Zinc caproate , CAS No.20779-08-2

CAS: 20779-08-2 Cat. No.: Z951836 Formula: C₁₂H₂₂O₄Zn Peso molecolare: 295.700

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CCCCCC(=O)[O-].CCCCCC(=O)[O-].[Zn+2]
• IUPAC Name: zinc;hexanoate
• InChIKey: PKJOUIVGCFHFTK-UHFFFAOYSA-L
• INCHI: 1S/2C6H12O2.Zn/c2*1-2-3-4-5-6(7)8;/h2*2-5H2,1H3,(H,7,8);/q;;+2/p-2
• Peso molecolare: 295.700

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Medium-chain fatty acids
• Alternative Parents: Straight chain fatty acids Carboxylic acid salts Organic transition metal salts Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic cations
• Molecular Framework: Not available
• Substituents: Medium-chain fatty acid - Straight chain fatty acid - Carboxylic acid salt - Organic transition metal salt - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organooxygen compound - Carbonyl group - Organic cation - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 295.700 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 294.081 Da
• Monoisotopic Mass: 294.081 Da
• Topological Polar Surface Area: 80.300 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 63.400
• 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: 3

XLogP3

Application Protocols

No validated bioassay protocols (WB, IHC, IF, FC, etc.) are associated with this small-molecule reagent.

General laboratory usage suggestions (non-validated; literature-informed):

• Preparing a catalytic solution: Dissolve the required mmol of zinc caproate in hot ethanol or isopropanol with stirring; cool to use. If solubility is limited, add a small amount of acetic acid or chelating ligand to aid dissolution.
• Coating/precursor solutions: Prepare 0.01–0.2 M solutions in 2-propanol or acetone; filter (0.45 µm PTFE) before deposition.

For any critical application, develop and document an internal SOP and confirm performance with small-scale trials.

Biological Roles

This product is supplied strictly for research use. No medical or clinical claims are made.

General biochemical context (literature; not specific to this product):

• Zinc(II) is an essential trace element and Lewis-acid cofactor in numerous enzymes (e.g., carbonic anhydrase, alcohol dehydrogenase, zinc finger transcription factors). In biological systems, Zn2+ is tightly regulated and typically coordinated by histidine/cysteine residues.
• Caproate (hexanoate) is a medium-chain fatty acid that can arise in lipid metabolism and microbial fermentation; its CoA thioester can enter β-oxidation.

Relevance to lab studies:

• As a model organozinc salt in organic media, zinc caproate can be used to study Zn2+ coordination to carboxylates and hydrophobic interactions, or as a non-aqueous zinc source in materials/biomaterials research. Any biological testing should ensure appropriate controls for zinc and fatty-acid effects.

Note: For biological experiments, buffer compatibility and solubility must be empirically established; hydrolysis in aqueous media can liberate hexanoic acid, affecting pH and membrane interactions.

Buffer Applications

Zinc caproate is not a buffering agent and is not typically used to prepare defined pH buffer systems.

• If aqueous use is attempted, hydrolysis and limited solubility may occur, and liberated hexanoic acid can acidify the medium. Choose standard buffer systems (e.g., phosphate, HEPES, Tris) for pH control and add zinc species separately if needed (e.g., zinc acetate/chloride for aqueous compatibility).

Green Alternatives

Green chemistry considerations involve solvent choice, metal content management, and energy efficiency. The compound itself is a zinc carboxylate; greener strategies often compare counterions, ligands, or processing conditions (literature-based guidance).

• Alternative zinc sources:
  • Zinc acetate: More water-soluble—enables aqueous or water-lean processes; easier wastewater treatment but less compatible with hydrophobic matrices.
  • Zinc stearate: More hydrophobic—often functions at lower loadings in nonpolar systems but can be harder to remove and less soluble.
• Alternative catalysts: Organic acids or enzyme catalysts (lipases) can replace metal carboxylates for some esterifications at ambient conditions, reducing metal waste but possibly increasing cost/time.
• Solvent choices (preferable where feasible):
  • Replace chlorinated/aromatic solvents with bio-based alcohols (EtOH, i-PrOH) or esters (EtOAc). 2-MeTHF and CPME can offer performance similar to toluene with better EHS profiles.

