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
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
224.340 g/mol
XLogP3
4.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Exact Mass
224.178 Da
Monoisotopic Mass
224.178 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
213.000
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
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Application Protocols
No assay-specific, platform-specific, or biologics application protocols are provided for this small-molecule ester. Typical laboratory uses are synthetic and analytical:
Example workflows (general):
Hydrolysis test: dissolve in anhydrous THF or MeOH, add standardized base, monitor by GC or 1H NMR.
Enzymatic screen: combine with immobilized lipase in MTBE or solvent-free, control water activity, analyze conversion by GC.
Purification: silica gel flash chromatography using hexane/EtOAc gradients; verify stability on silica.
Refer to your internal method SOPs and validate conditions. For any regulated applications, consult the CoA and SDS and develop fit-for-purpose protocols.
Biological Roles
No endogenous biological role is known for cyclohexylmethyl cyclohexanecarboxylate. It is a synthetic, hydrophobic, aliphatic ester.
General biochemistry context (literature):
Ester functionality: readily subject to enzymatic hydrolysis by carboxylesterases and lipases, especially in hydrophobic environments or at interfaces. The bulky cycloaliphatic groups may reduce hydrolysis rates relative to short-chain esters, enabling kinetic comparisons in enzyme studies.
Membrane interactions: strong hydrophobicity can promote partitioning into lipid phases, making it a potential probe for studying partition coefficients, micelle formation, or emulsification behavior in surfactant systems.
Metabolic fate (conceptual): upon hydrolysis, products would be cyclohexanecarboxylic acid and cyclohexylmethanol, which can undergo further oxidation in metabolic models. Actual metabolic processing depends on organism and enzyme complement; no specific pathways are assigned to this compound.
Usage note: Any references to biological processing herein are for laboratory research context only. This material is provided strictly for research use and is not intended for diagnostic, therapeutic, or other clinical applications.
Buffer Applications
This compound is a neutral, hydrophobic ester and is not used as a buffering agent or buffer component. It lacks acid/base functionality in aqueous media and is sparingly soluble in water.
For experimental systems involving this compound:
Prepare buffers independently (e.g., phosphate, Tris, HEPES) and introduce the ester via a compatible cosolvent (e.g., ≤1–2% v/v DMSO, ethanol) or as an emulsion/surfactant formulation if aqueous dispersion is required.
Consider cyclodextrin inclusion complexes or lipid vehicles for aqueous delivery in biochemical assays.
No buffer recipes are applicable to this product.
Green Alternatives
If this material is used as a solvent or processing medium (less common), consider greener substitutes with improved safety and sustainability profiles. If it is used as a substrate, greener process conditions (catalysts/solvents) can minimize environmental impact.
Greener options and trade-offs (general/literature):
2-Methyltetrahydrofuran (2-MeTHF): bio-based ether solvent, good for many reductions and Grignard reactions; higher hydrophobicity than THF and easier phase separation. Trade-off: peroxide formation risk; not suitable for strong acids.
Cyclic carbonates (e.g., propylene carbonate): polar aprotic, low volatility; good for certain catalyzed transesterifications. Trade-off: high viscosity; can participate in ring-opening under strong nucleophiles.
CPME (cyclopentyl methyl ether): low peroxide tendency vs MTBE/THF, higher boiling point; good for azeotropic water removal. Trade-off: may retain hydrophobic products strongly; odor considerations.
Bio-derived esters (e.g., methyl oleate, ethyl lactate): renewable, low toxicity; effective in extraction and some catalytic processes. Trade-off: can be more reactive (transesterification) and have strong odors or higher boiling points.
Process intensification:
Solvent-free or neat enzymatic transesterification using immobilized lipases can reduce solvent load.
Heterogeneous acid catalysts (Amberlyst-15, sulfated zirconia) allow easier separation and reuse compared with mineral acids.
Selection should balance EHS metrics (boiling point, VOC, toxicity), reaction compatibility, and recovery/recycling feasibility in your workflow.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is specified for this item. The product is sold for research use only.
