Sciencemadness Discussion Board

Chemicals from plants

ficolas - 9-6-2016 at 05:15

I have been looking up information about some chemicals that can be extracted for plants (Probably not in a big amount, but as a just-because its a plant, and its cool because nature). This came from some capsacinoids I extracted (in low purity though, I didnt have good ventilation or safety of any way, as I was doing it with high alcohol conc vodka, and it started to feel quite unconfortable to my lungs and nostrills)
I ended up with some really spicy sauce, that even wetting a spoon and moving it arround some bacon, made that bacon way too spicy. I planted some peppers, including carolina reapers, and I plant to repeat this when they grow, with the carolina reapers.

So this got me wondering, what other chemicals of "interest" could be extracted from plants?
I know toluene was named after the balsam of tolu, if im not mistaken a esential oil from a tree autoctonous in south america. If I had access to that plant, I would be trying it for sure, but its a tree, so planting it to harvest it would require too much time.
Another idea I had, is extracting formic acid and histamine from nettles, to watch the world burn. However it is kinda scary. I can harvest tons of nettles, since they grow a lot in the countryside.
Cianyde from apples, bitter almonds (Arround 50mg/almond acording to what I found online) However, again, kinda scary to play arround with cyanide for me without a formation.
Menthol from mint.
Alliicin from garlic.

I would like to know how viable it is to purify these (having a pretty crude product at the end still) and any other ideas of interesting compounds that could be stracted from plants.

[Edited on 9-6-2016 by ficolas]

NEMO-Chemistry - 9-6-2016 at 05:45

I am also into plant extractions although i am very new to it. I have recently extracted as yet unknown 'things' from cloves.

I am working on extracting menthol from mint. There is a old book on the net ironically called a modern herbal. It gives you a good idea what different plants contain.

I saved some papers from the mint and will post them when i find where i saved them!

This one was from eugenol i was trying to extract from cloves, there are some pics in the beginners section that i posted.
[Edited on 9-6-2016 by NEMO-Chemistry]

Attachment: eugenol.pdf (144kB)
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And the menthol one from ment and how to get the menthol crystals, i havnt completed this one yet.
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[Edited on 9-6-2016 by NEMO-Chemistry]

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Scalebar - 9-6-2016 at 10:50

Here's a link to Grieves herbal http://www.botanical.com/botanical/mgmh/mgmh.html

Even elements like iodine used to be extracted from plant material - sea weed and high quality silica from horsetails.

Formic acid would be an easy target as it can be distilled - used to be extracted from ants (good luck getting them into the flask)

Caffeine is a fun one to try - the chemistry is simple but it still takes a degree of care and attention

ficolas - 9-6-2016 at 11:16

Ants... killing ants while extracting formic acid... Sounds fun huehuehue
Is it ethical to put them inside the solvent alive? Or to boil them alive?
Ok just kidding, but there is an ant plague arround, so I may try this. However extracting it from nettles seems more ethical and less disgusting

There is another thread (http://www.sciencemadness.org/talk/viewthread.php?tid=66475) that was posted simoltaneously to this one, lets better use the other one, since it was posted first

[Edited on 9-6-2016 by ficolas]

Scalebar - 9-6-2016 at 11:25

I've never done it but I've seen it in ancient text books - it's a dry distillation, i can only assume that the ants were killed first as red ants get quite angry when fiddled with.
I make Birch tar from time to time but it's hardly extracting a pure chemical.

Some of the more exotic henbanes contain enough alkaloid that it forms ( microscopic) crystals in the dry leaves.

One i really fancy doing is something that bridges the chemical/life divide - extract enough tobacco mosaic virus to form a visible crystal but I'd basically have to kiss goodbye to every solanaceous plant in the garden and the allotment association would kill me.

Chem Rage - 10-6-2016 at 10:06

I am quite into Natural Product chemistry, too. I grow all manner of different plants for their essential oils and the constituent chemical components (e.g. terpenes) of these oils. A Soxhlet extraction apparatus comes in handy.

The Myrtaceae family, which includes eucalypts, have interesting phytochemicals.

http://www.pranarom.com/en/our-products/essential-oils/essen...

[Edited on 10-6-2016 by Chem Rage]

[Edited on 10-6-2016 by Chem Rage]

DraconicAcid - 10-6-2016 at 10:10

I'd assume you could extract oxalic acid from rhubard or skunk cabbage. Never tired, though.

