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Using Aspirin as a Growth Hormone

Cayenne

Member
There is more than 1 thread of past write-ups, DIY.....[I will try to find and post, using NEW SEARCH!]
I have evolved to use, raw honey and nettle juice. No more powders,gels, etc.

Acetylsalicylic acid is the active metabolite in Aspirin, it is the prodrug [precursor] of salicylic acid, ASacid once absorbed by the body, metabolizes to salicylic acid. Lack of empirical evidence always sways most of the crowd, but a legit DIY way to harness it repetitively, without always wondering, would be good.


this leads me to believe there has to be a way to utilize the acetylsalicylic acid aspirin contains to later use as a growth hormone. this would be beneficial for people who dont have access to willow trees. is there a way to metabolize the acetylsalicylic acid into salicylic acid without ingesting it?



Originally Posted by http://deepgreenpermaculture.com/diy-instructions/home-made-plant-rooting-hormone-willow-water/
Home Made Plant Rooting Hormone – Willow Water
weeping-willow-tree

Weeping Willow (Salix babylonica)

----

Willows are an amazing tree that have captivated humanity since time immemorial. They appear in the ancient legends, tales, folklore and customs of the Chinese, Egyptians, Greeks, Brits, Celts and American Indians. They even feature in three of William Shakespeare’s plays, Hamlet, Othello and Twelfth Night.

Some folklore associated with willows is fascinating – my two favourites are are that it is bad luck to tell a secret while standing under a willow, as the wind that blows through the leaves will reveal the secret to everyone, and that striking an animal or a child with a willow twig will stunt their growth! They did have some strange ideas way back in Medieval Europe!

Surely, there is something “magical” about these trees, for them to capture our attention so strongly.They have some interesting and unique properties, as we’ll explore in this article!





Willows – A Brief Introduction
Willows are fast growing, deciduous trees that are mainly found found in the the Northern Hemisphere, in cold arctic and north temperate zones, in regions with moist soils. The Weeping Willow appears to be a native of extra-tropical Asia, from Japan and China to Armenia and the banks of the Euphrates, and of Egypt and North Africa.

One of the most popular and familiar willows is the Weeping willow (Salix babylonica), it has exceptional form and beauty. When mature it exhibits graceful, wide-spreading, pendulous weeping branches, with a short trunk, and a broad rounded crown. Its leaves are thin and narrow, sometimes with whitened or silky undersides. It is fast growing, and adaptable to almost any soil conditions.



Willows are an incredibly useful tree, they have many useful functions:

