Acetaminosalol

Acetaminosalol
Names
	Preferred IUPAC name 4-Acetamidophenyl 2-hydroxybenzoate
Identifiers
CAS Number	118-57-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:250620 ;
ChEMBL	ChEMBL92590 ;
ChemSpider	1907 ;
ECHA InfoCard	100.003.875
EC Number	204-261-3;
MeSH	Salophen
PubChem CID	1984;
UNII	O3J7H54KMD ;
CompTox Dashboard (EPA)	DTXSID7045865 ;
	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−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

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References

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