Methyl 3-cyclohexyl-2-hydroxypropanoate - ≥95% , CAS No.1033777-74-0

CAS: 1033777-74-0 Cat. No.: M970874 Formula: C₁₀H₁₈O₃ Molecular Weight: 186.24 EC Number: 865-180-2 PubChem CID: 13925900

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

COC(=O)C(CC1CCCCC1)O

IUPAC Name

methyl 3-cyclohexyl-2-hydroxypropanoate

InChIKey

DQWADVKQCYOJTK-UHFFFAOYSA-N

INCHI

1S/C10H18O3/c1-13-10(12)9(11)7-8-5-3-2-4-6-8/h8-9,11H,2-7H2,1H3

Isomeric SMILES

COC(=O)C(CC1CCCCC1)O

PubChem CID

13925900

Molecular Weight

186.24

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Methyl esters Secondary alcohols Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Fatty acid ester - Methyl ester - Secondary alcohol - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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

Chemical and Physical Properties

• Molecular Weight: 186.250 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 186.126 Da
• Monoisotopic Mass: 186.126 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 162.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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‑validated bioassay or analytical application protocols are provided for this item.

• General laboratory usage notes (non‑validated)
  • For synthetic transformations, weigh neat material or prepare stock solutions in dry EtOAc, THF, DCM, or MeOH as required by the reaction. Record exact mass and solvent density for stoichiometry.
  • For LC analysis, prepare 1–10 mg/mL stocks in MeCN or MeOH; for reverse‑phase LC, dilute into water with 0.1% formic acid or ammonium acetate as needed to improve peak shape.
  • For bioassay research, dissolve initially in DMSO or MeOH to create a concentrated stock (e.g., 10–100 mM), then dilute into assay buffer maintaining final organic content at ≤1–2% v/v to avoid matrix effects.

Please refer to your internal SOPs and validate conditions for your specific use case.

Biological Roles

No specific biological role is assigned to this catalog item; it is offered strictly for research use as an organic intermediate.

• General context (literature)

  • α‑Hydroxy esters are structural motifs found in metabolic intermediates (e.g., lactate esters) and can participate in enzymatic transformations when presented in appropriate biological contexts. However, the β‑cyclohexyl substituent here substantially increases hydrophobicity and is not a common feature of native metabolites.
  • In medicinal chemistry, α‑hydroxy ester fragments can serve as pro‑functional handles: conversion to α‑keto esters enables covalent adduct formation in enzyme model systems, and the free –OH allows fine‑tuning of hydrogen-bond networks in ligand design (all statements are general, not product‑specific claims).

• ADMET considerations (general)

  • The –OH and –CO2Me groups may influence permeability and solubility; the cyclohexyl group increases lipophilicity and membrane affinity. Actual biological properties depend on the larger scaffold and are not defined for this item.

No therapeutic, diagnostic, or in vivo use is implied or supported. For any bioassay use, ensure appropriate control compounds and verify purity/identity from the CoA before interpreting results.

Buffer Applications

This compound is a hydrophobic α‑hydroxy methyl ester and is not a buffering agent. It does not provide a defined acid/base pair suitable for pH control in aqueous systems.

• Practical guidance
  • If used in biochemical assays, it will generally require a co‑solvent (e.g., DMSO, MeOH, or MeCN) prior to dilution into aqueous buffers. Keep final organic content at levels compatible with the assay system (commonly ≤1–2% v/v), and verify solubility/precipitation visually.
  • Choose standard buffers for pH control (e.g., phosphate, HEPES, Tris) as appropriate to your system; this compound itself should not be relied upon for buffering capacity.

Refer to assay SOPs for acceptable solvent systems and to the CoA for purity before use in any analytical or bioassay context.

Green Alternatives

While this product is a specific research intermediate, greener choices can be made around solvents, reagents, and related building blocks.