Source of Medicine – The use of willow bark dates back thousands of years, to the time of Hippocrates (400 BC) when patients were advised to chew on the bark to reduce fever and inflammation. Willow bark has been used throughout the centuries in China and Europe, and continues to be used today for the treatment of pain (particularly low back pain and osteoarthritis), headache, and inflammatory conditions such as bursitis and tendinitis. The bark of white willow contains salicin, which is a chemical similar to aspirin (acetylsalicylic acid). It is thought to be responsible for the pain-relieving and anti-inflammatory effects of the herb. In fact, in the 1800s, salicin was used to develop aspirin. White willow appears to be slower than aspirin to bring pain relief, but its effects may last longer. (Ref: University of Maryland Medical Centre, Medical Reference – Complementary Medicine – Willow Bark)
Source of Material for Construction and Manufacturing – Willow wood is used to make furniture, tool handles, wood veneers, and toys. It is used in wood turning as it is easily worked, and is also used to make cricket bats. Willows are a source of wicker for basketry (weaving of wicker baskets) and for making fish traps. The wood can also be used as a source of fibre for making rope, string and paper. Charcoal used by artists is exclusively made from willow.
Source of Energy – Willow is grown for biomass, a renewable energy source which reduces the need for fossil fuels and petroleum products. Willow can be converted into a variety of sustainable environmentally-friendly resources, including: 1. heat and electricity by direct combustion, co-firing with coal, and gasification; 2. biodegradable plastics and other polymers; 3. biofuels.
Willows are an ideal source of biomass because 1. Willows are easily propagated from unrooted cuttings; 2. High yields can be obtained in a few years, 3. Willow’s genetic diversity and short breeding cycle can be utilized to produce improved varieties; 4. Willows vigorously re-sprout after each harvest; 5. The amount of heat in a dry ton of willow is similar to other hardwoods.
Large scale projects to support willow as an energy crop are already at commercial scale in Sweden, and in other countries there are being developed through initiatives such as the Willow Biomass Project in the US and the Energy Coppice Project in the UK. (Ref: College of Environmental Science and Forestry – The Willow Biomass Project)
Ecological/Environmental Uses – Willows have many beneficial environmental uses. They can be used in the following areas:
Riparian buffers – Natural barriers that prevent chemicals from entering streams, ponds, and lakes.
Phytoremediation – Willows clean up toxins from contaminated sites.
Wastewater management (biofiltration) – Willows filter contaminants from wastewater, and can be used in ecological wastewater treatment systems.
Environmental protection and preservation – Willows are often used for land reclamation, streambank stabilisation (bioengineering), slope stabilisation, soil erosion control, shelterbelt and windbreak construction, soil building, and soil reclamation.
Environmental reconstruction – Willows are used for constructing wetlands and wildlife habitat.
Gardening – Willows are used for in the construction of hedges, “living fences” and other living garden structures and general landscaping
Living snowfences – Strategically planted willows trap drifting snow.
Farming – Willows can used by farmers as an animal forage to feed their stock.
Horticultural Uses – Willow bark contains natural plant growth hormones which can be used for rooting new cuttings. This is the area that we’ll be looking at in this article!
One of the most amazing properties of willows is their growth! Coppicing a willow (that is cutting it back to ground level) will result in numerous rods growing from the base that will grow at an amazing rate of 1.2-3.0m in a single season. A broken willow branch left in water will grow roots. Willows successfully root from very thick pieces of stem, this method is known as taking “trunk cuttings”, and a stem as thick as a human thigh will take root of put into damp ground. Willow cuttings can even grow if put in upside-down (but please do the right thing and put them in the right way up)! This property of willows is due to the naturally occurring plant rooting hormones that they contain. We can take advantage of this naturally occurring hormone, and make extracts that we can use to induce rooting on cuttings of other plants.





“Willow Water” – How it Works
“Willow Water” is a homebrew plant rooting hormone that is easily made and can be used to increase the strike rate (growth of roots) of cuttings that you’re trying to propagate.

The way that it works can be attributed to two substances that can be found within the Salix (Willow) species, namely, indolebutyric acid (IBA) and Salicylic acid (SA).

Indolebutyric acid (IBA) is a plant hormone that stimulates root growth. It is present in high concentrations in the growing tips of willow branches. By using the actively growing parts of a willow branch, cutting them, and soaking them in water, you can get significant quantities of IBA to leach out into the water.

Salicylic acid (SA) (which is a chemical similar to the headache medicine Aspirin) is a plant hormone which is involved in signalling a plant’s defences, it is involved in the process of “systemic acquired resistance” (SAR) – where an attack on one part of the plant induces a resistance response to pathogens (triggers the plant’s internal defences) in other parts of the plant. It can also trigger a defence response in nearby plants by converting the salicylic acid into a volatile chemical form.

When you make willow water, both salicylic acid and IBA leach into the water, and both have a beneficial effect when used for the propagation of cuttings. One of the biggest threats to newly propagated cuttings is infection by bacteria and fungi. Salicylic acid helps plants to fight off infection, and can thus give cuttings a better chance of survival. Plants, when attacked by infectious agents, often do not produce salicylic acid quickly enough to defend themselves, so providing the acid in water can be particularly beneficial.


Willow water can be made from cuttings of any tree or shrub of the willow family, a group of plants with the scientific name of Salix. The more cuttings that are used and the longer they are soaked in water, the stronger will be the resulting willow water. Recommendations for the exact method of soaking vary. Cold water can be used, and soaking times of four or more weeks are often quoted. Other gardeners use boiling water to steep the willow twigs and soak the mixture for around 24 hours.





How to Make “Willow Water”
Here is the procedure for making willow water:

Collect young first-year twigs and stems of any of willow (Salix spp.) species, these have green or yellow bark. Don’t use the older growth that has brown or gray bark.
Remove all the leaves, these are not used. Don’t waste good green material though, compost the leaves or throw them in the garden as mulch.
Take the twigs and cut them up into short pieces around 1" (2.5cm) long.
The next step is to add the water. there are several techniques to extract the natural plant rooting hormones:
a) Place the chopped willow twigs in a container and cover with boiling water, just like making tea, and allow the “tea” to stand overnight.

b) Place the chopped willow twigs in a container and cover with tap water (unheated), and let it soak for several days.

