Ethyl 7-hydroxy-7-phenylheptanoate , CAS No.112665-42-6

CAS: 112665-42-6 Cat. No.: E970973 Fórmula: C₁₅H₂₂O₃ Peso molecular: 250.330

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: CCOC(=O)CCCCCC(C1=CC=CC=C1)O
• IUPAC Name: ethyl 7-hydroxy-7-phenylheptanoate
• InChIKey: CBLRKMHGDTXYKT-UHFFFAOYSA-N
• INCHI: 1S/C15H22O3/c1-2-18-15(17)12-8-4-7-11-14(16)13-9-5-3-6-10-13/h3,5-6,9-10,14,16H,2,4,7-8,11-12H2,1H3
• Peso molecular: 250.330

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Fatty Acyls
      • Subclass Fatty alcohols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Fatty Acyls
• Subclass: Fatty alcohols
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty alcohols
• Alternative Parents: Fatty acid esters Benzene and substituted derivatives Secondary alcohols Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Fatty alcohol - Fatty acid ester - Monocyclic benzene moiety - Benzenoid - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Aromatic alcohol - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organic oxygen compound - Organooxygen compound - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six 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

Propiedades químicas y físicas

• Peso molecular: 250.330 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 250.157 Da
• Monoisotopic Mass: 250.157 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 222.000
• 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 assay or kit-style application protocols are specified for this item. As a general-purpose research chemical and synthetic intermediate, usage depends on the intended transformation.

• Weighing and dissolution

  • Bring the container to ambient temperature before opening to avoid condensation. Dissolve in an appropriate solvent (e.g., DCM, EtOAc, THF, toluene, or DMSO for bioassays). Filter if particulates are present.

• Example workflow contexts (general)

  • Oxidation to ketone: Dissolve in dry DCM (0.05–0.2 M), add DMP at 0 °C, warm to rt; quench and extract.
  • Saponification: Stir in MeOH/H2O with NaOH at rt until complete by TLC; neutralize and extract to obtain the acid.
  • Derivatization of the OH: Form the mesylate in DCM/Et3N at 0 °C; follow with nucleophilic substitution as needed.

• Analytical QC

  • Verify identity and purity by 1H/13C NMR, LC/GC, and HRMS as required. For chiral applications, use chiral HPLC/GC to assess enantiomeric composition.

Always consult internal SOPs and adapt solvent systems and conditions to the specific reaction and scale.

Biological Roles

This product is a synthetic aryl-alkyl ester with a benzylic secondary alcohol and is not known as a natural metabolite or cofactor.

• General context (chemistry knowledge)

  • The scaffold resembles a lipophilic fatty-acid-derived ester appended to a phenyl cap. Such motifs appear in medicinal chemistry libraries as hydrophobic fragments but are not recognized as specific biological metabolites.
  • The secondary benzylic alcohol can participate in hydrogen bonding, potentially impacting binding in biochemical assays, yet any such interactions are assay- and target-dependent and must be empirically determined.

• Experimental considerations

  • Poor aqueous solubility is expected; for biochemical assays, dissolve first in DMSO or EtOH, then dilute into buffered media while monitoring for precipitation.
  • Avoid interpretation of activity data without proper vehicle controls and solubility assessments (e.g., nephelometry).

No established physiological role, metabolic pathway, or enzymatic specificity is attributed to Ethyl 7-hydroxy-7-phenylheptanoate in the literature. Use is limited to research and development under appropriate laboratory conditions.

Buffer Applications

This compound is not a buffering reagent and has no defined pKa values in the biological buffering range that would make it suitable for buffer preparation.

• Practical guidance
  • If required in biochemical buffers (e.g., assay compound), dissolve first in a miscible organic cosolvent such as DMSO and then perform controlled dilution into the aqueous buffer with vigorous mixing.
  • Typical biological buffers (HEPES, PBS, Tris, MOPS) should be selected independently to control pH; this compound will not provide buffering capacity.

