Trolamine salicylate: Difference between revisions

{{Use dmy dates|date=February 2023}}

{{Distinguish|Trolamine}}

| verifiedrevid = 402707114

| ImageFile = Trolamine salicylate.png

| ImageSize = 250

| ImageAlt = Structural formula of trolamine salicylate

| ImageFile1 = Trolamine salicylate 3D ball.png

| ImageSize1 = 250

| ImageAlt1 = Ball-and-stick model of the component ions of trolamine salicylate

| PIN = 2-Hydroxy-''N'',''N''-bis(2-hydroxyethyl)ethan-1-aminium 2-hydroxybenzoate

| OtherNames = {{ubl|Tris(2-hydroxyethyl)ammonium 2-hydroxybenzoate<ref name=sigmaaldrich></ref>|Tris(2-hydroxyethyl)ammonium salicylate|TEA salicylate<ref name=pubchem></ref>|Triethanolamine salicylate<ref name=pubchem></ref>|Triethanolaminium salicylate<ref name=sigmaaldrich></ref>}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| CASNo = 2174-16-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H8O4040BHD

| PubChem = 25213

| SMILES = O=C(O)c1ccccc1O.OCCN(CCO)CCO}}

| C=13|H=21|N=1|O=6

| Appearance = Beige crystals or lumps<ref name=sigmaaldrich>[https://www.sigmaaldrich.com/GB/en/sds/sial/74412 Safety data sheet]</ref>

|Odor = odorless

| Density =

| MeltingPtC = 50

| MeltingPt_notes = <ref name=drugbank>{{cite web | url=https://go.drugbank.com/drugs/DB11079 | title=Trolamine salicylate }}</ref>

| BoilingPt = Decomposes<ref name=pubchem>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Trolamine-salicylate | title=Trolamine salicylate }}</ref>

| Solubility = Soluble,<ref name=pubchem></ref> 11.3 mg/mL (predicted)<ref name=drugbank></ref>

}}

| MainHazards = Serious eye damage

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|H302|H315|H319|H335}}

| PPhrases = {{P-phrases|P261|P264|P270|P271|P280|P301+P317|P302+P352|P304+P340|P305+P351+P338|P312|P319|P321|P330|P332|P317|P337|P362+P364|P403+P233|P405|P501}}

| FlashPt =

| AutoignitionPt =

| LD50 = 500 mg/kg (oral, estimated value)<ref name=sigmaaldrich></ref>

}}

'''Trolamine salicylate''' (Aspercreme, Aspergel) is an [[organic compound]] with the [[chemical formula]] {{chem2|[HN(CH2CH2OH)3]+C6H4(OH)(COO−)}}. It is a [[salt (chemistry)|salt]] of [[triethanolamine]] and [[salicylic acid]].

It is used as an ingredient in [[sunscreen]]s, [[analgesic]] creams, and cosmetics. The salicylic acid portion contributes to both the sun protection effect (by absorbing [[UVB radiation]]) and to the analgesic effect. The triethanolamine neutralizes the acidity of the salicylic acid. One benefit of this topical analgesic is that it has no odor, in contrast to other topical analgesics such as [[menthol]].

The [[US Food and Drug Administration]] has not reviewed any of the over-the-counter products listed in the [[Daily Med]] database that contain trolamine salicylate.<ref>From ''DailyMed'' (a publication of the National Institutes of Health) [http://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=trolamine+salicylate&x=13&y=10],{{dead link|date=February 2023}} retrieved 23 April 2011</ref> Also, the producers of trolamine salicylate products have not provided evidence to the FDA in support of claims that this chemical is directly absorbed through the skin into underlying tissue.<ref>Steven Pray, ''Nonprescription Product Therapeutics'', 2nd ed., Lippincott Williams & Wilkins (2006), {{ISBN|0-7817-3498-3}}, {{ISBN|978-0-7817-3498-1}}</ref> Due to health concerns, in 2019 the FDA issued a proposed rule classifying the sunscreen use of trolamine salicylate as "not generally recognized as safe and effective."<ref>FDA News Release, (FDA advances new proposed regulation to make sure that sunscreens are safe and effective) [https://www.fda.gov/news-events/press-announcements/fda-advances-new-proposed-regulation-make-sure-sunscreens-are-safe-and-effective], retrieved 13 December 2019</ref> One study reported that trolamine salicylate does penetrate into, and persist within, underlying muscle tissue. The test subjects used either the trolamine salicylate product or a placebo while engaging in an exercise regimen designed to induce muscle soreness. The experimenters observed that those using the trolamine salicylate product exercised longer before reporting the onset of soreness, reported less intense soreness, and reported that their soreness did not last as long as the people who used the placebo.<ref>"Effect of a Topical 10% Trolamine Salicylate Cream on Delayed Onset Muscular Soreness", ''Medicine and Science in Sports and Exercise'', vol. 20(2), Supplement, #141 (1988), online at [http://www.pponline.co.uk/encyc/0283.htm Peak Performance website]{{dead link|date=February 2023}} retrieved 23 April 2011</ref>

All of the trolamine salicylate-containing products listed in the two cited references are 10% solutions. These products are sold under various brand names, e.g. Aspercreme, and are marketed as topical analgesics for temporary relief of arthritis, simple backache, [[muscle strain]]s, and [[sprain]]s.

==See also==

*[[Methyl salicylate]] <!--An alternative salicylate in analgesic creams.-->

==References==

{{reflist}}

[[Category:Ethanolamines]]

[[Category:Sunscreening agents]]

[[Category:3-Hydroxypropenals]]