Clofibrate-d4 - ≥98 atom% D,≥98% , CAS No.1189654-03-2

CAS: 1189654-03-2 Cat. No.: C1005657 분자식: C₁₂H₁₁D₄ClO₃ 분자량: 246.72 PubChem CID: 71314923

GRADE & PURITY ≥98 atom% D,≥98%

Storage

Room temperature

Specifications

사양 및 순도

≥98 atom% D,≥98%

보관 조건

Room temperature

작업 유형

AGONIST

순수함

≥98 atom% D,≥98%

이름과 식별자

• 정식 스마일: CCOC(=O)C(C)(C)OC1=CC=C(C=C1)Cl
• IUPAC Name: ethyl 2-(4-chloro-2,3,5,6-tetradeuteriophenoxy)-2-methylpropanoate
• InChIKey: KNHUKKLJHYUCFP-KDWZCNHSSA-N
• INCHI: 1S/C12H15ClO3/c1-4-15-11(14)12(2,3)16-10-7-5-9(13)6-8-10/h5-8H,4H2,1-3H3/i5D,6D,7D,8D
• 이성체 SMILES: [2H]C1=C(C(=C(C(=C1OC(C)(C)C(=O)OCC)[2H])[2H])Cl)[2H]
• PubChem CID: 71314923
• 분자량: 246.72

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • 분류 Benzene and substituted derivatives
      • Subclass Phenoxyacetic acid derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 분류: Benzene and substituted derivatives
• Subclass: Phenoxyacetic acid derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenoxyacetic acid derivatives
• Alternative Parents: Phenoxy compounds Phenol ethers Chlorobenzenes Alkyl aryl ethers Aryl chlorides Carboxylic acid esters Monocarboxylic acids and derivatives Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxyacetate - Phenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid ester - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Organochloride - Organooxygen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organohalogen compound - Organic oxide - Aromatic homomonocyclic compound
• 설명: This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
• 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: 246.720 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 246.096 Da
• Monoisotopic Mass: 246.096 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 232.000
• Isotope Atom Count: 4
• 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 assay-specific protocols are provided in the Product Data. Typical usage as an LC–MS/MS internal standard includes:

• Prepare a primary stock (e.g., 0.5–1.0 mg/mL) in acetonitrile or methanol. Store aliquots to minimize freeze–thaw; verify stability per your SOP.
• Prepare working solutions by serial dilution into initial LC mobile phase or precipitation solvent to target ng/mL–μg/mL levels matching analyte concentration.
• Spike a fixed volume of the internal standard into each calibrator, QC, and sample before extraction to correct for recovery and matrix effects.
• Monitor MRM transitions offset by +4 Da relative to the unlabeled analyte; optimize collision energies and source parameters empirically.

These are general best practices for isotope-dilution LC–MS and are not item-specific instructions. Always follow your lab’s validated method.

Biological Roles

This section provides general, literature-based context for the clofibrate scaffold; it does not imply any clinical/therapeutic use of this product.

• Mechanistic class (literature)

  • Clofibrate is a classic peroxisome proliferator–activated receptor alpha (PPARα) agonist used as a biochemical tool compound in metabolic research. The d4 label enables selective MS quantification in complex matrices.

• Biotransformation (literature)

  • Primary pathway: ester hydrolysis to clofibric acid; subsequent conjugation (e.g., glucuronidation) may occur in biological systems.
  • Oxidative O-dealkylation and ether cleavage are lesser but documented routes under certain conditions.

• Research applications (laboratory)

  • Use of Clofibrate-d4 as an internal standard allows accurate assessment of extraction recovery, matrix effects, and instrument variability when studying uptake, distribution, or in vitro metabolism of clofibrate.

Note: All uses are for research only. No medical, diagnostic, or therapeutic applications are intended or implied.

Buffer Applications

Clofibrate-d4 is a hydrophobic aromatic ester and does not function as a buffering agent. It has no conventional role in preparing pH buffer systems. For experimental planning, focus instead on the Solvent Selection and Reaction & Applications sections for guidance on preparing stock solutions and LC–MS standards in compatible organic/aqueous-organic media.

