Pamoic acid

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Pamoic acid[1]
Structural formula of pamoic acid
Names
IUPAC name
4-[(3-Carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid
Other names
Embonic acid
Identifiers
130-85-8 YesY
901319
ChEBI CHEBI:50186
ChEMBL ChEMBL177880 YesY
ChemSpider 8228 YesY
EC Number 204-998-0
2920
Jmol 3D model Interactive image
Interactive image
MeSH Pamoic+acid
PubChem 8546
RTECS number QL2180000
UNII 7RRQ8QZ38N YesY
  • InChI=1S/C23H16O6/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h1-10,24-25H,11H2,(H,26,27)(H,28,29) YesY
    Key: WLJNZVDCPSBLRP-UHFFFAOYSA-N YesY
  • OC(=O)C1=CC2=CC=CC=C2C(CC2=C(O)C(=CC3=CC=CC=C23)C(O)=O)=C1O
  • C1=CC=C2C(=C1)C=C(C(=C2CC3=C(C(=CC4=CC=CC=C43)C(=O)O)O)O)C(=O)O
Properties
C23H16O6
Molar mass 388.38 g·mol−1
Melting point ≥300 °C
log P 6.169
Acidity (pKa) 2.675
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pamoic acid, also called embonic acid, is a naphthoic acid derivative. Salts and esters of pamoic acid are known as pamoates or embonates. It can be prepared by the reaction of 2-hydroxy-3-naphthoic acid with formaldehyde.

In pharmacology, the salt form of pamoic acid (pamoate ion) can be used as a counter ion of a drug compound to increase the solubility of the drug in water.[2] The presence of multiple oxygen atoms enables significant hydrogen bonding to occur. Hydrogen bonds facilitate the dissolution of compounds in water.

Pamoic acid has agonist activity for the orphan G protein-coupled receptor GPR35 by which it activates ERK and beta-arrestin2, and causes antinociceptive activity.[3][4] Although (like other drug salts) it has been considered an inactive compound by the FDA, these recent data suggest that its permitted uses may need to be reexamined.[citation needed]

References

  1. Merck Index, 12th Edition, 7136.
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