• Greener processing choices (general)

  • Solvents: prefer EtOAc, 2‑MeTHF, CPME, or MeOH over chlorinated solvents when compatible. Use heptane over hexane where feasible.
  • Oxidations: use catalytic TEMPO/bleach or IBX over chromium(VI). Dess–Martin is effective but consider workup and waste minimization.
  • Mitsunobu alternatives: employ azodicarboxamide surrogates with improved EHS profiles or use SN2 substitutions via activated carbonates/tosylates to avoid stoichiometric phosphine waste.

• Alternative feedstocks (context)

  • For developing greener analogs, bio‑based α‑hydroxy esters like methyl lactate provide similar functionality with improved biodegradability and established green solvent credentials; however, the β‑cyclohexyl motif in this product imparts distinct hydrophobicity and steric profile not replicated by methyl lactate.

• Comparison snapshot (literature/general)

  • Methyl 3‑cyclohexyl‑2‑hydroxypropanoate: hydrophobic, higher lipophilicity; suited to SAR where bulky nonpolar groups are required.
  • Methyl lactate: higher polarity, biodegradable solvent; suitable as a greener solvent/reagent but not a structural drop‑in.

• Waste and energy

  • Apply solvent swap and recycle where infrastructure allows; perform vacuum distillations at reduced temperature to cut energy.
  • Adopt in‑process controls to minimize rework and off‑spec waste.

These recommendations are general; validate compatibility with your target chemistry.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is provided for this item. It is supplied strictly for research and development.

• General formulation context (literature/general)

  • α‑Hydroxy esters are sometimes used as pro‑moieties or intermediates during API synthesis. The presence of a secondary alcohol allows selective derivatization (e.g., carbonate/ester pro‑groups) and subsequent unmasking under physiological or chemical conditions.
  • The β‑cyclohexyl group imparts hydrophobicity that can be leveraged in medicinal chemistry SAR for tuning membrane permeability and metabolic stability, but this item itself is not indicated for clinical or GMP use.

• Process considerations

  • If used as a process intermediate, standard ICH considerations apply: control of residual solvents, purge of reagents (e.g., coupling agents), and chiral purity if stereochemistry is relevant to the route.

No therapeutic claims are made. For any work approaching regulated development, obtain full quality dossiers and consider custom GMP production and release testing.

Physical Properties

Item-specific specifications (this lot)

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

Literature/computed expectations for this structural class (not product specifications)

• Physical state: typically a low-melting solid or colorless to pale liquid for C10 α‑hydroxy methyl esters with a cyclohexyl substituent.
• Boiling point: α‑hydroxy methyl esters of similar size often show BP in the ~240–290 °C range at ambient pressure; vacuum distillation is commonly used (literature, structural analogs).
• Density: esters with one ring and C10 backbone often fall near 1.00–1.05 g/mL at 20–25 °C (literature, analogs).
• Solubility: miscible with many organic solvents (EtOAc, MeOH, i-PrOH, acetone, CH2Cl2); low solubility in water due to hydrophobic cyclohexyl (general behavior).
• Partitioning: the cyclohexyl group increases hydrophobicity; logP is expected in the moderate range (>1, <3) for analogous α‑hydroxy esters (literature trend).
• Hydrogen bonding: intramolecular H‑bonding (OH→C=O) possible; OH engages in standard H‑bonding with donors/acceptors in solution, influencing chromatography.

Practical notes

• Viscosity may be modestly higher than simple methyl lactate due to the ring substituent.
• The free –OH can broaden NMR signals (exchange) and may cause tailing in normal-phase chromatography; add a trace of base or use reverse phase if needed.

Always confirm exact parameters for your lot in the CoA/Spec Sheet; do not treat the above ranges as specifications.

Quality & Grades

Item-specific grade and purity are not provided in the Product Data for this listing.

• Item-specific (from Product Data)

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

• Interpreting common grades (general guidance)

  • Research grade: suitable for most synthetic and analytical workflows; impurity profiles are controlled but not pharmacopeial.

  • 95–98% purity (if specified on CoA): adequate for most organic synthesis; chiral applications may require enantiomeric excess confirmation by chiral HPLC.

