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Acetaminosalol

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Acetaminosalol
Kekulé, skeletal formula of acetaminosalol
Names
Preferred IUPAC name 4-Acetamidophenyl 2-hydroxybenzoate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.875 Edit this at Wikidata
EC Number
  • 204-261-3
MeSH Salophen
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H13NO4/c1-10(17)16-11-6-8-12(9-7-11)20-15(19)13-4-2-3-5-14(13)18/h2-9,18H,1H3,(H,16,17)Key: TWIIVLKQFJBFPW-UHFFFAOYSA-N
  • InChI=1/C15H13NO4/c1-10(17)16-11-6-8-12(9-7-11)20-15(19)13-4-2-3-5-14(13)18/h2-9,18H,1H3,(H,16,17)Key: TWIIVLKQFJBFPW-UHFFFAOYAL
SMILES
  • CC(=O)Nc1ccc(OC(=O)c2ccccc2O)cc1
  • CC(=O)NC1=CC=C(OC(=O)C2=CC=CC=C2O)C=C1
Properties
Chemical formula C15H13NO4
Molar mass 271.272 g·mol
Density 1.327 g cm
log P 2.562
Acidity (pKa) 7.874
Basicity (pKb) 6.123
Hazards
Flash point 241.9 °C (467.4 °F; 515.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Acetaminosalol is an organic compound with the chemical formula C15H13NO4.

It is an esterification product of salicylic acid and paracetamol. It was marketed by Bayer under the brand name Salophen as an analgesic in the late 19th and early 20th centuries.

Action and uses

In a warm alkaline solution acetaminosalol is broken up into salicylic acid and paracetamol. It is decomposed in the intestines, even when given as an injection. It was used as a substitute for salicylic acid in acute rheumatism, and as an intestinal antiseptic. It was similarly effective and much safer than salol, another intestinal antiseptic commonly used at the time. The fact that it is tasteless renders it easy to administer.

Advertisement for early 20th century Bayer products, including Salophen

References


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