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Author: Subject: Zingerone
SM2
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[*] posted on 13-8-2014 at 12:18
Zingerone


So we extract our ginger ketone, dry, and condence 4.27g in 2M NaOH (aq), with a large abundance of MEK, 50ml min. The flocuent precipitate is quickly washed with cold water, dried, and dissolved in twice it's weight ethyl methacrylate monomer. The cheapest, easiest neat monoomer tou can buy from China via Ebay. A homogeneous, slightly straw looking transparent mixture is formed, which does not change, Now, PEA HCL is basified and washed/dried. 17,24G of the FB in 50ml MeOH, is slowly added to our above straw colored mixture, which over the 10 minute addition, has turned red, red/yellow, and then a lighter different shade of red. Upon watching, one can see the reddish heavy layer settle. 50ml brine is added, with heavy magnetic stirring, so the red portion forms small miscles, and eventually emulsify with the whole. Stirring is stopped after 10-15 minutes, and now the red layer is more defined, but floating on top. It is also cleaner looking. Add 50more ml H20, and finally extract the oil with toluene. First wash w/ gusto, 25 ML. 2ND WASH ONLY 10ML. 3RD WASH 15ML. Toluene conservation, a treasured OTC soon to go on a national level. Red extract is gently distilled until almost all the toluene is out, and the toluol is put in a container where it will be reprocessed at some later date, and not wasted!

Now, this red oil (not turkey red) could be reacted with a degradation product of tyrosine, but that is just the teaser. As it is now, it represents a very interesting molecule. But I have no GC/MS Quad|||| sitting around, so, I don't know. Und ich denka verleicht etwa could have been lost in translation. This is the Beginnings section, and here is a beginning.

[Edited on 13-8-2014 by SM2]




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[*] posted on 13-8-2014 at 19:24


I'm fairly confused as to what you did (or intended to do) here. Here is my take on the above:

Zingerone was reacted with a large excess of 2-butanone and base (how much 2M sodium hydroxide? Or did you mean 2 molar equivalents?) in water. Then the butanone adds to the tail of the zingerone twice to make a branched diketone? This is where my confusion begins to crescendo: next a precipitate (assumed to be the condensation product - likely a mixture) is isolated and washed, but there was no neutralization of the base... So was the product at this point a non-soluble phenolate? Or other sodium salt?

Then you go on to add ethyl methacrylate. I see how the later added phenethylamine would condense with one or two equivalents of this, but was the previous branched ketone intermediate supposed to to add to it? Was the (assumed) diketone supposed to cyclize? Etcetera...

Anyways, my curiosity had been roused and wouldn't mind seeing some clarification. Maybe some structures of the intended intermediates and product? Haha, here's to putting the madness in sciencemadness. Cheers.
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[*] posted on 13-8-2014 at 19:49


I couldna make heads or tails either, and ginger has been on my list of "interesting" substances to investigate.

Quick question: gingerol alledgedly decomposes to zingerone on cooking. Reflux powdered ginger in nonpolar solvent=zingerone?




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[*] posted on 13-8-2014 at 20:33


Not sure about that, but it can be made by condensing acetone with vanillin with a base then hydrogenating the double bond(analogous to the synthesis of rheosmin AKA raspberry ketone from p-hydroxy benzaldehyde).
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[*] posted on 13-8-2014 at 20:45


@Crowfjord--I have LOTS of powdered ginger, in fact a 112gm bottle--no vanillin (well, mebbe .3gm ethylvanillin).


And if I had any amount of benzaldehyde..........well, lets say I could do without booze for a while LOL




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[*] posted on 13-8-2014 at 21:30


Perhaps one could extract gingerol and the related compounds from the ginger with acetone or ethyl acetate and then react with aqueous base to form zingerone via retro-aldol reaction. Zingerone is "sparingly soluble" in water, according to Wikipedia. I wonder if it could be steam distilled?

Then again, with the other stuff in ginger, it might be better to do a bisulfite extraction or some such after the retro-aldol.

[Edited on 14-8-2014 by Crowfjord]
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[*] posted on 13-8-2014 at 21:43


I read the wiki too, what got me thinking about it. Zingerone looks VERY interesting to an insomniac LOL. Figured heat from reflux with EtAc would take gingerol>>>>zingerone? Maybe need pop over to the-collective and ask.....



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[*] posted on 16-8-2014 at 09:59


benzaldehyde can be made from the ozonolysis of styrene, the needed chemicals are very easy to get hold of, one made easily from a cheap readily available plastic, the other obtained from a cheap ozone generating car lighter thing
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[*] posted on 11-10-2014 at 08:26


Quote: Originally posted by rannyfash  
benzaldehyde can be made from the ozonolysis of styrene, the needed chemicals are very easy to get hold of, one made easily from a cheap readily available plastic, the other obtained from a cheap ozone generating car lighter thing


could you be more elaborate about the ozone generator
actually i am interested in the same reaction i.e making benzaldehyde from styrene

the reaction is actuallly ironic ,converting a stinky chemicla like styrene to a nice smelling one like benzaldehyde ,but i guess that's how chemistry is;)
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[*] posted on 11-10-2014 at 11:14


Benzaldehyde can also be made by oxidation of toluene (I have done it):

https://www.sciencemadness.org/whisper/viewthread.php?tid=22...




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