For pH control and ionic strength, use dedicated buffer systems; consult this product’s Solvent Selection and Application Protocols sections for handling in assays.

Green Alternatives

Greener practice considerations for using Ethyl 7-hydroxy-7-phenylheptanoate focus primarily on solvent and reagent choices during its handling and transformations.

• Prefer greener solvents when feasible

  • Replace DCM/CHCl3 with ethyl acetate or 2-MeTHF for many operations (workups, extractions, some oxidations and acylations).
  • Use toluene or isopropyl acetate instead of higher-toxicity aromatics or chlorinated solvents where solubility permits.

• Oxidations at the benzylic alcohol

  • Consider TEMPO/bleach (NaOCl) or Oxone®-based systems in biphasic greener solvents as alternatives to chromium(VI) reagents. Balance with chemoselectivity to protect the ester when needed.

• Ester transformations

  • For hydrolysis/re-esterification, biocatalytic options (lipases in 2-MeTHF or solvent-free systems) can reduce waste and metal residues.

• Energy and waste minimization

  • Employ microscale DoE to define minimal reagent excess and optimal temperature.
  • Favor catalytic protocols (organocatalysis or low-loading metal catalysis) over stoichiometric activators where compatible.

Comparison snapshot (general)

• DCM vs EtOAc: EtOAc offers lower toxicity and better biodegradability; DCM offers easier evaporation but higher environmental impact.
• THF vs 2-MeTHF: 2-MeTHF is bio-based with improved separations in aqueous workups; THF is more established but forms peroxides more readily.

Note: Selection must still meet performance and purity needs; verify compatibility by small-scale trials.

Pharmaceutical Uses

No pharmacopeial monograph or excipient listing is provided for this item. It should be treated strictly as a research chemical.

• Item-specific status

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Regulatory status: Not established; not intended for human or veterinary use.

• General R&D context (non-clinical)

  • Aryl-alkyl esters with benzylic alcohols are sometimes explored as intermediates in medicinal chemistry routes, enabling late-stage diversification (oxidation, etherification, or dehydration) while preserving an ester handle for further derivatization.
  • The ethyl ester can serve as a temporary protecting group for the acid; hydrolysis to the acid followed by amide coupling is a common route to explore analogs.
  • Physicochemical properties (lipophilicity, HBD/HBA count) place this scaffold in a range often used for fragment-to-lead elaboration, but any pharmaceutical relevance would derive from the final target molecule, not this intermediate.

No therapeutic, diagnostic, or clinical claims are made or implied. For formulation or ADME studies, select and qualify materials according to internal QA and regulatory standards.

Physical Properties

Item-specific physicochemical specifications are not provided in the Product Data. Do not use the following as product specifications; they are literature/computed context only.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Ester of this size is typically a high-boiling liquid/oil; literature values for close analogs are often >250 °C at ambient pressure.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Aliphatic/aryl esters of this size are commonly liquids at room temperature.)
• Density: Not specified for this item; refer to CoA/Spec Sheet. (Literature for related C15 esters: ~1.00–1.06 g/mL at 20–25 °C.)
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general): Expected to be insoluble in water and miscible/soluble in nonpolar to mid-polar organic solvents (e.g., toluene, dichloromethane, THF, ethyl acetate, hexanes) based on functionality.
• LogP/partitioning (qualitative): Aryl-alkyl ester with secondary alcohol is expected to have a moderate-to-high hydrophobicity (cLogP likely >3; computed/literature for comparable structures).
• pKa: The benzylic secondary alcohol typically exhibits pKa ~15–17 in water/MeOH (literature, very weak acidity); not suitable as an aqueous buffer component.

