Sciencemadness Discussion Board - Urushiol

Urushiol

Rhodanide - 19-8-2016 at 16:53

Evening, everyone. Up here in the Northeast, we tend to have lots of poison ivy. Being who I am, I can't help but try to extract the Urushiol from them. Personally, I seem to be practically impervious to Urush. (Trust me, it's been a carefully tested claim by myself.) I got about 50-100g of PI leaves from the roadside where I live, and tried dissolving the U out in Acetone, and Denatured alcohol. I'm waiting on the results. What I want to know is, will Acetone and EtOH both work for extraction? I don't have access to either ether or benzene. This stuff is pretty cool and I wish it was more studied than it already is.

[Edited on 20-8-2016 by Tetra]

Mailinmypocket - 19-8-2016 at 17:00

I would try requesting this in the references section perhaps:

http://pubs.acs.org/doi/abs/10.1021/ja01640a030?journalCode=...

DraconicAcid - 19-8-2016 at 17:01

According to wiki, it's soluble in alcohol, so it should be soluble in ethanol, and I'd be very surprised if it wasn't soluble in acetone as well. It's a phenol, so it should also be soluble in sodium hydroxide solution (although this may induce polymerization).

careysub - 20-8-2016 at 09:52

Just don't try to extract furanocoumarins from giant hogweed.

The mustard gas of the plant world.

Velzee - 20-8-2016 at 13:24

Quote: Originally posted by careysub

Just don't try to extract furanocoumarins from giant hogweed.

The mustard gas of the plant world.

I've always wanted to find and grow giant hogweed

But on the PI; I've always thought about extracting urish—I have live on Long Island for ten years(since I was seven) and I have always played in the woods—only about four years ago I knew exactly what poison ivy looks at like, and I realized that the woods were literally full of it. I have never had any poisons ivy rash, but I have never tested for sure if I was immune to it. I've just presumed that I'm immune; even all of my friends have gotten it even though I've been where they've been in the woods. I don't think I daren't touch any of the PI, but if you are successful in your extraction, I may consider attempting it, considering I have tons of PI in our neighborhood.

gdflp - 20-8-2016 at 16:20

All of you guys are lucky, I'm terribly allergic to urushiol. And of course I live in an area bursting with poison ivy as well. :mad:

Just thinking of attempting to extract it makes me shudder.

Praxichys - 20-8-2016 at 16:34

I had a similar experience to Velzee. Here in Michigan it grows extensively, even in my backyard. I spent a lot of time outdoors as a kid, tromping through the woods, and to no ill effect.

My father is immune to the stuff but my mother is quite allergic. Thinking I may have inherited his immunity, I purposefully inoculated myself with a crushed leaf to the shin one day. Turns out just brushing up against the stuff has basically no effect on me (and I think it has something to do with thick leg hair) but the intentional application produced the classic effect. Man, does that stuff ITCH.

myristicinaldehyde - 20-8-2016 at 17:46

Itch is an understatement. It is terrible! But, contact will hospitalize me. The last time I had an encounter, almost a decade ago I was put on heavy duty steroids. Do be careful.

In case you didn't know, a supposeв treatment is jewel weed sap- not sure it would help with straight urushol, but I heard it works on poison ivy. Jewel weed is quite common, with fleshy steams, matte leaves and most distinctively hood-like orange blooms hanging below the leaves. It grows in wet, cool places.

Magpie - 20-8-2016 at 18:08

Louis and Mary Fieser in their textbook Introduction to Organic Chemistry (1957) have a section showing various research projects including one for urushiol. It is an unsaturated catechol highly sensitive to air oxidation. They say "The principle of poison ivy...can be extracted from leaves and twigs of the plant with ethanol and processed for the removal of fats, waxes, and chlorophyll."

I'm quite sensitive to this vesicant. Twice when I have helped my brother-in-law remove his docks from a lake in Minnesota I have come in contact with it at the water's edge. The irritation will show up a few weeks later and last for a couple months.

[Edited on 21-8-2016 by Magpie]

mayko - 20-8-2016 at 20:47

Quote: Originally posted by Mailinmypocket

I would try requesting this in the references section perhaps:

http://pubs.acs.org/doi/abs/10.1021/ja01640a030?journalCode=...

Attachment: Poison Ivy Urushiol.pdf (697kB)
This file has been downloaded 785 times

[Edited on 21-8-2016 by mayko]

argyrium - 21-8-2016 at 15:01

You might find this of some interest. Less to do w/ urushiol but quite a bit on the chemistry of Urushi (oriental lacquer).

The attached file is part three of URUSHI, Proceedings of the Urushi Study Group June 10-27, 1985 Tokyo, published by THE GETTY CONSERVATION INSTITUTE.
FYI

Attachment: urushi3.pdf (7.4MB)
This file has been downloaded 1070 times

ave369 - 25-8-2016 at 10:50

Quote: Originally posted by Velzee

I've always wanted to find and grow giant hogweed

Do not. You won't be able to get rid of it and it will overrun your garden. Once a single plant of this monster sprouted in my garden. It only died after I buried the mown stump under an iron drum lid, weighted the lid with bricks and left it so for a full year.

Mabus - 25-8-2016 at 13:38

Had a not very fortunate encounter with some freshly cut hogweed some years ago. Got some really ugly blisters on my left arm and leg. Didn't know at that time what caused it, only found out later. The scars have now faded away, but still, it was an unpleasant experience. I try to avoid it as much as possible.

Quote: Originally posted by ave369

Only grew in my garden once or twice almost a decade ago. I dug the whole plant from the ground and didn't grew back. On the other hand every year I find plenty of hemlock growing in the tall grass from the back garden despite my best efforts to get rid of it.

Velzee - 14-5-2018 at 16:13

Oh, there are LOADS of hemlock over here; I considered running an extraction on them a while back, but that was too much, even for me!

@Rhodanide, how is the product?

[Edited on 5/15/2018 by Velzee]

[Edited on 5/15/2018 by Velzee]

DavidJR - 14-5-2018 at 16:21

Quote: Originally posted by ave369

Apparently injecting the plant with concentrated glyphosate solution works pretty well.

fusso - 14-5-2018 at 16:39

~~No wonder it looks so much like Japanese...~~

XeonTheMGPony - 14-5-2018 at 16:47

Quote: Originally posted by DavidJR

Quote: Originally posted by ave369

Apparently injecting the plant with concentrated glyphosate solution works pretty well.

works good for thistle too, do it just at the start of dusk for best effect

Rhodanide - 15-5-2018 at 06:49

Ahhh, this was an old thread. I remember that I got nothing from the extraction. @Velzee

CouchHatter - 15-5-2018 at 08:33

I just got covered in it last weekend. Guess I have it pretty good if it doesn't hospitalize me! Did you try extracting it with ether and/or benzene?

Edit: I saw that you didn't have access to either, just wondering if that changed. I have access to both if youre still interested.

[Edited on 15-5-2018 by CouchHatter]

inanium - 26-9-2024 at 22:11

Bringing this dead thread back to life(sorry).

You should be able to extract the urushiol with alcohol but then what? Exposure to air and heat will likely speed polymerization.

Here is a patent covering the extraction: https://patents.google.com/patent/US20150284308A1/en

but it requires solvents I do not have access to.

Is there a way to salt out/crash out the urushiol out of alcohol?

I don't think there is a solubility table for urushiol in alcohol, but I'm curious if dropping the temp a lot(i.e. dry ice/acetone bath) would precipitate it?

It would be interesting to obtain a pure(ish) oil and play around with coating wood with it to see how the coating behaves vs real laquerware.