Trolamine salicylate

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Trolamine salicylate
Trolamine salicylate.png
Trolamine salicylate 3D ball.png
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.847 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: UEVAMYPIMMOEFW-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C(O)c1ccccc1O.OCCN(CCO)CCO
Properties
C13H21NO6
Molar mass 287.312 g·mol−1
AppearanceBeige crystals or lumps [1]
Odor odorless
Melting point 50 °C (122 °F; 323 K) [3]
Boiling point Decomposes [2]
Soluble, [2] 11.3 mg/mL (predicted) [3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Serious eye damage
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P312, P317, P319, P321, P330, P332, P337, P362+P364, P403+P233, P405, P501
Lethal dose or concentration (LD, LC):
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

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

Related Research Articles

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Triethanolamine, or TEOA, is an organic compound with the chemical formula N(CH2CH2OH)3. It is a colourless, viscous liquid. It is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples may appear yellow because of impurities.

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Myrtecaine (Nopoxamine), sold as a combination product with diethylamine salicylate under the trade name Algesal and Algésal Suractivé among others, is a local anaesthetic in the form of a topical cream, or with laurilsulfate in rubefacient preparations. It is used to treat muscle strains, tendinitis or ligament sprains and joint pain. It is a surface anaesthetic, adds to the analgesic and anti-inflammatory actions of diethylamine salicylate by facilitating its penetration. Also myrtecaine has a muscle relaxant effect.

References

  1. 1 2 3 4 Safety data sheet
  2. 1 2 3 4 "Trolamine salicylate".
  3. 1 2 "Trolamine salicylate".
  4. ↑ From DailyMed (a publication of the National Institutes of Health) ,[ dead link ] 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) , 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 [ dead link ] retrieved 23 April 2011
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