Methyl 2-(4-hydroxycyclohexyl)acetate - ≥98% , CAS No.99183-13-8

CAS: 99183-13-8 Cat. No.: M1071247 Formula: C₉H₁₆O₃ Peso molecolare: 172.220 Numero EC: 820-532-4

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: COC(=O)CC1CCC(CC1)O
• IUPAC Name: methyl 2-(4-hydroxycyclohexyl)acetate
• InChIKey: FUDUBAPFCNGJJM-UHFFFAOYSA-N
• INCHI: 1S/C9H16O3/c1-12-9(11)6-7-2-4-8(10)5-3-7/h7-8,10H,2-6H2,1H3
• Peso molecolare: 172.220

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Alcohols and polyols
        • Level5 Secondary alcohols
          • Level6 Cyclohexanols

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Secondary alcohols
• Direct Parent: Cyclohexanols
• Alternative Parents: Methyl esters Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexanol - Methyl ester - Cyclic alcohol - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane 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

Proprietà chimiche e fisiche

• Peso molecolare: 172.220 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 172.11 Da
• Monoisotopic Mass: 172.11 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 148.000
• 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

No manufacturer-tested bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.

• General laboratory use (guidance)
  • For synthetic applications, see Reaction Conditions and Synthetic Utility sections.
  • For analytical characterization, typical methods include 1H/13C NMR (CDCl3, DMSO-d6, or acetone-d6 depending on solubility), IR (ester C=O ~1735 cm−1; O–H stretch broad ~3300–3500 cm−1), and LC–MS.
  • For biological assays (research use only), prepare stock solutions in DMSO or EtOH and dilute into assay buffer with appropriate co-solvent ceilings (often ≤1–2% v/v in final media). Validate solubility and stability empirically.

Refer to the product’s CoA/Spec Sheet for any lot-specific analytical data.

Biological Roles

• Item-specific biological role: Not specified for this item; refer to primary literature if a biological context is intended.
• General information (contextual, non-clinical)
  • This compound is a synthetic, non-natural small molecule. It contains functionalities common in lipophilic metabolites (cyclohexyl ring, ester) and a single secondary alcohol, but it is not known as a canonical metabolite or cofactor.
  • In chemical biology, related hydroxy-esters are occasionally used as pro-fragments or handles for conjugation (via ester hydrolysis to acids or alcohol derivatization) to generate probes or affinity tags; such applications require case-by-case validation.
  • The ester linkage is susceptible to hydrolysis by esterases in biological matrices (general observation for aliphatic methyl esters), which may be considered in assay design and stability studies; actual rates for this exact structure are not specified.

Research use only: No medical, diagnostic, or therapeutic use is intended or implied. For cellular or in vivo work, establish compound-specific cytotoxicity, permeability, and stability profiles experimentally.

Buffer Applications

This product is a neutral, largely hydrophobic organic reagent and is not a conventional buffering agent. It lacks a conjugate acid/base pair in the physiological pH range.

• Not typically applicable
  • No established buffer systems or buffer recipes are associated with this compound.
  • For aqueous handling, use co-solvents (e.g., DMSO, EtOH) and standard biological buffers (PBS, HEPES) as appropriate for your assay.

Refer instead to the sections on Reaction & Applications and Synthetic Utility for relevant laboratory uses.

Green Alternatives

While the substance itself is a synthetic building block, greener choices can be made in the solvents and reagents used for its transformations.

• Greener solvent options (literature/general)
  • Replace DCM/CHCl3 with ethyl acetate, 2-MeTHF, CPME, or anisole where compatible.
  • Substitute THF with 2-MeTHF (biomass-derived), maintaining similar polarity and stabilizing enolates effectively.
  • For hydrolysis/aminolysis, favor aqueous ethanol or isopropanol systems over DMF/DMSO when feasible.
• Greener reagent swaps
  • Use catalytic organobases (DBU, TBD) or carbonate bases instead of stoichiometric strong bases when doing transesterifications.
  • Prefer EDC·HCl with catalytic DMAP in EtOAc/MeCN over DCC in DCM for amidations to minimize urea waste handling.
  • Employ catalytic oxidation (e.g., TEMPO/bleach or O2 with Cu catalysts) for alcohol-to-ketone conversions where compatible, instead of chromium(VI) reagents.

Comparison (illustrative)

• DCM vs EtOAc: EtOAc is less toxic, biodegradable, and has a better EHS profile; however, DCM often offers superior solubility and faster phase separations.
• THF vs 2-MeTHF: 2-MeTHF is less miscible with water (easier workups) and has a higher boiling point; peroxide formation risk remains and should be controlled for either ether.

