Disodium pamoate monohydrate - ≥98% , CAS No.71607-30-2

CAS: 71607-30-2 Cat. No.: D972265 PubChem CID: 54678147

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Room temperature

Pureté

≥98%

Noms et identifiants

• Sourires canoniques: C1=CC=C2C(=C1)C=C(C(=C2CC3=C(C(=CC4=CC=CC=C43)C(=O)O)[O-])[O-])C(=O)O.O.[Na+].[Na+]
• IUPAC Name: disodium;3-carboxy-1-[(3-carboxy-2-oxidonaphthalen-1-yl)methyl]naphthalen-2-olate;hydrate
• InChIKey: DNQSGXVJKQBSMT-UHFFFAOYSA-L
• INCHI: 1S/C23H16O6.2Na.H2O/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);;;1H2/q;2*+1;/p-2
• Isomères SMILES: C1=CC=C2C(=C1)C=C(C(=C2CC3=C(C(=CC4=CC=CC=C43)C(=O)O)[O-])[O-])C(=O)O.O.[Na+].[Na+]
• CAS alternatif: 71607-30-2
• PubChem CID: 54678147

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Naphthalenes
      • Subclass Naphthalenecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Naphthalenes
• Subclass: Naphthalenecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthalenecarboxylic acids
• Alternative Parents: Naphthols and derivatives Salicylic acid and derivatives Dicarboxylic acids and derivatives Vinylogous acids Carboxylic acid salts Carboxylic acids Organooxygen compounds Organic sodium salts Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: 2-naphthalenecarboxylic acid - 2-naphthol - Hydroxybenzoic acid - Salicylic acid or derivatives - Dicarboxylic acid or derivatives - Vinylogous acid - Carboxylic acid salt - Carboxylic acid derivative - Carboxylic acid - Organic alkali metal salt - Organic oxygen compound - Organooxygen compound - Organic salt - Organic sodium salt - Hydrocarbon derivative - Organic oxide - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthalenecarboxylic acids. These are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Poids moléculaire: 450.300 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 450.069 Da
• Monoisotopic Mass: 450.069 Da
• Topological Polar Surface Area: 122.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 568.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 4

XLogP3

Application Protocols

Catalog-tested applications and conditions: Not specified for this item; refer to CoA/Spec Sheet.

General protocol example (research use only; adapt as needed):

• Preparation of a pamoate salt of a secondary amine
  1. Dissolve the amine in ethanol and add equimolar HCl in ethanol to form the ammonium salt (monitor by pH/conductivity).
  2. In a separate vessel, suspend/disperse disodium pamoate monohydrate in warm water/ethanol (1:1); stir to a fine suspension or partial solution.
  3. Slowly add the ammonium solution to the pamoate dispersion at 25–35 °C. Maintain pH 4–6.
  4. Seed if necessary; then cool to 5–10 °C to complete crystallization. Age 2–12 h.
  5. Filter, wash with cold ethanol/water (3:1), and dry under vacuum at ≤40 °C.
  6. Characterize by XRPD, DSC/TGA (hydrate state), and NMR/IR to confirm salt identity.

Note: This is illustrative literature-style guidance and not a specification for this catalog item.

Biological Roles

Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.

General context (non-clinical, literature-based):

• Pamoate (embonate) anion is not an endogenous metabolite. It is used in formulation science as a counter‑ion to modulate the solubility and solid‑state properties of cationic molecules, including in research formulations and model systems.
• Interaction profile: The large hydrophobic surface and dianionic charge support strong ionic pairing with protonated amines and can promote formation of dense, sparingly soluble lattices. No specific receptor or enzymatic roles are recognized.
• Biocompatibility considerations: As with many aromatic carboxylates, biocompatibility depends on dose, counter‑ion, and formulation; evaluation is application-specific in preclinical settings.

Reminder: This product is for research use only. No medical, diagnostic, or therapeutic claims are made.

Buffer Applications

Disodium pamoate monohydrate is not typically used as a buffering agent. While it contains carboxylate groups, its low aqueous solubility and strong tendency to form sparingly soluble salts with cationic species make it unsuitable for conventional buffer systems.

For buffer preparation needs, consider standard buffers (general guidance):

• Citrate, phosphate, acetate, HEPES, Tris — chosen based on desired pH range, ionic strength, and compatibility.

For this item, focus instead on sections detailing salt formation and crystallization behavior (see Reaction & Applications and Synthetic Utility).

Green Alternatives

Context: Disodium pamoate is selected primarily for its ability to form poorly water‑soluble salts with cationic species. From a green chemistry perspective, alternatives aim to reduce hazardous solvents and improve lifecycle impacts while achieving similar performance.

