Sciencemadness Discussion Board - Synthesis of Hydroxycitrate

Synthesis of Hydroxycitrate

Pasrules - 4-1-2015 at 05:32

I would like to synthesis hydroxycitrate from citric acid and have found nothing on a method to do so. My theory to produce this compound would be to take citric acid and dehydrate the central tertiary alcohol using sulfuric acid forming a double bond (symmetrical so no problem there) then use an oxidiser to introduce two Hydroxyl groups similar to producing a diol.

In stock I currently have food grade citric acid, 18M sulfuric acid which will be dilluted to 2M as per the recipe for aconitic acid and Potassium Permanganate

This is for a food grade application.

Also here is a procedure to produce aconitic acid which would be step one of my process http://www.orgsyn.org/demo.aspx?prep=cv2p0012

[Edited on 5-1-2015 by Pasrules]

Bert - 4-1-2015 at 06:38

Looks like extraction from plant material (Garcinia, spp) is the main source?

Yes, looks like there's not much to be quickly found by Google on synthetic production-

http://www.fda.gov/ohrms/dockets/dockets/95s0316/95s-0316-rp...

Curious as to your intended use of this? Apparently this stuff is related to a crap ton of diet related spamvertising I encounter around the net!

Some information on traditional use, along with various studies

Quote:

Thus, what appears to be the most thorough study of hydroxycitrate obtained negative results. In addition, one other recent study (Rothacker et al.) found results which were not statistically significant. The usefulness of this product remains to be demonstrated.

[Edited on 4-1-2015 by Bert]

Pasrules - 4-1-2015 at 06:58

The apatite suppression is why the university is so crazy about it for money of course but why grow tropical fruit when instead you could grow lemons and then just add a bit of oxidiser and catalyst.

Everything is so focused on the dieting factors that's it's impossible to find good synthesis papers that don't include the garcinia family.

My reason for making this is so I would have a positive control to test against once I have my fruit extract. Honestly I'm just going above and beyond for a task to research analytical methods rather than applying them.

Bert - 4-1-2015 at 07:11

No need to grow lemons! Commercial critic acid is mostly made by a fermentation process, using moulds to process cheap sugar or starch byproducts.

http://patentimages.storage.googleapis.com/pdfs/US4994609.pd...

You're going to University in chemical engineering?

Pasrules - 4-1-2015 at 07:43

I'm just starting second year in undergrad medical science so I've only completed introductory chemistry which was a joke. My chemistry background came out of nowhere but luckily I have a job in food & pharma which gives me access to every chemical this forum could want, however I like the humble approach of making it rather than buying it.
And the lemons was more of a joke on how expensive tropical fruits can be however thank you for the patent I can say I've learnt something.

Bert - 4-1-2015 at 08:06

Welcome to sciencemadness.org, please do take a couple of minutes and read the FAQ.

I'm going to leave this thread in organic chemistry, hoping to see your results if you do go "hands on" with this.

Pasrules - 4-1-2015 at 08:09

Thank you for the warm welcome, I will make sure to do a proper write up when I do perform this experiment so it suits the organic chemistry thread.

deltaH - 4-1-2015 at 22:32

Another way to make vicinal diol's from alkenes is via the epoxide prepared from hydrogen peroxide and formic acid.

Attached, an illustrative example using cyclohexene.

Perhaps you won't even need formic acid since you already have aconitic acid as your substrate, in your specific case. The peroxide is also a 'cleaner' reagent.

Reference:

Roebuck, A & Adkins, H. (1948). trans-1,2-CYCLOHEXANEDIOL.Org. Synth. vol. 28. p35.

Attachment: trans-1,2-CYCLOHEXANEDIOL.pdf (294kB)
This file has been downloaded 554 times

[Edited on 5-1-2015 by deltaH]

Pasrules - 4-1-2015 at 23:31

Thankyou for the information on vicinal diols as i haven't heard of that term and it has given me a new key word to research.

I was also considering combining citric acid with an KMnO₄ in the acidified medium then following the steps of extraction as per aconitic acid. Would that be viable for a trial?

And you are already a step ahead of me, i will be using peroxide in my final run however the purple permanganate will act as an indicator until then.