Adopt solvent recycling and minimal protecting-group strategies to further reduce environmental impact.

Pharmaceutical Uses

• Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
• General (non-clinical, manufacturing context)
  • As a bifunctional intermediate, methyl 2-(4-hydroxycyclohexyl)acetate can serve in the synthesis of drug-like molecules or prodrugs where ester hydrolysis or alcohol derivatization is leveraged. Any use in GMP settings would require independent qualification and full impurity profiling.
  • Esters such as this are occasionally used in medicinal chemistry SAR campaigns to tune lipophilicity and enable late-stage diversification (amidation after hydrolysis, carbonate/urethane formation from the alcohol).
  • No claims are made regarding therapeutic activity, safety, or efficacy. Any formulation or exposure work must be preceded by comprehensive preclinical evaluation.

For regulated applications, secure lot-specific CoA, residual solvent data, and trace impurity assessments. This catalog listing is for research use only.

Physical Properties

• Item-specific specifications
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed (non-spec) physical data for guidance only
  • Molecular weight: ~172.22 g/mol (computed from C9H16O3)
  • Expected physical state: low-viscosity liquid or low-melting solid for similar hydroxy-alkyl esters (literature/analogy).
  • Solubility: expected to be miscible with common organic solvents (EtOAc, THF, DCM, MeOH) and poorly soluble in water due to hydrophobic cyclohexyl moiety (literature/analogy).
  • Acid/base behavior: neutral compound containing a non-ionizable ester and a secondary alcohol; pKa of the cyclohexanol OH typically ~16–18 in water (literature, analogous cyclohexanols). The ester carbonyl does not ionize under neutral conditions.
  • Partitioning: logP anticipated to be moderate (≈2–3) given cyclohexyl plus one OH and one ester (literature/estimation).
  • Refractive index/density/boiling point/melting point/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Important: The above values are provided as general literature/computed guidance and are not item-specific specifications. For method development or regulatory documentation, use the CoA/Spec Sheet for this lot.

Quality and Grades

• Item-specific details
  • 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)
  • If supplied as research grade, typical expectations include compliance with internal specifications for identity (NMR/HRMS/IR) and purity (e.g., GC/HPLC/LC–MS) suitable for synthetic and analytical research. Specific impurity limits (water, peroxides, metals, UV cutoffs) are not specified for this item.
  • For chromatography-intensive applications, users may consider in-house pre-qualification (e.g., low-UV baseline scans, GC residual solvent screening) when the grade is not explicitly “HPLC grade” or similar.
• Documentation
  • For lot-specific purity, residual solvents, and analytical traces, refer to the CoA/Spec Sheet. Request additional documentation (SDS, TDS) if your workflow requires defined thresholds (e.g., genotoxic impurities, elemental analysis).
• Practical notes
  • Hydroxy-esters can slowly equilibrate via transesterification in alcoholic media; maintain appropriate solvent quality if purity is critical.
  • If trace acidity/basicity impacts your method, consider a quick acid/base wash or pass through a short plug of neutral alumina, validating recovery and integrity by NMR.

Reaction and Applications

As a bifunctional building block (secondary alcohol + methyl ester), methyl 2-(4-hydroxycyclohexyl)acetate is versatile in target-oriented synthesis and medicinal chemistry exploration.

• Transformations involving the ester
  • Hydrolysis to the carboxylic acid (saponification) under aqueous NaOH or K2CO3 (MeOH/H2O), followed by acidification.
  • Transesterification to other alkyl esters using acid (H2SO4, TsOH) or base (NaOMe) catalysis; enzymatic ester exchanges are also feasible.
  • Conversion to amides via activation: EDC/HOBt or DCC to form the active ester; alternatives include acid chloride formation (SOCl2, oxalyl chloride) then aminolysis.
• Transformations involving the ring alcohol
  • Protection: silylation (TBSCl/TBDMSCl), acylation (Ac2O, BzCl), or carbonate formation to modulate polarity/reactivity.
  • Oxidation to the corresponding ketone (4-oxocyclohexyl derivative) using Dess–Martin periodinane, PCC, or Swern (literature conditions). This can enable intramolecular aldol or Michael-type strategies.
  • Etherification: Williamson-type O-alkylation after deprotonation (NaH/NaHMDS) to give alkyl ethers; Mitsunobu reactions can invert and etherify if a stereocenter is defined.
• Alpha-functionalization adjacent to the ester
  • Enolate generation at the methylene (–CH2–CO2Me) with LDA or NaH for alkylation, acylation, or aldol-type couplings.
• Use cases (general)
  • Intermediate toward cyclohexylacetic acid derivatives, scaffold elaboration with orthogonal handles, and as a fragment for probe or monomer synthesis.

