Moxalone

pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
I can't find a database page for it at TGSC, where are you buying it from?
It looks like it might be a Givaudan Product...

I see that Wiki lists it a captive that's been released, but more than that I am lacking...

Thanks,
Paul Kiler
 

Skelly

Super Member
Jan 4, 2013
'In 1979, M. Klaus of F. Hoffmann-La Roche discovered by serendipity a new intense
musk odorant with some damascone-like and woody nuances. In the course of synthetic
work on aromatic retinoids he had synthesised the hexahydroindene 65, which because
of its powerful odour soon became internally known as klausenone (65) in Hoffmann-La
Roche and also at Givaudan, at that time the flavour and fragrance division of Roche. As
65 is structurally not an aromatic polycycle, the musk odour of 65 was rather surprising.
Attempts to develop an industrially feasible route to klausenone (65) turned out to be
more difficult than anticipated, and thus derivatives were also investigated [38]. The
corresponding alcohol, obtained by LAH reduction of 65, possessed as well a pronounced
musk note, indicating the carbonyl function was no prerequiste. Surprisingly, the epoxide
intermediate 66, en route to a methyl klausenone by acid-catalysed rearrangement, turned
out to be the best musk odorant of the whole series and it was introduced into perfumery
as Moxalone® (66). Moxalone® (66) had its debut in »Eden« (Cacharel, 1994) by Jean
Guichard and was even at 0.62% an important cornerstone in the unisex fragrance
»CK be« (C. Klein, 1996) created by René Morgenthaler.'


bib.convdocs.org/v38471/?download=1


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pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
Oh Yes, Skelly, that's a valuable resource, I had it already but great post from all of your response...
Thanks
PS, I think I should just print it out and bind it for the Perfumarium Library...
 

Plaisir

Super Member
Sep 7, 2012
Pkiler: Not buying it, but am potentially interested in it - if it is biodegradable.

Sorry, but I still wonder the same thing...maybe it is possible to deduce from the text Skelly kindly posted above whether Moxalone is biodegradable or not, but I don't have the expertise to do so. Anyone?
 

pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
Plaisir, Did you actually have a source to buy this? my new reasearch seems to say it's a captive...

PK
 

edshepp

Super Member
Sep 27, 2004
If it's very important to you whether or not it's quickly biodegradable, then to be on the safe side, don't use it or anything you think may or may not contain it. There you go.
 

parker25mv

Basenotes Dependent
Oct 12, 2016
I wonder if anyone here knows whether Moxalone is biodegradable or not.
I can give you my (expert/professional) opinion from looking at the molecular structure. It looks like the type of thing that will be very resistant to complete biodegredation and that its break-down products would persist in the environment for a long time, but will not be impossible to biodegrade.
(can see Effect of Chemical Structure on the Biodegradability of Aliphatic Acids and Alcohols F. F. Dias, Applied Microbiology, 1971 for additional detail)

Still not as bad as Galoxide.
 
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emrego

Super Member
Aug 4, 2016
Re-igniting Moxalone. An ingredient that is very little known of online as far as I can tell, except it is a Givaudan captive (could not find any release info). Anyone here somehow got more info, insider or not?

Appreciate it.
 

Alex F.

Super Member
Nov 29, 2019
Re-igniting Moxalone. An ingredient that is very little known of online as far as I can tell, except it is a Givaudan captive (could not find any release info). Anyone here somehow got more info, insider or not?

Appreciate it.

Moxalone was patented in the 80s, along with other epoxides derived from a Givaudan-musk called Klausenone (Klauscenone acc. to Herrmann, see below). The story behind the development can be read in Kraft, Philip et al.: Odds and trends - Recent developments in the chemistry of odorants, 2000, p. 3004 (link to publisher). It's structurally related to Cashmeran, but it's the only epoxide/oxirane musk on the market. (Herrmann, Andreas: The chemistry and biology of volatiles, 2010, pp. 188-189 and Ohloff, Günther et al.: Scent and Chemistry, ²2022, p. 354.)
The patents - Europe (German) and US - include demonstration formulas. (Moxalone is "epoxide 2", 6,7-Epoxy-1,1,3,4,4,6-hexamethyl-1,2,3,4,5,6,7,8-octahydronaphthalene.)

It's contained in a number of perfumes, e.g. in CK Be at around 0.62% (see Ohloff et al. cited above) and in Paris Baby Doll by YSL at ~1.2% (see Kraft et al. cited above).
 
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emrego

Super Member
Aug 4, 2016
Moxalone was patented in the 80s, along with other epoxides derived from a Givaudan-musk called Klausenone (Klauscenone acc. to Herrmann, see below). The story behind the development can be read in Kraft, Philip et al.: Odds and trends - Recent developments in the chemistry of odorants, 2000, p. 3004 (link to publisher). It's structurally related to Cashmeran, but it's the only epoxide/oxirane musk. (Herrmann, Andreas: The chemistry and biology of volatiles, 2010, pp. 188-189 and Ohloff, Günther et al.: Scent and Chemistry, ²2022, p. 354.)
The patents - Europe (German) and US - include demonstration formulas. (Moxalone is "epoxide 2", 6,7-Epoxy-1,1,3,4,4,6-hexamethyl-1,2,3,4,5,6,7,8-octahydronaphthalene.)

It's contained in a number of perfumes, e.g. in CK Be at around 0.62% (see Ohloff et al. cited above) and in Paris Baby Doll by YSL at ~1.2% (see Kraft et al. cited above).

