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Author: Subject: Vicine
aga
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Vicine

For over a year i've been trying to extract vicine from fava beans.

Today i picked up the latest tiny plastic pot of brown goo with the intention of throwing it out as yet another total failure.

When the pot was squeezed, it was crunchy.

Pouring off the nearly black supernatant (which had a crust on top) revealed crystals !

There isn't much, but at least there is something - finally !

Now for the scary part - recrystallising this micro-gramme amount, separating the convicine then recrystallising it again.

Happy days !

Madness is thinking i'm not drunk.
zed
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Vicine? You got a grudge against somebody with a glucose-6-phosphatase deficiency?
aga
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Quite the opposite.

Research is somewhat hampered by the $35,000 per-gramme cost of the stuff at analytical purity. Marquardt et al's process is a bit beyond an amateur in the form it states. Great googling btw. Madness is thinking i'm not drunk. SWIM National Hazard Posts: 263 Registered: 3-9-2017 Member Is Offline Mood: in a state of equaverpoise Do you have any Craig tubes? They're just great for re-crystalizing small quantities with minimal loss. (with a centrifuge, but you've got one of those.) They use them in microscale kits (that 14/10 stuff), but they must be available alone. Did you find an MP for that stuff? How are you planning to characterize it? The problem with quotes on the internet is that it's hard to determine their authenticity. -Abraham Lincoln. UC235 National Hazard Posts: 357 Registered: 28-12-2014 Member Is Offline Mood: No Mood Have you taken a look at DOI: 10.1002/jsfa.2740361210 ? The extraction looks fairly straightforward. zed International Hazard Posts: 1607 Registered: 6-9-2008 Location: Great State of Jefferson, City of Portland Member Is Offline Mood: Semi-repentant Sith Lord Did you mean to say: "Great Googly Moogly"? Stop being rude to people. Folks from where I went to school, know what Favism is.$30,000 a gram?

That might be worth the trouble.

https://www.sigmaaldrich.com/catalog/product/sial/78260?lang...

Yup!

[Edited on 6-6-2018 by zed]

[Edited on 6-6-2018 by zed]
aga
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 Quote: Originally posted by SWIM Do you have any Craig tubes?

No, i do not - did not even know they existed - thanks. Really good info.

I now suspect that Craig tubes are what Marquardt et al used when they said 'crystals recovered by centrifugation'.

 Quote: Originally posted by UC235 Have you taken a look at DOI: 10.1002/jsfa.2740361210 ? The extraction looks fairly straightforward.

Thanks for the reference. Yes, i've read that also.

Everything looks easy until you try and do it.

Seems to get harder at that point, especially when there is no 'No. 245 Carter Seed Cleaner' nor a 'Type 132 MP' on hand.

 Quote: Originally posted by zed ... Stop being rude to people.

I was congratulating you on your search skills, not trying to be rude.

The probability of addressing anyone with prior knowledge of vicine is vanishingly small, which i offer as an excuse for assuming it was googled.

 Quote: Originally posted by zed ... $30,000 a gram? Closer to$40,000. Around 35,000 euros a gramme.

... not that the production of vicine could ever make anyone anyone some actual money.

It can only really be used in research, where milligrammes are more than sufficient.

It could find applications - i only found it by accident when NurdRage was making Pyrimethamine back at the NaCN stage.

Seemed to me that vicine was already mostly what he wanted to make.

If you tried to make and store a whole gramme, chances are that it would have badly degraded before a buyer was found.

Madness is thinking i'm not drunk.
Tsjerk
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Can you state what you did? Very nice that you actually did some chemistry, but for all I know those are just funny looking NaCl crystals.

It would be preferable you explain your experiments in such detail that we could exclude other compounds forming these nice crystals.
zed
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Perhaps it is easier to extract Vicine from Bitter Melons? If indeed, it is actually present there.

Now, I love me my Fava Beans, fer eatin', but they are just chocked full of fibrous materials and highly pigmented, seemingly oxidizable other stuff.