Chem Rage - 10-6-2016 at 10:51

Quote: Originally posted by DraconicAcid  
I'd assume you could extract oxalic acid from rhubard or skunk cabbage. Never tired, though.


Indeed you could; it is a matter of harvesting enough raw material! Judging by the way things are going here in the UK (we are subjected to increasingly draconian EU restrictions and bans), one would have to resort to rhubarb for their oxalic acid. I can only hope that Britain leaving the EU nullifies these restrictions so that hobbyists here in Britain can once again enjoy good access to chemicals.

[Edited on 10-6-2016 by Chem Rage]

Cucurbit - 10-6-2016 at 10:56

Interesting ideas!

I once made a bit of benzoic acid from benzoin resin (styrax), cool.

Hmm, what else springs to mind...
- salicylic acid from willow bark
- limonene from orange peels (steam distillation)

Chem Rage - 10-6-2016 at 11:22

Quote: Originally posted by Cucurbit  
Interesting ideas!

I once made a bit of benzoic acid from benzoin resin (styrax), cool.

Hmm, what else springs to mind...
- salicylic acid from willow bark
- limonene from orange peels (steam distillation)


Methyl salicylate from wintergreen
Piperidine from black pepper
Bergamottin from bergamot orange (citrus bergamia)
1,8 cineole, etc, from eucalyptus
Myristicin from nutmeg
Cinnamaldehyde from cinnamon
Citronellol and citronellal from lemongrass
Crocetin and safranal from saffron crocus

clearly_not_atara - 10-6-2016 at 12:32

Coniine is a useful one, found in pretty good quantities in a very common plant -- poison hemlock.

http://en.wikipedia.org/wiki/Coniine

There are a handful of procedures in chemistry that call for "a secondary amine" to act as a catalyst, such as the synthesis of MVK from acetone + formaldehyde + diethylamine HCl; coniine may substitute for the inaccessible diethylamine.

http://www.orgsyn.org/demo.aspx?prep=CV4P0281
https://en.wikipedia.org/wiki/Methyl_vinyl_ketone#Production

Coniine may also react with organolithiums to produce lithium coniide, which is similar to but not quite as hindered as lithium diisopropylamide. Diisopropylamine is easier to make of course (isopropyl iodide + NH3) than diethylamine.

Advantages over piperine/piperidine: can be extracted by A/B methods, does not require hydrolysis.

Disadvantage: coniine is very toxic, but not too much moreso than some of the more caustic things we deal with. It just has to be treated with respect to the fact that it's more dangerous than it looks.

Mandelonitrile and benzaldehyde from bitter almond oil are also pretty useful, although I don't know if anyone has found a safe way to extract mandelonitrile reliably. Cyanide is nothing to trifle with.

NEMO-Chemistry - 11-6-2016 at 03:46

The other thing that would be handy is a way to test that we have correct product, i intend to use TLC to see what compounds have been extracted, i assume i need to put several dot on the plates, then test the bands with various reagents to see which which are alkaloids etc?

Slightly disjointed having two thread but choose one and i will post what i find in it, for reference the other thread is here http://www.sciencemadness.org/talk/viewthread.php?tid=66475

It would be easier to post papers etc in one place however.

I am particularly looking extraction that produce crystals, it would be nice to have a slightly different crystal collection.

NEMO-Chemistry - 11-6-2016 at 04:09

This seems pretty good, it details different methods and gives some plant families and the main oils obtained.



Attachment: Aromatic plant extr methods.pdf (2.2MB)
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Seems parsley is another source of myristicin, although at 38mg per Kg its hardly a huge source :D, but posted anyway in case its useful.



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BILLBUILDS - 9-3-2017 at 20:40

does anyone know how to make/distill birch oil/resin

JJay - 9-3-2017 at 21:46

Birch oil is methyl salicilate, right? Same as oil of wintergreen?

tsathoggua1 - 17-3-2017 at 13:47

You wouldn't have to kill the ants if one can find a wood ant nest (they sometimes form huge piles, favouring pinaceous tree needles, so look for them in acidic forests dominated by pines, larch etc (if your lucky there might be larch bolete and slippery jack mushrooms too, a type of bolete (Suillus to be precise) which are both common, in season and very good just fried in butter after removal of the slime surface layer which peels easily). Note certain folk are intolerant to the slippery jack, like some are to honey fungi or sulfur polypore, although for most both of these too are excellent edibles. And there is always the possibility of saffron milk-caps, Lactarius deliciosus (along with the very similar, also edible but not as tasty L.deterrimus, which stains with age more green)

Wood ants will spray formic acid when provoked into annoyance. Birds, especially the intelligent corvidae use this to rid themselves of parasites, by pissing off a wood-ant nest and then standing back to be hosed down in acid.

