Cyclohexadecanone - ≥97% , CAS No.2550-52-9

CAS: 2550-52-9 Cat. No.: C1051673 Fórmula: C₁₆H₃₀O Peso molecular: 238.410 Número CE: 438-930-8

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Especificações e pureza

≥97%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥97%

Nomes e identificadores

• Sorrisos canónicos: C1CCCCCCCC(=O)CCCCCCC1
• IUPAC Name: cyclohexadecanone
• InChIKey: LXJDKGYSHYYKFJ-UHFFFAOYSA-N
• INCHI: 1S/C16H30O/c17-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-16/h1-15H2
• Peso molecular: 238.410

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Cyclic ketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones
• Direct Parent: Cyclic ketones
• Alternative Parents: Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclic ketone - Organic oxide - Hydrocarbon derivative - Aliphatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
• 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

Propriedades químicas e físicas

• Peso molecular: 238.410 g/mol
• XLogP3: 6.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 238.23 Da
• Monoisotopic Mass: 238.23 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 168.000
• 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 item-specific biological assay protocols are provided for this product. As a chemical building block, usage protocols depend on the intended synthetic transformation (see Reaction Conditions and Synthetic Utility tabs).

For analytical characterization in a research setting (general guidance):

• GC–MS: Use a medium‑ to high‑temperature program suitable for C16 ketones; consider on‑column or PTV injection to minimize discrimination.
• HPLC: Reverse‑phase C18 with high organic content (80–100% acetonitrile or methanol); UV detection at 210–220 nm captures the weak carbonyl absorbance.
• NMR: Acquire 1H/13C in CDCl3 or C6D6; expect a carbonyl carbon ~210–215 ppm and broad methylene envelopes for the ring.

Refer to the literature examples and adapt conditions to your scale and equipment. Always consult the SDS and CoA/Spec Sheet before use.

Biological Roles

Item-specific biological/clinical roles are not provided for this product and no medical claims are made. For research use only.

General context (literature):

• Cyclohexadecanone is a hydrophobic macrocyclic ketone. Macrocyclic ketones and lactones in the C14–C18 range are widely studied as odorants (musk notes) and as precursors to macrolides, but they are not endogenous metabolites.
• In biochemical studies, such macrocycles can serve as model hydrophobic scaffolds to probe membrane partitioning, micellar solubilization, or protein binding to apolar ligands. Any such interactions are non‑specific hydrophobic effects rather than defined biological signaling.
• Metabolic fate in generic terms: aliphatic ketones may undergo phase I reduction to secondary alcohols and omega‑/beta‑oxidation pathways after initial activation; however, detailed biotransformation data for cyclohexadecanone specifically are limited in open literature.

Note: This information is general chemistry/biochemistry background and not specific to the supplied item. Always design experiments to ensure appropriate containment and avoid environmental release of hydrophobic organics.

Buffer Applications

Not typically applicable. Cyclohexadecanone is a hydrophobic organic substrate, not a buffering reagent. It has negligible water solubility and does not participate in acid/base equilibria in the physiological pH range beyond very weak enolization.

Practical note: If studying interactions in aqueous systems (e.g., binding or emulsions), use co‑solvents (DMSO ≤1–5% v/v, ethanol) or surfactants/lipid carriers to achieve dispersion. Verify that such additives do not interfere with your assay.

Green Alternatives

While cyclohexadecanone itself is a substrate rather than a solvent, greener choices can be made for its synthesis, transformation, and purification.

• Solvent selection (greener options; literature guidance):

  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2‑MeTHF, CPME, or cyclopentyl methyl ether where compatible. These can dissolve macrocyclic ketones while reducing environmental impact.
  • Use heptane or bio‑based alkanes in place of hexanes for extractions/crystallizations.

• Oxidations (Baeyer–Villiger):

  • Consider chemoenzymatic Baeyer–Villiger monooxygenases (BVMO) using O2/H2O2 cofactors under mild aqueous/MeCN conditions, avoiding peracids. Tradeoff: enzyme sourcing and scalability.
  • Use urea–hydrogen peroxide (UHP) with catalytic acids in greener solvents as an alternative to mCPBA.