When finished, separate the liquid from the twigs by carefully pouring out the liquid, or pouring it through a strainer or sieve. The liquid is now ready to use for rooting cuttings. You can keep the liquid for up to two months if you put it in a jar with a tight fitting lid and keep the liquid in the refrigerator. Remember to label the jar so you remember what it is, and write down the date you brewed it up, and to aid the memory, write down the date that it should be used by, which is two months from the date it was made!
To use, just pour some willow water into a small jar, and place the cuttings in there like flowers in a vase, and leave them there to soak overnight for several hours so that they take up the plant rooting hormone. Then prepare them as you would when propagating any other cuttings.
The second way to use willow water is to use it to water the propagating medium in which you have placed cuttings. Watering your cuttings twice with willow water should be enough to help them root.





In Summary
As you can see, this is a garden potion that is really easy to brew up, and it keeps in line with the Permaculture principles of avoiding waste and caring for the Earth – no purchased synthetic chemicals, containers, it’s all natural, and best of all, free! So, next time you’re out on a hot summer’s day enjoying the shade and natural cooling provided by a majestic willow, grab a few twigs and take them home to help you in propagating plants for your garden!
 

Cayenne

Member
found this, thought it might help


Origionally posted By Eri Luxton, eHow Contributor , last updated April 09, 2013
How to Make Simulated Stomach Acid Stomach Acid and Problems Digesting Foods
Things You'll Need
Muriatic acid or 0.1 M hydrochloric acid
Graduated cylinder
Show (3) More

Instructions
Replicating Stomach Acid for a Science Project

1
Assemble supplies, Hydrochloric acid, the active component of stomach acid, can burn the skin. 0.1 M hydrochloric acid (M, short for molarity, is a measure of the quantity of molecules of a chemical in solution.) This concentration simulates the strength of stomach acid.

2
Seek out "muriatic acid" at a hardware store if you cannot get a standardized solution. Hardware stores carry a hydrochloric acid solution as "muriatic acid," according to Frostburg State University, in a concentration of approximately one part HCl to two parts water.

3
Mix the muriatic acid, if this solution is being used, to a ratio of one part muriatic acid to 60 parts water. Add 120 mL of water to the glass beaker, then measure out 2 mL of muriatic acid solution and add it to the beaker. Double or triple this recipe for a larger quantity of your stomach acid replica. Always add acid to water, not water to acid, because adding them in the other order can cause spattering, which could lead to injury, according to the University of Wisconsin.

4
Use a pH test such as pH test strips (which show a full pH range) to determine that the solution has reached the correct pH for stomach acid, which ranges from 1 to 3 according to the University of Cincinnati. (see references 3) A pre-mixed 0.1 M solution of hydrochloric acid has a pH of 1 and will suffice on its own.
 

Oregonism

Active member
found this, thought it might help


Origionally posted By Eri Luxton, eHow Contributor , last updated April 09, 2013
How to Make Simulated Stomach Acid Stomach Acid and Problems Digesting Foods
Things You'll Need
Muriatic acid or 0.1 M hydrochloric acid
Graduated cylinder
Show (3) More

I am trying to find a tie-in between this [Hcl Acid] and the stuff I will post. It might be that enzymes acting on ASA are possibly ubiquitous in Hcl. But remember, there may be a precursor to a precursor. As in, they may use stomach acid to accelerate another substrate in Aspirin itself, that in turns inhibits the ASA enzymes, which then catalyze the ASA and render it into Salicylic acid [and technically only in vivo]

I myself am not clear on the entire cycle......but its rounding into shape of sorts....
 

