Sciencemadness Discussion Board

Curcumin Extraction Solvents

SPB - 8-4-2013 at 02:09

I want to extract the curcuminoids from Tumeric.

I have found two methods:
One from this forum uses 50:50 ethyl / methyl alcohol and heptane.

Another method uses ethylene dichloride and isopropyl alcohol:
http://nhsjs.com/2012/characterization-of-the-purity-of-curc...

Neither of these methods suit me as I don't have ethylene dichloride or heptane.

I do have methyl alcohol, isopropyl alcohol, methylene chloride.

Q: Can I use any of these solvents with any others readily available to perform this extraction?

Ideally, I also want a method that does not involve heating.

If someone cares to answer this, could they also explain how/why they came up with the solvent selections, as I'm interested to know this also.

Mailinmypocket - 8-4-2013 at 05:00

Dichloromethane (methylene chloride) works exceptionally well when refluxed with tumeric. I am actually halfway through this extraction as we speak (what left is just stripping the solvent from the extract, when time permits). If you can reflux it will speed up the extraction however I don't think there would be a problem with letting it extract in a closed vessel for say, a few days. Dichloromethane is nice because it has a very low bp which makes it quick and easy to distill/evaporate off from your extract.

[Edited on 8-4-2013 by Mailinmypocket]

Finnnicus - 8-4-2013 at 05:04

Sorry to look like an idiot, but what is curcumin for? I checked the wiki, but alas.

Mailinmypocket - 8-4-2013 at 05:42

Quote: Originally posted by Finnnicus  
Sorry to look like an idiot, but what is curcumin for? I checked the wiki, but alas.


It is a phenol with pharmacological properties(read up on that), it is also used as a dye as well as an indicator for borate determination.

Wikipedia: http://en.wikipedia.org/wiki/Rosocyanine

There is plenty of information about its properties and uses online

Finnnicus - 8-4-2013 at 05:54

Seems handy. Pharmacological being illicit? ;)

Finnnicus - 8-4-2013 at 06:06

Ok, always learning, check my bio. Thanks guys.

Not a particularly useful pharmalogical chemical, right? But very interesting, more research is needed.

Mailinmypocket - 8-4-2013 at 06:11

Quote: Originally posted by Finnnicus  
Seems handy. Pharmacological being illicit? ;)


No, pharmacological in the sense that it has potential for disease curing properties (anti tumor I believe). I myself haven't researched it much in that regard, I just need it for borate determination.

Hexavalent - 8-4-2013 at 10:33

I requested a paper on this topic exactly in the References section, for those interested.

I have previously extracted curcumin from tumeric using DCM, which worked well, for use in boron analysis of soil samples (it forms red-coloured rosocyanine complexes boron compounds).

Mailinmypocket - 8-4-2013 at 10:58

Quote: Originally posted by Hexavalent  
I requested a paper on this topic exactly in the References section, for those interested.

I have previously extracted curcumin from tumeric using DCM, which worked well, for use in boron analysis of soil samples (it forms red-coloured rosocyanine complexes boron compounds).


I especially love how the DCM extract will instantly stain everything, even glass, and require solvent rinsing. Right when I was expecting a somewhat simple clean up. I followed the same instructions in the paper you requested, all that is left to do is triturate with hexane tonight. Nice process :)

Boffis - 8-4-2013 at 17:43

n-Heptane, presumably of synthetic origins is now preferred to n-Hexane or petroleum ether boiling range 60-80 C because there is some evidence (discussed on this board I believe) that n-hexane is acutely toxic and there has been a tendency to substitute cyclohexane or n-heptane. Cyclohexane and old fashion petroleum ether will work just as well as will almost any non-polar solvent of similar boiling point, DCM has a rather lower boiling point but I am sure works too as does chloroform and 1,1,1-trichlorethane.

SPB - 8-4-2013 at 19:26

Quote: Originally posted by Mailinmypocket  
I am actually halfway through this extraction as we speak (what left is just stripping the solvent from the extract, when time permits).
[Edited on 8-4-2013 by Mailinmypocket]


So, are you using only the one solvent (DCM) for the whole process?

Could you please describe the whole process you're using, with a level of detail that includes ratios, filtering, etc.

Mailinmypocket - 9-4-2013 at 03:12

Quote: Originally posted by SPB  
Quote: Originally posted by Mailinmypocket  
I am actually halfway through this extraction as we speak (what left is just stripping the solvent from the extract, when time permits).
[Edited on 8-4-2013 by Mailinmypocket]


So, are you using only the one solvent (DCM) for the whole process?