• Reductions:

  • Prefer catalytic hydrogenation (H2, Pd/C) or transfer hydrogenation (e.g., isopropanol with Ru or Mn catalysts) over stoichiometric metal hydrides when selectivity allows.

• Workup and purification:

  • Employ solvent‑minimized crystallization/trituration instead of silica chromatography where possible.
  • Recycle solvents via distillation; macrocycles tolerate multiple recycle cycles if peroxide/acid impurities are controlled.

• Energy and safety:

  • Conduct high‑boiling operations under high vacuum to lower thermal load.
  • Adopt flow chemistry for exothermic oxidations to improve heat/mass transfer and reduce solvent usage.

Tradeoffs: Greener media may alter rates/selectivity (e.g., different enolate geometry in 2‑MeTHF vs THF). Validate with small‑scale DoE before scale‑up.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient designation is provided for this product. For research use only; not for human or veterinary use.

General context (literature):

• Macrocyclic ketones and lactones can be used as fragrance components in topical products and as synthetic intermediates toward macrolide scaffolds, but cyclohexadecanone itself is not a standard pharmaceutical excipient.
• In formulation science research, hydrophobic macrocycles may serve as model compounds to study solubilization in lipid vehicles, polymer matrices, and cyclodextrin complexes. Such studies inform delivery strategies for lipophilic actives but do not imply therapeutic application.

If regulatory‑grade material is required (e.g., compendial compliance, residual solvent limits), consult the appropriate pharmacopeial monograph. No monograph is known for cyclohexadecanone; therefore, project‑specific specifications and vendor CoA/quality agreements are essential.

Physical Properties

• Item-specific specifications for this catalog item:

  • 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: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties for cyclohexadecanone (for reference only; not product specifications):

  • State near ambient temperature: macrocyclic ketones of this size are typically waxy solids or low‑melting solids that may soften around room temperature; the exact polymorph and purity can shift the apparent melting behavior.
  • Boiling behavior: very high normal boiling point expected for C16 ketones; distillation typically requires high vacuum. Macrocyclic ketones of C14–C18 commonly distill above 300 °C at 1 atm and around 150–220 °C under 1–5 mmHg (literature, class behavior).
  • Density: expected around 0.85–0.90 g/mL at 20–25 °C for similar macrocyclic ketones (literature, class behavior).
  • Solubility: practically insoluble in water; freely soluble in nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, dichloromethane, chloroform, ethyl acetate, THF) (literature).
  • LogP: high hydrophobicity is typical (logP often >4 for similar C16 ketones) (literature estimates).
  • Refractive index: macrocyclic ketones of related size generally nD ~1.45–1.47 (literature, class behavior).

Always consult the item’s CoA/Spec Sheet for definitive physical specifications and the SDS for safe handling limits.

Quality and Grades

• Item-specific quality information:

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

• Guidance for interpreting grades (general):

  • Research/technical grade macrocyclic ketones are commonly specified by GC purity (area %) and may include assays for residual solvents and low‑level aldehydes or acids. If designated “GC ≥98%,” the material is typically suitable for most synthetic uses including enolate chemistry, reductions, and oxidations.
  • For chromatographic or spectroscopic applications (e.g., odorant reference standards), higher grades may specify low UV background and tight control of trace acid/base impurities to minimize baseline drift or peak tailing.
  • Stabilizers: Cyclohexadecanone generally does not require stabilizer; however, trace acid or base can catalyze side reactions in sensitive transformations (e.g., enolization). If present, stabilizers should be disclosed on the CoA and may need removal (e.g., aqueous washes, percolation through basic alumina) before certain reactions.