Green Alternatives

As an isotopically labeled reference material, Clofibrate-d4 itself is not replaceable for its analytical role. However, greener choices can be made around its use, especially solvent selection and sample preparation.

• Greener solvent choices for solution prep and LC–MS (general)

  • Prefer acetonitrile or ethanol over chlorinated solvents for routine handling.
  • Use aqueous-organic mobile phases with volatile buffers (ammonium formate/acetate) to minimize hazardous waste.

• Comparison (general guidance)

  • Acetonitrile vs. methanol: ACN often provides lower backpressure and sharper peaks; MeOH is less toxic and often cheaper but may require higher pressures and can change selectivity.
  • Replace DCM/CHCl3 in extractions with EtOAc or MTBE where method performance allows.

• Waste minimization

  • Prepare concentrated master stocks to reduce solvent usage in daily dilutions.
  • Adopt microvolume autosampler vials and low-flow LC to cut solvent consumption.

Trade-offs

• Method sensitivity and selectivity may dictate solvent choice; validate greener substitutions to ensure they meet assay performance targets.

Pharmaceutical Uses

For research use only; not for human or veterinary use.

• Role in pharmaceutical research (general)

  • Analytical standard/internal standard for method development, validation, and QC in the context of clofibrate-related research materials or legacy formulations.
  • Useful in evaluating extraction recoveries, matrix effects, and stability during sample handling and storage in preclinical laboratories.

• Regulatory/compendial status

  • No pharmacopeial grade or monograph is specified for this item. Any compendial relevance would pertain to the unlabeled drug substance; isotopically labeled materials are typically controlled by in-house specifications and supplier CoAs.

• Formulation relevance

  • While the unlabeled scaffold has historical formulation interest, the d4 analog is employed strictly as a chromatographic/mass-spectrometric reference.

Physical Properties

Item-specific specifications are not provided in the Product Data.

• Product Data specifics

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

• Literature/typical properties for the unlabeled clofibrate scaffold (for reference only; not item specifications)

  • Typical MW (clofibrate, unlabeled): ~242.65 g/mol; d4 analog expected ~4.03 g/mol higher (literature-based isotopic increment).
  • Physical state: crystalline solid or low-melting solid (literature).
  • Solubility: sparingly soluble in water; soluble in common organic solvents (methanol, ethanol, acetonitrile, DMSO, dichloromethane) (literature).
  • LogP: clofibrate is lipophilic (high logP; literature indicates strong hydrophobicity), supporting use in organic phases.
  • UV characteristics: aromatic chromophore absorbs in UV; exact cutoffs/ε not specified for this item.

• Computed/estimation notes

  • No computed values are provided for this catalog entry. For exact numeric specifications (mp, purity, residual solvents, isotopic enrichment), refer to the item’s CoA/Spec Sheet.

Quality and Grades

• 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 for this product class (analytical/isotopically labeled standards)

• Isotopic enrichment: For d4 materials, enrichment at labeled positions is usually reported as %D and %GC/LC purity on the CoA. This dictates suitability for quantitative LC–MS/MS.
• Analytical purity vs. isotopic purity: Both matter. High chemical purity minimizes interferences; high isotopic enrichment maximizes mass-resolving power and minimizes isotopic cross-talk.
• Residual solvents/water/peroxides/metal limits: Not specified for this item; see CoA. For LC–MS, low non-volatile residue and low background ions are preferred.
• Batch-to-batch documentation: Expect retention time match and identical fragmentation pathways to the unlabeled analyte; review the CoA for confirmation of exact labeling pattern.

What this means in practice

• Use this material as an internal standard or system suitability control when quantifying clofibrate or related analytes.
• Verify match to your method by comparing MS transitions (parent/product m/z shifted by +4 vs. unlabeled). Check CoA for exact transitions if provided.

Reaction and Applications

This product is primarily an isotopically labeled analytical standard rather than a synthetic reagent. Typical research applications include:

• Quantitative LC–MS/MS internal standard

  • Spike-in control for assay calibration, matrix-effect normalization, and recovery correction when measuring clofibrate or related metabolites.
  • Use in method validation (linearity, accuracy, precision, carryover, stability) per bioanalytical guidelines.