Could you please describe the whole process you're using, with a level of detail that includes ratios, filtering, etc.


Yes, DCM for extraction. Here is the extraction process copied from the paper in references:

Extraction Procedure
Twenty grams of ground turmeric in 50 mL of dichloro- methane was magnetically stirred and heated at reflux for 1 h. The mixture was suction-filtered and the filtrate was concen- trated in a hot-water bath maintained at 50 °C. The reddish- yellow oily residue was triturated with 20 mL of hexane and the resulting solid (0.57 g) was collected by suction filtration.

SPB - 9-4-2013 at 05:22

Quote: Originally posted by Mailinmypocket  

Extraction Procedure
Twenty grams of ground turmeric in 50 mL of dichloro- methane was magnetically stirred and heated at reflux for 1 h. The mixture was suction-filtered and the filtrate was concen- trated in a hot-water bath maintained at 50 °C. The reddish- yellow oily residue was triturated with 20 mL of hexane and the resulting solid (0.57 g) was collected by suction filtration.


Thanks.

So, can I substitute the hexane with IPA?

Mailinmypocket - 9-4-2013 at 06:47

Quote: Originally posted by SPB  
Quote: Originally posted by Mailinmypocket  

Extraction Procedure
Twenty grams of ground turmeric in 50 mL of dichloro- methane was magnetically stirred and heated at reflux for 1 h. The mixture was suction-filtered and the filtrate was concen- trated in a hot-water bath maintained at 50 °C. The reddish- yellow oily residue was triturated with 20 mL of hexane and the resulting solid (0.57 g) was collected by suction filtration.


Thanks.

So, can I substitute the hexane with IPA?


For the trituration stage you mean?

Boffis - 9-4-2013 at 09:04

No, the trituration stage is removing fats and oil and leaving most of the curcumin behind. If you use IPA you are more likely remove the curcumin but probably not without some of the fat.

Mailinmypocket - 9-4-2013 at 12:33

Nicely colored extract in DCM before stripping the solvent out

image.jpg - 74kB

Boffis - 20-11-2020 at 08:04

@Mailinmypocket, did you ever get any further with your prep of curcumin? Did you recrystallise it andif so in what solvent?

zed - 21-11-2020 at 08:41

Ummm. Tumeric has multiple uses. Used for liver ailments.

Combined with fresh Neem leaf, as a topical Scabicide

Basis in Curry compositions. Yummm!

Some folks, use it to "pack" a painful tooth. This works, but I prefer Cayenne. Like fire for a short time, and then zippo! Pain is gone!

I just bought 5 lbs. online. Twenty bucks! I assume it to be, a lifetime supply.

unionised - 21-11-2020 at 10:19

Has anyone tried aqueous alkali as a solvent?

Metacelsus - 22-11-2020 at 05:06

Just don't waste your time with it.

Anyway, alkali are unlikely to work. Curcumin has a half-life measured in minutes in aqueous alkali (0.1 M sodium carbonate, pH 10). Source: https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.6b00975

[Edited on 2020-11-22 by Metacelsus]

zed - 22-11-2020 at 06:33

https://www.worldofmolecules.com/antioxidants/turmeric.htm

Let's just say, medical usefulness; unconfirmed.

It isn't "nothing". It is something we don't fully understand.

As a toothache remedy, it has structures in common with other remedies.

Eugenol (AKA Clove Oil), Vanillin, Cayenne, Curcumin.

unionised - 22-11-2020 at 06:41

Quote: Originally posted by zed  


It isn't "nothing".

Yes it is.

"No double-blinded, placebo controlled clinical trial of curcumin has been successful."
From the abstract of paper Metacelsus cited.

I'd quite like to see the full paper: mainly to find out what the products of the decomposition are, but partly to see if thI can remove curry stains with washing soda.


zed - 22-11-2020 at 07:08

Stuff it in a painful dental cavity. Then repeat your ridiculous statement.

Also mentioned as a mood elevator. Might be.

Note: Curcumin shares some structures in common with Oleuropein. Is that "nothing"?

Perhaps, all Curcumin inquiries should cease forever, because you personally have concluded they will be "fruitless"?

