Hexyl cyclohexanecarboxylate - ≥95% , CAS No.27948-10-3

CAS: 27948-10-3 Cat. No.: H996069 Formule: C₁₃H₂₄O₂ Poids moléculaire: 212.330 Numéro CE: EINECS248-744-7

QUALITÉ & PURETÉ ≥95%

Storage

Room temperature

Spécifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

Sourires canoniques

CCCCCCOC(=O)C1CCCCC1

IUPAC Name

hexyl cyclohexanecarboxylate

InChIKey

QNVYTFRSSXVBQH-UHFFFAOYSA-N

INCHI

1S/C13H24O2/c1-2-3-4-8-11-15-13(14)12-9-6-5-7-10-12/h12H,2-11H2,1H3

Poids moléculaire

212.330

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Carboxylic acid derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Carboxylic acid esters
• Alternative Parents: Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Carboxylic acid ester - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
• 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: 212.330 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 212.178 Da
• Monoisotopic Mass: 212.178 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 171.000
• 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: 1

Application Protocols

Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule ester in the Product Data.

• For analytical use, general protocols include:
  • GC–FID/GC–MS sample prep: dilute 0.1–1.0 mg/mL in hexane or isooctane; inject 1 µL split 20:1; use nonpolar column 30 m × 0.25 mm × 0.25 µm.
  • NMR: dissolve 5–20 mg in CDCl3 (0.7 mL); acquire 1H (400 MHz), 13C, DEPT; reference to TMS.

These are general literature-style methods and not product certifications.

Biological Roles

This compound is a synthetic aliphatic ester without a known intrinsic biological role.

• General context (literature; not product-specific):

  • Aliphatic esters can serve as substrates for esterases/lipases in biocatalysis. Hydrophobic bulk esters like hexyl cyclohexanecarboxylate can be useful to probe enzyme activity in nonaqueous/biphasic systems.
  • In metabolic terms, simple esters are typically hydrolyzed to the corresponding alcohol and carboxylic acid; subsequent metabolism follows fatty-alcohol and fatty-acid pathways (β-oxidation, ω-oxidation), though cyclohexanecarboxylate is not a native fatty acid.
  • Low aqueous solubility means limited bioavailability in purely aqueous systems without surfactants or co-solvents.

• Practical lab implications:

  • For enzymatic studies, use emulsifiers or organic co-solvents (e.g., 5–20% v/v acetonitrile, DMSO, or ionic surfactants) to achieve substrate delivery while maintaining enzyme activity.
  • Monitor hydrolysis by GC or HPLC after derivatization of the liberated acid (e.g., methylation) if direct detection is challenging due to hydrophobicity.

No therapeutic or physiological claims are made; product is for research use only (per Product Data).

Buffer Applications

Not typically applicable. Hexyl cyclohexanecarboxylate is a hydrophobic, water-immiscible ester and is not used as a buffering agent or buffer component.

• Practical note: If working in aqueous systems (e.g., enzymatic hydrolysis), choose an appropriate buffer for the enzyme (e.g., phosphate, Tris, HEPES) and deliver the ester via co-solvent or emulsification. Focus instead on sections covering Reaction & Applications and Solvent Selection.

Green Alternatives

While hexyl cyclohexanecarboxylate is not a common process solvent, it may be used as a hydrophobic carrier or phase component. Consider greener options depending on the task.

• Greener carriers/solvents (literature perspective):

  • Ethyl acetate: bio-based availability, low toxicity profile, readily biodegradable; higher polarity than hydrocarbons but dissolves many hydrophobic esters.
  • 2-Methyltetrahydrofuran (2-MeTHF): biomass-derived ether with favorable EHS profile vs THF; good solvency for aliphatic esters; water-immiscible for easy separations.
  • Cyclopentyl methyl ether (CPME): low peroxide formation tendency, water-immiscible, broad solvency.
  • Bio-ester diluents (e.g., isopropyl myristate, glycerol triacetate): renewable and low volatility; useful as carriers in formulation studies.

• Comparison (general; not product-specific):

  • Criterion | Hexyl cyclohexanecarboxylate | Ethyl acetate | 2-MeTHF | CPME
  • Origin | Petro-/synthetic | Widely bio-based | Bio-based | Petro-/mixed
  • Biodegradability | Likely good for saturated esters | Good | Moderate-good | Moderate
  • Volatility | Low (high bp) | Moderate | Moderate | Moderate
  • Water miscibility | Immiscible | Slight | Immiscible | Immiscible

• Trade-offs:

  • Using a low-volatility ester carrier can reduce VOC emissions but complicates removal/purification.
  • 2-MeTHF/CPME offer better processability (distillable) with improved environmental metrics vs chlorinated solvents.