Thank you very much Alex, it was a fun read of patent (though I didn't understand 90% of it, 10% that made some sense was worth it).

My takeaway: It's a fruity-musk, pear-like, in the vein of Helvetolide, Ambrettolide, Edenolide etc. with top note effects.

I would still look forward to hear feedback from anyone who had a chance to smell.
 

Alex F.

Super Member
Nov 29, 2019
Thank you very much Alex, it was a fun read of patent (though I didn't understand 90% of it, 10% that made some sense was worth it).

My takeaway: It's a fruity-musk, pear-like, in the vein of Helvetolide, Ambrettolide, Edenolide etc. with top note effects.

I would still look forward to hear feedback from anyone who had a chance to smell.

😁 Yeah, patents are hardly ever fun to read. I forgot to add the second-hand odour descriptions: "a true musk, rich and powerful, and only accompanied by slightly fruity facets and woody accents" (Ohloff et al.: Scent and Chemistry, ²2022, p. 338), "almost fruity-lactonic which tells Moxalone must have been used" apropos of the base of Vanille fatale by Tom Ford (Scent and Chemistry FB), and "elegant fruity-lactonic blackberry note" in the top notes of Genetic Bliss by 27 87 (Scent and Chemistry FB).
 
Oct 3, 2016
Well I had the chance to smell it on a strip two weeks ago at the lecture in Göttingen.
It is _really_ very beautiful musky with (cashmeran-smooty) woody-fruity shades - and I thought 'ok that is the reason why they keep it captive'.
Synthesis involves a Birch reduction (industry standard) but then also oxidation with tert-butyl hydroperoxide.
(tert-butyl hydroperoxide explosions are rare but possible)
And looking at the molecular shape (something between cashmeran, isoE and galaxolide) I would say biodegradability is limited.

It is heavy 'ovedosed' in 'Genetic Bliss' (27 87 perfumes, 2018) by Jórdi Fernandez, but also hidden there in the bombastic peppery-ambery sandalwood accord with Akigalawood, Belambre, Georgywood, and Javanol.
My favorite scents with moxalone are 'Vanille fatale' (TF), 'Botafumeiro' (Carner) and 'Santal Cardamome' (Fragonard).
 

parker25mv

Basenotes Dependent
Oct 12, 2016
An assessment of biodegradability of quaternary carbon–containing fragrance compounds: Comparison of experimental OECD screening test results and in silico prediction data, Markus Seyfried, 2014

Summary: They looked at 27 fragrance compounds which contain "quaternary carbons" (four carbons all bonded to one carbon atom in the molecule) assessing the biodegradability. 37% were at least passably acceptable (perhaps not great).

I think we can also look at the biodegradability of Helvetolide, to possibly get some idea of how Moxalone might break down:
" In conclusion, this screening test shows that primary degradation of Helvetolide takes place, but the ultimate degradation is below the pass level of 60%. Therefore, Helvetolide is considered to be "not readily biodegradable". "
(EU Substance Evaluation Conclusion)

Several tests also showed that Iso E Super was "not readily biodegradable".

What can be said is that common fragrance compounds like damascenones and ionones that occur in nature do contain a quaternary carbon group, and seem to be generally accepted as at least somewhat biodegradable. Givaudan says that Ambrofix is biodegradable, and it contains one of these groups.

I decided to look up some information for 2,2-Dimethyl-1,3-propanediol (neopentyl glycol), since that seems similar to the type of major problematic breakdown product which a musk like Moxalone would leave behind.
" 2,2-Dimethyl-1,3-propanediol [...] is classified as "not readily biodegradable" by the results of the biodegradation test conducted as SIDS testing. The chemical is non-toxic to fish, daphnids and algae. In conclusion, although 2,2-dimethyl-1,3-propanediol is persistent and toxicological test showed moderate toxicity, no further testing is needed at present considering its exposure levels. "

My takeaway conclusion from this is, as I suspected before, it will take a long time for it to biodegrade. Fortunately there are no signs that it is very harmful to the environment.
 
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emrego

Super Member
Aug 4, 2016
It is _really_ very beautiful musky with (cashmeran-smooty) woody-fruity shades - and I thought 'ok that is the reason why they keep it captive'.
Very helpful! And how lucky you are!

It is heavy 'ovedosed' in 'Genetic Bliss' (27 87 perfumes, 2018) by Jórdi Fernandez
Genetic Bliss is exactly what triggered my curiosity on Moxalone. I was comparing it every now and then to my signature scent, CdG - Wonderoud, and trying to pick up these subtle differences side by side and maybe reach a conclusion to justify these captives. Happy to see some verifications from you which is 100% in line with what was I thinking. That abstract rotundone/peppery vibe with Akigalawood with some berry-pear nuance (trying to find to what extent Moxalone was responsible of it)...Though Wonderoud has a similar fruity note lurking in the background that's probably from Cashmeran/Iso E and perhaps a similar musk, but Genetic Bliss has a different charm in that aspect. For a regular user I think it wouldn't even matter much, but for perfumers and hobbyists I think it is quite intriguing. Thanks a ton!
 

parker25mv

Basenotes Dependent
Oct 12, 2016
I think if you want fully biodegradable musks, you should stick to macrocyclic musks.
(Not all of them are fully biodegradable though. Stay away from Exaltone, Civettone, Muscone, and Trimofix)
Ambrettolide, Habanolide, Polvolide, Exaltolide would all be good.
I found two different conflicting sources of information for ethylene brassylate. I think it should probably be biodegradable (because another source says that adipic acid esters have high biodegradability).
 

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