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Quaff
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[*] posted on 15-11-2017 at 10:47
Sulforaphane


Is anyone aware of a short synthetic method for sulforaphane ?
thank you.
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Vosoryx
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[*] posted on 15-11-2017 at 10:55


Perhaps an extraction might be possible?
I don't know if there is a quick and easy method for production, although there might be.

Crush up broccoli or cauliflower sprouts, let react, and extract the compound from that. Thats my theory.
Or perhaps individually extract or find the precursors and react it yourself.

Hopefully someone with more knowledge of organic sysnthesis can help you out.
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[*] posted on 15-11-2017 at 13:35


Some good posts in this thread:

http://www.sciencemadness.org/talk/viewthread.php?tid=75864





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[*] posted on 15-11-2017 at 16:19


Thanks ! Lots of folk talk about how it cured their cancer, so maybe its a good idea to know more. I saw where Sigma sells five milligrams for $100 and its only spc'd to 90% . So, that's $20,000 a gram. ok, in bulk one gets a better price, maybe wholesale its worth $3k or $4k a gram ? So, at least $ 100k per kilo I'd imagine, bulk wholesale ?
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clearly_not_atara
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[*] posted on 15-11-2017 at 19:19


I found a paper describing the extraction of sulforaphane from freeze-dried broccoli. Note that "lyophilized" means "freeze-dried".

http://www.pnas.org/content/89/6/2399.long

"Lyophilized SAGA broccoli was extracted three times with acetonitrile (35 ml/g) for 6 hr each at 4°C. The pooled extracts were filtered and evaporated to dryness under reduced pressure on a rotating evaporator (<40°C). About 1 g of residue from 640 g of fresh broccoli (64 g of lyophilized powder) contained 3.6 x 106 units of inducer activity. The residue was mixed thoroughly with 120 ml of methanol/water (25/75, vol/vol) and the insoluble fraction was discarded. Although not all of the residue obtained from the extraction was soluble in aqueous methanol, the solvent partition pro- cedure resulted in substantial purification without significant loss of inducer activity. Portions of the extract were dried in a vacuum centrifuge and dissolved in small volumes of dimethyl formamide (0.75-1.0 ml per 50 mg of residue), and 50-mg portions were subjected to HPLC (nine runs) as described in the legend of Fig. 1. Fractions 18-23 from all runs were pooled, evaporated to dryness, applied in aceto- nitrile to five preparative silica TLC plates (100 x 200 x 0.25 mm), and developed with acetonitrile, which was run to the top of each plate three times. Four major fluorescence- quenching components were resolved, and nearly all (99%) of the inducer activity migrated at Rf 0.4. The active bands were eluted with acetonitrile, pooled, and fractionated by two runs on a second preparative reverse-phase HPLC in a water/acetonitrile gradient (Fig. 2). Ultraviolet absorption and inducer activity were eluted in a sharp coincident peak (at 66% acetonitrile) that contained all of the activity applied to the column. Evaporation (<40'C) of the active fractions gave 8.9 mg of a slightly yellow liquid, which contained 558,000 inducer units (overall yield 15%) and migrated as a single band on TLC."

From about one and a half pounds of broccoli there is about one gram of acetonitrile-soluble residue which contains nine milligrams of sulforaphane after isolation with HPLC. I have trouble imagining that this is a practical method of obtaining it.
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maybe wholesale its worth $3k or $4k a gram ? So, at least $ 100k per kilo I'd imagine, bulk wholesale ?
It's not wise to hope you can get the same price Sigma does for a compound. Some compounds are highly priced on SA because SA is charging for laziness and knows they're the first place anyone will check.

[Edited on 16-11-2017 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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Quaff
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[*] posted on 15-11-2017 at 20:27


Thanks for that. I don't get the "35ml/g" It appears to mean 35 ml of CH3CN for every gram of broccoli, which would put one in the solvent recycling business. Fortunately, broccoli sprouts contain about 50X the level of sulf..ane as mature broccoli. But why CH3CN ?? I suppose any polar solvent should work, I'd probably look at ethanol. Need to think more on this, but first thought is macerate a shtload of broccoli sprouts with sufficient EtOH, then decoct at low temp, evap the EtOH with air stream, treat the residue with EtOAc, wash with H2O, then evap the EtOAc. Probably lots of enzymes and glycosides in there, so maybe add a little sorbate to quell unwanted rxns. I prefer to stay away from DMF and the nitrile. I bet it could be purified on a silica prep column using play sand.... Have to find the partition coefficients, and maybe the elution times are out there as well....

[Edited on 16-11-2017 by Quaff]
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[*] posted on 15-11-2017 at 20:35


Ethanol should work but it may dissolve much more unwanted material from the broccoli, while nitrile and DMF and most likely more selective. If you do choose to go with ethanol, you probably have to do a solvent extraction anyway with a more selective solvent to separate the sulforaphane from other unwanted impurities.



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clearly_not_atara
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[*] posted on 16-11-2017 at 11:18


Acetonitrile is not particularly dangerous and the synthesis from acetamide is OTC. What's wrong with that? I'd try acetone first if for some reason I couldn't use a proper solvent.

Also, how are you going to dehydrate it? Heating is probably not a good idea.




[Edited on 04-20-1969 by clearly_not_atara]
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