Comparison snapshot (general):

• Zinc caproate vs zinc acetate in esterification
  • Solubility in organic media: caproate higher; acetate lower.
  • Aqueous processing/waste: acetate preferable.
  • Odor/VOC from liberated acid: caproate (C6) has moderate fatty-acid odor; acetate milder.

Operational levers: lower catalyst loading, continuous water removal (energy-efficient azeotropy), and solvent recycling to lessen environmental impact.

Pharmaceutical Uses

No pharmacopeial grade or excipient status is provided for this item. This product is for research use only.

General context (literature; not product-specific and not a therapeutic claim):

• Metal soaps such as zinc stearate are used industrially as lubricants/glidants in tablet manufacture; zinc caproate is less common due to chain length/solubility balance.
• Potential research roles include: organophilic zinc source in nonaqueous formulations, catalyst for synthesis of excipient esters, or precursor for ZnO in topical formulation research (materials focus).

Regulatory note: For any GMP or clinical application, only pharmacopeial-listed excipients and validated grades should be considered. This SKU provides no such designation; consult relevant pharmacopeias and quality standards.

Physical Properties

Item-specific physico-chemical specifications are not provided in the Product Data for this SKU. Where helpful, general literature values are summarized for context (not product specifications; verify via CoA/SDS).

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Literature: white to off-white solid/powder typical of zinc carboxylates.)
• Melting behavior: Not specified for this item; refer to CoA/Spec Sheet. (Literature: many zinc Cn carboxylates show softening/melting with possible decomposition in the ~120–180 °C range, depending on chain length and structure.)
• Boiling point: Not applicable; metal carboxylates decompose before boiling (literature).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative, literature):
  • Water: low to very low solubility expected for mid-chain zinc carboxylates.
  • Organic: better solubility in alcohols (MeOH, EtOH, i-PrOH), polar aprotic solvents (e.g., acetone), and chlorinated solvents; limited in alkanes and aromatics unless modified/chelated.
• Partitioning/logP: Not routinely defined for ionic coordination aggregates; effective hydrophobic character increases with the C6 chains (literature qualitative note).
• Refractive index: Not applicable to solids; Not specified for this item.

Practical notes (general): Finely dividing the solid and gentle warming/sonication can aid dissolution in alcohols or ketones. Trace water can improve wetting but may change coordination state.

Quality and Grades

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

Guidance on grades (general, for context):

• Analytical/Reagent grade zinc salts emphasize low inorganic/metal impurities; metal carboxylates may also specify acid value, free acid content, and loss on drying.
• For catalysis or materials synthesis, parameters of interest often include: residual free hexanoic acid, basicity/neutralization number, water content (Karl Fischer), and trace metals (Fe, Cu, Ni) that can affect polymerization or color.
• For spectroscopic or electronic applications, ash content and organic residue profile may be specified to ensure clean thermal conversion to ZnO/Zn-containing films.

Stabilizers/additives: None are indicated in the Product Data. If present in a specific lot, they would be listed on the CoA.

Recommendation: Consult the lot-specific CoA for assay, acid value, loss on drying, and impurity profile relevant to your application (polymer catalysis, coatings drier, precursor for ZnO, etc.).

