Talk:Salicylic acid

Wiki Education Foundation-supported course assignment
This article was the subject of a Wiki Education Foundation-supported course assignment, between 30 March 2020 and 5 June 2020. Further details are available on the course page. Student editor(s): Paulyjkim.

Above undated message substituted from Template:Dashboard.wikiedu.org assignment by PrimeBOT (talk) 08:34, 17 January 2022 (UTC)

Mechanism of action
Previously, the mechanism of action of anti-diabetic effect claimed that salicylic acid did not work through AMPK, which is contradicted by the given source. Consequently, I edited it to say that it DOES work through AMPK. I duly note, and consequently left it in the article, that salicylic acid also can have its anti-diabetic effect through a yet-to-be described mechanism. BioSciEngr (talk) 18:29, 18 December 2012 (UTC)

Vitamin "S" section
The "Vitamin S" section needs work. The one reference cited (European Journal of Nutrition) seems OK, but are there any corroborating references available? It isn't clear if this is given much credence in the mainstream scientific world or if it is borderline quackery. In any case, the section is too long, poorly written, and so loaded with weasel words it reads more like a plea to accept the author's opinion than a statement of fact. If the Vitamin S stuff is kept, most of it should be moved to vitamin which already has a brief Vitamin S section and only a short pointer to it left here. Currently it's over half the article. (Another problem in passing: salicylate is used several times throughout the entry without any prior definition.) --66.188.84.209 07:14, 20 Jan 2005 (UTC)

I agree with the above post. Also, I believe the statement that salicylic acid could be argued as more important than vitamin A or D should be removed. The effects of vitamin A and D deficiency are well documented, and I don't believe I need to explain them here. There is no evidence of a salicylate deficiency related disorder.

Moved from article
I have moved the following section from the article here. Maybe somebody can write a critical/NPOV section for the article:

"Vitamin S"
"Vitamin S" is a proposed alternative name for salicylate, which would have the effect of classifying it as a vitamin. There is no generally agreed definition of what constitutes a vitamin, though salicylate meets at least one of the requirements:


 * It is present in our natural diet in fruit and vegetables, particularly if they have had to defend themselves against damage or disease
 * It is not produced by our bodies
 * Trace amounts, it has been suggested, are required for the maintenance of life

This last point is controversial because salicylate deficiency, unlike, say, Vitamin C deficiency, which causes scurvy, does not result in any particular known symptoms. A low salicylate intake seems to be related to longer term problems, resulting in higher risks of age-related chronic diseases.

Whereas most vitamins are enzyme cofactors, promoting cellular biochemical reactions - Vitamin C boosts production of collagen - salicylate is not, but then nor is Vitamin E, which is an antioxidant, like salicylate.

Lack of salicylate appears to predispose humans to:
 * Cancer
 * Heart attacks
 * Stroke
 * Alzheimer's disease

It can be argued that salicylate has a better claim to be called a vitamin than vitamins A and D.

Whether or not you choose to call aspirin a vitamin, there is still a case to be made that salicylate is an important micronutrient.

There is evidence that salicylates in past ages were much more common in human diets than they are now. Salicylates are produced by fruit as a defense mechanism: inducing damaged and diseased cells to commit suicide. Modern man's predilection for fruit and vegetables in a pristine condition - with shoppers often rejecting fruit with bumps of bruises - means that we eat less salicylates than in the past. A study has shown that organic vegetable soups contain nearly six times as much salicylate as non-organic equivalents (European Journal of Nutrition, vol. 40 p 289).

Comment: as far as I know going as far as calling salicylic acid a vitamin is complete nonsense and I haven't seen any reference to it as such in the literature.

Additionally, in reference to the paragraph quoting the E.J.N. article, the comparison between vegetable soups and human diet of "past ages" is almost a non sequitur since the history of crop selection is more complex than choosing over a bruised fruit; and while comparison between ancient and modern crops is a legitimate area of reserach, this article is not the place for that. My point is that the reference looks out of place and seems more like an attempt to legitimize a fringe theory that has little or no research to back it up. I'd support the removal of the dispute tag off this article. -- Rune Welsh | &tau;&alpha;&lambda;&kappa; | Esperanza  04:16, 22 October 2005 (UTC)


 * I think evidence is now emerging for the therapeutic effects of low-dose aspirin - see this paper presented at the 2012 NCRI conference: http://www.ncri.org.uk/ncriconference/programme/speakerAbstracts/2012_parallel_Nancy_Cook.asp Danensis (talk) 10:37, 9 November 2012 (UTC)
 * That doesn't seem really relevant to whether it is or has been known as "vitamin S" - Rod57 (talk) 10:41, 12 December 2019 (UTC)