Select the medium based on downstream separation, safety, and LCA considerations.

Pharmaceutical Uses

No pharmacopeial status or excipient grade is specified for this item; refer to CoA/Spec Sheet. The information below is general and not specific to this product.

• General formulation context (literature):

  • Hydrophobic aliphatic esters can function as nonaqueous carriers, plasticizers, or emollient-type diluents in research formulation studies. Selection is driven by stability, solvency, and sensory/viscosity targets.
  • For any use in regulated products, excipient compliance (e.g., NF/Ph.Eur.) and toxicological qualification would be required—this product is designated for research use only.

• Research formulation tips:

  • Solubility screening: pair with co-solvents such as ethanol, propylene glycol, or triacetin to adjust viscosity and solubilize actives.
  • Stability: avoid strong acids/bases and elevated temperatures in the presence of water to minimize hydrolysis; consider antioxidants only if data indicate need (saturated esters are generally not peroxide-forming).
  • Analytical: GC–FID with nonpolar columns provides clear separation from common formulation excipients.

No therapeutic claims are made; this product is for research use only.

Physical Properties

• Item-specific (Product Data):

  • Appearance: 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.

• Literature/computed (general reference values; not product specifications):

  • Calculated formula and MW (from structure rationale): C13H24O2; ~212.33 g/mol.
  • Physical state: typically a colorless to pale liquid for analogous C13 aliphatic esters (literature).
  • Boiling point: high-boiling ester, typically >250 °C at 1 atm for C13 saturated esters (literature range; consult specific source for exact value).
  • Melting point: often below 0 °C for analogous liquid esters (literature trend).
  • Density: esters of this size commonly 0.86–0.92 g/mL at 20–25 °C (literature range).
  • Refractive index: typical 1.43–1.46 at 20 °C for saturated aliphatic esters (literature range).
  • Vapor pressure: low at ambient temperature (literature trend for C>10 esters).
  • Solubility: practically insoluble in water; miscible with nonpolar and mid-polar organics (hexane, toluene, MTBE, DCM, EtOAc, alcohols) (literature).
  • LogP: expected high (≈4–6) reflecting strong hydrophobicity (literature/estimation).

• Practical implications:

  • Low volatility and high hydrophobicity suit it as a hydrophobic carrier or phase component.
  • Ester function is hydrolytically sensitive to strong acids/bases, especially at elevated temperature or in the presence of water.

Quality and Grades

• Item-specific (Product Data):

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

• Guidance on interpreting grade (general, not product-specific):

  • Research grade: suitable for most synthetic and materials applications. If UV transparency, GC residue, or trace metals are critical, verify via CoA.
  • GC or HPLC grade (if applicable): typically indicates low nonvolatile residue and low UV background; useful when using the ester as a diluent or reference in chromatographic methods.
  • ≥98–99% purity claims (if present on CoA): imply minimal byproducts such as the parent acid/alcohol or transesterification products. Water content and acid value may be reported; check these if hydrolytic sensitivity is a concern.

• Practical QA/QC tips:

  • Verify identity by GC–MS (base peak patterns of aliphatic esters) and 1H/13C NMR (quartet of carbonyl C around ~173–175 ppm; methylene alpha to O around 4.0–4.2 ppm).
  • Monitor acid value or residual alcohol by GC to assess hydrolysis during storage/use.
  • If critical applications require, request or review: peroxide value (usually low for saturated esters), water (Karl Fischer), and trace metals—even if not standard, Aladdin can often provide batch-specific CoAs.

Reaction and Applications

• Typical research uses (general for aliphatic esters):

  • Model substrate in studies of ester hydrolysis, transesterification, and enzymatic ester cleavage (lipases/esterases) due to its clear GC/NMR signatures and hydrophobicity.
  • Hydrophobic carrier or internal standard in fragrance/materials research where a nonvolatile, inert medium is required (verify compatibility with your analytical method).

• Representative reactions (literature guidance):

  • Hydrolysis: acid- or base-catalyzed cleavage to cyclohexanecarboxylic acid and 1-hexanol. Base conditions (e.g., NaOH, H2O/EtOH, reflux) give the carboxylate quantitatively; acid catalysis (H2SO4, aqueous) proceeds more slowly but avoids saponification salts.
  • Transesterification: acid (p-TsOH) or base (alkoxide) catalysis in anhydrous alcohols swaps the hexyl group for other alkyl groups; removal of the lower-boiling alcohol drives equilibrium.
  • Reduction: LiAlH4 (Et2O/THF, 0 °C to reflux) reduces the ester to cyclohexylmethanol plus 1-hexanol equivalents; DIBAL-H can give the corresponding aldehyde at low temperature (−78 to −40 °C) with careful quench.
  • Carbon–carbon formation: Esters undergo twofold addition with organolithium/Grignard reagents to furnish tertiary alcohols after workup (e.g., RMgX or RLi, ether/THF, 0 °C to reflux).

