Talk:Menthol

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Is menthol a covalent or ionic compound?

Menthol is covalent organic compound. --Mykhal 15:28, 31 Dec 2004 (UTC)

The previous version of this page stated that menthol is "actually extremely toxic", and proceeded to talk about amounts "as small as a teaspoon", taken every day. That can hardly be called "extremely" toxic. Many substances can be toxic when taken in large quantities (and a teaspoon is quite alot). Thus, I've changed the wordage to "quite toxic". (15/03/2005)

Is the information on homeopathy really necessary? Some radical theories suggest that skepticism similarly interferes with the potency of homeopathic remedies. --Thanks to whoever amended this - in hindsight, disclaimerising the pseudoscientific status of homeopathy was the right thing to do.

is menthol also used in peppermint schnapps? rthrust@gmail.com

I'm incerted LD50 (becouse "low" or "high" toxic is very indefinite). In drinks most use flavoring agents which consist of natural essential oils, synth. substances etc. Alexandrov 08:24, 29 September 2005 (UTC)

Would we want a picture of menthol in its crystalline form on the main page? I have the means to get a picture of it up here....Killerrobotdude 06:08, 25 April 2006 (UTC)

Yes, it has very pretty crystals. Most organics are pretty boring, but if you can get some nice large crystals that would really enhance the article. If you can't, I may be able to over the summer. Be sure to take the picture in natural light to get the contrast - flash pix of crystals are very flat. Walkerma 19:21, 25 April 2006 (UTC)

I'll use the largest crystals I can find.... From what I have, they would have to be only a few inches maximum.

Under "Properties", only solubility in water is listed. Shouldn't it also list solubility in alcohol? Troother (talk) 15:22, 22 September 2022 (UTC)

Diagram Labeling and (-)-menthol, Natural Form

The discussion of the diagram says, "Natural menthol exists as one pure stereoisomer, nearly always the (1R,2S,5R) form (bottom left of diagram below)." However, while the verbal description (1R,2S,5R) matches up with other reference sources, e.g. [[1]] indicates that l-menthol occurs in the upper left-hand corner of the diagram. I cross-checked this against the Merck Index, 14th edition, and it agreed with PubChem. Unfortunately, the diagram itself seems to be mislabeled or using a different convention from the other sources for diagramming the positions, thus resulting in a discrepancy. As I'm not a chemist, I would appreciate if someone would check the diagram and deal with the inconsistency.Iainuki (talk) 20:18, 7 April 2010 (UTC)

You're right, and your edit has fixed it. --Rifleman 82 (talk) 23:24, 7 April 2010 (UTC)

I've just come across this and I believe that the diagram is actually correct. You may have made a mistake when considering rotation of the compound to view the structure on Pubchem from the same angle as the diagram shown, but the structure on pubchem is the same as the one in the bottom left corner (as will be the one in the Merck Index). I've checked the Beilstein database just to make sure that the stereochemistry is correct and that the (1R,2S,5R) isomer corresponds to the laevorotatory optical isomer. Taking this into account I will revert the change to correct the paragraph. Sam Eyley (talk) 18:17, 15 April 2010 (UTC)

References don't work

I noticed that the references are cited, but they have manual superscripts. It should use the automatically numbered references so that the article can be edited without having to renumber all the superscripts. -- R'nway [ T C ] 02:57, 16 June 2006 (UTC)

Calcium Channel Blocker

If you look up Calcium Channel Blocker it lists Menthol in the "other" section.

Does it actually have that ability? Where can I get more information?

Interesting.

Thanks,

Ben

400 000 tons?

Article claims that 400 000 tons of menthol are manufactured each year, but primary external link: http://www.leffingwell.com/menthol1/menthol1.htm says 'in excess of 6,300' (which sounds a lot less). Which is right? quota 12:06, 13 August 2007 (UTC)

It may be a difference between menthol from natural sources, and synthetic menthol; whatever it is it needs a reliable source and some clarification. The Ryoji_Noyori article also gives the same figure, but that may have been taken from here. I've seen such large tonnages in books such as Noyori's book on asymmetric catalysis, but I should really try to verify this and add the source. Thanks for flagging it. Anyone got a copy of Noyori's book, or a newer source of information? Walkerma 16:39, 13 August 2007 (UTC)

GA Sweeps Review

This article was promoted to WP:GA on December 7, 2005, so it is clearly time for a re-review. Unfortunately, as the Good Article criteria have changed considerably since then, the article no longer meets the criteria. I find numerous issues with several criteria:

• The lead section is too short, and does not adequately summarize the article. Please see WP:LEAD for tips on improving this section.
• Insufficient inline citations in the article. There are entire sections lacking references (most obvious is the 'applications' section). There were previously two sections entitled 'references' (one for inline cites, and another for other material, which I have renamed to 'further reading'). "General references", which supposedly cover all of the material in the article, "as a whole", do not satisfy wikipedia's verifiability guidelines. Material should be cited directly using inline citations.
• The 'applications' section is really just a list; not really written very well, and not very helpful.
• Consider combining the biological properties & chemical properties sections. I would also promote this section to earlier in the article, so that it's closer to the infobox.
• The 'natural menthol' section is just two sentences. Should be expanded, or combined with another section.
• Perhaps the 'synthesis' section should come immediately after chemical properties, and be located earlier in the article. How is menthol synthesized in nature (biosynthesis)?
• The 'structure' section is unsourced, and has a link in the section header (violation of WP:MSH). It also has very little text and lots of images. Could be expanded.
• History could be expanded somewhat. It's quite short.