Always consult the CoA/Spec Sheet for this specific item before using any numeric property for process design or QC.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff/LC-MS background/metals: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for this molecule class (for selection and method development):

• Research grade organic building blocks such as aryl-alkyl esters with a benzylic alcohol are typically suitable for synthetic R&D, medicinal chemistry, and method development. For trace analyses (e.g., LC/GC or high-sensitivity MS assays), low-residual solvent and low-UV-absorbing profiles are beneficial.
• If employing this material in enantioselective synthesis (the C7 center is stereogenic), specify and verify enantiomeric ratio by chiral HPLC/GC as needed.
• For reactions sensitive to acid/base impurities (e.g., Mitsunobu couplings, Lewis-acid catalysis), consider pre-treating or verifying acid/base number on the lot CoA.
• If used in photochemical or oxidative contexts, verify the absence of oxidation byproducts (e.g., benzylic ketone) by NMR/LC before use.

Documentation and QC

• Request and review the lot-specific CoA/Spec Sheet for assay, residual solvents, and analytical data (e.g., 1H/13C NMR, HPLC/GC purity) prior to regulated or scale-up work.

Reaction and Applications

This molecule combines an ethyl ester (electrophilic at the carbonyl) with a secondary benzylic alcohol (nucleophilically derivatizable and oxidizable). These orthogonal handles support diverse transformations in synthesis and SAR exploration.

• Transformations of the benzylic alcohol (C7)

  • Oxidation to the corresponding ketone (7-oxo-7-phenylheptanoate) using Dess–Martin periodinane, PCC, Swern, or TEMPO-based systems (literature). Benzylic positions oxidize efficiently under mild conditions.
  • Conversion to leaving groups: mesylate/tosylate formation, or halides using SOCl2 or PBr3, enabling subsequent substitution/elimination to install heteroatoms or alkenes (E1 to yield 7-phenyl-6-heptenoate derivatives).
  • Etherification/esterification: Mitsunobu coupling to invert configuration and form C–O bonds to phenols/carboxylic acids; or direct acylation/alkylation under standard conditions.

• Transformations of the ethyl ester

  • Saponification to the free acid and re-esterification with alternative alcohols for pro-moiety tuning.
  • Reduction (DIBAL-H to aldehyde at low temperature; LiAlH4/borane to primary alcohol) for chain elaboration.
  • Amidation via activation (e.g., DCC/EDC after hydrolysis to acid) or direct aminolysis under forcing conditions.

• Strategic uses

  • Late-stage diversification at the benzylic stereocenter to explore stereochemical effects.
  • Serve as a lipophilic linker between an aryl cap and functionalized carboxylate terminus in medicinal chemistry scaffolds.
  • Precursor to benzylic ketones and styrene-like alkenes via dehydration/oxidation sequences.

Ensure moisture control when ester integrity is required and avoid strong acids/bases if racemization or dehydration is a concern.

Reaction Conditions

Guidance below reflects typical literature conditions for related functional groups and should be adapted by small-scale optimization. Not item-specific specifications.

• Oxidation of benzylic secondary alcohol → ketone

  • Dess–Martin periodinane (1.3–1.6 equiv), DCM, 0 °C to rt, 0.5–2 h. Workup with aq. NaHCO3/Na2S2O3. Typical isolated yields: 80–95% (literature for benzylic alcohols).
  • PCC on silica, DCM, rt, 1–4 h, 70–90% yields; minimize over-oxidation or acid-promoted side reactions of the ester.

• Activation/substitution at C7

  • MsCl/Et3N, DCM, 0 °C→rt, 1–2 h to give mesylate; subsequent SN1/SN2/E1 pathways depending on nucleophile/base and temperature. Benzylic substrates are typically reactive at rt–reflux.
  • SOCl2 (1.2–2.0 equiv), pyridine or DMF catalytic, DCM or toluene, 0 °C→rt, 1–3 h to give chloride.

• Dehydration to alkene

  • Acid-catalyzed elimination (e.g., p-TsOH, toluene, Dean–Stark) or POCl3/pyridine at 0 °C→rt to form the 6-alkenyl ester; monitor for regioselectivity.

