N-Octyl 4-hydroxybenzoate-d , CAS No.2708282-26-0

CAS: 2708282-26-0 Cat. No.: N1446018 Formula: C₁₅H₁₈D₄O₃ Peso molecolare: 254.36

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

N-Octyl 4-hydroxybenzoate-d 4 is the deuterium labeled N-Octyl 4-hydroxybenzoate.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

• Peso molecolare: 254.36

Application Protocols

No manufacturer-verified assay protocols are provided for this item. The following are general, literature-based examples for using deuterated parabens as analytical standards. Adapt to your method and validate internally.

• LC‑MS/MS calibration (example): • Stock: 1 mg/mL in acetonitrile (LC‑MS grade); store at −20 °C in amber vials.
  • Working solutions: serial dilutions to 0.5–500 ng/mL in 50:50 ACN/H2O with 0.1% formic acid (as compatible with method).
  • Spiking: add internal standard at constant concentration across calibrators, QCs, and samples (e.g., 50 ng/mL).
  • Column: C18, 2.1 × 50 mm, 1.7–3 µm; gradient water/ACN with 0.1% FA.
  • Detection: MRM transitions selected per instrument; adjust for +1 Da mass shift vs. native analyte.

• Enzymatic hydrolysis assay (example): • Prepare substrate in minimal ACN (≤1% v/v final) in phosphate buffer, pH 7.4.
  • Add esterase (per supplier units); incubate at 37 °C.
  • Quench aliquots with ice‑cold ACN containing internal standard; analyze by LC‑MS for substrate/product time course.

Note: Parameters above are illustrative (literature/good practice) and not product specifications. Optimize for your instrumentation and regulatory context.

Biological Roles

This section summarizes general, literature-based biology relevant to 4‑hydroxybenzoate esters and how deuteration can aid research. It does not imply any clinical or therapeutic use.

• Biotransformation: Aryl esters like octyl 4‑hydroxybenzoate are susceptible to enzymatic hydrolysis by carboxylesterases, yielding 4‑hydroxybenzoic acid (p‑HBA) and n‑octanol. Subsequent phase II conjugation of p‑HBA (e.g., glucuronidation, sulfation) is well documented for parabens (literature).
• Transport/partitioning: The long n‑octyl chain confers strong hydrophobicity, favoring membrane association and partitioning into lipid phases (literature). This can influence bioavailability in in vitro systems and recovery in extraction workflows.
• Deuterium label utility: The O–D at the phenolic site allows tracking of H/D exchange and can serve as a mass tag for isotope‑dilution assays, enabling discrimination from endogenous/unlabeled parabens.
• Enzyme kinetics: Using the deuterated analog as substrate permits monitoring of hydrolysis rates without isotopic interference in MS detection and can help correct for matrix effects through coelution.
• Photostability/oxidation: Phenolic aromatics may undergo photo‑oxidation under intense UV; routine laboratory lighting is typically not problematic, but amber storage is prudent.

Note: The above reflects general biochemical behavior of parabens in research contexts. For this specific item, no biological potency or binding data are provided; consult primary literature if mechanistic detail is required for your model system.

Buffer Applications

N‑Octyl 4‑hydroxybenzoate‑d is not a buffering reagent and is only sparingly soluble in water. Consequently, it is not typically used to prepare biological buffers.

Practical notes for aqueous work (literature/good practice):

• If inclusion in aqueous media is necessary (e.g., spiking controls), dissolve first in a water‑miscible organic solvent such as acetonitrile or methanol and then dilute into buffer with vigorous mixing; keep the final organic content as low as your system tolerates (often ≤1–5%).
• Avoid basic buffers if preserving the O–D isotopic label is critical; phenolate formation will induce rapid H/D exchange and can accelerate hydrolysis.
• For enzyme assays (e.g., esterases), typical buffers are phosphate or Tris near pH 7.4, but maintain low organic cosolvent and confirm solubility/aggregation behavior experimentally.

Green Alternatives

As an analyte/standard rather than a solvent or bulk reagent, the “green alternatives” discussion focuses on solvent and workflow choices that reduce environmental impact without compromising data quality.

Greener solvent choices (literature guidance):

• Prefer acetonitrile or ethanol over chlorinated solvents (e.g., CH2Cl2, CHCl3) for sample prep when chromatographic compatibility allows.
• For reversed-phase LC, use water/MeOH or water/ACN gradients; avoid unnecessary use of tetrahydrofuran or halogenated eluents.
• For extractions, consider ethyl acetate or MeTHF as alternatives to DCM where selectivity permits.

