Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: jparker9141 on June 17, 2020, 03:54:19 AM
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Urushiol is the clear oily resin that causes poison ivy dermatitis by reacting with skin cells. Experts say it takes 2-8 hours for the reaction to occur, and if the resin is removed from the skin before the reaction takes place, the dermatitis can be avoided. The resin is difficult to remove and cannot be seen. It remains active on tools and dead plants, sometimes for years.
My question: is there a non-toxic chemical solution that can be sprayed on the skin or tools that will rapidly react with the urushiol, and either 1) permanently deactivate it, or 2) make it change to a visible color so that it can be identified and removed?
The goal would be a product that, after working outside clearing brush, you could spray on to yourself and your tools to either deactivate the urushiol, or reveal where it is so that you can scrub the contaminated areas. Within the skin, the catechol portion of the urushiol molecule changes to a quinone, which is the highly toxic form that causes all the damage. Could this step be interrupted or accelerated to form a non-toxic molecule?
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Its a interesting problem. You need to do something fast if you get Urishiol on the skin, when it has penetrated the skin it will be difficult to neutralize. The oxidized form probably reacts fast with proteins in the skin so I dont think you can use something topical to stop this reaction. Maybe its just best to use gloves and long-sleeves?
https://en.wikipedia.org/wiki/Urushiol
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On a gardening forum I would expect to find a recommendation to wear protective clothing/gloves. I posted this on an organic chemistry forum to seek a chemistry-based solution to neutralizing urushiol. Yes, urushiol reacts with the skin, but every source I have found indicates it is a slow process, taking up to several hours. There must be a chemical that would react to the urushiol molecule more rapidly than skin, permanently deactivating it. I took organic chemistry in college over 30 years ago, so I don't recall the various reactions and reagents that may be applicable to this organic molecule.
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, but every source I have found indicates it is a slow process, taking up to several hours.
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From WIKI
https://en.wikipedia.org/wiki/Urushiol#Side_effects_and_treatment (https://en.wikipedia.org/wiki/Urushiol#Side_effects_and_treatment)
Before the urushiol has been absorbed by the skin, it can be removed with soap and water. It is important to do this quickly, as 50% of the urushiol can be absorbed within 10 minutes.[citation needed] Once urushiol has penetrated the skin, attempting to remove it with water is ineffective.
Check your sources but WIKI needs a citation as well
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After doing GOOGLE on
urushiol absorption rate
I found Additionally From
https://www.fs.usda.gov/Internet/FSE_DOCUMENTS/stelprdb5306114.pdf (https://www.fs.usda.gov/Internet/FSE_DOCUMENTS/stelprdb5306114.pdf)
• Be proactive in regards to removing the contaminate (urushiol) from the skin. There are three
options.
1. Soap and Water – this would only be helpful if a person could use it within 10 minutes of exposure.
2. Tecnu original – is a liquid skin clanser that can be applied directly to skin or gear to remove
urushiol, and can be used with or without rinse water. Tecnu can be applied, rubbed around and
wiped off with a towel or cloth.
3. Tecnu Extreme – is a mild scrub with micro-fine scrubbing beads to remove embeded urushiol from
the skin. Use within 8 hours after exposure to poison ivy. It is important to be diligent when
washing areas where skin creases because urushiol accumulates in these areas.
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Hi Billnotgatez, The TecNu Extreme product comes close to what I'm looking for.
However, it cost $2.80 per ounce. The ingredients are water, polyoxyethylene (4) lauryl ether, polysorbate 20, alcohol, silicon dioxide, carbomer, grindelia robusta extract, benzethonium chloride, aminomethyl propanol, and fragrance.
I'm looking for something simpler, that I can mix up by the gallon, without spending over $300. If I understood what chemicals work to neutralize the urushiol, that would be a start.
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I am showing you how to search for yourself.
We are limited on giving medical advice and the like.
This is a forum policy.
Click on the link near the top center of the forum page.
Forum Rules: Read This Before Posting.
http://www.chemicalforums.com/index.php?topic=65859.0
FYI I know that I am not knowledgeable enough to give much more than what is already on the internet
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Just so we are clear here, soap and water effectively removes this compound from the skin. If you suspect you have come in contact with urushiol, just wash with soap and water. If it has been on your skin too long, the body's own defenses have kicked into action and there is nothing you can do.
TecNu Extreme is indistinguishable from many other soaps.
So, would you consider hand soap and warm water something that can be made by the gallon from <$300? I'm sort of confused why a fancier option is being pursued.