• Practical tips:

  • Dry conditions and inhibitor-free solvents improve outcome in reduction and organometallic additions.
  • Monitor reactions by GC–FID or 1H NMR (disappearance of ~4.0–4.2 ppm O–CH2 signal and ~173–175 ppm 13C=O).

Reaction Conditions

General literature guidance for reactions involving this ester (not product specifications):

• Hydrolysis (saponification):

  • Conditions: 1–2 M NaOH or KOH in EtOH/H2O (1:1 to 4:1), 50–80 °C, 1–6 h.
  • Outcome: quantitative formation of cyclohexanecarboxylate salt and 1-hexanol; acidify to pH <2 to isolate the free acid.

• Acid-catalyzed hydrolysis:

  • Conditions: 0.5–2 M H2SO4 or HCl(aq), reflux (80–100 °C) in aqueous/MeOH or aqueous/THF mixtures, 6–24 h; slower but avoids soaps.

• Transesterification:

  • Base: sodium ethoxide or methoxide (1–5 mol%) in corresponding alcohol, 25–60 °C; remove hexanol to drive equilibrium.
  • Acid: p-TsOH (1–10 mol%) in anhydrous ROH with Dean–Stark (if using higher alcohols), 60–120 °C.

• Reduction:

  • DIBAL-H: 1.1–1.5 equiv, toluene or CH2Cl2, −78 to −40 °C, 1–3 h; careful quench at low temperature to favor aldehyde.
  • LiAlH4: 1.5–3 equiv, dry THF or Et2O, 0 °C to reflux, 1–4 h; work up with cautious water/NaOH then filter salts.

• Organometallic addition (tertiary alcohol formation):

  • RMgX or RLi (≥2 equiv) in dry THF/Et2O, 0 °C to reflux, 1–12 h; monitor by GC/NMR.

• Analytical monitoring:

  • GC–FID on nonpolar columns (DB-1/HP-5) at 120→280 °C ramps; 1H NMR disappearance of ~4.0–4.2 ppm O–CH2.

Adjust equivalents, temperature, and time based on scale, catalyst activity, and desired selectivity.

Safety and Handling

• Item-specific (Product Data):

  • GHS signal word: Not specified for this item; refer to SDS.
  • H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature (Product Data).

• General safety guidance for aliphatic esters (literature; not product-specific):

  • Hazard profile: typically combustible liquids; may cause skin/eye irritation and respiratory tract irritation upon vapor/aerosol exposure.
  • PPE: safety glasses or splash goggles, lab coat, and chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation of vapors or mists.
  • Incompatibilities: avoid strong acids or bases (catalyze hydrolysis/transesterification), strong oxidizers, and reducing agents (e.g., hydrides) that can reduce esters.
  • First aid: if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes and remove contact lenses if present; if inhaled, move to fresh air; if ingested, rinse mouth—seek medical attention in all cases. Follow SDS instructions.
  • Fire safety: use CO2, dry chemical, or foam for small fires. Vapors may form explosive mixtures with air if sufficiently heated; ensure grounding/bonding when transferring flammable liquids.
  • Spill response: absorb with inert material (vermiculite, sand). Prevent entry into drains. Dispose in accordance with local regulations.

Always consult the product SDS for authoritative hazard, exposure limits, and emergency procedures.

Solvent Selection

Hexyl cyclohexanecarboxylate is a hydrophobic analyte/reagent rather than a routine laboratory solvent. Selection below refers to media for dissolving/processing this ester.

• Polarity/miscibility (literature trends):

  • Polarity class: nonpolar to weakly polar aprotic (ester carbonyl present, but overall hydrophobic).
  • Water miscibility: practically immiscible.
  • Good solvents: hexane/heptane, cyclohexane, toluene/xylene, MTBE, ethyl acetate, dichloromethane, chloroform; moderate solubility in alcohols (EtOH, i-PrOH) at room temperature.

• Dielectric and H-bonding context (literature):

  • Does not donate H-bonds; weak H-bond acceptor at carbonyl O. Solubility benefits from dispersive and dipolar interactions—aromatics and chlorinated solvents often give higher solubility than alkanes at equal temperature.

