Knopff, J. Kuhne e C. Fehr, Enantioselective Intramolecular Aldol Addition/Dehydration Reaction of a Macrocyclic Diketone: Synthesis of the Musk Odorants (R)-Muscone and (R,Z)-5-Muscenone, in Angew. Chem. Int. Ed., vol. 46, n. 8, 2007, pp. 1307–1310, DOI:10.1002/anie.200604518.
D. R. Lide (Editor), CRC Handbook of Chemistry and Physics, Internet Version 2005, su hbcponline.com, CRC Press, Boca Raton, 2005. URL consultato il 9 dicembre 2017.
(DE) L. Ruzicka, Zur Kenntnis des Kohlenstoffringes VII. Über die Konstitution des Muscons, in Helv. Chim. Acta, vol. 9, n. 1, 1926, pp. 715-729, DOI:10.1002/hlca.19260090197.
(EN) C. Sommer, The Role of Musk and Musk Compounds in the Fragrance Industry, in G. G. Rimkus (a cura di), Synthetic Musk Fragrances in the Environment, Berlino, Springer, 2004, DOI:10.1007/b14173, ISBN 3-540-43706-1.
(DE) H. Walbaum, Das natürliche Moschusaroma, in J. Prakt. Chem., vol. 73, n. 1, 1905, pp. 488-493, DOI:10.1002/prac.19060730132.

Altri progetti

Wikimedia Commons contiene immagini o altri file su (±)-muscone

Collegamenti esterni

(EN) muscone, su Enciclopedia Britannica, Encyclopædia Britannica, Inc.

V · D · M

Chetoni

monochetoni

lineari/ramificati	Acetone · Calcone · Metiletilchetone · Metilisobutilchetone · Acetofenone · Pinacolone · 2-eptanone · Benzilacetone · β-damascenone · β-damascone · Tonalide
ciclici	Tujone · Cicloesanone · Canfora · Civetone · Habanolide · Muscone · Pinguinone
aromatici	Tropone · Benzantrone · Fenilacetone · 3-nitrobenzantrone · Benzofenone

dichetoni

lineari/ramificati	Acetilacetone
ciclici	Dimedone

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