• Metabolism and ADME research (preclinical, in vitro; research use only)

  • Tracking hydrolysis to clofibric acid and potential phase I ether cleavage by comparing unlabeled vs. d4 signals.

• Stability-indicating studies

  • Evaluate ester hydrolysis, oxidative degradation, and photolysis pathways by following isotopologue ratios.

General chemical behavior of the clofibrate scaffold (literature)

• Ester hydrolysis under acidic/basic conditions to give clofibric acid and ethanol (or d-labeled ethanol if label is on the ethyl group).
• Ether linkage is stable to mild conditions but can undergo O-dealkylation under strong conditions or specific enzymatic pathways.
• Aromatic chloride is typically inert toward nucleophilic substitution without activation; the phenoxy ether defines reactivity more than the C–Cl bond.

Reaction Conditions

As an analytical standard, Clofibrate-d4 is not typically “reacted.” The following literature-based conditions pertain to the chemical behavior of the clofibrate scaffold during stress testing or derivatization; they are provided for general guidance only.

• Hydrolysis (to clofibric acid)

  • Base-catalyzed: aqueous NaOH or KOH (0.1–1 M), MeOH/H2O or THF/H2O, 20–60 °C, hours; quenched and acidified to isolate acid (literature).
  • Acid-catalyzed: mineral acid (e.g., HCl) in MeOH/H2O, reflux to accelerate; milder rates at ambient temperature.

• Transesterification

  • Alkoxide in corresponding alcohol (e.g., NaOMe/MeOH), 0–25 °C to control side reactions; applicable to derivatization for GC methods.

• Stability for analytical use

  • Stock solutions in acetonitrile or methanol are typically stable for weeks at 2–8 °C and days at room temperature; always verify with your method’s stability protocol. Light protection is recommended due to aromatic chromophore.

• LC–MS notes

  • Positive/negative ESI both possible depending on method; the carboxylate favors negative ionization after hydrolysis. For the intact ester, APCI or ESI can be effective; optimize source conditions empirically.

All parameters above are general literature guidance for the unlabeled scaffold and are not item specifications.

Safety and Handling

• Product Data safety fields

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

• General laboratory handling (best practice; defer to SDS for authoritative guidance)

  • PPE: lab coat, safety glasses, and appropriate chemically resistant gloves. Handle powders/solids in a fume hood to avoid inhalation of dust/aerosols.
  • Avoid: inhalation, ingestion, and skin/eye contact. Prevent environmental release; dispose of waste via appropriate hazardous waste streams.
  • Incompatibilities (general for aryl ester ethers): strong bases/acids may induce hydrolysis; strong oxidizers may react with the aromatic ether; avoid prolonged exposure to strong nucleophiles.
  • First aid (general): rinse eyes/skin with water for ≥15 min upon contact; move to fresh air if inhaled; seek medical attention as needed. Consult the SDS for detailed measures.

• Special considerations for isotope-labeled standards

  • Treat as you would the unlabeled analog regarding hazards; deuteration does not typically change GHS classification.
  • To preserve isotopic integrity, avoid conditions that could exchange deuterium (if any D is on potentially exchangeable positions; the specific labeling pattern for this item is not provided).

Solvent Selection

Clofibrate-d4 is a non-polar to moderately polar aromatic ester, optimized for use in organic media and LC–MS sample prep.

• Polarity/miscibility (literature-based for clofibrate scaffold)

  • Water: very low aqueous solubility; avoid purely aqueous media.
  • Polar aprotic: readily soluble in acetonitrile, DMF, DMSO; commonly used for stock solutions in LC–MS.
  • Alcohols: soluble in methanol/ethanol; good for calibration solutions and spiking standards.
  • Halogenated/ethers: soluble in dichloromethane, chloroform, MTBE, THF.

• Practical selection

  • LC–MS calibration: acetonitrile or methanol with 0.1% formic acid or ammonium acetate (buffer kept volatile) are standard. Prepare concentrated stocks in ACN or MeOH, then dilute with initial mobile phase composition.
  • Sample extraction: for biological matrices, pair with protein precipitation (ACN/MeOH) or LLE (MTBE/hexane/EtOAc) depending on method.