 * I indirectly arrived at this article from B vitamins, which discusses vitamin B11 with some uncited arguments about vitamin S (disambiguation), which points to this page, where "vitamin S" isn't actually mentioned. Based on a search of reliable sources, what seems to have occurred is that a single author, GP Morgan, informally suggested the possible term in New Scientist [Morgan 2004], another author mentioned the proposal in the British Medical Journal [McMullen 2005], and bloggers and conspiracy theorists latched onto the term and treated it as scientific gospel. A 2013 book errantly referred to vitamin S as a former name for salicylic acid, and Morgan and New Scientist keep citing the idea from the original 2004 article ([Morgan 2007], [New Scientist 2011], to cite two examples) which keeps the term active (and keeps bloggers linking to the NewSci's paywall).


 * While “vitamin S” seems unmentioned among reliable sources outside NewSci and the references cited here, it has enough common usage that it seems worth mentioning the purely factual genesis of the term in the article. Setting aside whether salicylic acid's use as a micronutrient is a good, bad, or fringe idea, it will help others who arrive at the article trying to understand what people are talking about. I have included the following sentence, which I'm guessing may still be controversial; I'll leave others to decide its fate:
 * A 2004 article in New Scientist discussing the controversial idea of treating salicylates as micronutrients, “akin to vitamins and antioxidants,” suggested that “perhaps in future we might even call salicylate ‘vitamin S’.”


 * Some quotes and sources on the term:


 * “There is a case for regarding salicylate as a micronutrient, akin to vitamins and antioxidants, that is essential for maintaining good health – perhaps in future we might even call salicylate ‘vitamin S’.” [Morgan 2004]


 * “As reported in New Scientist, organically grown vegetable soups contain almost six times more salicylic acid than do non-organic vegetable soups. Morgan has suggested that salicylates are essential for good health and could be designated vitamin ‘S.’” [McMullen 2005]


 * “...and salicylic acid, previously known as vitamin S.” [Velisek 2013]






 * [NOTE: JOURNAL NOT A RELIABLE SOURCE; just illustrating Morgan citing his 2004 article for the proposal]






 * ––Agyle (talk) 23:17, 24 January 2014 (UTC)

Removed in 2005, Sad that article still has no mention of the 2004/Morgan/NewSci proposal to call it vitamin S. Perhaps we could (re)add that, and note if there have been any published arguments either way ? We could say the proposal has not gained [much] support, but it's harder to justify that with an RS.- Rod57 (talk) 10:36, 12 December 2019 (UTC)

SMILES
I changed the SMILES from  OC1=CC=CC=C1C(O)=O     =>     C1=C(O)C=CC=C1C(O)=O The first indicated that C1 is carrying the -OH group, and that the C1 is also carrying the acid group; my modification put it onto C2, but I'm only 90% sure of the system. Someone doublecheck my thinking? --Firien § 28 June 2005 14:27 (UTC)
 * Switched it back; I reckon the system's a little inconsistent in that the 1 above should be a (1), but something tells me the system will be too far along now to change ;) Case closed. --Firien § 30 June 2005 11:02 (UTC)

Plant hormone
Why is Salicylic acid (plant hormone) split off from this? Neither article is very long. Shouldn't they be merged? &mdash; Gwalla | Talk 8 July 2005 20:24 (UTC)
 * They just have been. Physchim62 13:35, 16 October 2005 (UTC)

Boiling point
I removed the following boiling point info from the table as it seems ludicrous to me. Maybe a typing error has got in there somewhere...
 * 211°C at 2666 Pa (reduced pressure), sublimes at 76°C

I will see what I can find for more reliable data. Physchim62 13:35, 16 October 2005 (UTC)
 * My 1960 Merck Index says the same thing. Clearly the 76 number is wrong, or else (more likely) an even lower pressure should be listed and isn't.  My rubber handbook (CRC) just gives the same 211 C at 20 torr figure, so I put that in.  The MP is right, we use it in our intro organic lab! Walkerma 07:44, 13 November 2005 (UTC)