Alternative counter‑ions (literature/general):

• Citrate, tartrate, malate (biogenic dicarboxylates): Renewable origin, often better aqueous processing. Tradeoff: typically produce more water‑soluble salts, reducing utility for controlled precipitation or sustained release.
• Terephthalate/adipate: Provide crystallinity and tunable solubility; may be less hydrophobic than pamoate, potentially increasing solubility.
• p‑Toluenesulfonate (tosylate)/mesylate: Good crystallinity and processability; not biogenic; can increase hygroscopicity.

Greener solvent systems for processing pamoates:

• Favor water/ethanol or water/iso‑propanol over chlorinated or high‑boiling aprotics. Use anti‑solvent crystallization to minimize solvent volumes.

Comparison table (qualitative):

• Pamoate: very low salt solubility; strong crystallization; aromatic, non-renewable.
• Citrate/tartrate: greener origin; higher salt solubility; may hinder isolation by precipitation.
• Adipate: intermediate properties; moderate greenness.

Practical guidance:

• If the goal is salt screening, include greener diacids in the panel and evaluate process metrics (PMI, solvent recyclability, mother liquor treatability) alongside physicochemical performance.

Pharmaceutical Uses

Item-specific pharmacopeial status/grade: Not specified for this item; refer to CoA/Spec Sheet.

General formulation context (no therapeutic claims):

• Counter‑ion for salt forms: Pamoate (embonate) is widely used in R&D to form salt versions of basic APIs, primarily to adjust solid‑state properties (crystallinity, polymorph control) and reduce aqueous solubility, which can be leveraged for depot or sustained‑release characteristics in research formulations.
• Manufacturing implications:
  • Enables precipitation/crystallization of target amine bases from mixed solvent systems for purification and isolation.
  • The hydrate state (e.g., monohydrate) can influence flowability, compressibility, and stability during downstream processing.
  • Solid-state characterization (XRPD, DSC, TGA) is essential to define polymorph and hydrate forms.
• Excipient considerations: Disodium pamoate can act as a reagent in salt selection studies; however, in regulated contexts, excipient-grade material and compliance with relevant compendia (if applicable) would be required.

Note: This catalog item is for research use only. For any formulation development beyond research scale, confirm excipient compliance and quality attributes via the CoA and regulatory guidance.

Physical Properties

Item-specific properties (from Product Data):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.

Storage/shipping (from Product Data):

• Recommended storage: Room temperature.

General/literature expectations (non-spec):

• Physical state: Typically an off-white to yellowish crystalline solid for many pamoate salts; hydrates are common (monohydrate in this item’s name).
• Solubility (qualitative): Pamoate salts are generally hydrophobic; the disodium pamoate form may display limited water solubility at neutral pH and increased solubility in basic aqueous media due to carboxylate formation. Solubility can improve in polar protic solvents or water/ethanol mixtures; conversely, it is usually poorly soluble in nonpolar solvents.
• Thermal behavior: Aromatic polycarboxylates often show high decomposition on heating rather than a sharp melting point; hydrates may lose water upon drying or heating.
• Partitioning: The hydrophobic aromatic core drives strong π–π stacking in the solid state; despite ionic sodium counterions, solutions often exhibit aggregation at higher concentrations.

Important: Do not treat the above as catalog specifications. For exact values (mp, water content, Na content, solubility limits, refractive index, etc.), consult the CoA/Spec Sheet for this lot.

Quality and Grades

Item-specific grade/purity (from Product Data):

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and considerations (general):

• Without an explicit grade (e.g., analytical, bio‑reagent, or excipient grade), the material should be treated as a research-grade reagent suitable for laboratory R&D.
• For applications sensitive to trace inorganic ions or water content (hydrate state), review the CoA for:
  • Assay (on anhydrous basis vs as-is)
  • Residual solvents and loss on drying (LOD)
  • Sodium content/stoichiometry (confirming disodium monohydrate form)
  • Heavy metals/elemental impurities (if applicable to your workflow)
  • Bioburden/endotoxin (only if relevant; often not specified for research reagents)
• If your use case involves salt screening or formulation development, verify:
  • Hydration state control: Monohydrate vs anhydrate can impact crystallinity and solubility.
  • Particle size distribution: Influences filtration, dissolution, and crystallization kinetics.
  • Residual moisture: Affects accurate stoichiometry in salt metathesis experiments.

Documentation:

• Request the CoA/Spec Sheet for lot-specific quality attributes, recommended test methods, and acceptance criteria aligned to your application.