Oregonism

Active member
Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria

Aspirin ingestion can induce a wide range of clinically recognized allergic reactions, including acetyl salicylic acid (ASA)-exacerbated respiratory disease (AERD), ASA-intolerant urticaria (AIU), chronic rhinitis, and anaphylaxis..............ASA is metabolized by UDP-glucuronosyltransferase 1A6 (UGT1A6), cytochrome P4502C9 (CYP2C9), and N-acetyl transferase 2 (NAT2). Inter-individual differences in the activities of these enzymes may be the underlying cause of adverse ASA-related symptoms such as urticaria.
Most Importante
The two polymorphic enzymes CYP2C9 and UGT1A6 are involved in hydroxylation and glucuronidation of ASA, respectively
Cytochrome P4502C9: an enzyme of major importance in human drug metabolism

Accumulating evidence indicates that CYP2C9 ranks amongst the most important drug metabolizing enzymes in humans. ......CYP2C9 activity in vivo is inducible by rifampicin [prescription only antibiotic produced by bacterium]. Evidence suggests that CYP2C9 substrates may also be induced variably by carbamazepine, ethanol and phenobarbitone.
 

Oregonism

Active member
unil_fbm.gif
ASPIRIN PHARMACOKINETICS

Aspirin is absorbed rapidly from the stomach and intestine by passive diffusion. Aspirin is a prodrug, which is transformed into salicylate in the stomach, in the intestinal mucosa, in the blood and mainly in the liver. Salicylate is the active metabolite responsible for most anti-inflammatory and analgesic effects (but acetylsalicylate is the active moiety for the antiplatelet-aggregating effect). Gastrointestinal intolerance to salicylate observed in some patients has prompted the development of formulations with enteric coating.
As mentioned above, aspirin is rapidly biotransformed into the active metabolite, salicylate. Therefore, aspirin has a very short half-life. Salicylate, in turn, is mainly metabolized by the liver. This metabolism occurs primarily by hepatic conjugation with glycin or glucuronic acid, each involving different metabolic pathways. The predominant pathway is the conjugation with glycin, which is saturable. With low doses of aspirin approximately 90% of salicylate is metabolized through this pathway. As the maximum capacity of this major pathway is reached, the other pathways with a lower clearance become more important. Therefore, the half-life of salicylate depends on the major metabolic pathway used at a given concentration and becomes longer with increasing dosage. Salicylate is said to follow nonlinear kinetics at the upper limit of the dosing range. Studies have shown that there is much inter-subject variation with respect to the relative contribution of the different salicylate metabolic pathways.
 

Oregonism

Active member
http://en.wikipedia.org/wiki/Salicin

Salicin is an alcoholic β-glucoside. Salicin is an anti-inflammatory agent that is produced from willow bark.

Salicin is closely related in chemical make-up to aspirin. When consumed, the acetalic etherbridge is broken down. The two parts of the molecule, glucose and salicylic alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid.
 

omera1

Member
why not use Acetylsalicylic acid? Acetylsalicylic acid works, many studies use Acetylsalicylic acid....
 

Only Ornamental

Spiritually inspired agnostic mad scientist
Veteran
Hi

Sorry for the interruption but I may have a stupid question: What has Aspirin and willow water in common (with regard to plant physiology)? Why bother with the whole pharmacokinetics in humans if it'll be easier to go for a walk and find a willow, a poplar, heartsease, or especially meadowsweet (Filipendula ulmaria syn. Spiraea ulmaria; the true source of Aspirin) which all contain certain if not important amounts of salicin, than trying to "kitchen-synthesise" salicylic alcohol from Aspirin?

Afaik, salicin or 2-hydroxybenzyl alcohol (aka salicylic alcohol) and (acetyl-) salicylic acid act not in a similar way in plants. The former
seem to be used as rooting hormone (I have no knowledge in that field and don't even know whether it is really the salicin in willow water which boosts root development), the latter play important roles in plant immune responses and, maybe most important for the users here, they inhibit ethylene formation and hence should/could theoretically cause females to grow male flowers; see post https://www.icmag.com/ic/showthread.php?t=268948 .

Why not simply buy 2-hydroxybenzyl alcohol? Many chemical suppliers do have that in stock (doesn't cost too much either but maybe privat persons can't order things there)...
Well, that would be the same than buy other (synthetic) root hormones like indoleacetic acid and derivatives...

Greetings
 

Oregonism

Active member
Hi

Sorry for the interruption but I may have a stupid question: What has Aspirin and willow water in common (with regard to plant physiology)? Why bother with the whole pharmacokinetics in humans if it'll be easier to go for a walk and find a willow, a poplar, heartsease, or especially meadowsweet (Filipendula ulmaria syn. Spiraea ulmaria; the true source of Aspirin) which all contain certain if not important amounts of salicin, than trying to "kitchen-synthesise" salicylic alcohol from Aspirin?

