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Author: Subject: Piperic acid oxidation to Piperonal
DraconicAcid
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[*] posted on 4-3-2023 at 16:26


I see that they have similar results from trying to recrystallize piperine. Goopy oil. Again.



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[*] posted on 6-3-2023 at 02:44


You can oxidize piperine to piperonal using an ozone generator supplied with oxygen from a oxygen concentrator.
In another stinging insect forum one can read all about it.
It will make peroxides (explosion hazard) so caution must be taken until the bisulfite adduct has been separated, then its peroxide free.
Use peroxide test strips.
Both piperine and styrene is working well.

But it would probably be easier (and also less dangerous) starting from vanillin, de-metylate with AlI3/DMSO to protocatechuic aldehyde then methylenate to piperonal.
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[*] posted on 6-3-2023 at 23:20


Quote: Originally posted by Mateo_swe  

But it would probably be easier (and also less dangerous) starting from vanillin, de-metylate with AlI3/DMSO to protocatechuic aldehyde then methylenate to piperonal.


One thing that occurred to me is that one could react said aldehyde with dibromoethane and get a six-membered ring. The resulting benzodioxancarbaldehyde doesn't seem to be very common in organic chemistry, which is kinda surprising to me- I thought six-membered rings were the most stable ones.

https://www.sigmaaldrich.com/CA/en/product/aldrich/264598

Anyone know anything about this compound, or why it's not so common?




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clearly_not_atara
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[*] posted on 7-3-2023 at 09:29


The amphetamines with that ring (affectionately "EDMA") do not produce the desired effect.

Quote:
You can oxidize piperine to piperonal using an ozone generator supplied with oxygen from a oxygen concentrator.

As I was mentioning on the last page, it would seem desirable to use ozonolysis on potassium piperate, in water (the sodium salt is poorly soluble), rather than on piperine, in a flammable organic solvent, since water is much less likely to explode. It is still important to consider that ozone is an extremely dangerous gas.

[Edited on 7-3-2023 by clearly_not_atara]




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[*] posted on 7-3-2023 at 11:54


Quote: Originally posted by clearly_not_atara  
The amphetamines with that ring (affectionately "EDMA") do not produce the desired effect.


While that is a fair point, it's also worth noting that amphetamines are not the only reason to do organic chemistry. The 6-membered version doesn't seem to appear in natural products, and doesn't even have a cool trivial name.

For the record, I want to find things that smell cool, or can be used as unknowns in my organic lab. (Admin won't let me buy piperonal.)




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[*] posted on 7-3-2023 at 21:03


I suppose it's also notable that the unsubstituted dioxane is a carcinogen, and the dibenzo-fused version is none other than the infamous dibenzodioxin, so the remaining benzo[b]dioxane is not from a very reputable family of rings.

EDIT: Ring fusion notation was misinterpreted as bold

[Edited on 8-3-2023 by clearly_not_atara]




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[*] posted on 7-3-2023 at 21:25


Also a fair point, but the infamously toxic dioxins are all chlorinated. Most of the references I've found to the aldehyde are about it being tested as an anti-inflammatory.

I'm just surprised that it never shows up anywhere.

[Edited on 8-3-2023 by DraconicAcid]




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[*] posted on 8-3-2023 at 05:36


Some derivatives of benzodioxane are used as pharmaceuticals such as piperoxan which was also the first antihistamine to be discovered.



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[*] posted on 8-3-2023 at 17:03


Quote: Originally posted by andyloris  
Some derivatives of benzodioxane are used as pharmaceuticals such as piperoxan which was also the first antihistamine to be discovered.

Interesting, but Wikipedia says about it:

"Piperoxan and analogues themselves were not clinically useful due to the production of toxic effects in humans and were followed by phenbenzamine (Antergan) in the early 1940s, which was the first antihistamine to be marketed for medical use."
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