Macrocyclic musks

Muscone, a macrocyclic musk

A class of artificial musk consisting of a single ring composed of more than 6 carbons (often 10-15). Of all artificial musks, these most resemble the primary odoriferous compound from Tonkin musk in its "large ringed" structure. While the macrocyclic musks extracted from plants consists of large ringed lactones, all animal derived macrocyclic musks are ketones.^[2]

Although muscone, the primary macrocyclic compound of musk was long known, it was only in 1926 that Leopold Ruzicka was able to synthesize this compound in very small quantities. Despite this discovery and the discovery of other pathways for synthesis of macrocyclic musks, compound of this class were not commercially produced and commonly utilized until the late 1990s due to difficulties in their synthesis and consequently higher price.^[4]

About half the human population are anosmic (unable to smell) to macrocyclic musks, possibly due to its high molecular weight. Common macrocyclic musks include:

• Ethylene brassilate
• Globalide (also available as Habanolide, trademark of Firmenich SA)
• Ambrettolide
• Muscone
• Thibetolide (Exaltolide)
• Velvione

Alicyclic musks

Helvetolide, an alicyclic musk

Alicyclic musks, otherwise known as cycloakyl ester or linear musks, are relatively novel class of musk compounds. The first compound of this class was introduced 1975 with Cyclomusk, though similar structure were noted earlier in citronellyl oxalate and Rosamusk^[5]. Alicyclic musks are dramatically different in structure than previous musks (aromatic, polycyclic, macrocyclic) in that they are modified akyl esters^[6]. Although they were discovered more than 10 years before, it was only in 1990 with the discovery and introduction of HELVETOLIDE at Firmenich that a compound of this class was produced at a commercial scale^[5]. ROMANDOLIDE, a more ambrette and less fruity alicyclic musk compared to HELVETOLIDE was introduced ten years later^[6]. Common musks of this class include:

• Cyclomusk
• Helvetolide (trademark of Firmenich SA)
• Romandolide (trademark of Firmenich SA)