5-Methoxycoumarin , CAS No.51559-36-5

CAS: 51559-36-5 Cat. No.: M1048519 PubChem CID: 10899191

Storage

Room temperature

Specifications

보관 조건

Room temperature

이름과 식별자

정식 스마일

COC1=CC=CC2=C1C=CC(=O)O2

IUPAC Name

5-methoxychromen-2-one

InChIKey

XYFXTIBDEAZMAH-UHFFFAOYSA-N

INCHI

1S/C10H8O3/c1-12-8-3-2-4-9-7(8)5-6-10(11)13-9/h2-6H,1H3

이성체 SMILES

COC1=CC=CC2=C1C=CC(=O)O2

대체 CAS

51559-36-5

PubChem CID

10899191

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • 분류 Coumarins and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• 분류: Coumarins and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarins and derivatives
• Alternative Parents: 1-benzopyrans Anisoles Pyranones and derivatives Alkyl aryl ethers Heteroaromatic compounds Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin - Benzopyran - 1-benzopyran - Anisole - Phenol ether - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Lactone - Oxacycle - Ether - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• 설명: This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
• 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

화학 및 물리적 특성

• 분자량: 176.170 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 176.047 Da
• Monoisotopic Mass: 176.047 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 234.000
• 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 validated, item-specific application protocols are provided for this product.

• General examples (for research use; adjust to your system)
  • Preparation of stock solutions for fluorescence assays: Dissolve 5-methoxycoumarin at 10–50 mM in anhydrous DMSO or ethanol. Store aliquots protected from light. Dilute into assay buffer to ≤1% cosolvent.
  • Thin-film or solid-state studies: Dissolve in volatile solvent (EtOAc, CHCl3), cast on substrate, dry under nitrogen, and anneal as needed. Record spectra promptly to minimize photobleaching.
  • Demethylation setup: Under N2, cool BBr3 in CH2Cl2 to 0 °C, add substrate solution dropwise, stir to completion (TLC/HPLC), then carefully quench with MeOH/H2O and extract.

These are illustrative, non-validated outlines. Consult primary literature and adapt conditions to your laboratory SOPs. For authoritative handling and safety, refer to the product’s SDS.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to primary literature for detailed biochemical properties of 5-methoxycoumarin.

• General context (coumarins in biology; literature)

  • Occurrence: Coumarin scaffolds are widespread in plants (secondary metabolites). Methoxy substitution patterns modulate lipophilicity and electronic properties, which can influence membrane interaction and photophysical behavior in biological environments.
  • Photophysics and probing: Coumarins serve as microenvironment-sensitive fluorophores. While 7-substituted analogs are more common in biolabeling, 5-methoxy derivatives can be adopted as alternative reporters or scaffolds for probe development after further functionalization (e.g., installing linkers at positions 3, 6, 7, or 8).
  • Metabolic considerations: Etherified phenols can undergo O-demethylation by oxidative enzymes (general observation for methoxy aromatics), potentially yielding hydroxycoumarins in biological systems. Specific metabolic rates and pathways for 5-methoxycoumarin should be sourced from dedicated ADME studies.

Note: No medical, diagnostic, or therapeutic uses are claimed or supported for this catalog item. For research use only.

Buffer Applications

5-Methoxycoumarin is a neutral, poorly water-soluble aromatic lactone and is not itself a buffering agent. It does not form conventional buffer systems in aqueous media.

• Practical notes
  • If aqueous use is required (e.g., fluorescence in buffers), prepare concentrated stocks in DMSO or ethanol, then dilute into the target buffer (PBS, HEPES, Tris) ensuring final cosolvent content is compatible with the experiment (often ≤1–2% v/v).
  • Surfactants or cyclodextrins may be used to enhance apparent aqueous solubility; verify that additives do not alter fluorescence undesirably.

For buffer formulation guidance, refer instead to standard buffering agents; this product is best considered a hydrophobic analyte/label rather than a buffer component.

Green Alternatives

Where compatible with your chemistry and performance targets, consider greener solvent and process choices for handling and transforming 5-methoxycoumarin.

• Solvent substitution (general guidance)

  • Replace chlorinated solvents (e.g., CH2Cl2) with EtOAc or dimethyl carbonate for extractions and medium-polarity reactions when feasible.
  • Substitute THF with 2-MeTHF or CPME for organometallic or Lewis-acid-mediated steps, noting differences in coordination and water content.
  • Favor bio-based or low-toxicity solvents (EtOH, isopropanol) for recrystallization and chromatography when resolution permits.