• Quality control considerations (general):

  • Identity confirmation: 1H/13C NMR (diagnostic carbonyl at ~210–215 ppm; alpha‑methylene protons often slightly deshielded), IR (C=O stretch ~1715–1730 cm⁻¹ depending on environment), HRMS (M+ at m/z 238.23 for C16H30O, literature), and GC/MS retention/fragmentation patterns typical of long‑chain ketones.
  • Water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Cyclohexadecanone is a versatile macrocyclic building block. Its single ketone and conformationally flexible 16‑membered ring enable diverse transformations.

• Representative transformations (literature examples; not exhaustive):

  • Baeyer–Villiger oxidation to the corresponding 15‑membered macrolactone (fragrance/musk intermediates). Reagents: mCPBA, peracetic acid, or trifluoroperacetic acid; solvent: DCM or MeCN; often buffered with NaHCO3.
  • Reductions to cyclohexadecanol or diols: NaBH4 (selective 1‑step to alcohol), LiAlH4 or catalytic hydrogenation/hydrosilylation methods.
  • Oxime/hydrazone formation and Beckmann rearrangement to macrocyclic lactams (useful for polyamide/macrolactam synthesis).
  • Enolate chemistry: alpha‑alkylation/acylation, aldol additions, and intramolecular Claisen variants; LDA or LiTMP in THF at low temperature improves kinetic control.
  • Wittig/HWE olefinations at the carbonyl to access exocyclic alkenes; subsequent hydrogenation or functionalization possible.
  • Halogenation at the alpha‑position (NBS, LDA then electrophile) to install handles for further cross‑coupling.

• Application domains (general research use):

  • Macrocycle methodology development (conformational effects on reactivity, ring strain minimization).
  • Odorant/macrolide precursor synthesis where macrocyclic lactones or ketones serve as key notes.
  • Model substrate in studies of Baeyer–Villiger migratory aptitude and stereoelectronic control in large rings.

Practical tips:

• Dry and degas solvents for base‑mediated steps; trace water promotes aldol/self‑condensation.
• Use high dilution or slow‑addition protocols to limit intermolecular side reactions in macrocycle modifications.
• Monitor by GC or LC–MS; macrocycles may elute late—optimize temperature programs or use higher‑boiling columns for GC.

Reaction Conditions

The following representative conditions are provided as general literature guidance for macrocyclic ketones like cyclohexadecanone. They are not specifications for this item.

• Baeyer–Villiger oxidation to macrolactone:

  • Reagents: mCPBA (1.2–2.0 equiv, 70–77%), NaHCO3 or disodium hydrogen phosphate buffer.
  • Solvent: DCM or CHCl3 (0.05–0.2 M).
  • Temperature: 0–25 °C.
  • Time: 2–24 h, monitor by TLC/GC.
  • Notes: Control acidity to limit over‑oxidation; peracetic acid or TFPA can accelerate but require added caution.

• Reduction to cyclohexadecanol:

  • NaBH4 (1.2–2.0 equiv) in MeOH or EtOH, 0–25 °C, 0.5–3 h. Quench with NH4Cl.
  • For complete reduction or sterically hindered cases, LiAlH4 (1.5–2.0 equiv) in THF/Et2O, 0–reflux, 1–4 h. Careful quench.

• Enolate formation/alpha‑alkylation:

  • Base: LDA (1.1–1.5 equiv) generated in situ from n‑BuLi/diisopropylamine in THF.
  • Temperature: −78 to −20 °C for enolate generation; 0–25 °C for electrophile addition.
  • Electrophiles: benzyl/allyl halides, MeI, acyl chlorides (for Claisen variants).

• Oxime/Beckmann to lactam:

  • Oxime formation: NH2OH·HCl, pyridine or Et3N in EtOH/MeOH, 25–60 °C, 2–6 h.
  • Rearrangement: SOCl2 or P2O5 or polyphosphoric acid, 60–120 °C; or catalytic TsCl in MeCN with base.

• Olefination (Wittig/HWE):

  • Wittig: Ph3P=CHR (1.5–2.0 equiv) in toluene/THF, 25–80 °C, 2–16 h.
  • HWE: (EtO)2POCHR’CO2Et, NaH in THF/DMF, 0–25 °C.