Afaik, salicin or 2-hydroxybenzyl alcohol (aka salicylic alcohol) and (acetyl-) salicylic acid act not in a similar way in plants. The former
seem to be used as rooting hormone (I have no knowledge in that field and don't even know whether it is really the salicin in willow water which boosts root development), the latter play important roles in plant immune responses and, maybe most important for the users here, they inhibit ethylene formation and hence should/could theoretically cause females to grow male flowers; see post https://www.icmag.com/ic/showthread.php?t=268948 .

Why not simply buy 2-hydroxybenzyl alcohol? Many chemical suppliers do have that in stock (doesn't cost too much either but maybe privat persons can't order things there)...
Well, that would be the same than buy other (synthetic) root hormones like indoleacetic acid and derivatives...

Greetings

Thanks for the input, I was mainly interested in tracing the metabolic pathways and see if they could be "isolated" from other substrates.

It should be worth noting that there are two different pathways at least, Salician and synthesized ASA are two starts of different paths, but both end up as SA. ASA is metabolized as an salt[ester] containing O...i.e. -ate, before catalyzing into SA.

It just so happens that most of the background of that metabolic process is from journals about human health because its aspirin.
There isn't a whole lot of documented info about ASA and other derivatives and specific isolation techniques and substrates unique to the plant kingdom and hence the post I guess. But I am glad you chimed in, I have to keep reading!

Quote:Oregonism
Salicin is closely related in chemical make-up to aspirin. When consumed, the acetalic etherbridge is broken down. The two parts of the molecule, glucose and salicylic alcohol, then are metabolized separately. By oxidizing the alcohol function the aromatic part finally is metabolized to salicylic acid.


Why not simply buy 2-hydroxybenzyl alcohol?
Good suggestion, I will look into this, basically oxidize the 2-HbA and hopefully you would have SA?

However, I am into fermentation as well and it seems functionally on the surface, that SA could be isolated from fermented willow bark.
 

mofeta

Member
Veteran
Looks like you are learning a lot! Good for you.

I thought I'd let you know that what you are looking for is a lot simpler than you are thinking.

Google "aspirin decomposition".

You will find out that if you dissolve aspirin in warm water, it decomposes rapidly into salicylic acid and acetic acid.

Lots of people use "aspirin water" in their grows, for various purposes. Google that too ("aspirin water", that is).
 

RetroGrow

Active member
Veteran
I've been singing the praises of aspirin for years, with many people questioning it. I always keep it in my rez. It boost the plants natural immune response, and helps fight against any kind of infection, including the toxins injected by Broad/Cylclamen mites. One aspirin tablet, 325 MG. per gallon does the trick. Don't use enteric (coated) aspirin. Just plain old cheap generic aspirin.
 

Oregonism

Active member
Looks like you are learning a lot! Good for you.

I thought I'd let you know that what you are looking for is a lot simpler than you are thinking.

Google "aspirin decomposition".

You will find out that if you dissolve aspirin in warm water, it decomposes rapidly into salicylic acid and acetic acid.

Lots of people use "aspirin water" in their grows, for various purposes. Google that too ("aspirin water", that is).


And that helps a bit, especially for the OP. However, I am trying to analyze the metabolic pathway for isolation because it exists beyond just aspirin in other alternative forms. [chime] Queueing........ Dr Duke......

That is why I added the fermentation, bit. You could also just starve willow bark of oxygen. Soaking in a water menstrum after the bacteria have torn open the lignin from enzymatic amylase and attached to all the glucose. [i.e. sitting in a bucket for a week]....although it wouldn't all be SA either at that point.

Easy is relative!
[but I get the point] I tend to over analyze but I want to comprehend the why, not the just "because". :good:
 

Only Ornamental

Spiritually inspired agnostic mad scientist
Veteran
You guys made me thinking, so I was searching a bit on pubmed.com for physiological effects of salicylic acid in plants and found an interesting and fortunately free article beyond immune response CLICK ME as well as one on its biosynthesis in plants (which doesn't go via ASA) CLICK ME TOO.

