What would react with octenol?

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Mavrisa
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What would react with octenol?

Postby Mavrisa » Mon Jun 21, 2010 7:49 am UTC

I recently got bitten by 25 mosquitoes and decided I'd go to Wikipedia to see how they actually find their targets. Apparently it's a combination of CO2 and oct-1-en-3-ol.
This year in chemistry, I only briefly learned about reactions of alcohols. I'm wondering: is there any chemical that would readily react with octenol that could safely be sprayed on the skin, or perhaps could be put into those candles without any respiratory effects? I read that DEET was supposed to work by disabling octenol detection in the mosquitoes, but at the point where the mosquito is close enough to you for that to work, wouldn't it be too late? I would also think this would just cause DEET resistant mosquitoes to eventually become the norm.
I guess someone's probably thought of all of this before, but I thought it was worth asking.
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Re: What would react with octenol?

Postby The EGE » Mon Jun 21, 2010 2:59 pm UTC

It's a pretty standard alcohol, and IIRC most alcohol reactions occur at the OH group. So, presumably, anythign that reacts with ethanol would react with octenol as well, neh?
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Re: What would react with octenol?

Postby Mavrisa » Mon Jun 21, 2010 4:10 pm UTC

What about the double bond? We never learned that much about how reactive various functional groups are, so that may be a useless thing to ask.
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Re: What would react with octenol?

Postby morvita » Mon Jun 21, 2010 4:25 pm UTC

The EGE wrote:It's a pretty standard alcohol, and IIRC most alcohol reactions occur at the OH group. So, presumably, anythign that reacts with ethanol would react with octenol as well, neh?

In some cases that may be true, however ethanol is a primary alcohol and oct-1-en-3-ol is a secondary alcohol, so they do react differently in some cases, like the standard organic chemistry alcohol tests. I am not an organic chemist, though, so I do not remember what specifically would react with something like octenol.
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Re: What would react with octenol?

Postby Whelan » Mon Jun 21, 2010 5:02 pm UTC

The only things I could think of would be halogens undergoing electrophillic addition with it to remove the C=C double bond. Problem being the toxicity of them. That and whatever will react with a secondary alcohol.
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Re: What would react with octenol?

Postby Minerva » Tue Jun 22, 2010 12:02 am UTC

What about a Fe2+ solution, to catalyse the natural oxidation of the alcohol by enzymes on your skin into the ketone? That should be relatively non-toxic.

Or maybe a dilute solution of bromine to add across the double bond, which hopefully wouldn't be too toxic or corrosive if it was dilute?
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Re: What would react with octenol?

Postby redgrowth » Tue Jun 22, 2010 12:20 am UTC

Minerva wrote:What about a Fe2+ solution, to catalyse the natural oxidation of the alcohol by enzymes on your skin into the ketone? That should be relatively non-toxic.

Or maybe a dilute solution of bromine to add across the double bond, which hopefully wouldn't be too toxic or corrosive if it was dilute?

I would not want even a dilute bromine solution on my skin. It is not a pleasant chemical. Maybe a brominated compound if it was bound to something that kept it from penetrating skin, and reacting with skin, while still adding across the double bond.

What I would do instead is design a chemical that blocks the same receptor as 1-octen-3-ol, spray that in the air, and tada "blind" mosquitoes.

Or you could buy some bug spray.

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Re: What would react with octenol?

Postby bane2571 » Tue Jun 22, 2010 4:00 am UTC

Perhaps you're going about it the wrong way, maybe rather than removing Octenol from yourself, you should blanket the environment with it. It's be amusing to swap an aerosole repelant can for a can of CO2/octenol mixture. :twisted:

Apparently, some bug killers use octenol attractants.

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Re: What would react with octenol?

Postby Mavrisa » Tue Jun 22, 2010 4:33 am UTC

redgrowth wrote:What I would do instead is design a chemical that blocks the same receptor as 1-octen-3-ol, spray that in the air, and tada "blind" mosquitoes.
How would you get it to stay suspended? Also, wouldn't that perhaps be dangerous if you inhaled it?

redgrowth wrote:Or you could buy some bug spray.
If only it worked... I had lots of bug spray on that night. People were running around with cans of it. It was weird (and tasted like crap).

bane2571 wrote:Perhaps you're going about it the wrong way, maybe rather than removing Octenol from yourself, you should blanket the environment with it. It's be amusing to swap an aerosole repelant can for a can of CO2/octenol mixture. :twisted:

Apparently, some bug killers use octenol attractants.
I suppose this would confuse them. Then again, they would still eventually catch on I would think, and perhaps 10 times as many would come to the area as a result... so maybe that's not the best idea :P
And yeah, the electric ones use octenol. I love those things. They make such lovely music.
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Re: What would react with octenol?

