Texium
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Tomato Leaf Extraction
A while ago in this thread, I expressed interest in extracting the compound that creates the smell of tomato leaves. It was a mostly unrelated thread though, so
I figured I should start a new one for this.
It's about the end of tomato season here now, so I have a lot of tomato leaves and stems to play with, but only for a matter of time before the plants
become unusable.
In the other thread, I was able to find out that the smell originates in a nameless "yellow goo" that seeps out of special cells on the leaves and
stems. I did extensive internet searching about what the components of this goo are, and found absolutely nothing.
So basically, my goal is to extract and concentrate this compound, and if possible, determine what it is somehow and if it is possible to synthesize
it, so that I may have access to that lovely tomato plant smell all year long!
What I need to do first is figure out how to properly extract the nice smelling compound(s) from the plants. What I had in mind was to use a Soxhlet
extractor with ethanol or isopropanol as the solvent.
I'd be jumping into the deep end with this though, as I only very recently acquired the extractor along with a lot of other equipment, and have never
used one before.
I'm open to any advice/better ideas, particularly since I may just be over-eager to try out my new toys, possibly missing something much more obvious
and easy!
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arkoma
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| Quote: | Phytochemicals
These are typical phytochemicals found in tomato: phytoene, phytofluene, beta-carotene, flavonoids, carotenoids, lycopene, quercetin, polyphenols,
kaempferol. |
From here
I have found out from "hard experience" some of these good smelling plant compounds get badly degraded even at the boiling temp of acetone. I picked
some wonderful smelling flowers in Nevada, refluxed in acetone, and ended up with stuff that smelled like wet hay 
Good Luck, have fun, and watch those ticks back yonder--don't laugh, I have Lyme Disease from a daggum Oklahoma deer tick.
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Texium
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Quote: Originally posted by arkoma  | | Quote: | Phytochemicals
These are typical phytochemicals found in tomato: phytoene, phytofluene, beta-carotene, flavonoids, carotenoids, lycopene, quercetin, polyphenols,
kaempferol. |
From here
I have found out from "hard experience" some of these good smelling plant compounds get badly degraded even at the boiling temp of acetone. I picked
some wonderful smelling flowers in Nevada, refluxed in acetone, and ended up with stuff that smelled like wet hay
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Yeah, well, that seems mostly concerned with the chemicals in the fruit. It seems that there is very
little research about the compounds that exist in the stems in leaves, which is what I'm interested in.
Thank you for the advice about the boiling temperatures– that's something I hadn't thought of at all. I'll try extracting a small amount with
boiling alcohol the way I had planned. I'd use acetone, but I'm afraid that the smell of the acetone would overpower the desired smell. I'll also try
letting some simply sit in alcohol, and some in water at outdoor/garage temp overnight and see if that would extract any of the smell. If I stumble
upon a method that works well, then I'll process the rest of the tomato leaves in the same manner.
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arkoma
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good clean acetone leaves NO smell behind. I buy the Wally World 99%, 97 cent bottles of acetone polish remover and distill them to get rid of the
bitrex.
I've reading about "supercritical" extraction of oils with CO2 and I've done butane extractions of "certain herbs". Today I ran across a
method using R134a refrigerant, which my brother happens to have a few cans of laying around. If I figure out and appropriate homebuilt rig to do it,
I'll pass it on to you.
Research BHO (warning cannabis chemistry), but you'll get an idea of what I wanna try with R134a. Cannabis ALSO contains its active oils in trichomes
trichomes on my friends Blue Dream female two years ago:
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Zyklon-A
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| Quote: |
trichomes on my friends Blue Dream female two years ago: |
Nice, I had three female Blue Dream kush plants not half a year ago. (I tent to get rid of any males as they can ruin the females)
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Texium
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Alright alright, this doesn't need to turn into a stoner thread now! You guys go on and start one in Whimsy.
We're talking about tomatoes here, not pot! 