Note: Choose conditions to avoid undesired ester hydrolysis when manipulating the alcohol, and conversely protect the alcohol when strong base or oxidants are employed.

Reaction Conditions

The following are general literature conditions for common transformations of hydroxy-esters like methyl 2-(4-hydroxycyclohexyl)acetate; optimize for your substrate and scale.

• Saponification to acid
  • Reagents: NaOH (1–2 equiv) in MeOH/H2O (4:1 to 9:1).
  • Conditions: 0–25°C to reflux; 0.5–6 h. Quench into cold dilute acid to pH ~2; extract with EtOAc. Typical yields: high (70–95%) for unencumbered esters (literature).
• Amidation via carbodiimide coupling
  • Reagents: EDC·HCl (1.1–1.5 equiv), catalytic DMAP, amine (1.2–2.0 equiv) in DCM or EtOAc.
  • Conditions: 0°C to rt, 2–16 h. Workup with aqueous NaHCO3 and brine. Yields: 60–90% (substrate-dependent; literature).
• Alcohol protection (TBS)
  • Reagents: TBSCl (1.2–1.5 equiv), imidazole (2.0 equiv) in DMF or DCM.
  • Conditions: rt, 2–6 h. Typical yields: 80–95% (literature).
• Oxidation to ketone (ring OH → 4-keto)
  • Dess–Martin periodinane (1.3 equiv) in DCM, rt, 1–3 h; or TEMPO/bleach (pH ~8.6, NaHCO3 buffer) for greener variant. Yields: 70–90% (literature).
• Enolate alkylation at –CH2–CO2Me
  • Base: LDA (1.1–1.5 equiv) in THF, −78 to −20°C; electrophile: primary alkyl halide.
  • Quench at low temperature; warm and work up. Yields: 40–80% depending on sterics (literature).
• Transesterification
  • Acidic: catalytic TsOH in MeOH/ROH, reflux; or basic: NaOMe/ROMe at rt–reflux. Monitor to avoid ring OH participation.

Note: Avoid strong acid or base for prolonged times to minimize concurrent hydrolysis or intramolecular acyl transfer. Protect the alcohol when using strong bases.

Safety and Handling

• Item-specific hazard data
  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements/Pictograms: Not specified for this item; refer to SDS.
• General safety considerations for aliphatic hydroxy-esters (literature/best practice)
  • Potential hazards: combustible liquid; may cause skin/eye irritation. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
  • PPE: wear lab coat, safety glasses or chemical splash goggles, and suitable gloves (e.g., nitrile). Use in a fume hood to avoid inhalation exposure during weighing or transfers.
  • Incompatibilities: strong oxidizers (risk of exotherm); strong bases and acids can promote hydrolysis/transesterification; avoid reactive acylation agents without proper control.
  • First aid (overview; defer to SDS): rinse eyes with water for at least 15 minutes if contacted; wash skin with soap and water; if inhaled, move to fresh air; if ingested, rinse mouth and seek medical attention. Provide SDS to responders.
  • Spill/cleanup: contain with inert absorbent (vermiculite, spill pads); collect in appropriate waste. Prevent entry into drains.
  • Fire response: use CO2, dry chemical, or foam; cool containers with water spray. Combustion may produce CO/CO2.

Always consult the product SDS for authoritative, current hazard classification and response guidance.

Solvent Selection

This product is a neutral, moderately polar organic molecule with both hydrogen-bond donor (secondary alcohol) and acceptors (carbonyl, alkoxy, ring oxygen is absent). It dissolves well in many organic solvents; water solubility is expected to be low to moderate.

