Trolamine salicylate

Not to be confused with Trolamine.

Trolamine salicylate

Names
Preferred IUPAC name

2-Hydroxy-N,N-bis(2-hydroxyethyl)ethan-1-aminium 2-hydroxybenzoate

Other names

* Tris(2-hydroxyethyl)ammonium 2-hydroxybenzoate[1]
* Tris(2-hydroxyethyl)ammonium salicylate
* TEA salicylate[2]
* Triethanolamine salicylate[2]
* Triethanolaminium salicylate[1]

Identifiers

CAS Number

* 2174-16-5 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 23549 Y

PubChem CID

* 25213

UNII |

* H8O4040BHD Y

InChI

* InChI=1S/C7H6O3.C6H15NO3/c8-6-4-2-1-3-5(6)7(9)10;8-4-1-7(2-5-9)3-6-10/h1-4,8H,(H,9,10);8-10H,1-6H2 Y

Key: UEVAMYPIMMOEFW-UHFFFAOYSA-N Y

* InChI=1/C7H6O3.C6H15NO3/c8-6-4-2-1-3-5(6)7(9)10;8-4-1-7(2-5-9)3-6-10/h1-4,8H,(H,9,10);8-10H,1-6H2

Key: UEVAMYPIMMOEFW-UHFFFAOYAM

SMILES

* O=C(O)c1ccccc1O.OCCN(CCO)CCO

Properties

Chemical formula

| C13H21NO6
Molar mass | 287.312 g·mol−1
Appearance  | Beige crystals or lumps[1]
Odor | odorless
Melting point |  50 °C (122 °F; 323 K) [3]
Boiling point | Decomposes[2]

Solubility in water

| Soluble,[2] 11.3 mg/mL (predicted)[3]
Hazards
Main hazards | Serious eye damage
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| HH302Script error: No such module "Preview warning".Category:GHS errors, HH315Script error: No such module "Preview warning".Category:GHS errors, HH319Script error: No such module "Preview warning".Category:GHS errors, HH335Script error: No such module "Preview warning".Category:GHS errors

GHS precautionary statements

| PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP270Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP301+P317Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP305+P351+P338Script error: No such module "Preview warning".Category:GHS errors, PP312Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP330Script error: No such module "Preview warning".Category:GHS errors, PP332Script error: No such module "Preview warning".Category:GHS errors, PP317Script error: No such module "Preview warning".Category:GHS errors, PP337Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP403+P233Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 500 mg/kg (oral, estimated value)[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Trolamine salicylate (Aspercreme, Aspergel) is an organic compound with the chemical formula [HN(CH
2CH
2OH)
3]+

4(OH)(COO−
). It is a salt of triethanolamine and salicylic acid, i.e. the compound consists of protonated triethanolamine and the conjugate base of salicylic acid, salicate.

It is used as an ingredient in sunscreens, 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.[4] 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.[5] 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."[6] 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.[7]

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 strains, and sprains.

## See also

* Methyl salicylate

## References

1. ↑ 1.0 1.1 1.2 1.3 Safety data sheet
2. ↑ 2.0 2.1 2.2 2.3 "Trolamine salicylate". https://pubchem.ncbi.nlm.nih.gov/compound/Trolamine-salicylate.
3. ↑ 3.0 3.1 "Trolamine salicylate". https://go.drugbank.com/drugs/DB11079.
4. ↑ From DailyMed (a publication of the National Institutes of Health) [1], retrieved 23 April 2011
5. ↑ Steven Pray, Nonprescription Product Therapeutics, 2nd ed., Lippincott Williams & Wilkins (2006), ISBN 0-7817-3498-3, ISBN 978-0-7817-3498-1
6. ↑ FDA News Release, (FDA advances new proposed regulation to make sure that sunscreens are safe and effective) [2], retrieved 13 December 2019
7. ↑ "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 Peak Performance website retrieved 23 April 2011

* v
* t
* e

Sunscreening agents approved by the US FDA or other agencies

* UVA: 400–315 nm
* UVB: 315–290 nm
* chemical agents unless otherwise noted

UVA filters|

* Avobenzone (Parsol 1789)
* Bisdisulizole disodium (Neo Heliopan AP)
* Diethylamino hydroxybenzoyl hexyl benzoate (Uvinul A Plus)
* Ecamsule (Mexoryl SX)
* Menthyl anthranilate

UVB filters|

* Amiloxate
* 4-Aminobenzoic acid (PABA)
* Cinoxate
* Ethylhexyl triazone (Uvinul T 150)
* Homosalate
* 4-Methylbenzylidene camphor (Enzacamene)
* Octyl methoxycinnamate (Octinoxate)
* Octyl salicylate (Octisalate)
* Padimate O (Escalol 507)
* Phenylbenzimidazole sulfonic acid (Ensulizole)
* Polysilicone-15 (Parsol SLX)
* Trolamine salicylate

UVA+UVB filters|

* Bemotrizinol (Tinosorb S)
* Benzophenones 1–12
* Dioxybenzone
* Drometrizole trisiloxane (Mexoryl XL)
* Iscotrizinol (Uvasorb HEB)
* Octocrylene
* Oxybenzone (Eusolex 4360)
* Sulisobenzone
* hybrid (chemical/physical): Bisoctrizole (Tinosorb M / Eversorb M)
* physical:
* Titanium dioxide
* Zinc oxide

See also: Photoprotection, Sun protective clothing, Sun tanning, and Sunburn

* v
* t
* e

Salicylates

* Salicylic acid
* Aspirin
* Aloxiprin
* Methyl salicylate
* Magnesium salicylate
* Ethyl salicylate
* Bismuth subsalicylate
* Sodium salicylate
* Salicylamide
* Salicin
* Benorilate
* Salsalate
* Ethenzamide
* Diflunisal
* Trolamine salicylate
* Homosalate
* Salicylmethylecgonine
* Octyl salicylate
* Aluminon
* Benzyl salicylate
* Copper aspirinate
* Potassium salicylate

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