Also birch produces two other interesting compounds, betulin and betulinic acid. with anti-cancer properties, betulinic acid being the more bioavailable, and synergistic against certain cancer types, particularly those stemming from neurological progenitors. IIRC its (betulin the less bioavailable, but naturally available given the profusion in the northern hemisphere of silver birch) also a GABAa positive allosteric modulator, benzodiazepine binding site IIRC.

http://cat.inist.fr/?aModele=afficheN&cpsidt=20572488

A Halogenated Substance - 17-3-2017 at 15:43

I've read about octyl acetate being present in citrus fruits (there are also oils that smell of citrus that likely contain a higher concentration). However, I've haven't tried it myself as of yet.

http://www.hmdb.ca/metabolites/HMDB38602
https://en.wikipedia.org/wiki/Octyl_acetate
https://pubchem.ncbi.nlm.nih.gov/compound/Octyl_acetate
http://www.sciencemadness.org/smwiki/index.php/Octyl_acetate


Osage oranges (which I think are generally exclusive to the southeast U.S) supposedly contain a flavonol called Morin.




Morin 3d structure.png - 44kB

I've seen these oranges around where I live. I think I may try to extract it.
Apparently it creates fluorescent complexes with tin and aluminium in solution which would be a good indicator of a successful extraction.

Osage Orange: https://en.wikipedia.org/wiki/Maclura_pomifera#Distribution
Morin: https://en.wikipedia.org/wiki/Morin_(flavonol)
Morin MSDS : http://www.sciencelab.com/msds.php?msdsId=9926149

JJay - 17-3-2017 at 16:47

They use them in the Northeast as hedges, and they can occasionally be found growing wild even in pretty cold climates. The fruits look and smell like green oranges but have a milky latex sap and are seemingly inedible.

A Halogenated Substance - 17-3-2017 at 18:11

Quote: Originally posted by JJay  
They use them in the Northeast as hedges, and they can occasionally be found growing wild even in pretty cold climates. The fruits look and smell like green oranges but have a milky latex sap and are seemingly inedible.


I had gone to a camp and asked about their edibility. The camp leaders said they were poisonous but people in older days had cooked Osage oranges and were then able to eat them after the poisonous substances were leeched out.

In contrast, these sites say they're edible but the seeds are poisonous only...

http://www.eattheweeds.com/maclura-pomifera-the-edible-inedi...

http://www.wildflower.org/expert/show.php?id=5764

https://hortnews.extension.iastate.edu/1997/10-10-1997/hedge...

http://web.extension.illinois.edu/dmp/palette/061022.html

Some sites support it in use of home-made insect repellents or home remedies.

Most sites also seem to focus on the edible and 'positive' parts of it but I couldn't find much information on what substances could be the toxins in the seeds of the orange.

I assume that if I were to attempt an extraction of Morin, I could likely just remove the seeds the first then attempt an extraction?

tsathoggua1 - 18-3-2017 at 07:48

Generally one should avoid eating or drinking from plants with milky sap, as a general rule of thumb. Most are toxic. The barrel cacti are one of the main exceptions, but its vital to make sure that they are not in fact, Euphorbia or within that family. It packs some really pretty noxious, corrosive phorbol esters in many of them, and some species can be lethal. Also the sap of many or most Euphorbia can blind if it gets into the eyes. And many of them look a lot like true cacti.



Valeriana officianalis contains some intriguing compounds, GABAa positive allosteric modulators, and compounds close in structure to valproate (epilim, the anticonvulsant). Mild to moderate sedative properties. The interesting bit is that at least one of its constituents, not sure which, binds to the loreclezole-sensitive allosteric site on GABAa as a positive allosteric modulator. I find that taking a high dose of root extract is the most potent and effective oneirogen I've ever encountered. Would love to bioassay loreclezole itself to see if this is the cause since I have never ingested anything else that is an agonist of this binding site on GABAaRs. Just be prepared for a bit of a kicking in terms of intensity.