Never tasted them until I was 40ish, and I grew my own. Delicious! Sometimes called Windsor Beans, Broad Beans, or English Broad Beans. They were not a common food on the West Coast of the U.S.A., at least when I was a boy. In California, the Pinto, the Pinquito, and other New World Beans, reigned supreme.

Is it as it appears? That the toxic part of Vicine is not the nitrogenous ring, but rather the form of glucose it delivers as it is metabolized?

Reminds me of Solasodine (aka Curaderm), of which it is reputed, that it delivers to cancer cells, a type of sugar, that because of the cell's abnormal metabolism, kills them.

https://www.ncbi.nlm.nih.gov/pubmed/2257540

About Favas in the U.S..... Circa 1984, most people had never heard of them.

https://www.nytimes.com/1984/04/11/garden/a-bean-called-fava...

[Edited on 10-6-2018 by zed]

[Edited on 10-6-2018 by zed]

[Edited on 10-6-2018 by zed]
The Volatile Chemist
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The beans and the deficiency that results in favism are discussed in the popular AP Biology suggested class-read book 'Survival of the Sickest', and I suppose that many have heard of the bean and the disease from this book. This is certainly an interesting extraction, and I would love to hear how you did it Aga.

My write-ups are on here...
http://www.MeltThe.Ga or http://ptp.x10.mx
aga
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 Quote: Originally posted by Tsjerk Can you state what you did? Very nice that you actually did some chemistry, but for all I know those are just funny looking NaCl crystals.

Very Good point.

I was just getting used to the idea that nobody cared how anything is actually done, with just random words required instead of actual work, or details.

Over about 20 experiments, the process has been pretty much the same, using Marquardt et al's 1983 paper, but with amateur adjustments/bodges.

First the frozen beans were thawed in water, then separated from their 'testa' by hand.

The separated cotelydons were liquidised in a kitchen food blender.

(several other things were tried, the following was the last attempt)

An NaOH solution was prepared, mixed with acetone and the whizzed-up bean cotelydon mush was stirred by hand with the NaOH solution + acetone for around 15 minutes.

1 metre of 40mm diameter water pipe was used, with 4 holes drilled at one end to accept two wooden skewers to make a cross, also two holes at the opposite end to accept supporting string.

A small wad of cotton was blown from the other end to form a plug.

A small quantity (about 100g) of fine sand was then poured into the top of the pipe, with water passed through to ensure that the filtering assembly was moist.

The filter/pipe was then hung by string from a support.

The bean mush was placed in a towel and hung up so the dissolved material could drip out. This took about 2 days each time.

The pre-filtered green stuff was then put into the pipe-filter and left to filter for about 4 days.

The vast quantity of other stuff in plants makes it a slow process.

Eventually there is a lot of brown liquid in a pot.

Lacking a cyclone evaporator, it just got Boiled down, then ignored for about a month.

The Second time i did all this there were crystals - since then there were none.

That little pot with possibly-table-salt with brown goo in the photo represents a lot as far as i am concerned.

It's some crystals of something after a great many 'no-crystal' experiments.

The separation/recrystallisation isn't going well. It's a very small amount.

That part is also non-trivial it seems.

Madness is thinking i'm not drunk.
The Volatile Chemist
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I know a few people from SM that might offer you NMR analysis of your product, if this is indeed vicine that is quite the success. I will have to look up that paper myself. I wonder if there's info on the crystallography of vicine, it looks like you've got a pretty consistent and identifiable shape in those crystals. I'm always interested in these biological extractions.

My write-ups are on here...
http://www.MeltThe.Ga or http://ptp.x10.mx
fusso
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What are the masses of the beans and crude crystals?
What solvent u used?

[Edited on 11/06/18 by fusso]

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 Sciencemadness Discussion Board » Fundamentals » Chemistry in General » Vicine Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication Non-chemistry   » Forum Matters   » Legal and Societal Issues   » Detritus