130-85-8

Basic information

• Product Name: Pamoic acid
• Synonyms: PAMOIC ACID;EMBONIC ACID;EMBIONIC ACID;2,2'-DIHYDROXY-1,1'-DINAPHTHYLMETHANE 3,3'-DICARBOXYLIC ACID;4-[(3-CARBOXY-2-HYDROXY-NAPHTHALEN-1-YL)METHYL]-3-HYDROXY-NAPHTHALENE-2-CARBOXYLIC ACID;4,4'-METHYLENE BIS-(3-HYDROXY-2-NAPTHOIC ACID);4-4'-METHYLENE-BIS-[2-HYDROXY-3-NAPHTHOIC ACID];4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLIC ACID)
• CAS NO: 130-85-8
• Molecular Formula: C₂₃H₁₆O₆
• Molecular Weight: 388.37
• EINECS: 204-998-0
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Bioactive Small Molecules;Biochemicals and Reagents;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Cell Biology;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Lipids;Organic Building Blocks;P;Straight Chain Fatty Acids;Antiparasitic Agents
• Mol File: 130-85-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: ≥300 °C (dec.)
• Boiling Point: 434.1°C (rough estimate)
• Flash Point: 356.5ºC
• Appearance: Yellow to yellow-green/Crystalline Powder
• Density: 1.2472 (rough estimate)
• Vapor Pressure: 2.13E-17mmHg at 25°C
• Refractive Index: 1.4593 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in nitrobenzene, pyridine
• PKA: 2.67±0.30(Predicted)
• Water Solubility: PRACTICALLY INSOLUBLE
• Merck: 14,7005
• BRN: 901319
• CAS DataBase Reference: Pamoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Pamoic acid(130-85-8)
• EPA Substance Registry System: Pamoic acid(130-85-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-48-41-37/38-20/21/22
• Safety Statements: 26-36-45-36/37/39-22
• WGK Germany: 3
• RTECS: QL2180000
• TSCA: Yes
• Hazardous Substances Data: 130-85-8(Hazardous Substances Data)

Usage

Chemical Properties

Pamoic acid is yellow to yellow-green crystalline powder

Uses

Different sources of media describe the Uses of 130-85-8 differently. You can refer to the following data:
1. Agonist of the orphan G protein-coupled receptor GPR35: a potent activator of extracellular signal-regulated kinase and β-arrestin2 with antinociceptive activity. Used as an inhibitor in the real-time fluorescence enzymatic characterization study of specialized human DNA polymerases.
2. Pamoic acid is used in preparation of repository derivatives of medicinal agents, used in pharmacology to increase the solubility of a drug in water.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Safety Profile

Poison by intraperitoneal route. An eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/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)/p-2

Synthetic route

formaldehyd (50-00-0) + 3-Hydroxy-2-naphthoic acid (92-70-6) → Pamoic acid (130-85-8)

Conditions	Yield
With sulfuric acid In acetic acid for 10h; Heating;	95%
With sodium hydroxide
With sulfuric acid; acetic acid
With sodium hydroxide

formaldehyd (50-00-0) + acetic acid (64-19-7) + 3-Hydroxy-2-naphthoic acid (92-70-6) → Pamoic acid (130-85-8)

9-(3-Carboxy-2-hydroxy-naphthalen-1-ylmethyl)-2,4-dioxo-4H-1,3-dioxa-2λ5-phospha-anthracen-2-ol anion → Pamoic acid (130-85-8)

Conditions	Yield
With water at 40℃; Rate constant; var. pHs;

formaldehyd (50-00-0) + 3-Hydroxy-2-naphthoic acid (92-70-6) + alkali → Pamoic acid (130-85-8)

formaldehyd (50-00-0) + 3-Hydroxy-2-naphthoic acid (92-70-6) + acid solution → Pamoic acid (130-85-8)

formaldehyd (50-00-0) + 3-Hydroxy-2-naphthoic acid (92-70-6) + alkaline solution → Pamoic acid (130-85-8)

vortioxetine (508233-74-7) + Pamoic acid (130-85-8) → vortioxetine semi pamoic acid salt

Conditions	Yield
With acetic acid; sodium hydroxide In water at 20℃; for 2h;	100%

racemic bupivacaine (14252-80-3, 2180-92-9, 27262-45-9, 27262-47-1, 38396-39-3) + Pamoic acid (130-85-8) → bis(bupivacaine) pamoic acid

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Solvent;	99.6%
In methanol; acetone Heating;	39.6%

triethylamine (121-44-8) + Pamoic acid (130-85-8) → bis(triethylammonium) pamoate