Acne treatment
I am wondering if Salicylic acid for acne treatment is to be left on the skin indefinately or washed off. There are products with differing instructions. How long does Salicylic acid need to remain on the skin to be effective, and is there a risk of leavingit on too long? --Jeiki Rebirth 01:58, 2 February 2006 (UTC)
 * It depends on the concentration of the acid used. Stronger concentrations(i.e. 5%) usually means that you need to wash them off after a period of time, and lower ones(i.e. 0.5%) are deisigned to be left on the skin.--Chicbicyclist 22:26, 2 February 2006 (UTC)

Plant Hormone
The section about SA as a plant hormone needs to be rewritten. What means "cells capable of syntesizing"? Synthesizing what? Could also not find SA und the page "SA", isn't this the official abbreviation? At least I've seen it like that in plant papers. massa 14:18, 26 February 2006 (UTC)

Bell foundries that cast bells in bronze - analloy of copper and tin stir the moulten bronze with a willow stick. The salicylic acid degasses the moulten metal which avoids pinholes in the finished article.
 * —Preceding unsigned comment added by 86.29.134.205 (talk • contribs) 20:58, 26 September 2006

Antiseptic? Anti-biotic?
I think the line stating that SA is an 'anti-biotic' either needs to be reworded or referenced. I don't dispute the accuracy of the statement in principle, but I'm not sure if 'anti-biotic' is the best term to use. If it is, I think it should have a citation. The statement elsewhere that it is an antiseptic is similar, and there is also 'anti-microbal' (not in the article, but a similar term). It depends I guess on how it acts upon microbes (does it actually kill bacteria through dispersal in the bloodstream when ingested, or just on contact or when topically applied?), and also how specific the term 'antibiotic' is: even with the hyphen, can it be used for something that is not in the normal pharmacological range in current use? Volume1 09:04, 31 October 2006 (UTC)

Effect of cooking on naturally occuring SA in food
The melting point of SA is easily achievable on a stovetop: does it simply melt and then solidify again as the food cools, or is it lost or altered due to sublimation or reaction with cookware, air, water, or other chemicals in food?
 * —Preceding unsigned comment added by 24.141.153.20 (talk • contribs) 07:40, 17 December 2006

Salicylanilide
Can anyone start an article about this? Or you can just tell me what it is and what it does. I also have a question, I have a soap that has both sulfur + salicylic acid. What would be the probable ratio of the mixture? Thanks.202.138.180.33 04:36, 5 January 2007 (UTC)


 * See http://www.alanwood.net/pesticides/salicylanilide.html for details.


 * Ben 13:29, 5 January 2007 (UTC)

ph and concentrations used in cosmetics
I got this information from Paula Begouns books, you can find it on the www.cosmeticscop.com site. I thought it was interesting as it relates to skin care but maybe needs more evaluation before its posted. I usually trust what she says because she evaluates products only based on medical journals that are legitmate and not funded by companies, or journals that just anyone can publish in (which is a bigger problem then you might think), and she usually states when the studies aren't big enough to draw conclusions. Although, she started selling her own line now which definitly hurts her credibility; her reputation before that was as a debunker of expensive and ineffective ingredients, based on pseudoscience or inconclusive evidence.

"BHA works best at concentrations of between 1 and 2%, and at an optimal ph of 3, diminishing in effectiveness as you go past a ph of 4" She goes on to give tips about use such as testing with ph paper before you buy. And that willow bark (which is often touted as the natural salicylic acid) actually contains salicin which can be converted into salicylic acid, but is by no means as direct as is often stated. She argues against higher concentrations for daily use but then lists some common peels that use higher concentrations (20-30% for the most high-powered peel) and says they can be more effective or better to start with then ahas peels of high concentrations because of their anti-inflammatory properties. She recommends bha for men's and women's grooming for the same properties, to reduce swelling and redness after shaving. She recommends a 5-10% solution for calluses on the feet and a 1.8% to 3% for psoriasis because it softens skin layers on psoriatic lesions.

I also read this, but can't find a direct reference, 1-2% daily, 2-8% irritaions may become more apparent, and at 8-13% may experience some bigger side effects. And I assume something as high as 20-30% is an only once in a blue moon, downtime treatment but I'm not sure.

Finally, I know that aspirin and salicylic acid are related and not necasarily the same but I thought this might be valid to mention in a cosmetics section, because its a cheap relatively afforadable option. I know from my own experience that using crushed up aspirin (uncoated) on the face is a common beauty treatment to get rid of blackheads, usually mixed with honey or a cream or just plain water. Given that you need a lower ph for salicylic acid, I personally use a little lemon juice ph2, diluted with water neutral 7. I don't know if that is the best method or even applicable for aspirin since they are slightly different, so I don't recommend it but I know that the honey or water and aspirin method is tested and true and you can probably look it up online somewhere. —Preceding unsigned comment added by 71.235.115.115 (talk) 18:06, 5 September 2007 (UTC)

tris chelate/phenol test
Dumping this section here until someone has the time to find refs/disprove. --Rifleman 82 (talk) 09:08, 25 September 2008 (UTC)

==Analysis== Salicylic acid is an enol of a β-keto carbonic acid and therefore forms purple complexes with iron(III) salts:



This tris(chelate) complex forms more readily in basic solution.