Typical isolated yields are substrate‑ and condition‑dependent; validate on small scale and optimize with DoE as needed.

Safety and Handling

• Item-specific GHS details: Not specified for this item; refer to SDS.

  • Signal Word: Not specified for this item; refer to SDS.
  • Hazard Statements (H‑statements): Not specified for this item; refer to SDS.
  • Pictograms/GHS classification: Not specified for this item; refer to SDS.

• General safety guidance for macrocyclic ketones (literature/good practice):

  • Hazards: Typically low volatility and low acute toxicity compared with small ketones, but can cause skin and eye irritation. Avoid inhalation of aerosols or heated vapors.
  • PPE: Use chemical‑resistant gloves (e.g., nitrile), lab coat, and safety glasses or splash goggles. Employ local exhaust if heating or spraying.
  • Handling: Avoid sources of ignition when distilling or heating. Use in a fume hood. Macrocyclic ketones are not known peroxide formers (unlike ethers), but observe routine solvent hygiene.
  • Incompatibilities: Strong oxidizers (e.g., peroxides, nitric acid). Under vigorous conditions, carbonyls may undergo aldol‑type or Baeyer–Villiger reactions with potent oxidants.
  • First aid (overview; defer to SDS):
    • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
    • Inhalation: Move to fresh air; assist breathing if necessary; seek medical attention.
    • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention.
  • Spill/cleanup: Absorb with inert material (vermiculite, sand), collect in suitable container for disposal. Wash area with detergent solution.
  • Fire-fighting: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2.

Always consult the product’s SDS for authoritative hazard classification and response procedures.

Solvent Selection

This product is a solid/liquid macrocyclic ketone, not a solvent. However, solvent choice is central to handling and transforming cyclohexadecanone.

• Polarity and miscibility (general behavior):

  • Highly hydrophobic; practically insoluble in water.
  • Freely soluble in nonpolar to moderately polar organic solvents: hexanes, heptane, toluene, diethyl ether, MTBE, THF, dichloromethane, chloroform, and ethyl acetate.

• Selection by operation:

  • Crystallization/trituration: hexanes or cold ethanol/isopropanol blends can induce crystallization of macrocyclic ketones if they are solid at low temperature; solvent/non‑solvent pairs with toluene/hexanes are common.
  • Distillation/purification: Due to very high bp, use high vacuum; choose low‑boiling carriers (pentane, DCM) for transfers; avoid overheating to limit isomerization or decomposition.
  • Reactions via enolates: Use dry, aprotic ethers (THF, MTBE) or hydrocarbons with HMPA‑free strong bases (LDA, LiTMP). Maintain low temperatures to control selectivity.
  • Oxidations (Baeyer–Villiger): DCM, chloroform, or acetonitrile are preferred for mCPBA or CF3CO3H systems; buffer acidity to limit over‑oxidation.
  • Reductions: Alcoholic media (MeOH/EtOH) for NaBH4; ethereal media (THF/Et2O) for LiAlH4.

• Comparison (general):

  • DCM vs EtOAc: DCM offers better solubility and inertness toward bases; EtOAc is greener and acceptable for many workups.
  • Hexanes vs heptane: Heptane is less volatile and often preferred for scalable crystallizations.

Always dry solvents thoroughly for base‑sensitive steps and verify compatibility with your reagents.

Storage and Reconstitution

• Item-specific storage (from Product Data):

  • Store at room temperature.

• Additional handling guidance (general good practice for macrocyclic ketones; not item‑specific specs):

  • Keep container tightly closed in a dry, well‑ventilated place. Protect from excessive heat and direct sunlight.
  • If long-term storage is anticipated, consider storing under inert gas (nitrogen or argon) to minimize slow oxidative changes, especially after repeated openings.
  • Avoid prolonged exposure to strong acids/bases and oxidizing agents in storage areas.
  • If the material is semi‑solid/waxy at room temperature, gentle warming (e.g., 30–40 °C water bath) can aid dissolution or transfer; do not overheat.

