ISOMERS, HOMOLOGS, AND ANALOGS OF MUSK AMBRETTE

83-66-9; MUSK AMBRETTE; Amber musk; 4-tert-Butyl-3-methoxy-2,6-dinitrotoluene; ..

offers a wide range of products which includes musk ambrette

Created through organic synthesis, musks are important to fragrance as indispensable elements of diffusion and tenacity. They are often called ‘white musks’ as opposed to natural, animal musk, which they have almost totally replaced. Their scents develop clean, fresh, skin notes. They can also be reminiscent of blackberry, ambrette and ambergris.

Musk ambrette crystals

Musk Ambrette | C12H16N2O5 | 676789 | 83-66-9

Polycyclic Musk - in 1948 some chemists of Givaudan realised that when synthesizing an aromatic nitro derivative, that turned out to be odourless, an intermediate one without nitro-groups had a pleasant musky odour, this is how Ambral was born from which then polycyclic musks originated. The first was launched in 1952 under the name Phantolid, because the structure was really still unknown. The most famous polycyclic musk is Galaxolide, synthesized in 1976 by two chemists of IFF.

Musk ambrette is now prepared commercially by the following multistep synthesis.

Synthetic musks have been used, for far more acceptable costs, to spice up a myriad of products: detergents, Toiletry products, perfumes and body lotions, insecticides and foods such as chocolate, liquorice, sweets, chewing gums. Even the fruit flavours and vanilla used in the kitchen contain some (5). Between 1995 and 2000, from 200 to 300 tonnes of Musk Ketone and Musk Xylene were produced and only in the year 2000, at least 4.000 tonnes of polycyclic musks have been consumed (6). The European market for synthetic musks has accounted for 95% for four substances, Musk Ketone, Musk Xylene, Tonalide and Galaxolide (7) which is the "clean smell" of almost all detergents, softeners and environment deodorants and even toothpastes. Because of their widespread use in detergents and products such as shampoo and bath foam, they end up in water and since they are not easily metabolised, they are reintroduced into the food chain. Accumulations have been found in animal and human tissues. Actually, there is still no certain data on their direct toxicity, but they are under careful investigation and research is today oriented in finding alternative substances that are more easily biodegradable. Of course one cannot imagine a perfumery without Musk!

musk ambrette have been used since the early i 900s as fragrance ingredients in perfumes


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The chemical is also used to a lesser extent as an artificial flavor in compositions such as cherry, nut, spice vanilla, and mint.

and as stated by the researchers,

"Musk ambrette, a nitro-musk compound widely used as a fixative in fragrance formulations and found to a lesser degree in flavor compositions, produces hindlimb weakness when administered in the diet or applied to skin of rats for periods up to 12 weeks.

Ambrette Musk, Ambrette Musk Suppliers and …

Explosives were big in the 19th century, much of the infrastructure we associate with the period of the Industrial Revolution could not have happened without them, like railway tunnels through mountains. and 2,4,6- trinitromethylbenzene (TNT) were key to this. Albert Baur was trying to make a super-TNT, so he investigated trinitrocompounds with more alkyl groups. In 1888, he carried out a Friedel-Crafts reaction between toluene and isobutyl bromide (using an AlCl3 catalyst) and nitrated it, obtaining 2--butyl-4-methyl-1,3,5-trinitrobenzene. Like many scientists, he did not obtain the result he expected, as the product had weakly explosive properties, but did have a strong musk smell; this became the perfume ingredient known as "Musk Baur". He went on to make even better musk molecules. These became known as Musk Xylene (synthesis below), Musk Ambrette and Musk Ketone, the last-named being believed to be the nearest to natural musk.

Musk ambrette: P: Neurotoxicity and photosensitization: 0:

The 1920s were a key decade in the development of musks, as Kerschbaum found a macrocyclic lactone, C16H28O2, in the plant, which was commercialised as Ambrettolide. In general, musks from animals are ketones, and plant musks are lactones (cyclic esters). But important things had happened in musks in the late 19th century.

musk xylene, musk ketone, and musk ambrette.

That is a very significant point. Chemists had found the molecular formulae of the compounds, and knew that they were both ketones, with muscone being C16H30O and that civetone was C17H30O. It was the great Croatian-born chemist Lavoslav (Leopold) Ružicka (1887-1976) (picture, right) who carried out key researches on macrocycles. In his research at ETH Zurich, he determined that muscone was 3-methylcyclopentadecanone (it was subsequently shown to be the (-)-()-isomer) and that civetone was (9)-1-cycloheptadec-9-enone. Up to that time (the mid-1920s), chemists believed that rings with more than eight atoms were unstable and could not exist. Ružicka went on to develop the Ružicka large-ring synthesis, by pyrolysing heavy-metal salts (Y, Ce, Th) of a long-chain dicarboxylic acid. Though this only gave very low yields (Exaltone; this is a component of the musk made by the Louisiana muskrat (), along with cycloheptadecanone. Ružicka was to share the 1939 Nobel Prize for Chemistry for his researches.