I believe that the above complex is inaccurate, as Iron (III) chloride is the test for a phenols and the complex forms in the presence of C=C-OH group and the above complex is shows a C=O that is not present in phenol itself.

Role in herbalism
Salicylic acid is effective against a plethora of skin ailments. Salicylic acid is a keratolytic agent. That is, it catalytically dissolves keratin, the skin protein. Keratin is most noted for its role in skin callus formation. Skin malformations employ keratin as a building block. Destruction of the keratin with salicylic acid destroys the skin malformation without destroying the healthy skin around or underlying the malformation. Thus salicylic acid is curative for many skin disorders. While the chemical, 2-hydroxybenzoic acid by IUPAC name, is named salicylic acid for its presence in Salix, its most common botanical source is Aloe vera. It is found in many plant sources, including many species of ice-plant and in wandering Jew. Its biological role in plants is as a protection against being eaten by animals. Enough salicylic acid eventually causes the inside of the animal’s mouth to become raw. (The proteolytic enzyme in raw pineapple does similarly if you would like to home experiment.) As a proteolytic, salicylic acid is antagonistic to the body’s larger biochemistry. Salicylic acid in the blood stream is ejected through the intestinal tract. My Flatley (talk) 14:56, 14 July 2011 (UTC)

Link broken
The external link to the MSDS does not work. 160.62.4.100 (talk) 13:39, 30 September 2014 (UTC)
 * . I replaced the broken link with a working one. Thanks for catching the problem and reporting it here.  -- Ed (Edgar181) 14:29, 30 September 2014 (UTC)

Proposed merge with Salicylic acid (medical use)
The article with the medical use does not contain much content, and would likely fit better if merged. iczero (talk) 21:41, 18 December 2017 (UTC)
 * Support. Readily fits into the main article which already contains adequate description of medical uses. --Zefr (talk) 22:29, 18 December 2017 (UTC)
 * Oppose We often create articles that go into detail on specific uses. Yes the medical uses can be expanded. Without splitting people than complain that the overview article is too medicine centric. Doc James  (talk · contribs · email) 04:01, 20 December 2017 (UTC)
 * oppose generally agree w/ Doc James reason here--Ozzie10aaaa (talk) 00:40, 21 December 2017 (UTC)


 * Oppose Firstly, as Doc James says, secondly, the medical uses article really needs some attention and the outcome might make merging even less advisable. Possibly even some of the material in the current chemical article should be moved to the medical article. And besides, "adequate description of medical uses" is by no means clear; some of the material is so curtailed as to be misleading. To expand it in situ would clutter this article, but cold enrich the medical article. Any particular editor's preferences are not cogent in such matters in the face of interest from other editors and users, as long as the material is encyclopaedic. JonRichfield (talk) 14:14, 8 February 2018 (UTC)

History
This article repeats the widespread myth that willow back was used as a painkiller. As far as I can make out, this is completely untrue, and attributions to Hippocrates and other early sources are all recent and incorrect. Salicylic acid is too dangerous to be taken internally and it is not the same as acetylsalicylic acid. Here's a good article on the subject: https://theconversation.com/hippocrates-and-willow-bark-what-you-know-about-the-history-of-aspirin-is-probably-wrong-148087. Can we edit to remove this misinformation? Apart from accuracy, it could also be hazardous to people who try to treat pain with willow. E Wusk (talk) 19:43, 28 December 2021 (UTC)
 * You are welcome to edit. The article has pretty convincing references to ancient medicine published in real journals vs your "theconversation.com". If you are correct, then your proposed edits would be influential.  I would not be surprised if the use of willow bark as a painkiller is in fact untrue because so many people are convinced of the wisdom of the ancients. So go for it.--Smokefoot (talk) 20:42, 28 December 2021 (UTC)

Thank you for the encouragement, Smokefoot

Illustrations
Can someone add reaction mechanism or atleast molecule structures in reactions and production? Clepenji1150 (talk) 13:00, 21 February 2023 (UTC)