• Workup and purification

  • Employ minimal solvent volumes; consider antisolvent crystallization (EtOAc/hexanes, EtOH/water) to reduce silica usage.
  • Explore supercritical CO2 for particle engineering or impurity removal where infrastructure exists.

• Energy and safety

  • Conduct reactions at ambient temperature/pressure when possible; use flow photochemistry for coumarin photoreactions to improve light-use efficiency and safety.

• Comparison snapshot (general)

  • CH2Cl2 vs EtOAc: EtOAc offers lower toxicity and better biodegradability with similar polarity; note higher boiling point and potential transesterification under strong base.
  • THF vs 2-MeTHF: 2-MeTHF has a higher boiling point and lower peroxide tendency in practice; may afford improved phase separations.

These are general green-chemistry recommendations; validate solvent effects on reactivity and photophysics for your specific application.

Pharmaceutical Uses

No pharmacopeial/excipient designation or formulation grade is provided for this item.

• Item-specific status

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Intended use: For research use only (as provided). Not for human or veterinary use, not for diagnostic or therapeutic applications.

• General context (literature; non-claim)

  • Coumarin derivatives are common scaffolds in discovery chemistry and as fluorescent tracers in formulation research (e.g., permeability studies, imaging excipients). 5-Methoxycoumarin may serve as a model chromophore or intermediate to access other coumarin-based reporters after functionalization.
  • If considering use as an analytical tracer/excipient in development settings, ensure impurity, residual solvent, and photostability profiles meet internal quality requirements; confirm extractables/leachables and fluorescence interferences as appropriate.

Always consult regulatory guidance and internal QC for any use beyond basic laboratory research.

Physical Properties

• Item-specific specifications

  • Physical constants (mp, bp, density, refractive index, water/peroxide content, trace metals, UV cutoffs): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties for 5-methoxycoumarin (for reference only; not product specifications)

  • Physical state: typically a crystalline solid
  • Color: off-white to pale yellow (typical for coumarin derivatives due to conjugation)
  • Solubility profile: low solubility in water; good solubility in polar aprotic and moderately polar organic solvents (e.g., DMSO, DMF, acetone), and moderate solubility in alcohols and chlorinated solvents (EtOH, MeOH, CH2Cl2, EtOAc)
  • Acid–base behavior: neutral lactone; phenolic acidity is masked by the methoxy ether; O-demethylation regenerates phenolic acidity at C5
  • Partitioning: expected moderate logP consistent with aromatic lactones bearing a methoxy substituent (qualitative)
  • Optical: coumarin chromophore exhibits UV–vis absorption in the near-UV; intrinsic fluorescence is typical for coumarins (exact maxima depend on solvent and substitution pattern)

Notes

• All numerical physical constants are intentionally omitted here because they are not specified for this catalog item. For exact values applicable to released lots, consult the item’s CoA/Spec Sheet and SDS.

Quality and Grades

• Item-specific grade/purity, appearance, and stabilizers

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

• General guidance on interpreting grade (context for research chemists)

  • Research-use grade materials typically emphasize identity and assay with routine impurity profiling suitable for synthesis, screening, and materials development. If low-UV absorbance, trace-metals control, or bioburden/endotoxin limits are required (e.g., for photophysics, catalysis, or bioassays), request the detailed specification/CoA or an elevated grade.
  • For fluorescent studies, background fluorescence from trace aromatic impurities or residual solvents can affect spectra. Ensure the grade meets your photophysical requirements (e.g., “spectroscopy grade” if needed).

• CoA/verification

  • For each lot, verify assay, related substances, and residual solvent levels via the CoA. If quantitative water content (e.g., KF), residual metals, or UV cutoffs are critical, these are Not specified for this item; refer to CoA/Spec Sheet.
  • If application requires stringent color/appearance criteria (e.g., thin-film optics), confirm with QC prior to use.

Reaction and Applications

• Representative research uses (general for coumarins)

  • Photophysics: Coumarins are established fluorophores; 5-methoxy substitution modulates absorption/emission and quantum yield. Useful as a reference scaffold for structure–photophysics studies, solvatochromism, and as a core for dye development.
  • Probe/scaffold development: The 5-position methoxy group can be diversified (e.g., O-demethylation → 5-hydroxycoumarin, followed by etherification/ether–linker installation) to generate reporter dyes or conjugates.