[Edited on 7-17-2014 by zts16]
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violet sin
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I was happy to see this open as I want to give it a try also. after reading the first bit I had a thought,.. given that I spend a LOT of time in the
emerald triangle( doing *completely* unrelated work) I first thought of using "bubble bags" to acquire the resin glands. exactly as one would do for
marijuana plant resin. the bags have diff size mesh at the bottom, and are filled with plant material, water and ice. the ice stiffens up the resin,
sloshing around causes it to fall off into solution, and straining each bag out in order traps the appropriate size particles in the mesh. I don't do
this, but living here you cant help but learn a few things 
I also LOVE the smell of tomatoes and had set aside a large amount of our tomato plants for extraction via the previously mentioned alcohols last
fall. the material went bad( not even cut down) in 2 days. we ended up with an early frost snap, ruptured all the cells and freed the wonderful
smells I was after. only the wet hay smell left
in my research to find out what was responsible for the wonderful smell, I found very little. several headaches from lots of looking but the useful
data was hidden in THOUSANDS of irrelevant house hold tips for growing tomato's. even after using the advanced search options and scientific wording
it was a full scale brute force approach. every one thinks they have the best tips for growing the plant, and posts their drivel about it.. LAME.
the few bits I found useful seemed to imply that the smell was actually a very minor constituent, and delicate at that. I don't have the papers I
found, Home compy, but it was suggested they might be present in hormone scale, so very very very small amounts.
but I guess getting the resin glands off would tell a tale pretty quick, as to whether it was minor/major constituent.
one thing I learned while reading was, for delicate smells, afraid of heat/oxygen, they used to spread lard or oil( thick at room temp) in a pan or
tray, and press the plant in it. cover with more layers and set aside for some time. usually flowers. afterward the scent laden fat could be used in
soaps or what have you, or extracted with solvents(in the absence of what would normally come out if only an alcohol pull).
thankfully I have quite a while before my t'maters stop growing. more time to plan. bubble bags might be easy enough to mimic with out buying pot
specific instruments( + them is spendy). a few patches of the screen, same as in a silk screen printing shop, should work on the small scale I have
in mind. I just happen to know a screen printer it would be pretty sweet to
nail this down, as I have always said I love the smell so much I would make incense out of it if I could. I won't be able to help out for at least 3
weeks though, still working away from home, so Ill keep reading hoping to find some more definitive info.
though I briefly touch on the marijuana subject, it is only to highlight a process I want to use for science, not drugs. so don't take this comment
as some marijuana glorification. I am QUITE interested in the tomato smell, and have FAR too much to lose to mess with pot processing. they treat it
like methamphetamine manufacture here, even if you only use water and ice. so... I choose to stay legit
[Edited on 17-7-2014 by violet sin]
[Edited on 17-7-2014 by violet sin]
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arkoma
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| Quote: Originally posted by zts16 | Alright alright, this doesn't need to turn into a stoner thread now! You guys go on and start one in Whimsy.
We're talking about tomatoes here, not pot!
[Edited on 7-17-2014 by zts16] |
it actually was on topic  trichomes, plant resins, extractions
Edit--this is my idea. attach a cheap automotive A/C charge kit to it, and turn the can upside down for liquid flow.
[Edited on 7-17-2014 by arkoma]
Found this link today
[Edited on 7-17-2014 by arkoma]
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violet sin
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and I got to second hand brag about my kid, on point too I have no probs with
what people do on their own time, I just don't want it to look like I manufacture because I know a little bit. ya know
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arkoma
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well violet, when it comes to plant oils, the methods and chemistry are the same from one herb to another and depending on hows its used all knowledge
is good knowledge.
Having done the BHO thing a couple time, then seeing that link today about 134a, the HUGE bulb lit over my head. Non toxic, non flammable quick clean
extraction of all sorts of lovely plant oils. I'm not ashamed to admit it, I want some daggum rose oil--love the smell--and if ya read the link stuff
extracted with 134a meets food purity standards in the EU, something a DCM or acetone one probably would not. Pretty cool really, and I think there
is enough stuff in brothers garage for me to clobber something up tomorrow......................