  • HPLC grade solvents/reagents: minimized UV‑active impurities for analytical work; for this product, “HPLC grade” would be relevant only if used as a mobile phase additive/standard.

• Stabilizers/inhibitors

  • No stabilizer is indicated for this item. If a stabilizer or antioxidant is present in a specific lot, it will be declared on the CoA/Spec Sheet and may affect certain reactions (e.g., radical or oxidation chemistry).

• Release documentation

  • CoA typically includes identity (1H NMR/13C NMR/IR), purity assay (GC/HPLC), and water content (Karl Fischer) when applicable. For chiral materials, an ee specification is only applicable if stated; otherwise assume racemate.

For regulated or high‑precision applications (e.g., chiral synthesis, quantitative analytical standards), verify full impurity profile, residual solvents, water content, and (where relevant) enantiomeric composition on the CoA.

Reaction & Applications

As a bifunctional α‑hydroxy methyl ester with a β‑cyclohexyl substituent, this reagent serves as a versatile intermediate in synthesis, medicinal chemistry, and materials derivatization.

• Transformations at the alcohol (C2)

  • Selective acylation (Ac2O, DMAP) to give α‑acyloxy esters.
  • Mitsunobu inversion (DEAD/DIAD, PPh3) with chosen nucleophiles to access inverted α‑substituted derivatives; useful for setting C2 configuration from racemate via resolution strategies.
  • Oxidation to α‑keto ester (Dess–Martin, Swern) enabling further C–C bond constructions (e.g., nucleophilic additions, enolizations).

• Transformations at the ester (C1)

  • Hydrolysis (acidic or basic) to 3‑cyclohexyl‑2‑hydroxypropanoic acid; subsequent coupling (EDC/HATU) introduces diverse amides/esters.
  • Transesterification to alternative alcohols (Fischer acid catalysis or base-catalyzed under anhydrous conditions) to tune lipophilicity.

• C–C bond formation at the α‑position

  • Via oxidation to α‑keto ester followed by reductive amination or nucleophilic addition.
  • Direct α‑functionalization through temporary protection of –OH (silyl ethers, carbonate), then enolate chemistry (LDA, LiHMDS) under carefully controlled temperatures.

• β‑Cyclohexyl handle

  • Provides hydrophobic bulk for SAR; undergoes standard ring functionalizations (oxidation at benzylic-like positions absent; remote C–H oxidations require directed strategies).

• Practical tips

  • Protect –OH (TBS, TMS, benzyl carbonate) to avoid side reactions during strong base steps.
  • Control temperature and quench carefully to prevent ester saponification.
  • For chiral applications, consider enzymatic resolution or chiral derivatization after Mitsunobu to access single enantiomers (literature strategies).

Reaction Conditions

The following conditions are general literature guidance for α‑hydroxy methyl esters and should be optimized for your substrate and scale.

• Protection of –OH (to enable base chemistry)

  • TBS protection: TBSCl (1.2–1.5 eq), imidazole (2.0 eq), DMF or DCM, 0–25 °C, 1–4 h; typical yields 80–95% (literature, general).
  • Carbonate protection: p‑nitrophenyl chloroformate or Boc2O/DMAP in DCM, 0–25 °C, 1–3 h.

• Mitsunobu inversion at C2

  • Alcohol (1.0 eq), acid nucleophile (1.1–1.5 eq), PPh3 (1.2–1.5 eq), DIAD (1.2–1.5 eq), THF or toluene, 0 °C→RT, 2–12 h; workup with hydrazine or scavengers to remove byproducts (typical yields 60–85% for secondary alcohols; literature ranges).

• Oxidation to α‑keto ester

  • Dess–Martin periodinane (1.3 eq), DCM, 0–25 °C, 0.5–2 h; quench with aqueous NaHCO3/Na2S2O3; yields 70–90% (literature).
  • Swern: DMSO/oxalyl chloride, −78→−20 °C; Et3N base; typical 60–85%.