Waffles SS - 18-3-2017 at 08:14

Quote: Originally posted by A Halogenated Substance  
I've read about octyl acetate being present in citrus fruits (there are also oils that smell of citrus that likely contain a higher concentration). However, I've haven't tried it myself as of yet.

http://www.hmdb.ca/metabolites/HMDB38602
https://en.wikipedia.org/wiki/Octyl_acetate
https://pubchem.ncbi.nlm.nih.gov/compound/Octyl_acetate
http://www.sciencemadness.org/smwiki/index.php/Octyl_acetate



That is true.Octyl acetate has citrus fruits odor and is very similar to orange fruit smell.(I have made it from 2-Octanol and 1-Octanol)

One of interesting natural extraction that i did is Stevia sugar(steviol glycosides) from Stevia plant.

Separation steviol glycosides from poly phenols(cause bitter taste) is challenge able and need special technique.

It is 200-300 times sweeter than table sugar

https://en.wikipedia.org/wiki/Stevia

[Edited on 18-3-2017 by Waffles SS]

unionised - 18-3-2017 at 08:17

Figs and dandelions are also exceptions to the "milky juice = bad" rule, but it's still a good starting point.
Extracting dyes form plants is a fairly common starting point- not least because you can tell where the stuff is when you do extractions etc.

tsathoggua1 - 18-3-2017 at 09:06

Yes, there are exceptions, I was just pointing out that GENERALLY its an indicator that the plant has likely noxious character. Some of the Euphorbiales are not too bad but there are some exceptionally virulent species also. Manchineel (Hippomane mancinella) for example will apparently blister and strip the paint off cars, just from the exudates washed during rain off the leaves. And caribbean tribespeople would use the sap as an arrow poison, and even being near the tree will blister and burn flesh. I've read of people using it to kill people by means of tying them to the tree trunk and leaving them there, to be slowly flayed alive as a method of execution/murder.

Booze - 20-3-2017 at 17:04

Well, for extracting capsacinoids I used 95% ethanol I made. It made a really thick, red oil that was really spicy, even an amount I couldn't see with my naked eye burned for a few hours.

PirateDocBrown - 20-3-2017 at 17:17

As someone who's done a LOT of extractions, I recommend learning the difference between:

Tinctures
Concretes
Absolutes
Attars
and Essential Oils.

The right route, using the right solvent, is what will often determine if you get what you want.

j_sum1 - 20-3-2017 at 17:37

Quote: Originally posted by PirateDocBrown  
As someone who's done a LOT of extractions, I recommend learning the difference between:

Tinctures
Concretes
Absolutes
Attars
and Essential Oils.

The right route, using the right solvent, is what will often determine if you get what you want.

Because it might be useful in the context of this thread, would you care to give a brief one line definition of these and maybe an explanation of why it is important? (I have not heard of "concrete" used in this context before.)

PirateDocBrown - 20-3-2017 at 23:05

Very well.

Tincture = an extraction done at or near ambient temperature, usually using a solution of at least 25% ethanol, though Tinctures are sometimes made with acetic acid, ethyl ether, ethyl acetate, glycerin, or even propylene glycol.
People who make their own vanilla extract by putting a vanilla bean in some vodka are making a Tincture.
Tinctures of medicinal plants would be recombined with the ashes of the same plant to produce "Spagyrics" in alchemical medicine. Likely the alkaline materials in the ashes would make soaps from oils in the tinctures to effect the change.

Essential Oil = most essential oils are extracted by means of steam distillation, although for certain materials, it's possible to simply use high pressure to express the oil.

Attar = A specific type of EO. Some materials yield an EO that's a gummy resin, tar, or solid, not a liquid. These are called Attars. Rose "oil" is likely the most famous of these. Attar can be spelled several ways, at it's a transliteration from the Sanskrit. Ittar, Otto, etc., are all used.

Fragrance Oil = A diluted scent composed of the odor-carrying extract mixed with a carrier oil. This is sometimes done for economy (i.e. to cut the product for more profit), but can also be done to make an Attar more usable or salable.

Concretes = These would be produced like Tinctures, but would always use a non-polar solvent, most commonly hexane, but benzene, toluene, or petroleum ether could also be used. This could also be done at reflux temperature, and in the modern lab could be facilitated by a Soxhlet or other extractor. After evaporation, these are often waxy or resinous.