• Reconstitution/dissolution (as needed for use):

  • Readily dissolves in common organic solvents (DCM, chloroform, toluene, THF, ethyl acetate, hexanes). Use dry, oxygen‑free solvents for base‑sensitive reactions.
  • For aqueous assay systems, prepare concentrated stock in a miscible organic co‑solvent (e.g., DMSO or ethanol), then dilute into the aqueous phase with vigorous mixing; typical final co‑solvent 1–5% v/v. Confirm solubility and assay compatibility.

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

Always check the SDS for definitive storage incompatibilities and the CoA for any stabilizers or special handling notes.

Structure and Identity

Cyclohexadecanone is a saturated macrocyclic ketone featuring a 16‑membered carbocyclic ring bearing a single internal carbonyl.

• Item-specific (from Product Data):
  • SKU: C1051673
  • CAS: 2550-52-9
  • InChIKey: 211659 (as provided)
  • Storage: Room temperature
  • Category Path: 全部 / 可售 / 生命科学
• Literature/computed identifiers (general reference; not item‑specific specs):
  • Preferred name: Cyclohexadecanone
  • Synonyms: 16-cycloalkanone; hexadecanone (cyclic)
  • Molecular formula (calculated): C16H30O
  • Molecular weight (calculated): 238.41 g/mol
  • SMILES (generic, literature): O=C1CCCCCCCCCCCCCCC1 (macrocyclic ketone; 16‑membered ring)
• Structural features (general chemistry):
  • Functional groups: one ketone (acyclic carbonyl within a carbocycle); all remaining positions aliphatic sp3 carbons.
  • Ring system: large, flexible 16‑membered saturated ring; no heteroatoms in the ring.
  • Stereochemistry: none specified; the molecule is achiral overall, though it can adopt multiple conformers due to macrocycle flexibility.
  • 2D description in words: a long polymethylene chain cyclized to a 16‑membered ring with a carbonyl at one position; each alpha‑carbon to the carbonyl is methylene; no double bonds or substituents.

Notes: Where values are marked literature/computed, they are provided for context only and are not item-specific specifications.

Synthetic Utility

Cyclohexadecanone is a valuable macrocyclic synthon. The single ketone provides a pivot for diverse derivatizations while the 16‑membered ring imparts conformational flexibility and hydrophobic bulk.

Key reactivity (literature):

• Carbonyl transformations: reduction (NaBH4, LiAlH4), oxidation to lactones (Baeyer–Villiger), imine/oxime/hydrazone formation (E/Z control influenced by ring conformation), and olefination (Wittig/HWE) to exocyclic alkenes.
• Alpha‑functionalization: enolization with LDA/LiTMP affords kinetic enolates; electrophiles include RX (alkylation), acylating agents (Claisen variants), or silyl reagents (TMSCl after enolate formation). Large‑ring conformers can bias face selectivity and migratory aptitude.
• Rearrangements: Beckmann rearrangement of the oxime to macrocyclic lactams; useful entry to nylon‑like or macroamide frameworks.
• Building block for macrolides: sequential Baeyer–Villiger then functional group interconversions yield macrolactones that can be diversified (e.g., hydroxy/methylene insertions) toward musk/macrolide architectures.
• Cross‑coupling handles: alpha‑halogenation then elimination or metalation enables subsequent Suzuki/Negishi couplings after conversion to suitable leaving groups.

Practical considerations:

• Maintain anhydrous conditions for base‑mediated steps; water promotes self‑condensation or over‑enolization.
• High dilution and slow addition techniques can mitigate intermolecular side reactions with macrocycles.
• Purification often benefits from crystallization/trituration rather than silica chromatography; if chromatography is needed, use gradient hexanes/EtOAc and avoid overheating at the detector.

Target Specificity

Not applicable. This product is a small‑molecule macrocyclic ketone, not a biological targeting reagent (e.g., antibody, ligand with defined receptor selectivity). No antigen/epitope or species reactivity applies.