• Ester manipulations

  • Saponification: NaOH (1–2 M) in MeOH/H2O, 0 °C→rt, 1–4 h to acid; acidify and extract. Typical yields: 85–98%.
  • Transesterification: ROH (5–20 equiv), catalytic H2SO4 or p-TsOH, reflux; or NaOMe-catalyzed in MeOH at rt–reflux.
  • Reduction: DIBAL-H (1.1–1.5 equiv), toluene or DCM, −78 to −20 °C to aldehyde; LAH (2–3 equiv), THF, 0 °C→reflux to primary alcohol.

• Purification/analysis

  • Normal-phase silica gel with hexanes/EtOAc. Monitor by TLC (anisaldehyde/UV). Confirm by 1H/13C NMR; chiral HPLC/GC if enantioenrichment is relevant.

Safety and Handling

• GHS information (item-specific)

  • 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 (chemistry knowledge; not item-specific)

  • Organic esters and benzylic alcohols are generally of low acute hazard, but may cause skin/eye irritation on contact and respiratory irritation if aerosols/vapors are generated.
  • Avoid ingestion and minimize inhalation of mists/vapors. Benzylic alcohols can undergo air oxidation; limit prolonged air exposure for long-term storage.

• Handling recommendations

  • Use in a fume hood with standard PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Avoid open flames/ignition sources when using volatile organic solvents with this material.
  • Prevent contact with strong oxidizers (risk of exotherm) and strong acids/bases if ester hydrolysis or dehydration is undesirable.

• First-aid overview (refer to SDS for authoritative guidance)

  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory irritation.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.

• Fire and reactivity

  • Combustible organic compound; use CO2, dry chemical, or foam for small fires. Combustion may produce CO/CO2 and irritant vapors.

Always consult the product-specific SDS for definitive hazard and response information.

Solvent Selection

This compound is a moderately bulky, hydrophobic aryl-alkyl ester with a secondary benzylic alcohol, favoring organic media.

• Polarity/miscibility (general)

  • Poorly soluble in water; readily soluble in ethyl acetate, dichloromethane (DCM), chloroform, toluene, and THF; variable solubility in hexanes/MTBE depending on temperature and composition.
  • The benzylic OH adds slight polarity and hydrogen-bonding capacity, improving solubility in mid-polar solvents (EtOAc, THF, MeCN) relative to completely nonpolar esters.

• Choosing solvents by task

  • Workup/extraction: EtOAc/hexanes or DCM/water biphasic systems are effective; avoid strong aqueous base if ester integrity must be preserved.
  • Chromatography: Start with hexanes/EtOAc (e.g., 8:2 to 6:4) or toluene/EtOAc gradients. Benzylic alcohol often elutes slightly more polar than a non-hydroxylated analog.
  • Reactions of the OH group: Use aprotic solvents (DCM, THF, toluene) for derivatizations (e.g., acylation, Mitsunobu). For oxidations (e.g., DMP, PCC), DCM is common.
  • Hydrolysis/transesterification of the ester: MeOH/EtOH with catalytic acid/base or in the presence of NaOMe/acid catalysts.

• Quick comparison (general)

  • DCM: excellent solubility and low boiling for easy removal; chlorinated waste.
  • EtOAc: greener than DCM, good solubility, compatible with many steps.
  • THF/2-MeTHF: broad solubility; 2-MeTHF offers greener profile and facilitates phase splits with water.

Storage and Reconstitution

• Storage (item-specific)

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

• General storage guidance (chemistry knowledge)

  • Keep container tightly closed in a cool, dry, well-ventilated place. Protect from moisture and prolonged exposure to air or light to minimize slow benzylic oxidation or ester hydrolysis over extended periods.
  • For long-term storage, consider amber glass and an inert headspace (N2/Ar), especially after first opening.