• When to choose which solvent:

  • For GC/analytical prep: hexane or isooctane are common carriers for hydrophobic esters.
  • For synthetic transformations (e.g., hydrogenation, transesterification): toluene or heptane provide good thermal stability; ethyl acetate or MTBE can aid catalyst dispersion.
  • For hydrolysis studies: biphasic systems (water/THF or water/acetonitrile with a phase-transfer catalyst) can be used; note potential ester cleavage.

• Small comparison (general guidance):

  • Hexane: lowest polarity, best for nonpolar matrices; slow dissolution if viscosity high.
  • Toluene/DCM: higher solvency; good for kinetics and spectroscopy; monitor toxicity considerations.
  • Ethyl acetate: greener profile vs chlorinated; good balance of polarity and volatility.

Storage and Reconstitution

• Item-specific (Product Data):

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

• General handling guidance (literature; not product-specific):

  • Store tightly closed in a dry, well-ventilated place away from strong acids/bases and oxidizers to minimize hydrolysis or degradation.
  • Protect from prolonged exposure to moisture and heat. Keep container tightly sealed when not in use to limit alcohol exchange or odor absorption.
  • If trace hydrolysis is a concern for sensitive applications, consider storing under inert gas (N2/Ar) and using dry transfer techniques.

• Reconstitution/dispensing:

  • The product is expected to be ready-to-use as a liquid (appearance not specified). If solidified by cold, warm gently to ambient and homogenize before sampling.
  • For preparing analytical standards, gravimetrically prepare stock solutions in hexane, toluene, or ethyl acetate; store solutions in sealed amber vials at 2–8 °C when long-term stability is required.

• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

For research use only (per Product Data). Consult the SDS for detailed storage incompatibilities and safe handling procedures.

Structure and Identity

A hydrophobic aliphatic–alicyclic ester formed from cyclohexanecarboxylic acid and 1-hexanol.

• Item-specific (Product Data):

  • SKU: H996069
  • Product name: Hexyl cyclohexanecarboxylate
  • CAS: 27948-10-3
  • PubChem CID: 119761
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and features (for reference; not product specifications):

  • Molecular formula (from structure rationale, ester of C6H11–COO–C6H13): C13H24O2 (literature/computed)
  • Molecular weight: ~212.33 g/mol (literature/computed)
  • Representative SMILES (literature): CCCCCCOC(=O)C1CCCCC1
  • Functional groups: one saturated carboxylate ester (–COO–); fully saturated cyclohexyl ring; linear n-hexyl chain.
  • Structural description (2D): a cyclohexyl ring bearing a carboxylate at C1, esterified to a straight-chain hexyl alcohol. No stereocenters; conformational isomers arise from cyclohexane chair flips and alkyl chain rotation.

• General notes:

  • The absence of unsaturation and heteroatoms beyond the ester makes the molecule nonpolar with modest polarizability from the carbonyl and ether oxygens.
  • Isomerism: constitutional isomerism is minimal for the named compound (n-hexyl ester of cyclohexanecarboxylic acid).

Synthetic Utility

As a saturated ester, hexyl cyclohexanecarboxylate is useful both as a substrate and as a protected carboxyl functionality.

• Functional group behavior (literature):

  • Carbonyl electrophile (ester): engages in nucleophilic acyl substitution (alcoholysis, aminolysis) and in reductions to aldehydes/alcohols.
  • Protecting-group role: the carboxyl function of cyclohexanecarboxylic acid is masked as an ester; it can be regenerated under controlled hydrolysis.

• Named/representative transformations:

  • Transesterification (Fischer–Speier, acid-catalyzed) to access a panel of alkyl cyclohexanecarboxylates.
  • Krapcho-type demethoxycarbonylation is not applicable, but general ester exchange and Baeyer–Villiger oxidation are not typically favored on saturated esters lacking activating groups.
  • Reduction with DIBAL-H (to aldehyde) or LiAlH4 (to diols via full reduction) expands access to cyclohexylmethyl alcohol derivatives.
  • Amidation via activation: convert ester to acid (hydrolysis) then to amide through acid chloride (SOCl2/oxalyl chloride) or coupling reagents (EDC/HOBt, DIC/DMAP) to introduce amide functionality on the cyclohexyl moiety.

• Analytical/processing advantages:

  • High boiling point allows use as an internal standard or solvent-like diluent in elevated-temperature studies without rapid evaporation.
  • NMR: distinct O–CH2 (hexyl) and ring methylenes simplify integration and tracking of reaction progress.

Target Specificity

Not applicable. This product is a small-molecule ester, not a biological targeting reagent (e.g., antibody, ligand with defined receptor selectivity). No antigen, epitope, clone, or species reactivity is relevant.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 27948-10-3, the molecular formula is C13H24O2, and the molecular weight is 212.330 g/mol. InChIKey QNVYTFRSSXVBQH-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.