ninhydric1 - 31-7-2017 at 18:15
I recently stumbled across an infographic stating the discovery of sulforaphane as a possible agent for preventing and treating diabetes. I briefly
researched this compound; sulforaphane has been discovered to possibly prevent and treat skin and breast cancer. I also read that sulforaphane exists
naturally in foods such as kale and broccoli. I immediately put myself to the task of isolating this interesting compound, either by extraction or
synthesis.
Extraction seems to be a simple method to obtain this compound, but a study (linked below) was only able to obtain a concentration of 1021.8 μmol per
kg fresh weight of Brussels sprouts. This wouldn't result in a tangible amount.
Then there is synthesis. I read many articles on the synthesis of sulforaphane, and the simplest one I found (linked below) used 4-aminobutan-1-ol.
Sadly, I don't have access to the article. So I was thinking, would be possible to start with butan-1,4-ol and use reagents such as thiocyanic acid to
make up the two ends of the molecule?
Of course, if it isn't that simple for the amateur chemist, it would be ideal for a possibly theoretical method.
References:
Study on concentration: https://link.springer.com/article/10.1007/s13765-012-2123-4
Study on synthesis: https://www.thieme-connect.com/products/ejournals/abstract/1...
[Edited on 8-1-2017 by ninhydric1]
CuReUS - 31-7-2017 at 23:19
the easiest way,IMO,would be to start of with homomethionine and decarboxylate it.After that you would end up with 4-methylsulfanylbutan-1-amine which
can be converted to the target compound in 2 steps(either using scheme 1 in the thieme paper with CSCl2/mCPBA or using
CS2/H2O2 according to this-http://onlinelibrary.wiley.com/doi/10.1002/hlca.19480310608/... )
ninhydric1 - 1-8-2017 at 11:55
Homomethionine doesn't seem very accessible IMO.
Loptr - 1-8-2017 at 11:59
It's an essential amino acid. I see it for sale on eBay.
EDIT:
Sorry, I see that it has one more carbon atom.
[Edited on 1-8-2017 by Loptr]
karlos³ - 1-8-2017 at 12:15
Not sure how you would proceed from there, but sodium glutamate is very accessible and may be convertable to your product? At least experimentation
would be very cheap, considering it´s price.
clearly_not_atara - 1-8-2017 at 12:38
I think you could put the whole carbon skeleton together by reacting the anion of DMSO (dimsyl sodium) with acrylonitrile, then selectively reduce the
nitrile and react with CS2 or CSCl2.
However, if DMSO won't form an anion, you could dimethylate thioglycolic acid (Nair) to methyl thiomethylacetate, which is oxidized to the sulfoxide
and then undergoes the Michael reaction with acrylonitrile. Reducing the nitrile should probably happen first, then base hydrolysis of the ester will
give an acid that should decarboxylate almost spontaneously (since the sulfoxide resembles a beta-keto), then reaction with CS2 gives the product.
Acrylonitrile can be made from glutamic acid, so karlos was going in the right direction there.
CuReUS - 1-8-2017 at 21:29
another way would be to react allyl cyanide with MeSH to get 4-methylsulfanyl butanenitrile which would then be reduced to amine and converted to
isocyanate -http://actachemscand.dk/pdf/acta_vol_08_p0295-0298.pdf (pg 296, pg 2 of pdf)
allyl cyanide could be made from NaCN + allyl-OH/Br which in turn could be made from glycerol
Waffles SS - 5-8-2017 at 00:08
All possible way for synthesis Sulforaphane by reaxys
Attachment: Sulforaphane.pdf (205kB)
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