• Synthetic transformations (examples)

  • O-Demethylation: BBr3, BCl3, AlCl3/thiols, or HI can convert the methoxy to phenol (5-hydroxycoumarin) under controlled conditions. Avoid overreaction or lactone opening by temperature control and stoichiometry.
  • Electrophilic substitution on the aromatic ring (SEAr): Nitration, halogenation, or Friedel–Crafts-type acylation are feasible with appropriate directing effects; protection of the lactone may be necessary.
  • Conjugate (1,4-) addition to the enone of the coumarin system by soft nucleophiles (e.g., thiols, malonates) under base or Lewis acid catalysis.
  • Cross-couplings: After halogenation (e.g., 6- or 8-bromo derivatives), perform Suzuki, Sonogashira, or Buchwald–Hartwig couplings to elaborate the chromophore.

• Practical tips

  • Dry, oxygen-free conditions are not strictly required for most electrophilic substitutions, but moisture control helps avoid lactone hydrolysis under basic conditions.
  • For fluorescence measurements, use anhydrous, spectroscopic-grade solvents and work under low-light to minimize photodegradation.

Reaction Conditions

General literature guidance for typical transformations of 5-methoxycoumarin (not product specifications):

• O-Demethylation to 5-hydroxycoumarin

  • Reagents: BBr3 (1–3 eq) in dry CH2Cl2; 0 °C to rt, 1–6 h. Quench with MeOH/water. Alternatively, HI (48%) reflux or AlCl3/thiol systems under anhydrous conditions.
  • Notes: Control temperature to limit lactone opening. Work under inert atmosphere to minimize side reactions.

• Electrophilic halogenation (to enable cross-coupling)

  • Reagents: NBS/NCS in AcOH or DMF; catalytic acid may assist. Typical rt to 60 °C, 1–12 h.
  • Follow-up: Suzuki (Pd(PPh3)4, base, dioxane/H2O, 50–90 °C), Sonogashira (Pd/Cu, amine base, THF/Et3N), or Buchwald–Hartwig as appropriate.

• Michael additions to the coumarin enone

  • Nucleophiles: malonates, thiols, amines under base (e.g., DBU, piperidine) or Lewis acid catalysis (e.g., ZnCl2). Temperatures: rt to 80 °C; times: 2–24 h.

• Photophysical measurements

  • Solvents: spectroscopic-grade EtOH, MeCN, or PBS with ≤1% DMSO. Record spectra under low-light; use quartz cuvettes. Degassing can improve reproducibility.

• Purification

  • Typical by silica gel chromatography (EtOAc/hexanes or DCM/MeOH). Recrystallization from EtOH/EtOAc is common.

These conditions are representative from the literature. Optimize stoichiometry, temperature, and time for your substrate and scale.

Safety and Handling

• Item-specific safety designations

  • GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

• General safety information for coumarin derivatives (literature/guidance; not item-specific)

  • Likely hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Avoid dust generation and inhalation.
  • Photosensitivity: Conjugated coumarins can undergo photochemical reactions; minimize light exposure during handling and storage when feasible.
  • Peroxide formation: Not typically a peroxide-forming class (unlike ethers); no special peroxide precautions beyond routine solvent controls.
  • Incompatibilities: Strong bases (may open the lactone at elevated temperature), strong acids (possible hydrolysis), strong oxidizers.

• Recommended PPE and engineering controls

  • Use in a chemical fume hood. Wear safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid ingestion and inhalation; prevent contact with skin and eyes.

• First-aid overview (consult SDS for definitive procedures)

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse thoroughly with water for at least 15 minutes; remove contaminated clothing.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always defer to the product’s SDS and institutional SOPs for authoritative safety and spill/cleanup procedures.

Solvent Selection

5-Methoxycoumarin is a neutral, moderately aromatic, conjugated lactone with an anisole substituent.

• Polarity and miscibility (general)

  • Polarity class: weakly to moderately polar aromatic lactone
  • Expected solubility: good in DMSO, DMF, acetone, acetonitrile, CH2Cl2, EtOAc; moderate in EtOH/MeOH; poor in water
  • Hydrogen bonding: H-bond acceptor (lactone carbonyls); no donor groups present

• Practical solvent choices

  • Stock solutions for spectroscopy and bioassays: DMSO or ethanol; dilute into buffered aqueous media with surfactant/cosolvent if needed.
  • Synthesis/functionalization: CH2Cl2, THF, acetonitrile, or toluene depending on reaction (e.g., demethylation, electrophilic substitution, cross-coupling after halogenation).

• When to choose alternatives

  • If water compatibility is required, use mixed solvent systems (e.g., DMSO/H2O, MeCN/H2O) or formulate via cyclodextrins/micelles.
  • For greener processing, consider EtOAc, EtOH, or 2-MeTHF in place of CH2Cl2/THF when compatible with the transformation.