• Comparison snapshot (general)

  • Acetonitrile: strong protein-precipitating power, low viscosity, excellent for LC–MS; preferred for calibration mixes.
  • Methanol: strong solvent, often improves solubility; slightly higher viscosity; common in LC–MS.
  • DMSO: excellent solubility for concentrated stocks; limit final % to avoid chromatographic/ionization effects.

Storage and Reconstitution

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

Best practices for this product class (analytical standards)

• Long-term storage: although room temperature is indicated, many labs store isotopically labeled standards at 2–8 °C or -20 °C (desiccated, light-protected) to maximize stability. Follow your internal SOPs and verify stability.
• Container: keep tightly closed in an inert container with desiccant. Minimize headspace moisture and light exposure.
• Reconstitution/stock solutions: dissolve in high-purity acetonitrile or methanol to prepare a primary stock (e.g., 0.1–1 mg/mL). Vortex until fully dissolved; filter if particulate is observed.
• Aliquoting: dispense single-use aliquots to avoid repeated opening. For frozen aliquots, avoid multiple freeze–thaw cycles.
• Aqueous work: due to low water solubility, first prepare an organic stock, then dilute into aqueous-organic mixtures (e.g., 50:50 ACN:H2O) immediately before use.

Note: Exact concentration, purity, and isotopic enrichment are Not specified for this item; refer to the product CoA/Spec Sheet and SDS for definitive instructions.

Structure and Identity

Clofibrate-d4 is the deuterium-labeled analog of clofibrate, an aryloxyisobutyric acid ethyl ester. The label provides four deuterium atoms incorporated into the parent framework for mass spectrometric discrimination.

• Product Data (as provided)

  • SKU: C1005657
  • CAS: 1189654-03-2
  • CID: 71314923
  • InChIKey: 184605 (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 for clofibrate scaffold)

  • Core scaffold: ethyl 2-(4-chlorophenoxy)-2-methylpropanoate (aryloxyisobutyrate ester).
  • Functional groups: aryl chloride, aryl–O–alkyl ether linkage (phenoxy), tertiary α-carbon bearing two methyl groups, ethyl carboxylate ester.
  • Isotopic labeling: four non-exchangeable deuterium atoms (positions vary by supplier specification; typically on the tert-alkyl methyls and/or ethyl group). Exact labeling pattern for this item is not specified; refer to CoA.

• 2D description (general)

  • A para-chloro-substituted phenyl ring connected through an ether oxygen to a quaternary (tertiary) carbon that also bears two methyl groups and a carboxylate; the carboxylate is esterified as an ethyl ester. The d4 label substitutes four hydrogens with deuterium on the alkyl moiety of this framework.

Synthetic Utility

Clofibrate-d4 is not commonly used as a building block in multistep synthesis; its principal value is as an isotopically labeled analog for analysis. Nevertheless, understanding the functional group chemistry can aid in stress-testing and degradation studies.

• Functional group reactivity (general for clofibrate scaffold)

  • Carboxylic ester: susceptible to acid-/base-catalyzed hydrolysis to clofibric acid; transesterification under alcoholysis conditions.
  • Aryl–O–alkyl ether: typically robust; can undergo cleavage under strong Lewis acids or specialized reagents; enzymatic O-dealkylation is a biological pathway.
  • Aromatic C–Cl: relatively inert under mild conditions; requires activated nucleophiles/catalysis for substitution.

• Isotopic considerations

  • Deuterium retention: labels are generally on non-exchangeable C–D bonds; avoid harsh protic acid/base at elevated temperature that may promote H/D scrambling if benzylic/α positions are involved. Exact labeled positions for this item are not specified; consult CoA.

• Use in synthetic method development

  • As an internal standard to monitor reaction progress or product stability of the unlabeled analog via LC–MS, enabling accurate mass-balance and impurity tracking.

Target Specificity

Not applicable. This product is a small-molecule analytical standard and has no antibody/biological target specificity. No antigen, epitope, clone, or isotype information applies.