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violet sin
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the pressure needed to keep it liquid isn't too bad if the temp is kept ambient(70'F) or lower. in the neighborhood of 100psi. a pressurized vessel
would allow for longer soak times, though that may lead to more crap gettn taken along for the ride. a can of dust off, is the same thing as the AC
refill kits and a fair amount cheaper with out the special fittings for your car. ~8$
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arkoma
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Mebbe check out this paper?
Fresh tomato aroma volatiles: a quantitative study
Ron G. Buttery , Roy Teranishi , Louisa C. Ling
J. Agric. Food Chem., 1987, 35 (4), pp 540–544
DOI: 10.1021/jf00076a025
Publication Date: July 1987
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violet sin
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I will check that paper out this evening, thanks also, arkoma, note I mentioned
ambient temp as 70'F because I remember seeing you are in a HOT climate, where you'd have to cool "ambient" to match the standard. lol. the r134A
seems interesting. just wish there was an easy way to recycle it so you weren't constantly poping for cans of it.... well dry ice may be the key. I
don't know what the vapor pressure would be at -78'C in a dryice/acetone cooled reciever, but it would be liquid mp, -103.3'C bp, -26.3'C. one of those double walled steel single cup size thermos might work good for that.
DI/Acetone inside cup like normal and vapors would enter the vacuum shielded area( obviously drilled with two ports, and hose barbs top and bottom)
and drain out the bottom as a liquid. its NOWHERE as dangerous as trying to keep butane, and in small amounts if it leaks its not gonna kill ya. be
nice to see/calculate what kind of pressure would be developed in a freezer setting? garage freezer, not in the house
-Violet Sin-
edited, spelling
[Edited on 17-7-2014 by violet sin]
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arkoma
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Ya, butane scares the HELL out of me especially since I'm not in the boondocks ATM. I just really wanna do a "proof of concept" on it.
The butane thing also invites hateful visits from folks like Fire Marshall's, understandably.
Edit--proof of concept with R134a that is, not butane
[Edited on 7-17-2014 by arkoma]
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Texium
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I'm beginning a hot extraction with isopropanol, in case it does work, and also because I want to try out my new equipment. The extract is a pleasant
lime green color. Hopefully it will smell like tomato plants and not like wet hay! If it doesn't work out, I'll try the cold methods.
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Texium
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Well, the good news is that I completed the extraction, and it's difficult to tell, but it seems like underneath the choking odor of isopropanol, the
tomato plant smell can be slightly detected. The bad news is that I spilled most of my extract when I was taking it off of the hot plate. I have the
rest evaporating outside on my front porch in a watch glass. Rather inconveniently though, despite it being hot and dry all month, it decided to be
cool and rainy today...
Hopefully whatever is left behind will smell strongly of tomato plant. If not, I'll move on to other methods. This was worth it to me even if it
doesn't work out just for the opportunity to try out my Soxhlet extractor. It was so cool and satisfying to get to see the siphon tube automatically
fill the boiling flask with bright green extract.
[Edited on 7-18-2014 by zts16]
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arkoma
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I bet the soxhlet was cool to watch!! Keep us posted--I love this kinda thing if ya couldn't tell.
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Texium
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Ok, the compound that was extracted has been fully dried. Unfortunately, it doesn't smell like tomato plants. The good thing though is that it doesn't
smell like wet hay either. Instead, it has a pleasant aroma of what I could best describe as a cross between freshly brewed tea and rose petals. I'm
not sure how that smell came from tomato leaves, but it's very nice!
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arkoma
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do you have a picture? you've almost got me wanting to grow some 'maters now.
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Texium
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Left is the extraction in progress, you can see the green extract beginning to enter the siphon, right is the final product. It is very sticky and
oily, and I'm not entirely sure how I will be able to remove it from the watch glass in a manner that would allow me to store it somehow. The nice
floral aroma has gotten stronger since it has completely dried out.
 
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arkoma
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do you have a picture? you've almost got me wanting to grow some 'maters now.
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Texium
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Um, I just posted two pictures, can you not see them?
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arkoma
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somehow I double posted (?) Think I hit "Back" . Ya I can see them.
Edit--added attachment
[Edited on 7-19-2014 by arkoma]
Attachment: tomatos.pdf (92kB)
This file has been downloaded 457 times
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