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Trolamine salicylate

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(Redirected from Aspercreme)

Not to be confused with Trolamine.
Trolamine salicylate
Structural formula of trolamine salicylate
Ball-and-stick model of the component ions of 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
  • Tris(2-hydroxyethyl)ammonium salicylate
  • TEA salicylate
  • Triethanolamine salicylate
  • Triethanolaminium salicylate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.847 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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,1-6H2Key: UEVAMYPIMMOEFW-UHFFFAOYSA-N
  • 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,1-6H2Key: UEVAMYPIMMOEFW-UHFFFAOYAM
SMILES
  • O=C(O)c1ccccc1O.OCCN(CCO)CCO
Properties
Chemical formula C13H21NO6
Molar mass 287.312 g·mol
Appearance Beige crystals or lumps
Odor odorless
Melting point 50 °C (122 °F; 323 K)
Boiling point Decomposes
Solubility in water Soluble, 11.3 mg/mL (predicted)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Serious eye damage
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements 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):
LD50 (median dose) 500 mg/kg (oral, estimated value)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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, 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. 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. 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." 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.

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

References

  1. ^ Safety data sheet
  2. ^ "Trolamine salicylate".
  3. ^ "Trolamine salicylate".
  4. From DailyMed (a publication of the National Institutes of Health) , 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 retrieved 23 April 2011
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
UVB filters
UVA+UVB filters
See also: Photoprotection, Sun protective clothing, Sun tanning, and Sunburn
Salicylates
Categories:
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