General formulation context (literature/industry):
Hydrophobic esters can sometimes serve as model compounds for studying ester stability, enzymatic hydrolysis, or partitioning relevant to formulation science (e.g., lipid-based delivery, emulsions). Cyclohexylmethyl cyclohexanecarboxylate’s low polarity and high boiling point may make it a convenient non-volatile model in pre-formulation studies.
As an excipient or solvent: not established for this specific compound; any such use would require rigorous toxicological, stability, and regulatory evaluation.
Regulatory note: Absent explicit pharmacopeial compliance (USP/NF, EP, JP) or GMP statements, do not use in clinical manufacturing or human/animal administration. Consult CoA and SDS for quality and safety attributes if considering advanced development work in a non-clinical research setting.
Physical Properties
Item-specific specifications are not provided in the Product Data for this listing. Consult the CoA/Spec Sheet for authoritative values.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (General/literature expectation for C14 saturated esters is a high boiling point in the hundreds of °C.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet. (Aliphatic esters of this size often have densities slightly below or near 1 g/mL at 20–25 °C; literature varies.)
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general/literature):
Water: expected very low solubility due to hydrophobic, saturated framework.
Organic: miscible with nonpolar and moderately polar aprotic solvents (e.g., hydrocarbons, ethers, chlorinated solvents); generally soluble in esters and ketones.
LogP and pKa: Not specified for this item; refer to CoA/Spec Sheet. (Neutral ester; no Brønsted acidity/basicity in water.)
Vapor pressure: Not specified for this item; refer to CoA/Spec Sheet.
Practical handling implications (general): high hydrophobicity and ester functionality suggest sensitivity to strong acids/bases (hydrolysis) and low volatility compared with lighter esters. Always verify exact property values on the specific batch documentation for process design.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance):
If provided as “neat, research grade,” the material is typically suitable for synthetic and analytical development work where ultra-low UV background or trace-metal control are not critical. Actual assay (GC or NMR), water content, and residual solvent limits should be verified on the batch CoA.
If an HPLC or LC/MS grade were specified (not indicated here), it would imply low UV absorbance/background and filtration suitable for chromatography; this product’s saturated, non-conjugated ester generally shows low UV absorbance >210 nm, but item-specific UV cutoffs are Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: None indicated. For esters of this type, stabilizers are uncommon; purity is usually maintained by limiting moisture and avoiding strong acids/bases.
Metals/ionic impurities: Not specified for this item; refer to CoA/Spec Sheet. If using in catalysis or surface-sensitive applications, consider pre-rinsing through a small plug of neutral alumina/silica or performing microdistillation if volatility allows (confirm thermal profile first).
Recommendation: Consult the lot-specific CoA for assay, GC profile, water content (Karl Fischer), and any residual solvents before use in quantitative or regulated workflows.
Reaction and Applications
Use this saturated dialkyl ester as a model substrate or intermediate in transformations that engage the ester functional group without complications from aromatic conjugation.
Representative research applications (general/literature):
Hydrolysis studies: kinetics of base- or acid-catalyzed ester hydrolysis in nonpolar matrices; evaluation of phase-transfer catalysts for saponification of hydrophobic esters.
Enzymatic catalysis: lipase-mediated transesterification or interesterification in organic media, probing substrate scope with bulky, cycloaliphatic alcohol/acid components.
Transesterification/Alcoholysis: exchange with lower alcohols under acid catalysis (p-TsOH) or basic catalysts (NaOMe), or with heterogeneous acids (Amberlyst). Water removal (Dean–Stark) improves conversions.
Reduction chemistry: conversion to corresponding alcohols using LiAlH4 or DIBAL-H (literature). Chemoselectivity considerations are simplified in the absence of aromatic or additional reducible groups.
Amidation: activation via mixed anhydrides (e.g., isobutyl chloroformate) or direct catalytic amidation (e.g., boron-based or Ti(IV) catalysts) to access cyclohexanecarboxamides with retention of the cyclohexylmethyl fragment in exchanged products.
Extraction/partition models: due to strong hydrophobicity, useful for studying partition behavior, emulsification, and phase separation in surfactant systems.
Practical tips:
Maintain anhydrous conditions if the native ester must be preserved; trace base or acid plus moisture will induce slow hydrolysis.
