Acetaminosalol

Acetaminosalol

Names
IUPAC name (4-Acetamidophenyl) 2-hydroxybenzoate[1]
Identifiers
CAS Number	118-57-0
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:250620
ChEMBL	ChEMBL92590
ChemSpider	1907
ECHA InfoCard	100.003.875
EC Number	204-261-3
MeSH	Salophen
PubChem	1984
UNII	O3J7H54KMD
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	271.27 g·mol^−1
Density	1.327 g cm^−3
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 [77 °F], 100 kPa).
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Infobox references

Acetaminosalol is an organic compound with the chemical formula C₁₅H₁₃NO₄.

It is an esterfication 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

1. "salophen - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.