• Reconstitution/handling

  • Typically provided neat. If solidification or crystallization occurs on cooling, warm gently to room temperature and swirl to homogenize.
  • To prepare stock solutions, dissolve in a suitable organic solvent (e.g., DCM, EtOAc, THF, toluene, or DMSO). Record solvent, concentration, and date; store solutions at 2–8 °C where compatible and check for precipitation before use.

Always refer to the product’s CoA and SDS for lot-specific guidance and safety information.

Structure and Identity

Ethyl 7-hydroxy-7-phenylheptanoate is an aryl-substituted aliphatic ester bearing a secondary benzylic alcohol at the ω-end of a heptanoate chain.

• Item identifiers (Product Data)

  • SKU: E970973
  • CAS: 112665-42-6
  • InChIKey: 39798 (as provided)
  • Category Path: 全部 / 可售 / 生命科学
  • Research Use Note: For research use only

• Core structural features (general description)

  • Functional groups: ethyl ester (–COOEt) and secondary alcohol at C7; phenyl (C6H5) substituent at the same C7 center (benzylic to the phenyl ring).
  • Carbon skeleton: a heptanoate chain (C1 = carboxyl carbon) with substitution at C7 = C(OH)(Ph)–.
  • Stereochemistry: the C7 carbon is a stereogenic center; material is typically obtained as a racemate unless otherwise specified (no enantiomeric info is provided for this item).

• Computed/literature identifiers (not item specifications)

  • Typical molecular formula (computed from name): C15H22O3 (literature/computed)
  • Typical molecular weight (computed): ~250.34 g/mol (literature/computed)
  • Representative SMILES (literature/computed): CCOC(=O)CCCCCC(O)c1ccccc1

• 2D structure in words (general)

  • From the ethyl ester carbonyl, a five-methylene spacer leads to a terminal carbon bearing both OH and phenyl groups, giving a benzylic secondary alcohol appended to an aliphatic chain esterified as the ethyl ester.

Synthetic Utility

Ethyl 7-hydroxy-7-phenylheptanoate offers orthogonal reactivity at the benzylic secondary alcohol and the ethyl ester.

• Functional group leverage

  • Benzylic OH: susceptible to oxidation (to ketone), activation (tosylate/mesylate), substitution (to halides), or Mitsunobu coupling (inversion with acids/phenols).
  • Ethyl ester: can be hydrolyzed, transesterified, reduced (DIBAL-H to aldehyde; LAH/borane to alcohol), or converted to amides after acid formation.

• Strategic disconnections

  • Retrosynthesis often disconnects at the C7–O(H) bond (arriving from a ketone by reduction) or at the C7–Ph bond (e.g., via addition of phenyl nucleophiles to a 7-oxo precursor or via Friedel–Crafts-type approaches on suitably activated intermediates).
  • The C7 stereocenter allows access to enantioenriched derivatives via asymmetric reduction of the corresponding ketone or resolution at the alcohol stage.

• Library diversification

  • Rapid generation of analogs through: (a) varying the alkoxy of the ester (RO-), (b) oxidizing/derivatizing the benzylic position, and (c) functionalizing the phenyl ring (SEAr, borylation/halogenation followed by cross-coupling).

• Protection strategies

  • The benzylic OH can be protected as silyl ethers (TBS/TBDPS) or carbonate/benzoate esters when downstream conditions threaten dehydration/oxidation.

This dual-handle architecture makes the compound a versatile intermediate for target- and property-driven synthesis.

Target Specificity

This product is a small-molecule building block, not a biological affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity is applicable.

• Targeting data: Not applicable.
• Tested reactivity/applications: Not applicable.

For biochemical assay use, any target engagement must be empirically determined for the final designed molecules incorporating this scaffold.

Preguntas frecuentes

How should this product be stored?

Store at room temperature.

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

The CAS Number is 112665-42-6, the molecular formula is C15H22O3, and the molecular weight is 250.330 g/mol. InChIKey CBLRKMHGDTXYKT-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.