Reaction and Applications

While no Manufacturer Applications are provided for this SKU, zinc carboxylates (including zinc caproate) have well-documented roles in synthesis and materials science (literature, for context):

• Lewis-acid catalysis: Promotes esterification and transesterification, often at 0.1–5 mol% Zn, enabling polyester formation and small-molecule ester synthesis. The hydrophobic C6 chains can enhance solubility in organic-rich matrices compared to acetate.
• Ring-opening polymerization (ROP): Zinc carboxylates can catalyze ROP of lactones and related monomers to polyesters under melt or bulk conditions.
• Urethane/epoxy systems: Functions as an additive/catalyst in polyurethane curing and epoxy esterification studies (mechanism: coordination to carbonyl or isocyanate increasing electrophilicity).
• Precursor to zinc oxide (ZnO): Thermal decomposition of zinc carboxylates yields ZnO; caproate offers intermediate volatility/organic content, useful for films or nanoparticle generation.
• Metal–organic frameworks (MOFs) and coordination polymers: Serves as a zinc(II) source with a carboxylate ligand; can participate directly or via ligand exchange to assemble Zn–O carboxylate nodes.

Practical tips:

• Drying: If water-sensitive processes are intended, dry the reagent in vacuo at modest temperature to minimize adsorbed moisture.
• Ligand exchange: Adding a small excess of the target carboxylic acid or chelating donor can tune solubility and catalytic activity.
• Byproduct control: In esterifications, remove water continuously (Dean–Stark or molecular sieves) to drive conversion.

Reaction Conditions

Illustrative conditions from the literature (general guidance; not product specifications):

• Esterification/transesterification:

  • Catalyst loading: 0.1–5 mol% Zn relative to carbonyl substrate.
  • Solvent: neat alcohol; or toluene/xylene with Dean–Stark to remove water.
  • Temperature: 70–140 °C depending on substrate volatility.
  • Notes: Continuous water removal increases rates; small amounts of added carboxylic acid can modulate catalyst speciation and solubility.

• Ring-opening polymerization of lactones (e.g., ε-caprolactone):

  • Catalyst: zinc carboxylate (including C6) with an alcohol initiator.
  • Conditions: bulk or solution; 80–140 °C; inert atmosphere; time 2–24 h to desired Mn.
  • Notes: Control via [M]/[I] ratio and temperature; avoid moisture for better control.

• ZnO precursor processing:

  • Dissolve in alcohol/ketone; deposit by spin/dip/print; dry; calcine 300–500 °C in air to convert to ZnO.
  • Byproducts: CO2, volatile organics; ramp rates influence film morphology.

Always verify solubility and optimize loading for the specific substrate set. Monitor reactions by GC/GC–MS, NMR, or GPC (for polymers).

Safety and Handling

Authoritative safety information resides in the SDS for this product. The Product Data do not list GHS classifications or hazard statements for this SKU.

• GHS/CLP: Not specified for this item; refer to SDS.
• Signal word / H- and P-statements: Not specified for this item; refer to SDS.

General safety considerations for zinc carboxylates (literature-based; not product-specific):

• Hazards: May cause skin/eye irritation; harmful if swallowed in quantity; zinc compounds are toxic to aquatic life with long-lasting effects—avoid environmental release.
• Incompatibilities: Strong acids (liberates hexanoic acid), strong oxidizers. Thermal decomposition can release irritating fumes (e.g., zinc oxides, organic fragments).
• Peroxide formation: Not applicable (no ether functionality).
• PPE: Laboratory coat, safety glasses, appropriate gloves (e.g., nitrile). Use dust control (avoid inhalation of particulates). Work in a fume hood when heating or preparing concentrated solutions.
• First aid (overview):
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/Disposal: Avoid release to the environment; collect solids by sweeping with minimal dust; dispose of in accordance with local regulations for heavy metal-containing waste.

Solvent Selection

Zinc caproate is a solid reagent/coordination compound; solvent choice is primarily about preparing homogeneous solutions or slurries for catalysis, coatings, or precursor processing.

General miscibility/solubility tendencies (literature, qualitative):

• Better solubility in polar protic and moderately polar aprotic solvents: methanol, ethanol, isopropanol, n-butanol; acetone and methyl ethyl ketone can also be effective.
• Limited solubility in nonpolar alkanes and aromatics; solubility may be improved with co-solvents or by adding small amounts of coordinating ligands (e.g., pyridine) or carboxylic acid to form basic/neutral complexes.
• Water solubility is generally low for mid-chain zinc carboxylates.