Conditions	Yield
In water for 1h; pH=~ 8.5 - 9;	99%

pramipexole (104632-26-0) + Pamoic acid (130-85-8) → pramipexole pamoate

Conditions	Yield
In dimethyl sulfoxide; ethyl acetate at 20℃;	99%

zyprexa (132539-06-1) + Pamoic acid (130-85-8) → olanzapine pamoate monohydrate

Conditions	Yield
Stage #1: Pamoic acid With ammonium hydroxide In water Stage #2: zyprexa With hydrogenchloride; water at 25 - 30℃; Reagent/catalyst;	97%
Stage #1: zyprexa; Pamoic acid In dimethyl sulfoxide at 20 - 25℃; for 0.333333h; Stage #2: With water In dimethyl sulfoxide at 20 - 40℃; for 1.16667h;

impramine (50-49-7) + Pamoic acid (130-85-8) → imipramine pamoate

Conditions	Yield
In ethyl acetate at 20 - 50℃; Solvent; Temperature;	96%

racemic bupivacaine (14252-80-3, 2180-92-9, 27262-45-9, 27262-47-1, 38396-39-3) + Pamoic acid (130-85-8) → mono(bupivacaine) pamoic acid

Conditions	Yield
In methanol; acetone Heating;	90%
In methanol; acetone	90%

{(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (830346-49-1) + Pamoic acid (130-85-8) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 3-[2(R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4(1H,3H)-dione pamoic acid salt

Conditions

Yield

Stage #1: {(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester; (2-fluoro-3-methoxyphenyl)boronic acid With sodium carbonate In 1,4-dioxane; water for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 95 - 100℃; Inert atmosphere; Stage #3: Pamoic acid Further stages;

90%

7-amino-2,4-dimethyl-1,8-naphthyridine (39565-07-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + Pamoic acid (130-85-8) → C10H11N3*C23H16O6*C3H7NO

Conditions	Yield
In methanol at 20℃;	88.23%

Galantamine hydrobromide (1953-04-4, 98125-73-6) + Pamoic acid (130-85-8) → galantamine bishydroxynaphthoate

Conditions	Yield
Stage #1: Galantamine hydrobromide With sodium hydroxide In ethanol for 0.5h; Stage #2: Pamoic acid In dimethyl sulfoxide at 20℃; for 6h; Temperature; Solvent;	88.2%
In dimethyl sulfoxide at 25℃; for 6h; Solvent; Temperature;	78.55%

1-(8-bromopyrido[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)-N-methylazetidin-3-amine + Pamoic acid (130-85-8) → 1-(8-bromopyrido[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)-N-methylazetidin-3-amine 4,4'-methylenebis(3-hydroxy-2-naphthoic acid) salt

Conditions	Yield
In ethanol at 20℃; for 20h;	88%

(R)-(+)-tolterodine (124937-51-5) + Pamoic acid (130-85-8) → tolterodine palmoate

Conditions	Yield
In water at 20℃; for 4h; Temperature;	87.27%

3-[2(R)-{3-cyanopropylamino}-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione (832720-85-1) + Pamoic acid (130-85-8) → C32H29F5N4O3*C23H16O6

Conditions	Yield
In methanol at 60 - 65℃; for 3h;	87%

5-bromo-6-(imidazolin-2-ylamino)-quinoxaline (59803-98-4) + Pamoic acid (130-85-8) → brimonidine pamoate (1084892-10-3)

Conditions	Yield
In ethanol; dimethyl sulfoxide at 20 - 65℃; Product distribution / selectivity;	86%
In 1-methyl-pyrrolidin-2-one; water at 70℃; Product distribution / selectivity;
at 60 - 70℃; Product distribution / selectivity;

imipramine hydrochloride + triethylamine (121-44-8) + Pamoic acid (130-85-8) → imipramine pamoate mono-triethylammonium salt (1357157-28-8)

Conditions	Yield
In water for 3h;	86%

benzyl bromide (100-39-0) + Pamoic acid (130-85-8) → C51H40O6 (217327-71-4)

Conditions	Yield
With potassium carbonate	85%

tapentadol (175591-23-8) + Pamoic acid (130-85-8) → tapentadol hemiembonate

Conditions	Yield
In ethanol for 1h;	83.3%

4-methyl-1,3-benzothiazol-2-amine (1477-42-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + Pamoic acid (130-85-8) → 4C8H8N2S*2C23H16O6*4C3H7NO

Conditions	Yield
In ethanol at 20℃;	80.42%

Ropinirole (91374-21-9) + Pamoic acid (130-85-8) → ropinirole pamoate

Conditions	Yield
In water; dimethyl sulfoxide at 20℃;	80.4%

titanium(IV) isopropylate (546-68-9) + propan-1-ol (71-23-8) + ethylenediamine (107-15-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + Pamoic acid (130-85-8) → (Me2NH2)8[(Ti4(embonate)6)]·4(n-propanol)·2(ethylenediamine)·6(N,N-dimethylformamide)