Monitor reactions by GC-FID or GC–MS; high boiling point may favor GC analysis with temperature programming, or HPLC-ELSD/RI if UV response is weak.
For enzyme screens, verify that the bulky, saturated rings do not exceed enzyme pocket constraints; adjust temperature and solvent to balance activity and stability.
Reaction Conditions
General literature guidance for ester transformations (not item-specific specifications):
Hydrolysis (saponification):
Conditions: 1–2 M NaOH or KOH in MeOH/H2O or EtOH/H2O, 20–60 °C.
Typical outcome: complete conversion in 1–6 h depending on solvent composition and temperature; yields of the acid/alcohol typically high after neutralization and extraction.
Acid-catalyzed hydrolysis:
Conditions: 0.5–2 M mineral acid (H2SO4, HCl) in aqueous alcohol or dioxane/water, reflux.
Notes: equilibrium-controlled; use excess water and heat; Dean–Stark with toluene for the reverse (esterification).
Transesterification:
Base-catalyzed: 1–10 mol% sodium alkoxide in the corresponding alcohol, 25–60 °C; remove formed alcohol to drive equilibrium.
Acid-catalyzed: 1–5 mol% p-TsOH in toluene or neat alcohol, 60–110 °C with water removal.
Enzymatic: immobilized lipases (e.g., CALB) in MTBE, heptane, or solvent-free at 30–60 °C; water activity control critical.
Reduction to alcohols:
LiAlH4 (THF, 0–25 °C) or DIBAL-H (toluene, −78 to 0 °C for partial reductions in other substrates). Workups require careful quench protocols.
Amidation:
Activation via acid chloride (SOCl2, oxalyl chloride) then amine coupling in inert solvent (DCM, toluene) with base (Et3N). Alternatively, catalytic amidation systems under azeotropic water removal.
Monitoring: GC-FID/MS with temperature-programmed methods (bp expected high), or HPLC with ELSD/RI. Adjust conditions to account for steric bulk and low polarity of the substrate.
Safety and Handling
Safety information is not specified in the Product Data for this item. Always review the SDS for definitive guidance.
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General laboratory safety for aliphatic esters:
Likely hazards: combustible liquid; may cause mild skin/eye irritation; aspiration hazard potential depends on viscosity—check SDS. Not expected to present acute toxicity typical of more volatile, low-MW solvents, but handle with standard precautions.
PPE: safety glasses, lab coat, and suitable chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of vapors/aerosols.
Incompatibilities: strong acids or bases (risk of ester hydrolysis), strong oxidizers. Avoid prolonged contact with moisture if purity must be maintained.
First aid (overview; defer to SDS):
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 if present and easy to do; continue rinsing.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: use CO2, dry chemical, or foam. Cool containers with water spray if exposed to fire.
Spill handling: absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains.
Research Use Note: For research use only.
Solvent Selection
This product is itself a hydrophobic, aprotic ester liquid and is typically treated as a substrate or medium rather than a routine process solvent. When solvent choice around this compound is required:
Polarity class (general/literature): low-polarity, non-protic; dielectric constant expected to be low (typical of aliphatic esters without conjugation).
Miscibility profile (general):
Water: immiscible or only sparingly soluble.
Organic: soluble in hydrocarbons (hexanes, toluene), ethers (THF, MTBE), ketones (acetone, MEK), chlorinated solvents (DCM, chloroform), and common esters (EtOAc).
Selection guidance:
For reactions involving hydrolysis or transesterification, use anhydrous, non-nucleophilic solvents (toluene, heptane) or remove water via Dean–Stark when acid-catalyzed.
For enzymatic (lipase) processes, solvent-free or solvent systems like MTBE, heptane, or ionic liquids are commonly employed; confirm enzyme compatibility.
For purification, normal-phase silica gel chromatography with hexane/EtOAc gradients is typical for esters; avoid strong acid sites on silica for prolonged contact to minimize transesterification/hydrolysis.
Comparison (general):
Versus aromatic esters (e.g., benzyl esters): lower UV absorbance and often lower polarity; fewer side reactions under hydrogenolysis.
Versus short-chain esters (e.g., ethyl acetate): much lower volatility and water miscibility; better for high-temperature or reduced odor processes but less suitable as a volatile extraction solvent.