I ran quickly over the pages... What's most important is the concentration and species dependent effect on growth. Arabidopsis thaliana (a common model organism in research) produced less trichomes upon SA treatment whereas other plants grew faster etc...
Furthermore, it seems to induce flowering in a broad set of plants.

As I know that not everyone knows reading (and understanding) scientific publications (not even our students...): Let me know if you need some help with it!

But I still don't get the fuss about self-made SA, sorry... :thinking:

An easier/faster way to degrade ASA into SA would be basic hydrolysis; p. ex. sodium hydroxide instead of hydrochloric acid (but then you end up with the SA in the water soluble salt form).

Converting salicylic alcohol into SA gets messy pretty fast when using kitchen chemistry ;) . Alcohol oxidation (there are quite a few "common" chemicals doing the trick) runs via an aldehyde intermediate and at this stage is prone to side reactions (especially with a phenol close by). Enzymatic oxidation might be cleaner but then you need a pure enzyme; bacteria will do a lot of other things with it.

Isolation (from whatever mixture/extract you have) of SA is rather simple because it is an acid and you can play with its solubility in water and organic solvents. In short, you add a strong acid to your mixture (the SA gets protonated, e.g. becomes neutral; incubate long enough and the ASA degrades to SA) and extract with an organic (non-water soluble) solvent such as ethyl acetate. Then you add a base in water (at this point, you may have ASA and SA in solution, incubate and shake the base for a certain time will degrade the remaining ASA to SA) to the separated ethyl acetate (the SA becomes deprotonated, e.g. a charged salt) and goes into the water (fat-soluble impurities remain in the org. solvent). Separate the water and adjust its pH as desired. You may also do the whole thing the other way round to end up with the free acid form of SA in the org. solvent (which can easily be dryed for storage). A similar procedure is commonly employed for quantitative alkaloid extraction; total extraction of organic acids is used less often because plants contain too many different acids and you still end up with a rather complex mixture at the end. Additionally, acids often degrade faster than alkaloids under the employed conditions.

Hope that you can profit a bit from that :D .
 

Cayenne

Member
You guys made me thinking, so I was searching a bit on pubmed.com for physiological effects of salicylic acid in plants and found an interesting and fortunately free article beyond immune response CLICK ME as well as one on its biosynthesis in plants (which doesn't go via ASA) CLICK ME TOO.

I ran quickly over the pages... What's most important is the concentration and species dependent effect on growth. Arabidopsis thaliana (a common model organism in research) produced less trichomes upon SA treatment whereas other plants grew faster etc...
Furthermore, it seems to induce flowering in a broad set of plants.

As I know that not everyone knows reading (and understanding) scientific publications (not even our students...): Let me know if you need some help with it!

But I still don't get the fuss about self-made SA, sorry... :thinking:

An easier/faster way to degrade ASA into SA would be basic hydrolysis; p. ex. sodium hydroxide instead of hydrochloric acid (but then you end up with the SA in the water soluble salt form).

Converting salicylic alcohol into SA gets messy pretty fast when using kitchen chemistry ;) . Alcohol oxidation (there are quite a few "common" chemicals doing the trick) runs via an aldehyde intermediate and at this stage is prone to side reactions (especially with a phenol close by). Enzymatic oxidation might be cleaner but then you need a pure enzyme; bacteria will do a lot of other things with it.

Isolation (from whatever mixture/extract you have) of SA is rather simple because it is an acid and you can play with its solubility in water and organic solvents. In short, you add a strong acid to your mixture (the SA gets protonated, e.g. becomes neutral; incubate long enough and the ASA degrades to SA) and extract with an organic (non-water soluble) solvent such as ethyl acetate. Then you add a base in water (at this point, you may have ASA and SA in solution, incubate and shake the base for a certain time will degrade the remaining ASA to SA) to the separated ethyl acetate (the SA becomes deprotonated, e.g. a charged salt) and goes into the water (fat-soluble impurities remain in the org. solvent). Separate the water and adjust its pH as desired. You may also do the whole thing the other way round to end up with the free acid form of SA in the org. solvent (which can easily be dryed for storage). A similar procedure is commonly employed for quantitative alkaloid extraction; total extraction of organic acids is used less often because plants contain too many different acids and you still end up with a rather complex mixture at the end. Additionally, acids often degrade faster than alkaloids under the employed conditions.

