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Author: Subject: Neutralization of capsaicinoids?
math
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shocked.gif posted on 8-7-2013 at 06:36
Neutralization of capsaicinoids?


Hello,

I think that it's common knowledge that capsaicin and its analogs or related "spicy" compounds can be washed off the skin with milk or some other fat-containing liquids due to their lipidic solubility.

I'm however interested if there is any compound (or different compounds) which can be used to either wash the skin (and hence are non-toxic and non-corrosive) or to wash inert surfaces (and hence they can be slightly corrosive or toxic).


Thank you
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killer_lapin
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[*] posted on 8-7-2013 at 16:46


Soap...

maybe you should be more specific!
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bfesser
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[*] posted on 8-7-2013 at 17:05


<a href="http://en.wikipedia.org/wiki/Capsaicin#Capsaicinoids" target="_blank">capsaicinoids</a> <img src="../scipics/_wiki.png" />
<a href="http://en.wikipedia.org/wiki/Capsaicin" target="_blank">
Quote:
soluble in alcohol, ether, benzene
slightly soluble in CS<sub>2</sub>, HCl, petroleum <img src="../scipics/_wiki.png" />
</a>
Please put in a little effort before starting another thread.

[Edited on 7/9/13 by bfesser]




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math
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[*] posted on 9-7-2013 at 06:17


I however asked for compounds that can NEUTRALIZE capsaicinoids, aka transform them into something else, not spicy, which won't bind to vanilloid receptors.


Thank you

<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: removed unnecessary quoting]

[Edited on 7/9/13 by bfesser]
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Manifest
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[*] posted on 13-7-2013 at 04:20


I'm pretty sure Capsaisin is alkaline so you could add vinegar.
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unionised
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[*] posted on 13-7-2013 at 07:15


I'm at least as certain that it isn't. Adding vinegar to chilli is likely to make a sauce, but not to neutralise it.
However it is an amide so it could be hydrolysed by strong alkali.

Presumably it's susceptible to other forms of reaction too. It would, for example, burn if heated in air.
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ElectroWin
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[*] posted on 13-7-2013 at 12:20


i believe capsaicin is soluble in oils; milk products (yogurt, sour cream) are effective at reducing the burning sensation.

find out what it is, in milk, that helps
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Paddywhacker
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[*] posted on 13-7-2013 at 19:50


The aromatic portion of the molecule is phenolic, so it may be extractable into dilute NaOH. As a phenol it should also be easily nitrated or brominated, but you'd have to be careful not to hydrolyze the amide group.
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[*] posted on 14-7-2013 at 10:39


Quote: Originally posted by ElectroWin  
i believe capsaicin is soluble in oils; milk products (yogurt, sour cream) are effective at reducing the burning sensation.

find out what it is, in milk, that helps


Can you read?
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[*] posted on 14-7-2013 at 13:13


Would sodium bicarbonate be a sufficiently strong base to deprotonate the aromatic part of the ring, which is phenolic and thus would migrate into the aqueous phase?



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[*] posted on 14-7-2013 at 13:56


Once at a new years eve party we ate Habaneros just for the fun, and one of us discovered that fresh mango silenced the burn instantly, and I mean silenced it totally. I tried it to and it did indeed stop any burning sensation a whole chewed Habanero gave me.

Never tried the combo after that party so I can't verify it that way. Anyone else had a similar experience?





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ElectroWin
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[*] posted on 15-7-2013 at 12:05


Quote: Originally posted by Manifest  
Quote: Originally posted by ElectroWin  
i believe capsaicin is soluble in oils; milk products (yogurt, sour cream) are effective at reducing the burning sensation.

find out what it is, in milk, that helps


Can you read?


Doh! i guess not, sorry i dont know how i overlooked the fact that my suggestion was little more than a rehash of the original post
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[*] posted on 15-7-2013 at 15:51


@Hexavalent: phenols are generally too weak of acids (pKa ~9-10) to be deprotonated by weak bases such as carbonates or amines. Strong bases like alkali hydroxides are necessary.

As to the rest of the topic, it seems to me the best solution (in vivo) would be to use a vanillin receptor antagonist to block the action of capsaicin. Eugenol comes to mind as a good candidate; it is well known as a local anesthetic (analgesic?). Vanillin may work as well. According to Arch Pharm Res. 2009 Nov;32(11):1643-9. doi: 10.1007/s12272-009-2119-8, vanillin has some antinociceptive properties in mice.

I may just test these hypotheses when I get home. I have plenty of capsaicin-containing foods as well as vanilla extract and clove oil (distilled it myself :D) so why not?
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