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5392257/



[Edited on 22-11-2020 by zed]

unionised - 22-11-2020 at 09:31

Quote: Originally posted by zed  
Stuff it in a painful dental cavity. Then repeat your ridiculous statement.

[Edited on 22-11-2020 by zed]

What did you use as the control experiment?

"Curcumin shares some structures in common with Oleuropein. Is that "nothing"?"

It shares some structures in common with morphine.
Do you think it should be a controlled drug?
Or do you realise that it takes rather more than a handful of atoms to define biological function?

"Perhaps, all Curcumin inquiries should cease forever,"
No, but they should be done properly- a controlled experiment with a placebo as the reference.
Because, by doing things properly, you get answers fit to be posted on a science page.


Also, is there any actual basis for the idea that Oleuropein is any good for you?

zed - 22-11-2020 at 19:30

The suggestion of the original poster was...... Just don't waste your time with it.

True, Curcumin remains a cipher. So far, a frustration.

So what? Most experiments fail. Success is built on the foundation of past failures.

Now, lots of papers have been published on Turmeric and Curcumin. Unfortunately, those papers often sport Indian surnames, and may not meet Western criteria for excellence.

[Edited on 23-11-2020 by zed]

DraconicAcid - 22-11-2020 at 20:41

What does it decompose to in basic solution?

Boffis - 23-11-2020 at 03:48

Oh dear.....!

When you guys have have stopped slagging each other off can we get back to my original question? Irrespective of whether curcumin (di-ferulylmethane where ferulyl = 3-(3-methoxy-4-hydroxyphenyl)-2-propenoyl unit) is a potential drug of abuse or effective pharmaceutical my question was whether anyone had ever obtained it in a crystalline form. I have extracted some from 100g of turmeric and now have about 4.5g of crude orangy yellow powder and would like to try recrystallising it. Any useful comments?

@DraconicAcid, since curcumin is a 1,3-diketone I suspect that under basic conditions the carbonyl groups on one molecule will condense with the active methylene group on another and very soon will result in polymerised crap :). Another possibility would appear to be a reverse Aldol resulting in vanillin and a ketonic residue.

zed - 23-11-2020 at 04:33

Yielding Vanillin might require Ozoneolysis.

Reverse Aldol, I think not. But it is and interesting idea.

Polymerization seems likely.

TriiodideFrog - 26-11-2020 at 18:40

Ethanol works well. Isopropanol also works, but I prefer ethanol.

DraconicAcid - 26-11-2020 at 21:14

I wonder if it would make acac-like complexes with transition metals.

I really should google instead of idly wondering: https://pubs.rsc.org/en/content/articlehtml/2015/cs/c5cs0008...

[Edited on 27-11-2020 by DraconicAcid]

Boffis - 27-11-2020 at 05:57

@DraconicAcid, That is an interesting find! Looks like further purification of my curcumin will be worth while after all. I like the sound of the ligands derived from oxime, semicarbazones etc.

Metacelsus - 27-11-2020 at 08:17

Quote: Originally posted by DraconicAcid  
What does it decompose to in basic solution?


I'm not sure because the paper didn't say, but I'd guess that when it's deprotonated, it's easily oxidized by atmospheric oxygen (like most other electron-rich phenols). The enolate (easily formed from the 1,3-diketone moiety) might also react with things.

Boffis - 30-11-2020 at 12:20

I tried to recrystallise my de-oiled from methanol. I dissolved 0.5g in increasing amounts of boiling methanol, I eventually ended up with 25ml of solution but it was still hazy so I added a pinch of charcoal and kieselguhr and filtered it hot. Very little crystallised on cooling the deep yellow solution so I left it to evaporate. At first dark orange pompoms and blades formed with a few coarse golden yellow blades. However, by the time the methanol had almost evaporated the dark orange crystals were by far the more abundant, I presume these to be the curcumin. Methanol is not a good solvent for the recrystallisation of curcumin though, its solubility is too low and the temp/solubility curve too flat.

Anyone have any ideas for a better solvent?

pneumatician - 28-5-2021 at 04:37

tested cucurmin powder if contain lead cromate???

karlos³ - 28-5-2021 at 07:47

Quote: Originally posted by pneumatician  
tested cucurmin powder if contain lead cromate???

You mean, how to test for lead chromate in turmeric?
Thats seems pretty simple, click that link: test for lead chromate in turmeric

pneumatician - 28-5-2021 at 09:12

wow, I are saying if the guy make this test!