Pamoic acid

Names

[ CAS No. ]:
130-85-8

[ Name ]:
Pamoic acid

[Synonym ]:
Pamoic
1,1'-Methylene-bis(2-hydroxy-3-naphthoic acid)
2-Naphthalenecarboxylic acid, 4,4'-methylenebis[3-hydroxy-
4,4-Methylenebis(3-Hydroxy-2-Naphthoic Acid)
EMBIONIC ACID
PAMOIC ACID FREE ACID
2,2'-Dihydroxy-1,1'-dinaphthylmethane-3,3'-dicarboxylic Acid
4,4'-Methylenebis(3-hydroxy-2-naphthoic acid)
Pamoic acid
PAMOIC ACID pure
Embonic acid
4,4'-Methylenedi(3-hydroxy-2-naphthoic Acid)
EINECS 204-998-0
MFCD00004079

Biological Activity

[Description]:

Pamoic acid is a potent GPR35 agonist with an EC50 of 79 nM. Pamoic acid exhibits neuroprotective and anti-inflammatory properties[1][2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Research Areas >> Neurological Disease

Signaling Pathways >> Stem Cell/Wnt >> ERK

[Target]

EC50: 79 nM (GPR35)[1]

[In Vitro]

GPR35 activation by Pamoic acid may increase the phosphorylation of ERK1/2, which in turn initiates an anti-inflammatory signal by suppressing NF-κB-dependent inflammatory genes[1].

[In Vivo]

In a mouse model of stroke, that GPR35 activation by Pamoic acid (s.c.; 50-100 mg/kg) is neuroprotective. Pharmacological inhibition of GPR35 reveals that Pamoic acid reduces infarcts size in a GPR35 dependent manner. Pamoic acid treatment results in a preferential increment of noninflammatory Ly-6CLo monocytes/macrophages in the ischemic brain along with the reduced neutrophil counts[1].

[References]

[1]. Ozayra Sharmin, et al. Activation of GPR35 protects against cerebral ischemia by recruiting monocyte-derived macrophages. Sci Rep. 2020 Jun 10;10(1):9400.

[2]. Pingwei Zhao, et al. Targeting of the orphan receptor GPR35 by pamoic acid: a potent activator of extracellular signal-regulated kinase and β-arrestin2 with antinociceptive activity. Mol Pharmacol. 2010 Oct;78(4):560-8.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
642.7±55.0 °C at 760 mmHg

[ Melting Point ]:
≥300 °C (dec.)

[ Molecular Formula ]:
C₂₃H₁₆O₆

[ Molecular Weight ]:
388.38

[ Flash Point ]:
356.5±28.0 °C

[ Exact Mass ]:
388.094696

[ PSA ]:
115.06000

[ LogP ]:
6.35

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.782

[ Water Solubility ]:
PRACTICALLY INSOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL2180000

CHEMICAL NAME :: 2-Naphthoic acid, 4,4'-methylenebis(3-hydroxy-

CAS REGISTRY NUMBER :: 130-85-8

BEILSTEIN REFERENCE NO. :: 0901319

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C23-H16-O6

MOLECULAR WEIGHT :: 388.39

WISWESSER LINE NOTATION :: L66J CQ DVQ B1- BL66J CQ DVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982

TYPE OF TEST :: Rinsed with water

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 390 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 13,381,1978

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
QL2180000

[ HS Code ]:
2917399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

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