Hope that you can profit a bit from that :D .

I want to thank you so much for researching ASA and SA and posting in this thread, i will be testing the Isolation method mentioned in your post. I also have access to a willow tree and hope to test willow water side by side with isolated SA. Stay tuned for more exciting science!
 

Only Ornamental

Spiritually inspired agnostic mad scientist
Veteran
@Cayenne
You're welcome.

What do you intend to use as SA source for the isolation? Aspirin tablets? They may be tricky because many tablets and especially the better ones contain polymers which really fuck up a proper isolation. I tried several different tablets (research @ work) and different approaches and it was just bad... Those polymers (often polyacrylates) are often soluble in water and organic solvents (often just when acid or basic but they don't tell), clog filters and silica gel columns, and give you a bad phase separation (water and solvent become an emulsion). Go for the really cheap tablets with a rough surface (they at least contain no coating). Sometimes, granulates or instant tablets (both contain other additives like colours, flavours and sweeteners) or effervescent tablets/granulates (they also contain a lot of sodium citrate after the bubbles are gone -> that buffers your solution which may be good or bad) work better...
Oh, and DON'T heat the water during a tablet extraction! Tablets usually contain starch or cellulose powder which will become a gel when heated and you obtain something like a Jell-O ;) .

Tips (as I have no idea on your ability and knowledge in chemistry but are still kind of recommending "stupid and dangerous" things to you):
A one molar (1 M) acid or base solution usually does the trick nicely (in case of heating: 5 minutes to one hour are often long enough for esters and other fragile bonds to hydrolyse). The rule of thumbs is: every 10°C accelerates a chemical reaction by two and you may calculate the time it takes when working only at room temperature (or estimate how long you shouldn't wait when you don't want a chemical breakdown). To adjust pH, use also 1 M solutions which you add bit by bit to water; a final 0.1 M is usually strong enough by far to just adjust the pH and play with a compounds solubility.

Concentrated hydrochloric acid is ~37% or 12 M: dilute 12 times (add the acid to the water)
Sodium hydroxide: 40 g per liter (add the pellets to the water)
Remember: Always add an acid or a base to cold water and not vice versa! Usually the stuff gets pretty hot and doing it the wrong way round may cause boiling and splatters in your face!

Acids and bases work differently in organic solvents: Measure the pH (with a pH paper) in the aqueous part (add the acid/base, shake the two liquids, let it settle and take out a drop of the water without the organic solvent for pH testing)!

Salicylic acid has a pKa of 3: That means, 50% are deprotonated (salt form) at a pH of 3 (so you get only the other 50% into the organic phase): Use a pH of 1 and you have 99% in the protonated/neutral form (so organic solvent soluble and no more water soluble) or a pH of 6 to have 99.9% in the salt form (water soluble, solvent insoluble).

Use safety glasses and gloves when doing such things! Especially bases are highly aggressive for the skin and a drop of 1 M NaOH in you eye and you're blind for good!

Feel free to ask if you need to know more ;) . Couldn't sleep well when you get hurt due to my recommendations and propositions....
 

Cayenne

Member
@Cayenne
You're welcome.

What do you intend to use as SA source for the isolation? Aspirin tablets? They may be tricky because many tablets and especially the better ones contain polymers which really fuck up a proper isolation. I tried several different tablets (research @ work) and different approaches and it was just bad... Those polymers (often polyacrylates) are often soluble in water and organic solvents (often just when acid or basic but they don't tell), clog filters and silica gel columns, and give you a bad phase separation (water and solvent become an emulsion). Go for the really cheap tablets with a rough surface (they at least contain no coating). Sometimes, granulates or instant tablets (both contain other additives like colours, flavours and sweeteners) or effervescent tablets/granulates (they also contain a lot of sodium citrate after the bubbles are gone -> that buffers your solution which may be good or bad) work better...
Oh, and DON'T heat the water during a tablet extraction! Tablets usually contain starch or cellulose powder which will become a gel when heated and you obtain something like a Jell-O ;) .