Absolutes = Once possessing a Concrete, an Absolute can be prepared. A further extraction of the Concrete, using a polar solvent, usually ethanol or sometimes ethyl acetate. The Concrete residue still often contains a pleasant scent in its own right and is usually used in soap formulations. The Concrete/Absolute method is used for materials that are too inert to be removed by steam distillation, or those who would be destroyed by the higher heat of the steam. Absolutes can simply be Tinctures of Concretes, or they can be carried out at reflux. Absolutes are usually very concentrated, and only tiny amounts are used in perfumery.

Pomades = Absolutes can also be obtained by means of a Pomade. Here, fats or oils are used instead of a Concrete extraction, in a mechanical mixing process with the source material. The Absolute is then removed as a Tincture as before. Spent fat still retains some scent, and is then used in soap. This is a traditional method, but still used in some circumstances.

In modern times, some extractions are done using supercritical CO2.

[Edited on 3/21/17 by PirateDocBrown]

[Edited on 3/21/17 by PirateDocBrown]

[Edited on 3/21/17 by PirateDocBrown]

j_sum1 - 21-3-2017 at 00:08

And there is post worthy of bookmarking. Thanks PDB,

PirateDocBrown - 21-3-2017 at 01:41

Glad to help!

PirateDocBrown - 21-3-2017 at 01:45

I guess I should also point out the source of "waters" in fragrance production.

In the use of steam distillation, the condensate has the oil in it, but naturally, most of the condensate is the condensed steam. It nevertheless picks up some fragrance, and can be used. This is the source of rosewater, lilac water, lavender water, and so forth. These are often used directly as toiletries.

tsathoggua1 - 24-3-2017 at 04:48

Rosewater makes a great addition to a cup of tea. Lady grey works really well, with a handful of chopped fresh lemon balm (Melissa officianalis, both for taste, and the GABA-transaminase inhibitor compounds that help smooth out the caffeine and file off its rough edges, so to speak) used to make an infusion, and that used to make the tea, with a tablespoonful of rosewater added as well, some honey to sweeten. The balm is best young and tender, and in flower is the best period, so the nectar is extracted into the tea with the rest of the goodness to be had from the plant. Goes down a real treat.

yobbo II - 24-3-2017 at 17:27

Quote: Originally posted by j_sum1  
And there is post worthy of bookmarking. Thanks PDB,


Definitely!

I have often wondered about taxine. It is contained in Yew trees. A ferocious poison.

tsathoggua1 - 25-3-2017 at 06:49

I read something interesting about taxine/taxol once.

Apparently the product was originally produced by the trees alone, but an endophytic fungus took up the genetic pathways for biosynthesis and amplified them, at least in some species of Yew, not sure if it applies to them all. The fungal symbiote then increased production.

Taxus alkaloids aren't just poisons though, some have value in treating certain cancers, particularly oestrogen-dependent tumours, since this family of compounds is known to possess members with aromatase inhibitor activity. (source-'The Genus Claviceps' by Kren and Kvac)

yobbo II - 25-3-2017 at 07:42

A small nibble of the leaves/needles to a horse or a sheep is certain death I am told. Hens heating small amounts of shavings have been known to 'heal up'.
They were planted in graveyards to stop the locals from putting an animal in to graze (allegedly).

The wood was used to make bows (bow and arrow) back in the day though that in stuff for a physics forum!

It is difficult to get information on taxine.

[Edited on 25-3-2017 by yobbo II]

symboom - 21-1-2018 at 10:38

I thought this was interesting nit much is even known about many plants many plants reseachers have only begin to understand what compounds they contain

One would be surprised what the chinese herbs that are used
https://en.m.wikipedia.org/wiki/Chinese_herbology#50_fundame...
Some are actually illegal in the U.S.

Sinicuichi
Heimia salicifolia is reported to be an auditory hallucinogen, but the effects of H. salicifolia are not well known.

Plant based
DRI
Scutellaria baicalensis (or Baikal skullcap)
Chaenomeles speciosa (commonly known as flowering quince, Chinese quince or as zhou pi mugua)

Simular compounds
Ephedra
Sida cordifolia

Kratom
Mitragyna Javanica
Mitragyna Hirsuta
Kanna
Rhodiola Rosea
Yohimbe
Akuamma

[Edited on 21-1-2018 by symboom]

WangleSpong5000 - 2-2-2018 at 16:47

There are just so many amazing an awesome things that are produced inside the myriad special life forms that build shit with light.

Cool stuff... too cool for school a lot of it. Trying to attain some of them is akin to that whole 'garden of Eden, Apple..' Shiz. Eat the forbidden fruit and Dad will fucking lose it etc.

Lol