Due to the many issues with this article, I think the best thing to do is to delist. It can be renominated at WP:GAN once the issues are addressed and it meets the Good Article criteria. Cheers! Dr. Cash (talk) 17:19, 10 December 2007 (UTC)

Is the 'Chair Form' correct

A hydrogen atom is shown alongside the hydroxide, and two hydrogens together. Should the extra hydrogens appear in the vacant places on the other side?

WikiProject Food and drink Tagging

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A topic of .....

L-Menthol has been added based on the following http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=W266590%7CALDRICH&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC --58.38.45.229 (talk) 12:57, 29 June 2009 (UTC)

Evolutionary biology

Any information about plant adaptation and the reasons plants produce menthol would be a welcome addition to this article. . . --71.111.194.50 (talk) 10:40, 28 October 2009 (UTC)

Menthol as spermicide?

Does menthol destroy spermatozoa on contact?

Toxicology data

If someone wants to do the work of paraphrasing/extracting the important information, The toxicology data on Menthol can be found here, http://www.inchem.org/documents/jecfa/jecmono/v042je04.htm research and meta-analysis courtesy of the World Health Origination.

ref: Safety evaluation of certain food additives. WHO Food Additives Series, No. 42, 1999, no 930 on INCHEM. 219.90.192.25 (talk) 03:31, 9 February 2011 (UTC)

minor problems

Infobox - Melting point - What is "35-33-31"? What is the difference between "(-)-form" & "(-)-isomer"? Note that the biosynthesis also includes an oxidation (along with "several reduction and isomerization steps"). Applications - typo - diastereomERic (last sentence) 69.72.92.88 (talk) 06:53, 3 October 2014 (UTC)

Stereoisomers

The article tells nothing about the differences betwean the stereoisomers. For some reason menthol is always used in "levomenthol" form, wich is probably the same isomer as the natural one. Are the rest of the isomers ineffective? Or just inconvinient to produce? 84.236.68.24 (talk) 08:26, 14 October 2016 (UTC)

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Diarrhea

This article doesn't mention the diarrhedic properties of menthol. As someone who has taken dextromethorphan on a regular basis, menthol is the ingredient in cough syrup that causes severe diarrhea for abusers. Floydian ^τ _¢ 15:38, 3 August 2022 (UTC)

The chemical molecule diagram seems to be missing

Could someone put the molecule diagram on the main article Treonsverdery (talk) 10:14, 14 April 2023 (UTC)

Damage vein

Under knee cap vain is damage can be healed with the right product I’m looking at molecule for healing 2600:1003:B017:D0F3:A9B6:D7B5:1AE5:6D5D (talk) 20:08, 23 November 2023 (UTC)

Hi this is what I text I need help hoping that molecule can help I don’t want to have surgery I was told by my vascular surgeon that I can live along time the way that I am or have the surgery not going to be the same after the surgery just hoping for some type of product that could help me heal or feel better again. Kennethpridgen (talk) 20:22, 23 November 2023 (UTC)

Negative reactions

The article states as an absolute fact that menthol produces a cooling sensation. This isn't true, and the absoluteness of the statement is not sourced (nor could it be). Some people experience a burning session, which is possibly an allergic reaction to it or to the mint family. You can find many references to this online, and people (like me) are not making it up. Yes, I am not a reliable source for the article, but that doesn't make me wrong about what I know to be true.

There are articles that mention this in passing but in a very brief search, I have not found a good source, and it doesn't appear that anybody knows what percentage of the population is allergic to menthol and/or mint.

I suggest (a) the article be corrected to say "For most humans ..." in the intro and perhaps elsewhere, and (b) anybody working on improving the sourcing for the article consider if sources can be found that document the negative reactions in a way that they can actually be included beyond (a). RoyLeban (talk) 11:05, 1 October 2024 (UTC)

Do you mean this sentence: "In humans, menthol produces a cooling sensation when inhaled, eaten, or applied to the skin,...". That is not stating as an absolute fact. It is easy to interpret that sentence as including some uncertainty and/or that it can or may produce a cooling sensation some of the time in some people. E.g., "Carelessness causes wildfires" does not mean that all carelessness causes a wildfire. But do feel free to be bold. Find a WP:MEDRS compliant reference, and make the text better by adding relevant referenced text. Jaredroach (talk) 12:32, 1 October 2024 (UTC)

Thanks, @Jaredroach. That sentence is an obvious place, but I think other places in the article imply it as well.

This article does not have good sources, and my quick read of the sources do not say "all humans". If I'm understanding you correctly, you think the sentence in the intro already means "For many people". If you are right, and this is the normal interpretation of that sentence, then my changing it to say "For many people" is a non-change, just a clarification of what it already means. It also changes changing the awkward "humans" to "people." So I'm going to make this change. I would actually be ok with "For most people," as I believe that to be true, but I think that would require a source that makes that claim. Should somebody think that it means and should say "all people," they should find a source that makes that stronger claim.

WRT the statement "carelessness causes wildfires", it's a bit different, but it does always irk me when I see a statement like that. There's an entire clause like (with campfires in the woods) that is omitted and implied. In such a case, adding the explanatory clause would not change the intended meaning of the statement either. RoyLeban (talk) 10:08, 2 October 2024 (UTC)