Container: Store tightly closed in an inert, compatible container (e.g., amber glass) to minimize exposure to moisture and airborne acids/bases that can catalyze hydrolysis.
Atmosphere: In general, a dry environment is preferred. For long-term storage, consider a desiccator or inert gas blanket if frequent opening is expected.
Light sensitivity: No specific sensitivity expected for saturated esters; protect from excessive heat/light as good practice.
Reconstitution: Not applicable—supplied neat. If preparing stock solutions, use dry, compatible solvents (e.g., hexanes, toluene, ethyl acetate). Document solvent lot and water content for reproducibility.
Freeze–thaw: Not relevant; avoid unnecessary temperature cycling which can draw moisture into containers.
Stability: Esters may slowly hydrolyze in the presence of moisture and acids/bases. Keep away from strong reagents and store at recommended conditions to maintain assay.
Always consult the product CoA for any lot-specific stability or storage notes before use in critical applications.
Structure and Identity
Cyclohexylmethyl cyclohexanecarboxylate is a dialkyl ester formed from cyclohexanecarboxylic acid and cyclohexylmethanol, featuring two saturated cycloaliphatic rings linked by an ester –O–CH2– bridge and a carbonyl.
Item-specific identifiers (from Product Data):
CAS: 2611-02-1
PubChem CID: 75786
InChIKey: 429038 (as provided; format appears atypical—verify against CoA/SDS)
SKU: C192383
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structure description (general/literature):
Functional groups: one ester carbonyl (–C(=O)–O–), one methylene linker (–CH2–) between oxygen and a cyclohexyl ring.
Ring systems: two cyclohexane rings (saturated, chair-conformational).
Stereochemistry: none specified (molecule contains no stereogenic centers in the idealized structure).
2D depiction in words: cyclohexanecarbonyl group attached to an alkoxy oxygen, which is bonded to a methylene that is bound to a cyclohexyl ring; the acyl side terminates in a second cyclohexyl ring.
SMILES (literature/computed, for reference): O=C(OCc1CCCCC1)C1CCCCC1
InChI (literature/computed, summary): an acyclic ester connecting two C6 alicyclic rings via –CO2–CH2–; full identifier should be confirmed from primary databases.
Note: Identity elements not explicitly specified in the item listing should be confirmed on the product CoA/Spec Sheet prior to regulated use.
Synthetic Utility
Functional group profile and reactivity (general/literature):
Ester group: participates in nucleophilic acyl substitution, transesterification, hydrolysis, reduction to alcohols, and conversion to amides or acids under standard conditions.
Aliphatic rings: chemically robust under many conditions; provide steric bulk that modulates reaction rates and selectivity (e.g., slower hydrolysis than short-chain esters).
Typical transformations:
Hydrolysis/saponification: base (NaOH, KOH) or acid (H2SO4, HCl) catalysis to yield cyclohexanecarboxylic acid and cyclohexylmethanol.
Transesterification: catalytic acid (p-TsOH, H2SO4), base (alkoxides), or enzymes (lipases); remove alcohol byproduct or water to drive equilibrium.
Reduction: LiAlH4 or DIBAL-H to the corresponding diols (reducing both carbonyl and maintaining/alcoholizing the alkoxy fragment). Borane can also reduce esters under controlled conditions.
Amidation: via activated esters, mixed anhydrides, or catalytic systems (e.g., B(OCH2CF3)3-mediated, Ti(OiPr)4-assisted) to access amides of cyclohexanecarboxylic acid.
Alpha-functionalization (indirect): enolization is minimal for this saturated acyl fragment, but converting to the acid chloride permits further acylations.
Strategic considerations:
The bulky cycloaliphatic groups can influence solubility and phase behavior, aiding separations.
Low UV response suggests monitoring by GC, HPLC-ELSD/RI, or 1H NMR.
Stability: avoid strong acids/bases and moisture when preservation of the ester is desired; otherwise leverage those conditions for purposeful cleavage.
Target Specificity
Not applicable. This product is a small-molecule ester, not a biological targeting reagent or antibody. No antigen, epitope, species reactivity, clone, or isotype information applies.
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