Tips (as I have no idea on your ability and knowledge in chemistry but are still kind of recommending "stupid and dangerous" things to you):
A one molar (1 M) acid or base solution usually does the trick nicely (in case of heating: 5 minutes to one hour are often long enough for esters and other fragile bonds to hydrolyse). The rule of thumbs is: every 10°C accelerates a chemical reaction by two and you may calculate the time it takes when working only at room temperature (or estimate how long you shouldn't wait when you don't want a chemical breakdown). To adjust pH, use also 1 M solutions which you add bit by bit to water; a final 0.1 M is usually strong enough by far to just adjust the pH and play with a compounds solubility.

Concentrated hydrochloric acid is ~37% or 12 M: dilute 12 times (add the acid to the water)
Sodium hydroxide: 40 g per liter (add the pellets to the water)
Remember: Always add an acid or a base to cold water and not vice versa! Usually the stuff gets pretty hot and doing it the wrong way round may cause boiling and splatters in your face!

Acids and bases work differently in organic solvents: Measure the pH (with a pH paper) in the aqueous part (add the acid/base, shake the two liquids, let it settle and take out a drop of the water without the organic solvent for pH testing)!

Salicylic acid has a pKa of 3: That means, 50% are deprotonated (salt form) at a pH of 3 (so you get only the other 50% into the organic phase): Use a pH of 1 and you have 99% in the protonated/neutral form (so organic solvent soluble and no more water soluble) or a pH of 6 to have 99.9% in the salt form (water soluble, solvent insoluble).

Use safety glasses and gloves when doing such things! Especially bases are highly aggressive for the skin and a drop of 1 M NaOH in you eye and you're blind for good!

Feel free to ask if you need to know more ;) . Couldn't sleep well when you get hurt due to my recommendations and propositions....

I will be using potassium hydroxide (KOH solution) as a base solution.
Do you know how long it takes for ASA or SA to break down when in a base solution? This would give me an idea as of wether or not to leave it sit for a while so that all the SA is guaranteed dissolved into the solution. Would it be a good idea to bring the solution up to neutral ph with either lemon juice or vinegar or do you think this would cause the SA to degrade?
 

mofeta

Member
Veteran
Hi Cayenne

Are you mainly interested in experimenting with salicylic acid on plants?

Or are you just doing this as a vehicle to increase your understanding of chemistry?

If you just want to obtain salicylic acid, it is readily available and very inexpensive (<$20/lb). You can also get willow bark powder, willow bark extract powder and willow bark extract tincture easily and inexpensively.

And really, to use aspirin, just dissolve it in hot water. It rapidly decomposes into salicylic acid.

I totally get it if you are doing this as an exercise in chemistry, I am a big DIY exploration kind of guy myself, so don't think I'm criticizing you, but if you just want the salicylic acid, obtaining it is trivial.
 

Only Ornamental

Spiritually inspired agnostic mad scientist
Veteran
@mofeta
If you just want to obtain salicylic acid, it is readily available and very inexpensive
That's the point I don't get either :D . But hell, already as a boy I did a lot of useless stuff just because it was fun! It's certainly better to degrade some drugs than to misuse them or fool around with explosifs ;) .

@Cayenne
Cooking ASA in water will still take some hours to complete degradation if you just use water. So you should (or might) add at least one mol. equivalent of KOH per mol ASA so you end up with 100% potassium salicylate after maybe a few hours at room temperature; add an excess as posted before and you get a pretty fast degradation. If you want to extract it afterwards with an organic solvent (one which isn't miscible with water), then opt for an acidic hydrolysis (so that the product is already in the solvent soluble form)... Just plan wisely before you lounch the experiment.

Still, it'll be good to know what you're going to use as source for your ASA and also what you wan't to do with it afterwards (not that you kill of your plants by using the wrong chemicals)!

If you want to stock the SA in solution, adjust it to a pH of around 3 or even a bit more acidic (just a guess from its structural features) because it will oxidise in its deprotonated form (in basic medium; most certainly at a pH over 7-8) and degrade over time. But its solubility in water is a bitch at that pH... For some days to weeks in the fridge it may be ok to stock it at pH 6 as a compromise. But it's always best to stock the things in the dry form ;) .

Any reason why you want to use vinegar or lemon juice? Pure chemicals might be better for this (especially because KOH might overpower the natural stuff due to it's purity)... such as citric acid or ascorbic acid (vitamin c) if you don't like mineral acids ;) .
 

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