Selection tips by application:

• Catalysis (esterification/transesterification): alcohol substrates as both reactant and solvent; toluene or xylene as azeotroping solvent with Dean–Stark where water removal is required.
• Coatings/drier research: oxygenated solvents (alcohols, esters, ketones) to ensure dissolution and uniform film formation.
• Precursor routes to ZnO/MOFs: polar aprotic solvents (DMF, DMAc) or alcohols aid dissolution/ligand exchange; consider coordinating additives if needed.

Small comparison (literature):

• Zinc caproate vs zinc acetate: acetate is more water-soluble (better for aqueous systems); caproate is more organophilic (better for organic media/coatings).

Storage and Reconstitution

• Storage conditions: Room temperature (per Product Data). Protect from excessive humidity and direct sunlight. Keep container tightly closed.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Stability: Not specified for this item; refer to CoA/Spec Sheet. (General: stable under dry, ambient conditions; prolonged exposure to moisture/acids can alter composition.)

Reconstitution/preparation notes (general):

• To prepare solutions, use dry alcohols (MeOH, EtOH, i-PrOH) or ketones (acetone, MEK). Gentle warming and sonication can assist dissolution. If needed, a small amount of compatible acid (e.g., hexanoic/acetic acid) or donor ligand can adjust speciation and solubility.
• For aqueous dispersions, expect limited solubility; pH and ionic strength may influence hydrolysis and aggregation.

Freeze–thaw: Not applicable to solids. If preparing stock solutions, store in airtight containers under inert gas to limit moisture uptake; avoid repeated freeze–thaw by aliquoting.

Research use note: For research use only.

Structure and Identity

Zinc caproate is the zinc(II) salt of caproic (hexanoic) acid, typically formulated as the dialkanoate Zn(OOCC5H11)2.

• SKU: Z951836
• Product name: Zinc caproate
• CAS: 20779-08-2
• CID: 6432226
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists: 279738)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature for zinc dihexanoate: C12H22O4Zn)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature for zinc dihexanoate: ~295.7 g/mol)

Structural features (general description; literature):

• Metal carboxylate (“metal soap”) consisting of a Zn2+ center coordinated by two hexanoate (caproate) carboxylates; extended coordination/polymeric aggregation is common in the solid state via bridging carboxylates.
• No stereocenters; aliphatic C6 chain per carboxylate (–CH3(CH2)4CH2–COO–).
• 2D description: central Zn2+ bound to two carboxylate groups (each –O–C(=O)–), with each carboxylate attached to a linear n-hexyl chain.

Note: Exact connectivity/oligomeric state in the solid may vary (bridged vs chelating carboxylates); consult crystallographic literature for specific polymorphs.

Synthetic Utility

Functional attributes (literature; general):

• Zinc(II) carboxylate behaves as a mild Lewis acid and as a source of carboxylate base/ligand. The hydrophobic C6 chain imparts organophilicity, improving compatibility with organic substrates/polymers compared to short-chain salts.

Representative uses:

• Esterification/transesterification: Activates carbonyls and stabilizes tetrahedral intermediates; effective for polyester synthesis and small-molecule ester exchange.
• Ring-opening polymerization: Catalyzes ROP of ε-caprolactone and related monomers, yielding aliphatic polyesters with tunable molecular weights.
• Precursor chemistry: Thermolysis affords ZnO; useful for preparing ZnO nanoparticles or films with organic residue profiles influenced by C6 ligands.
• Ligand exchange chemistry: Can undergo carboxylate exchange with other acids, enabling in situ generation of tailored zinc carboxylates.

Retrosynthetic value:

• Serves as a masked Zn2+ source where aqueous zinc salts are undesirable. The caproate ligand can be displaced by stronger donors (phosphines, amines, multidentate carboxylates) to form defined Zn complexes in organic media.

Target Specificity

Not applicable. This product is a small-molecule zinc carboxylate and does not possess antigen/epitope specificity, clone information, or species reactivity. No antibody/biological targeting attributes are associated with this SKU.