• Ester transformations

  • Hydrolysis (basic): MeOH/H2O, NaOH (1–2 eq), 0–25 °C, 1–4 h; acidify to isolate acid.
  • Transesterification (acidic): ROH (solvent, 10–20 eq), catalytic TsOH or H2SO4, Dean–Stark if applicable, 40–80 °C; remove MeOH for Le Châtelier drive.

• Enolate chemistry (after –OH protection)

  • LDA or LiHMDS (1.1–1.5 eq) in THF at −78 to −40 °C; electrophiles: alkyl halides, aldehydes; quench at low temperature to minimize retro‑processes.

All conditions should be validated by TLC/LC–MS/NMR monitoring; maintain anhydrous, oxygen‑free conditions where sensitive.

Safety & Handling

Authoritative safety information resides in the product SDS; the following provides general laboratory guidance for α‑hydroxy esters.

• Item-specific hazard information (from Product Data)

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

• General hazards and precautions (literature/general)

  • May cause eye/skin irritation and respiratory discomfort upon prolonged exposure; handle in a fume hood to avoid inhalation of vapors or aerosols.
  • Avoid contact with strong oxidizers and strong bases (base-catalyzed transesterification/saponification) and strong acids (acid-catalyzed transesterification/dehydration).
  • Secondary alcohols and esters are combustible; keep away from ignition sources. Ground/bond containers during bulk transfer.
  • PPE: lab coat, safety glasses or splash goggles, and nitrile gloves; change gloves regularly when handling liquids.

• First aid (overview; follow SDS/site SOPs)

  • Skin/eye contact: rinse with copious water for ≥15 minutes; remove contaminated clothing; seek medical evaluation if irritation persists.
  • Inhalation: move to fresh air; monitor for respiratory irritation; seek medical attention if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Waste & spill response

  • Absorb small spills with inert material (vermiculite, sand), place in appropriate organic waste.
  • Dispose according to local regulations; segregate halogenated from non‑halogenated solvent waste if used in solutions.

Solvent Selection

This compound is an α‑hydroxy methyl ester with a hydrophobic cyclohexyl substituent, giving amphiphilic behavior: polar functionality (–OH, –CO2Me) with substantial nonpolar surface area.

• Polarity and miscibility (general/literature)

  • Expected to be freely soluble in polar aprotic and moderately polar protic solvents: EtOAc, acetone, MeCN (warm), MeOH/i‑PrOH, THF, DCM.
  • Limited solubility in water due to the cyclohexyl ring; co‑solvents (MeOH, acetonitrile) assist aqueous workups or analytical sample prep.

• Chromatography considerations

  • Normal phase: may show tailing from –OH; add 0.1–1% Et3N or use EtOAc/hexanes with a base modifier.
  • Reverse phase: C18 with water/MeCN or water/MeOH plus 0.1% formic acid (or NH4OAc) often affords sharp peaks by suppressing secondary interactions.

• When to choose specific solvents

  • Drying/activation steps: for reactions sensitive to water (e.g., Mitsunobu, acylation), use rigorously dry solvents (molecular sieves or distillation) to limit ester hydrolysis/transesterification.
  • Recrystallization (if solid): EtOAc/hexanes or MTBE/hexanes are common combinations for α‑hydroxy esters; actual behavior depends on lot and polymorph.

• Small comparison (general)

  • EtOAc: green(er), excellent solvent for esters; easy removal, good for extraction.
  • THF/2‑MeTHF: strong solvency; 2‑MeTHF offers improved sustainability and water immiscibility.
  • MeOH/i‑PrOH: enable hydrogen bonding; useful for derivatization and as mobile phase components.

Storage & Reconstitution

Item-specific storage and handling

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

General storage guidance for α‑hydroxy esters

• Store tightly sealed under inert atmosphere (optional but beneficial) to minimize slow hydrolysis or oxidation. A desiccator or dry cabinet helps limit moisture uptake.
• Protect from prolonged heat and direct sunlight. If performing long‑term storage (>12 months), refrigeration (2–8 °C) can further enhance stability, though room temperature is indicated for this item.
• Avoid contact with strong acids/bases which can catalyze transesterification or hydrolysis.