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Billnotgatez,
For the record, there is nothing in the forum rules about giving medical advice. However, I'm an MD, and not asking for medical advice. I'm asking if any experts in organic chemistry know or can figure out what might work to deactivate urushiol, a well described catechol variant. For example, what would a solution of potassium permanganate do?
Widfyr,
My internet research and personal experience with soap and water is that they can remove the oil, but not very effectively. I'm looking for something to deactivate the chemical, not just remove it.
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https://patents.google.com/patent/US5443847A/en
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Hey, I like that one! Manganese salts! Maybe manganese ion with a long chain fatty acid to make it more greasy and able to penetrate skin better.
Manganese stearate quickly jumps to mind
https://www.scbt.com/p/manganese-stearate-3353-05-7#:~:text=Manganese%20Stearate%20is%20a%20carboxylate%20salt%20compound%20which,used%20in%20organic%20synthesis%20reactions.
Or managanese octanoate for something with a shorter chain
https://www.americanelements.com/manganese-octoate-15956-58-8
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For the record, there is nothing in the forum rules about giving medical advice.
Due to their potential health hazards, we will also not help you prepare your own medicines or cosmetics.
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Manganese itself is toxic, so its use can be problematic.
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It says; "avoid get on skin" but is not very toxic but seems to be mutagenic. Question is, does the mangan need to penetrate skin to be effective? Probably if you use it after the irritant has been absorbed. Then one could ask; does mangan penetrate the skin? Is that really a good thing? I dont think you want to get manganese chloride on your skin. The patent does not present any evidence that this really works, it more seems like a desktop-product.
https://www.fishersci.com/store/msds?partNumber=AC223610100&productDescription=MANGANESE%28II%29+CHLORIDE%2C+10GR&vendorId=VN00032119&countryCode=US&language=en
One very important this is that the LD50 is acute-toxicity, much smaller doses prolonged time can give toxicity.
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AWK,
Thanks for that patent link. very interesting.
Looks like MnSO4, MnSO4 hydrate, MnCl2, MnCl2 •4H2), Mn(C7 H3 O2)2, Mn(C2 H3 O2)2 •4H2), and Mn(CHO2)2 •H2 O in aqueous solutions may work as a chelate to deactivate urushiol. The inventor thought they would be safe. I will try to find out what happened. This patent expired a long time ago.
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What about Fe(II) and Fe(III)? They both have strong interactions with catechol (same functional group) and are totally harmless. Both should be checked, they do different chemistry.
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Hi Wildfyr,
There is a good discussion in the patent document about various metal salts that would work equally well as manganese, but he rejects them for various reason. Apparently ferric chloride would work well to deactivate the urushiol, but can discolor the skin.
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If you want to sell this kind of ointment or spray you would have to make clinical trials, MnCl2 would never be possible to use. If you yourself want to try it once or twice its fine I think. I think its completely useless.
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Hi rolnor,
I'm not looking to sell the product. In fact, I just did some searching and it's already for sale on Amazon as Dr West's Poison Ivy Wash. Dr. West (now deceased) is the inventor of the patent mentioned on this thread. He was a chemistry professor at LSU.
He uses Manganese sulfate. All the testimonials are favorable, so maybe it really works. At $15 for a 4 oz bottle I'd rather mix up my own.
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This brings up a question for the chemistry experts here. In your opinion, from what you know of the chemical nature of urushiol, would manganese sulfate (in an aqueous solution) react with, and deactivate it?
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The question is if this solution need to be applied imidiatley after exposure, then there is some chans it can react with the catechol. It seems unlikely that it can penetrate the skin and react fast enough to deactivate. The slow process is the allergic reaction but then its to late, the toxin is already bonded to protein in the skin, mangan can not break this bond I think. The fact that it is commercially available does give it som credability but it can be useless or near-useless.
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There are products that use bentoquatam - a type of bentonite clay. Used to be called "IvyBlock" but that brand isn't around anymore. Idea was to put it on the skin BEFORE possible exposure. The bentonite was supposed to absorb the uroshiol so it doesn't get on the skin.
Now there is one called IvyX that is supposed to do the same thing - but it has different ingredients - it is an aloe gel based material.
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That sounds better, or just use gloves...
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I can see uses for each type of product:
You are going out to do yard work or to go for a hike - you know you might be exposed to poison ivy. A preventive compound spread on any exposed skin would seem to be best.
You are outside - didn't expect to encounter posion ivy, but think you might have been exposed to it - a wash that destroys or chelates the uroshiol is useful.
I have also seen a scrub called Zanfels that is supposed to get the uroshiol out of the skin - I think it used micron sized polystyrene beads (which may no be banned, come to think of it).