Conditions	Yield
at 100℃; for 72h; High pressure;	78%

rotigotine (99755-59-6) + Pamoic acid (130-85-8) → rotigotine pamoate

Conditions	Yield
In water; dimethyl sulfoxide at 20℃;	77.4%

Upstream product

• 50-00-0 formaldehyd 
• 64-19-7 acetic acid 
• 92-70-6 3-Hydroxy-2-naphthoic acid 

Downstream Products

• 27757-79-5 3-hydroxy-4-phenylazo-[2]naphthoic acid 
• 217327-71-4 C₅₁H₄₀O₆ 
• 68902-24-9 1-methyl-2-hydroxy-3-naphthoic acid 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 221373-18-8 olanzapine pamoate monohydrate 
• 1357157-24-4 D-methylphenidate mono-triethylammonium pamoate 
• 10075-24-8 imipramine pamoate 
• 1221273-08-0 [Cd(pamoic acid(2-))(1,10-phenanthroline)(H2O)]n 

Related news

Development and evaluation of a 68Ga labeled Pamoic acid (cas 130-85-8) derivative for in vivo visualization of necrosis using positron emission tomography09/29/2019

In this study, we labeled N,N′-bis(diethylenetriamine pentaacetic acid)-pamoic acid bis-hydrazide (bis-DTPA-PA) with the generator produced PET radionuclide gallium-68 and evaluated 68 Ga-bis-DTPA-PA as a potential tracer for in vivo visualization of necrosis by positron emission tomogr...detailed

Construction of Two New Metal–Organic Frameworks from Pamoic acid (cas 130-85-8) and N-Containing Auxiliary Ligands09/28/2019

Two new metal–organic frameworks; namely, [Cd2(pam)2(bpe)1.5(DMF)2(H2O)] n ·2n(DMF) (1) and [Cd(pam)(bix)] n (2) (H2pam = pamoic acid, bpe = 1,2-di(4-pyridyl)ethylene, bix = 4,4′-bis(imidazol-1-ylmethyl)benzene, DMF = N,N′-dimethylformamide), were solvothermally synthesized via varying the ...detailed

Hydrothermal synthesis of tin-doped indium oxide nanoparticles using Pamoic acid (cas 130-85-8) as an organic additive and their photoluminescence properties10/01/2019

We report a facile hydrothermal method using the disodium salt of pamoic acid (Na2PA) as an organic additive, In(NO3)3·xH2O as an indium precursor, and SnCl2·2H2O as a tin precursor for preparation of ITO nanoparticles (NPs) at low temperature (200 °C). After drying at 110 °C, the as hydroth...detailed

Relevant articles and documents

Synthesis of dihomocalix[4]naphthalenes: First members of a new class of [1.2.1.2](1,3)naphthalenophanes

-

ALKYLENEBISNAPHTOL DERIVATIVES AND CHARGE CONTROL AGENT COMPRISING THE SAME

The present invention provides an alkylenebisnaphthol derivative represented by formula [I]: and a salt thereof. The compound of the present invention has an excellent triboelectric charge property and useful as charge control agent for electrophotographic toners.

Participation of two carboxyl groups in phosphodiester hydrolysis. 2. A kinetic, isotopic, and 31P NMR study of the hydrolysis of a phosphodiester with carboxyl groups fixed in an attack conformation

The phosphodiesters of 4,4′-methylenebis(3-hydroxy-2-naphthoic acid) (4) and 3-carboxy-2,2′-dihydroxydiphenylmethane (5) are constrained into a cyclic structure such that the oxygens of the two o-carboxy groups of 4 and the single o-carboxy group of 5 have restricted stereospecific positions with an o-CO2- oxygen to phosphorus distance of 3.7 ?. In the hydrolysis of 4, 31P NMR and HPLC data show the existence of an intermediate cyclic acyl phosphate in the g,g conformation. The 18O isotopic effects on 31P chemical shifts show incorporation of two 18O atoms in the product H3PO4. This observation is consistent with intramolecular o-CO2- nucleophilic attack on phosphorus to provide an acyl phosphate intermediate which undergoes hydrolytic cleavage by HO-/H18O- attack on phosphorus {one 18O incorporation} to provide a phosphate monoester which also undergoes hydrolysis with a second 18O incorporation on phosphorus. For hydrolysis of 4, the pH vs log kobsd profile, the values of the deuterium solvent kinetic isotope effect, and the activation entropy accord a mechanism which involves intramolecular attack of o-CO2- on the phosphate phosphorus assisted by the o-CO2H as a general acid catalyst. The latter can involve o-CO2H hydrogen bonding to the -(PO2-)- oxygen(s) and/or leaving phenolic oxygen. At neutrality, 4 hydrolyzes ca. 104 fold faster than 5 which only has one o-carboxy group and 108-109-fold faster than diphenyl phosphate.