Reaction and Applications

Primary laboratory application (general):

• Counter‑anion for salt formation: Disodium pamoate is widely used to prepare pamoate (embonate) salts of basic amines and APIs to modulate solubility, crystallinity, and release properties. The hydrophobic, rigid dianion favors low aqueous solubility of the resulting salts, facilitating isolation and purification.

Use cases in R&D and process chemistry:

• Salt screening: Pair with candidate amines under controlled pH to assess saltability, polymorphism, and solid‑state properties (HSM/DSC, XRPD).
• Crystallization aid: The bulky aromatic dianion promotes crystallinity; selective precipitation can separate target amines from impurities.
• Ion‑pair extraction: Formation of sparingly soluble pamoate salts can transfer cationic species between phases for purification.

Procedural notes (literature-informed):

• Generate the cation (RNH3+) by protonating the amine (e.g., with HCl). Combine with an aqueous solution/suspension of disodium pamoate; adjust pH to ~4–6 to avoid free acid precipitation while maintaining amine protonation. Monitor conductivity/pH.
• Solvent systems: Water/ethanol or water/acetone are commonly effective; seed to control polymorph; age the slurry to complete ripening.
• Filtration/washing: Use cold solvent blends with low pamoate solubility to maximize yield and purity.
• Characterization: Confirm stoichiometry (often 1:1 dianion to diamine or 2:1 to monocation), assess hydrate state by TGA/LOD, and verify crystallinity by XRPD.

Note: The above are general guidelines; tailor to your substrate’s pKa, solubility, and polymorph behavior.

Reaction Conditions

General guidance for forming pamoate salts (literature-informed; not item specifications):

• Substrate preparation: Convert amine to its conjugate acid (e.g., with HCl or acetic acid) to ensure high cation concentration.
• Pamoate source: Use disodium pamoate monohydrate as an aqueous or hydroalcoholic solution/suspension.
• Solvents: Water/ethanol or water/acetone blends are common. DMSO or DMF can aid dissolution if needed, followed by anti‑solvent addition to induce crystallization.
• pH control: Target mildly acidic conditions (approx. pH 4–6) to keep the amine protonated yet avoid excessive protonation of the pamoate that may cause free acid precipitation.
• Temperature: 20–40 °C typical for dissolution and mixing; cool slowly to promote controlled crystallization. Aging the slurry (1–16 h) can improve crystal quality.
• Stoichiometry: 1 equivalent pamoate dianion per dication, or 0.5 equivalents per monocation when forming 2:1 salts. Verify by elemental analysis or NMR.
• Isolation: Filter, wash with cold anti‑solvent (e.g., ethanol/ether or aqueous acetone), and dry under reduced pressure. Monitor LOD/TGA to confirm hydrate level.

Expected outcomes:

• Yields: Often high for well‑behaved amines due to low solubility of the pamoate salt; polymorph/hydrate diversity may affect apparent yield and filtration rate.

Always optimize to the specific amine’s pKa, solubility, and desired solid form.

Safety and Handling

Item-specific hazard data (from Product Data):

• Signal Word: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• H-Statements / Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance (not a substitute for SDS):

• Primary hazards (typical for organic salts): May cause eye, skin, or respiratory irritation as a particulate; dust may be nuisance dust—avoid inhalation. Not known as a strong oxidizer/reducer.
• PPE: Safety glasses, lab coat, appropriate gloves (e.g., nitrile). Use a dust mask or work in a fume hood when weighing fine powders.
• Handling: Minimize dust generation. Avoid contact with strong acids (can liberate the free diacid) and strong oxidizers. Keep containers tightly closed to avoid moisture uptake or loss of waters of crystallization.
• First aid (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses; seek medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spills: Avoid raising dust. Sweep with minimal disturbance; place in appropriate container for disposal per local regulations.
• Fire: Combustible organic solid; use water spray, CO2, dry chemical, or foam. Combustion may produce irritating fumes (CO/CO2, aromatic fragments).

Always consult the product’s SDS for authoritative hazard classification and response measures.

Solvent Selection

Context: Disodium pamoate monohydrate is an ionic organic salt with a large hydrophobic aromatic core and carboxylate groups coordinated to Na+.

General solvent behavior (literature-based, non-spec):

• Water: Limited solubility at neutral pH is common for pamoates; solubility may increase in basic aqueous media (pH > 9) due to full carboxylate deprotonation and disruption of π–π interactions.
• Alcohols: Methanol/ethanol can aid wetting and partial dissolution; water–alcohol blends may be optimal for salt metathesis or recrystallization steps.
• Polar aprotic (DMSO, DMF): Often dissolve aromatic dicarboxylate salts more effectively, especially with small water content. Use judiciously for processing due to toxicity and removal challenges.
• Nonpolar solvents (toluene, hexanes): Generally poor solubility; can be used as anti-solvents to precipitate pamoate salts.