• Small comparison (general)

  • DMSO: highest solvating power; good for concentrated stocks; may quench some photochemistry.
  • EtOH/MeOH: greener, volatile; may participate in transesterification under strong acid/base.
  • CH2Cl2: excellent dissolver and inert; environmental and safety drawbacks; avoid for scale-up if possible.

Storage and Reconstitution

• Storage conditions (item-specific)

  • Store at room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.

• Additional best practices (general for coumarin derivatives)

  • Protect from light to preserve photophysical integrity; use amber vials/foil wrap.
  • Avoid prolonged exposure to heat and moisture; the lactone can hydrolyze under strongly basic aqueous conditions.

• Reconstitution/solution preparation

  • Solubility: Readily prepared as concentrated stocks in DMSO or ethanol; also soluble in acetone, acetonitrile, and dichloromethane.
  • Filtration: If particulate is present, filter through a PTFE syringe filter (0.2 µm) under subdued light.
  • Aliquoting: For spectroscopy or screening, prepare single-use aliquots to minimize freeze–thaw and light exposure.

• Stability

  • Long-term stability is formulation- and storage-dependent. Exact shelf-life, assay, and impurity limits are Not specified for this item; refer to CoA/Spec Sheet.

Always follow your institution’s storage SOPs and consult the SDS for detailed handling and incompatibility information.

Structure and Identity

5-Methoxycoumarin is a methoxy-substituted benzopyran-2-one (coumarin) scaffold, featuring a fused benzene–α-pyrone system with an anisole (–OCH3) substituent at the 5-position of the aromatic ring.

• Item-specific identifiers (from Product Data)

  • CAS: 51559-36-5
  • SKU: M1048519
  • Storage: Room temperature
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (The provided value appears incomplete.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (general reference values; not item specifications)

  • Common name: 5-Methoxycoumarin
  • Synonyms: 5-Methoxy-2H-1-benzopyran-2-one; 5-Methoxy-1,2-benzopyrone
  • Molecular formula (literature): C10H8O3
  • Molecular weight (literature): ~176.17 g/mol
  • Core functional groups: lactone (α-pyrone), aryl methoxy ether, conjugated enone within the coumarin ring
  • Structural features: planar, conjugated chromophore; methoxy is meta to the lactone oxygen within the benzene ring framework

• 2D structural description (general)

  • The structure consists of a six-membered benzene ring fused to a six-membered unsaturated lactone. At the 5-position of the benzene portion, an anisole-like –OCH3 group replaces hydrogen. The lactone carbonyl (C=O) and the C=C bond of the pyrone ring form an extended conjugation path across the bicyclic system, characteristic of coumarin fluorophores.

Synthetic Utility

5-Methoxycoumarin is a versatile intermediate within the coumarin family, offering both an electronically tuned chromophore and a transformable methoxy handle.

• Functional group reactivity (general)

  • Lactone (α-pyrone): participates in conjugate addition and, under forcing conditions, ring-opening to o-hydroxycinnamate derivatives.
  • Aromatic methoxy: convertible to phenol (O-demethylation) enabling further diversification (etherification, esterification, carbonate/urethane linkages).
  • Aromatic ring: amenable to SEAr (nitration, halogenation) at positions governed by the coumarin electronics; subsequent cross-couplings expand diversity.

• Retrosynthetic value

  • Accessible via Pechmann condensation from appropriately substituted phenols and β-ketoesters or via Knoevenagel/lactonization strategies, making it a convenient node in coumarin libraries.

• Downstream elaborations

  • Install solubilizing groups (amines, sulfonates) via demethylation → phenol → alkylation/sulfonation to tune photophysics and solubility.
  • Create donor–acceptor systems by aryl–aryl coupling (e.g., 6- or 8-aryl derivatives) to shift absorption/emission for dye development.
  • Introduce click handles (azide/alkyne) through sidechains from the phenolic oxygen or via halogenation/cross-coupling enabling bioconjugation.

• Practical considerations

  • Protect the lactone if strong base or high-temperature conditions are needed to avoid ring opening.
  • For photophysical applications, rigorous purification minimizes background fluorescence from aromatic impurities.

Target Specificity

This product is a small-molecule chemical (coumarin derivative) and not a biological targeting reagent.

• Item-specific targeting data (antigen, epitope, clone, isotype, species reactivity): Not applicable and not specified for this item.

For applications requiring biomolecular specificity, use appropriate antibodies, ligands, or engineered probes; 5-methoxycoumarin can serve as a fluorescent scaffold after suitable bioconjugation chemistry.