• Miscibility and polarity (literature/analogy)
  • Good: DCM, CHCl3, EtOAc, THF, acetone, MeOH/EtOH, toluene (warming may help), acetonitrile (moderate).
  • Limited: hexanes/heptane unless co-solvent is used; solubility improves with slight polarity.
  • Aqueous: typically poor; co-solvent systems (MeOH/H2O or ACN/H2O) can aid in workups or analytical methods.
• Selection by task
  • Reaction medium for acylation/esterification: anhydrous DCM, THF, or toluene with base (e.g., pyridine, DIPEA) or acid catalyst as appropriate.
  • Hydrolysis/aminolysis: alcohol/water mixtures (MeOH/H2O, EtOH/H2O) or polar aprotics (DMF, DMSO) when coupling/activation is used.
  • Purification: normal-phase silica with hexanes/EtOAc or DCM/MeOH gradients; reverse-phase (C18) with ACN/H2O + 0.1% acid for LC if needed.
• Comparison (general)
  • Versus more hydrophobic esters, the ring OH improves solubility in slightly polar solvents (EtOAc, acetone) and can support H-bonding interactions; compared with diols, it remains largely organophilic.

For preparative scale, select solvents considering downstream workup (phase separation, environmental profile) and stability (avoid prolonged exposure to strong acids/bases that can hydrolyze the ester).

Storage and Reconstitution

• Item-specific storage
  • Storage Conditions: Room temperature (per Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• General handling
  • Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and strong acids/bases that can promote hydrolysis or transesterification.
  • If long-term storage is planned, consider storing under inert gas and away from light to minimize oxidative or acid/base-catalyzed degradation.
• Reconstitution and solution handling
  • If received as a liquid, use as supplied; if semi-solid at lower temperature, gently warm to ambient to liquefy, then mix thoroughly before aliquoting.
  • Prepare stock solutions in dry organic solvents (e.g., DCM, EtOAc, THF, MeOH, DMSO) according to downstream needs. Filter through a PTFE syringe filter if particulate is observed.
  • For aqueous applications, dissolve first in a compatible co-solvent (DMSO, EtOH) and dilute immediately before use. Assess stability in chosen solvent by LC–MS or HPLC over time.
• Shelf-life/Spec limits
  • No item-specific stability or impurity limits are provided here. Not specified for this item; refer to CoA/Spec Sheet.
• Research Use Note: For research use only.

Structure and Identity

Methyl 2-(4-hydroxycyclohexyl)acetate is an aliphatic hydroxy-ester featuring a secondary alcohol on a cyclohexane ring and a methyl ester tethered via a methylene spacer.

• Item-specific identifiers (from Product Data)
  • CAS: 99183-13-8
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • SKU: M1071247
• Computed/literature (non-spec) identifiers and composition
  • Functional groups: secondary alcohol (cyclohexanol, para to the side chain), methyl ester (–CO2Me), methylene linker (–CH2–) between ring and carbonyl.
  • Molecular formula (computed from name): C9H16O3 (literature/computed)
  • Molecular weight (computed): ~172.22 g/mol (literature/computed)
• Structural description (general)
  • The structure consists of a cyclohexane ring bearing an OH at the 4-position (relative to the side-chain attachment point). The ring carbon at the 1-position is substituted by a –CH2–CO2Me group. No stereocenters are specified at the ring carbon bearing OH (can exist as racemic mixture if not otherwise stated). The ester carbonyl is conjugated only to the alkoxy; no additional unsaturation or aromaticity is present.

Note: Where exact identifiers (SMILES/InChIKey) are required for registration or computational work, consult the product CoA/Spec Sheet or generate from a verified structure drawing.

Synthetic Utility

• Functional group handles
  • Secondary alcohol on cyclohexane: amenable to protection (silyl, acyl), oxidation to ketone, etherification, and carbonate/urethane formation.
  • Methyl ester: convertible to acid, amide, or alcohol (via reduction) and serves as an enolate-stabilizing unit for alpha-functionalization.
• Disconnections (retrosynthetic logic)
  • Disassemble to 4-hydroxycyclohexylacetic acid (or the acid chloride) and methanol for ester formation.
  • Alternatively, derive from 4-hydroxycyclohexanone via alkylation/oxidation–reduction sequences followed by esterification.
• Strategy notes
  • Orthogonal protection: protect the alcohol to survive strong base during alpha-alkylation of the acetate methylene; remove under mild conditions (e.g., TBS deprotection with TBAF, or acetate cleavage with methanolic K2CO3).
  • Leveraging conformational bias: oxidation to the 4-keto analog can enable intramolecular aldolizations or Robinson annulations for ring-fused targets.
  • Late-stage diversification: rapid access to amide libraries after saponification and coupling; carbonate/ether variants from the alcohol diversify polarity and H-bonding features.

Overall, the combination of a cyclohexyl core and two orthogonal handles makes this compound a practical scaffold for fragment growth and complexity-building sequences.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, inhibitor with defined target, or probe with validated specificity). No antigen/epitope, species reactivity, clone, or isotype information applies.