Reconstitution and handling

• Typically supplied neat; no reconstitution is required. If solidified/crystallized, warm gently (e.g., 30–40 °C) to liquefy before aliquoting.
• For solution prep, use dry, oxygen‑free solvents where reactions are moisture‑sensitive. Prepare single‑use aliquots to limit repeated air/moisture exposure.

Stability notes (general)

• The free –OH and ester are generally stable under neutral, dry conditions. Track any changes by NMR/LC over time if material is stored in solution.

Always consult the current CoA and SDS for lot‑specific guidance and follow institutional storage SOPs.

Structure & Identity

Methyl 3-cyclohexyl-2-hydroxypropanoate is an α-hydroxy methyl ester bearing a β-cyclohexyl substituent, making it a useful, bifunctional building block (free secondary alcohol + methyl ester) for stereocontrolled synthesis.

• Item-specific (from Product Data)

  • SKU: M970874
  • Product Name: Methyl 3-cyclohexyl-2-hydroxypropanoate
  • CAS: 1033777-74-0
  • PubChem CID: 13925900
  • InChIKey: 70481 (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)

  • Functional groups: secondary alcohol (at C2), methyl ester (at C1), cyclohexyl at C3 (β-position).
  • Stereochemistry: the C2 center is stereogenic; materials may be racemic unless otherwise declared (no stereochemical grade specified for this item).
  • 2D description: a three‑carbon chain bearing a terminal methyl ester (–CO2Me) at C1; the α‑carbon (C2) carries –OH; the β‑carbon (C3) is bonded to a cyclohexyl ring (chair conformation favored). The alcohol and ester are separated by one carbon (α‑hydroxy ester motif).

• Identity context (general)

  • The α‑hydroxy ester motif is versatile: it can be oxidized to an α‑keto ester, engaged in Mitsunobu inversion at C2, or hydrolyzed/transesterified at the methyl ester. The β‑cyclohexyl unit provides hydrophobic bulk and conformational bias for SAR or materials tuning.

Synthetic Utility

Key functional elements of Methyl 3‑cyclohexyl‑2‑hydroxypropanoate enable diverse transformations:

• α‑Hydroxy center (C2)

  • Protection: silyl ethers (TBS/TIPS), benzylation, or carbonate formation to mask –OH during strong base chemistry.
  • Inversion/substitution: Mitsunobu reaction with carboxylic acids, thiols, or azides to introduce new functionality with stereochemical control (from racemate or resolved material).
  • Oxidation: DMP/Swern to the α‑keto ester, enabling nucleophilic additions (e.g., cyanide, organometallics under controlled conditions) and formation of α‑amino esters via reductive amination.

• Ester handle (C1)

  • Hydrolysis (to acid) followed by amide coupling (EDC/HATU/DIC) or esterification (Fischer, Steglich) to diversify the scaffold.
  • Transesterification to alter lipophilicity and volatility (choice of alcohol controls properties and downstream separations).

• β‑Cyclohexyl group (C3)

  • Contributes steric bulk and hydrophobicity for SAR; ring C–H functionalization (radical or directed methods) can introduce further diversity (e.g., oxygenation, halogenation) though typically with lower site selectivity.

• Retrosynthetic value

  • Accessible from cyclohexyl‑substituted aldehydes/epoxides via aldol-type or epoxide opening strategies, or from β‑substituted lactates.

• Purification/analysis tips

  • 1H/13C NMR readily distinguishes the α‑CH–OH and methoxy signals; IR shows strong C=O near ~1735–1750 cm⁻¹ (ester) and broad O–H. For chiral work, use chiral HPLC or Mosher ester analysis to determine ee (general methods).

Target Specificity

Not applicable. This product is a small‑molecule organic intermediate and is not an antibody, enzyme, or targeted biological reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.

Frequently Asked 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.

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

The CAS Number is 1033777-74-0, the molecular formula is C10H18O3, and the molecular weight is 186.24 g/mol. InChIKey DQWADVKQCYOJTK-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.