Postby bane2571 » Tue Jun 22, 2010 4:47 am UTC

10 times as many would come to the area as a result... so maybe that's not the best idea

Ahh..yeah, good point, octenol water bombing the neighbours' yards? I'm reaching here.

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Re: What would react with octenol?

Postby Mavrisa » Tue Jun 22, 2010 5:43 am UTC

bane2571 wrote:I'm reaching here.

A little :P
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Re: What would react with octenol?

Postby Eebster the Great » Tue Jun 22, 2010 7:40 am UTC

If DEET is failing, you are unlikely to find superior chemicals just lying around. And if chlorine solutions don't confuse or repel insects (they do not), I doubt bromine would be effective.

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Re: What would react with octenol?

Postby Minerva » Tue Jun 22, 2010 8:36 am UTC

redgrowth wrote:What I would do instead is design a chemical that blocks the same receptor as 1-octen-3-ol, spray that in the air, and tada "blind" mosquitoes.


Isn't that re-inventing the wheel with regards to existing proven anti-insect compounds such as DEET?
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Re: What would react with octenol?

Postby Whelan » Tue Jun 22, 2010 6:41 pm UTC

Eebster the Great wrote:If DEET is failing, you are unlikely to find superior chemicals just lying around. And if chlorine solutions don't confuse or repel insects (they do not), I doubt bromine would be effective.

If Cl and Br don't work then we try F. if that fails, I. In the event that none of those work, then we move to At, although that probably won't be electrophillic enough to even react. Go for the -OH then, it'll be easier than the C=C and probably more effective.
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Re: What would react with octenol?

Postby Bobber » Tue Jun 22, 2010 8:09 pm UTC

As an additional bonus, applying an iodine solution to the skin doesn't sound that bad.
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Re: What would react with octenol?

Postby Whelan » Tue Jun 22, 2010 10:01 pm UTC

Not when you consider that aqueous Iodine is used as a disinfectant for cuts no. I think it's I(aq) anyway, it may be an Iodine-containing compound of some kind.
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Re: What would react with octenol?

Postby Eebster the Great » Wed Jun 23, 2010 12:41 am UTC

Haha, Whelan, I think fluoride is pretty unlikely to blind insects. It is a very small atom compared to the Cl, Br, C=C, and even the OH we were considering. Cl would probably be your best bet, but pools don't seem to help much, so you would have to concentrate it much more than that, which would dry out your skin and smell.

Your BEST bet is probably DEET.


E: Oh, and Iodine is not all that electronegative. And astatine is the rarest naturally occuring element on Earth.

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Re: What would react with octenol?

Postby PM 2Ring » Fri Jun 25, 2010 6:15 pm UTC

Wikipedia has some info about Iodine solutions.
http://en.wikipedia.org/wiki/Iodine_tincture
Tincture of iodine is a disinfectant, usually 2-7% potassium iodide or sodium iodide, and elemental iodine, dissolved in a mixture of ethanol and water. As in the case of Lugol's iodine, the role of iodide and water in the solution is to increase the solubility of the elemental iodine, by turning it to the soluble triiodide anion I3-. However, since iodine has moderate solubility in ethanol, it is also assisted by this solvent directly.

Thus, iodine tincture solutions are characterized by the presence of alcohol, and more elemental iodine than iodide. Lugol's iodine, by contrast, has no alcohol, and has twice the amount of iodide as elemental iodine.

But I don't think mixing an iodine solution with octenol is going to do much. And I don't see why inorganic esters of octenol would necessarily block mosquito octenol receptors; I think it'd be better to investigate organic esters of octenol. Or just use DEET. :)

FWIW, entomologists often use CO2 traps to catch mozzies. These can use a simple acid + bicarbonate reaction to generate the CO2, but the simplest just use a chunk of Dry Ice.

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Re: What would react with octenol?

Postby Sizik » Fri Jun 25, 2010 6:40 pm UTC

Minerva wrote:
redgrowth wrote:What I would do instead is design a chemical that blocks the same receptor as 1-octen-3-ol, spray that in the air, and tada "blind" mosquitoes.


Isn't that re-inventing the wheel with regards to existing proven anti-insect compounds such as DEET?

Nope.
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Re: What would react with octenol?

Postby Mavrisa » Fri Jun 25, 2010 7:08 pm UTC

PM 2Ring wrote:entomologists often use CO2 traps to catch mozzies.

Ever since reading HHGTTG, I tend to read entomologists as etymologists... so this confused me for a moment.
I'm thinking perhaps the spray that was used before was just old or something, because yesterday I think I only got one bite, but I had on a lot less spray.. ah well.
I also read (crap, can't find the link) that mosquitoes look for around 70 different chemicals, so perhaps just dealing with octenol would be useless anyway.
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