Practical selection tips:

• For preparing other pamoate salts via metathesis with protonated amines, use aqueous ethanol or water/acetone systems to balance solubility of the amine and controlled precipitation of the pamoate salt.
• To make stock solutions for analytical work, start with DMSO or basic aqueous (e.g., dilute NaOH) and back‑titrate if needed.

Comparison (qualitative):

• Water (neutral) – lowest dissolution; Water (basic) – improved; Alcohol–water – tunable; DMSO/DMF – highest dissolution; Nonpolar – precipitating/anti‑solvent.

Storage and Reconstitution

Item-specific storage (from Product Data):

• Storage Conditions: Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General storage advice for aromatic dicarboxylate salts (non-spec):

• Store in a tightly sealed container, protected from excessive humidity to maintain the monohydrate state. If exact hydration is critical, record loss on drying before use.
• Avoid prolonged exposure to strong acids/bases in storage; segregate from strong oxidizers.

Reconstitution and solution prep (general guidance):

• For aqueous work: Begin with warm water or mildly basic aqueous (e.g., dilute NaOH) to aid dissolution; adjust pH as required after dissolution.
• For mixed solvents: Water/ethanol or water/acetone blends enhance wetting and dispersion. For maximum solubility, small amounts of DMSO can be used, then diluted with water or alcohol while monitoring for precipitation.
• Filter solutions through 0.45 µm if particulate persists.

Stability:

• Solid is generally stable at ambient conditions; avoid temperatures that could induce dehydration or discoloration. Prepare fresh solutions for reproducible results.

Always consult the product CoA/SDS for lot-specific handling and stability details.

Structure and Identity

Brief overview: Disodium pamoate monohydrate is the disodium salt (monohydrate) of pamoic (embonic) acid, a rigid, polyaromatic diacid commonly used as a hydrophobic counter‑anion for forming poorly water‑soluble salts of basic compounds.

Item-specific identifiers (from Product Data):

• Product Name: Disodium pamoate monohydrate (SKU: D972265)
• CAS: 71607-30-2
• InChIKey: 68152 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature description):

• Backbone: Derived from pamoic (embonic) acid, structurally related to a methylene-bridged binaphthyl-like diacid featuring two naphthalene rings connected through a central methylene carbon.
• Functional groups: Two carboxylate groups (as disodium salts) and two phenolic oxygens; extensive conjugated aromatic system.
• Ionic state: Disodium salt of a dianionic dicarboxylate; supplied as a monohydrate (per item name).
• 2D description in words: Two naphthalene systems para to a central –CH2– bridge; each naphthalene bears a carboxylate and a phenolic substituent in positions consistent with 3‑hydroxy‑2‑naphthoate units; overall dianion charge balanced by two Na+ and one equivalent of waters of crystallization.

Notes:

• The exact stereochemistry is not applicable (achiral polyaromatic). For canonical identifiers (SMILES/InChI), consult the CoA/SDS for this catalog item.

Synthetic Utility

Role in synthesis (general):

• Salt metathesis reagent: Disodium pamoate serves as a dianionic partner to form pamoate salts of protonated amines, diamines, and quaternary ammonium species. The resulting salts often crystallize readily, enabling purification and isolation.
• Solid‑state engineering: The rigid, polyaromatic framework encourages π–π stacking and robust lattice energies, making it useful in crystallization‑driven separations and in probing supramolecular interactions.

Applications and strategies:

• Resolution/purification: Convert a basic substrate to its pamoate salt to remove neutral or weakly basic impurities by filtration; subsequently revert to the free base if desired by basification and extraction.
• Polymorph screening: Evaluate solvent systems and seeding to obtain distinct hydrates/solvates; characterize by XRPD and thermal methods.
• Stoichiometry control: Match cation charge with the dianion (e.g., 1:1 with dications, 2:1 with monocations) to direct crystallization behavior.

Practical notes:

• Prepare a clear solution or fine suspension of disodium pamoate in water/alcohol, then add the protonated amine under stirring. Control temperature (often ambient to 40 °C) and pH to prevent free diacid precipitation while ensuring full cation formation.
• Wash isolated solids with cold, low‑solubility solvent mixtures to maximize purity; dry under vacuum at mild temperatures to maintain the desired hydrate state.

Target Specificity

Not applicable. Disodium pamoate monohydrate is a small‑molecule inorganic–organic salt used for chemical and formulation purposes and does not possess biological target specificity such as an antibody, enzyme inhibitor, or ligand. Refer to Reaction & Applications and Synthetic Utility for relevant use cases.