fumaric acid esters?

[JesusBuiltMyHotRod]

While looking online for food grade fumaric acid powder I keep running across capsules of FAE. I've been looking around online trying to find anything on whether they can be used in place of formic acid powder but keep coming up empty. Could anyone explain to me the difference between the food grade and FAEs and how it might effect a reaction? Pardon my ignorance but I'm having a little bit of a hard time understanding how esters act/react.

 

[benzyme]

nucleophilic acyl substitution.

aha, someone is a ministry/1000 homo djs fan too.

 

[JesusBuiltMyHotRod]

Could you explain that a bit in laymens terms for me? Also, how could/would that possibly effect the conversion of the alkaloid from the freebase form to the salt if used in place of fumaric acid? Sorry if I'm asking stupid or basic questions here, I know enough chemistry to do certain basic extractions and purifications but I'm still far from knowledgeable on all the specifics.

And you are correct sir, I'm glad that somebody else is here is a fan, bonus points if you know what song my signature comes from!

 

[benzyme]

johnny cash?

*shrugs*

fumaric acid shouldn't be too hard to find. it's a simple dicarboxylic acid, like tartaric acid. in fact, tartaric acid may be used alternatively. it has different pKa's, so observe that when making solutions.
www.chemicalize.org
www.wolframalpha.com

the first link can be used to look up pKa of a molecule.
for fumaric or tartaric acid, you want the pH range between the first and second pKa, the points where the lines intersect.

the second link can be used to prepare solutions. just enter a concentration of fumaric or tartaric acid,
(ex. 0.01 M tartaric acid)

and it tells you how to prepare it, and the pH at that concentration.

 

[JesusBuiltMyHotRod]

My friend solved the problem and decided to just spend the money rather than substitute with what was available locally. Thank you for the information and links though, great info and much appreciated!

About tartaric acid.. Will it precipitate in a similar manner to fumaric acid in the FASA process or is it very hygroscopic like the other salts? Just curious since my friend has noticed that the local health food store seems to have everything you could need for organic chemistry, it's ridiculous. He wishes he found this out years ago.

It was Supernaut by Ministry but thanks for playing :thumb_up:

 

[benzyme]

Supernaut was initially done by Black Sabbath....it was remixed by 1000 Homo DJs in 1991, and that is referenced in your avatar sig, hence my initial post. I was looking at your sig below your posts...but thanks for playing.

yes, tartaric is hygroscopic like fumaric.

 

[JesusBuiltMyHotRod]

Fair enough on the one up, most people don't know who Ministry/1000 Homo DJ's/the other side projects, even fewer people I know knew the song that well. Your vast knowledge of seemingly everything shows through your posts and is simply amazing, truly something that I'm envious of.

I know that the salts are hygroscopic to some extent but is it comparable to the fumaric salt in the sense that it doesn't turn into goo with the ambient humidity? He is just interested in the properties of the different salts as well as their solubility and the information is few, far and buried in forums.

EDIT: 133g/100mL of water compared.to .63g/100mL, answered my own question. What about a Valerate? 4.87g/100mL seems much better than tartric for stability in air, but I'm not the chemist here.

Again, much appreciation for the help and repeated replies. The welcome has been much warmer here than any other forum I've visited.

 

[benzyme]

that's a good point, some of the acid salts are more hygroscopic than others.
Tartaric would possibly leave a goo by absorbing ambient humidity, because it has several OH groups which water can bind to. Valeric only has one, and it would bind DMT's terminal amine group at acidic pH.

 

[Infundibulum]

Dmt tartrate is a goo at ambient humidity, hard to work with,

Dmt fumarate can be a goo at first, but can be dried and made to a powder that stays a powder at ambient humidity.


JesusBuiltMyHotRod, fumaric acid esters are not a substitute for fumaric acid, as they are not fumaric acid...in simple terms they are derived from fumaric acid and after esterification they do not act as acids any more.

 

[JesusBuiltMyHotRod]

Wow, I'm honored that you think that I made a good point lol.. Could you explain the part about valeric to me in simpler terms? Sorry.

And thank you for answering my question about FAE! I didn't think it would substitute but I don't exactly understand esters that well.

 

[benzyme]

the "functional groups" in the carboxylic acids and esters in question are, R-CO-OH, and R-CO-OR', respectively, where R and R' represent a carbon chain (typically). the H bound to the oxygen is the key part of an acid (and it is lacking in the ester), because it acts as a proton. the OH group is called a proton-donor.

valeric is a single carboxylic acid (tartaric and fumaric are both dicarboxylic acids), so it is has one pKa, and can form a salt with an alkaloid, with relatively lower hygroscopic potential, because it only has one other oxygen to accept protons (essentially, bind ambient moisture)

 

[Shadowman-x]

:lol: this thread is full of learning. :thumb_up:

 

[JesusBuiltMyHotRod]

the "functional groups" in the carboxylic acids and esters in question are, R-CO-OH, and R-CO-OR', respectively, where R and R' represent a carbon chain (typically). the H bound to the oxygen is the key part of an acid (and it is lacking in the ester), because it acts as a proton. the OH group is called a proton-donor.

valeric is a single carboxylic acid (tartaric and fumaric are both dicarboxylic acids), so it is has one pKa, and can form a salt with an alkaloid, with relatively lower hygroscopic potential, because it only has one other oxygen to accept protons (essentially, bind ambient moisture)

Ok, that makes a lot of sense now that I know how the the ester is lacking a donor. So if I'm understanding this correctly, valeric acid would be about as good or possibly better than fumaric acid for a FASA type extraction, or at least a better salt that would be less hygroscopic and more stable in air?

Man, it's much easier to understand these concepts with you explaining them to me, thank you so much for your continued help and answers!

Kind of off topic but would you possibly be willing to explain what a carbamate is? I've always been curious since I founf that Soma and some of the other super awesome muscle relaxants are carbamates and not traditional salts or bases (right?).

EDIT: One more slightly off topic question, will DMT citrate ever precipitate from acetone? My friend has an extraction that has been sitting while he waits and some bark sediment that was at the bottom seems to to have gotten more orange and is now seemingly stuck. With the large amount of acetone relative to alkaloids it doesn't seem probable that the citrate is the cause.

 

[benzyme]

looks like they're derived from amines and carbamic acid.
anything with the suffix -ates, means it's a salt derived from an acid and basic compound.. a cation and an anion.

 

[JesusBuiltMyHotRod]

Hmm, interesting indeed. I have a lot more I'd love to ask you but I'm sure you have better things to do with your time than answer my simple and scattered questions.

Any chance you could take a look at the edit I posted above while you wrote that post? Last thing I ask from you, I promise!

 

[benzyme]

those might be some plant glycosides.
citrates should be soluble in acetone.

 

[JesusBuiltMyHotRod]

So it would seem that even more garbage has settled aside from particulate, gluing the particulate to the bottom of the glass? Sweet, less work for my friend.

So I'm assuming that it is safe for him to pipette off the golden goodness and scrub out the gunk before he salts? Just want to make sure he isn't doing anything counterproductive.

Any chance you would care to give your thoughts on dmt fumrate compared to dmt valerate in terms of stability and potential as a fumaric acid substitute?

Also, any idea why light beige ACRB turns crimson red when mixed with sodium carbonate and enough water to make a thick paste? My guess is something involving the tannins since they are used in darker dyes, but I figured you might have some insight. I don't think it's anything significant, just interesting.