Comparison (general):

• ACN vs DCM: ACN is less hazardous, fully miscible with water, and widely compatible with LC‑MS; DCM offers strong solvency but with higher environmental/health concerns.
• Ethyl acetate vs chloroform: EA provides good solvency and easier waste handling; chloroform should be avoided where possible.

Process considerations:

• Miniaturize calibrations and use low‑volume autosampler vials to reduce solvent consumption.
• Prepare concentrated master stocks and dispense microliter aliquots to minimize waste and repeat freeze‑thaws.
• Implement solid‑phase extraction (SPE) with aqueous methanol or ethanol eluents when feasible to reduce halogenated solvent use.

Note: No greener “substitute molecule” exists for isotopically matched internal standards; isotopic fidelity to the target analyte is critical for quantitative accuracy.

Pharmaceutical Uses

No therapeutic or clinical claims are made for this product. Content below is general, literature-based context for formulation and analytical development.

• Excipient context (literature): Parabens (alkyl 4‑hydroxybenzoates) have historically been used as antimicrobial preservatives in non‑parenteral formulations. Octyl paraben is more hydrophobic than lower alkyl parabens and is less commonly used due to solubility constraints.
• Analytical development: The deuterated analog serves as an internal standard for assay development, stability studies, and extractables/leachables testing where octyl paraben may be present or used as a model hydrophobic preservative.
• Method validation: Isotope‑dilution LC‑MS/MS with deuterated internal standards supports accuracy/precision across complex matrices by correcting for ion suppression and recovery.

Item-specific status:

• Pharmacopeial listing, impurity limits, and excipient grade status: Not specified for this item; refer to CoA/Spec Sheet and relevant pharmacopeias if required.

Formulation cautions (general):

• Low aqueous solubility complicates aqueous dosage forms; co‑solvents or surfactants may be needed in research formulations.
• Hydrolysis risk increases in alkaline media and at elevated temperatures; stress studies should control pH and temperature.
• If isotopic integrity matters (e.g., mass balance studies), minimize exposure to protic media to limit O–D/H exchange.

Physical Properties

Only item-specific storage/shipping is provided. All other values below are general literature guidance for octyl 4‑hydroxybenzoate or calculated estimates; they are NOT product specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (literature, octyl 4‑hydroxybenzoate): typically a low‑melting solid or waxy/viscous liquid near ambient; exact MP varies with purity/isomer content; consult primary literature for specific values.
• Boiling point: Not commonly reported due to decomposition before distillation; high BP expected from C8 chain (literature).
• Density: Not specified; expect <1 g/mL for liquid forms (literature trend for alkyl parabens).
• Solubility (qualitative, literature): • Water: very low (hydrophobic C8 chain dominates) • Readily soluble in organic solvents: methanol, ethanol, acetonitrile, acetone, ethyl acetate, DMSO, chloroform, toluene
• LogP: High (literature trend increases with alkyl chain length; octyl > butyl > methyl). Specific value not provided here.
• pKa (phenolic, literature for 4‑hydroxybenzoate esters): ~8–9 for the phenolic OH; deuteration does not materially change acidity in practical handling.
• UV/Vis: Aromatic ring/phenol gives UV absorbance in the 240–300 nm region (literature); exact cutoff/ɛ not specified for this item.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Storage and shipping (item-specific):

• Storage: Store at −20 °C.
• Shipped: Ice chest + ice pads to maintain low temperature.

Quality and Grades

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

Guidance on interpreting grade for this product class (general):

• Isotopic labeling: For deuterated analytical standards, suppliers often specify isotopic enrichment (atom % D at the phenolic site and/or overall). If your application is quantitative LC‑MS or NMR, verify isotopic enrichment, residual proton content, and any site-specific labeling on the CoA.
• Chemical purity vs. isotopic purity: Distinct parameters. Chemical purity (e.g., ≥98%) addresses organic impurities and residual solvents; isotopic purity (e.g., ≥98 atom % D) addresses deuterium incorporation. Both may be critical for mass spectrometric internal standards.
• Stabilizers/inhibitors: Not commonly added to parabens; if any stabilizer or antioxidant is used, it should be disclosed on the CoA. Absence/presence of stabilizers can impact baseline in trace analysis.
• Low-UV/LC grade solvents relevance: If using as an LC‑MS internal standard, prepare stocks in LC‑MS grade solvents to minimize background.

What to check on receipt (best practice):

• Verify CAS, lot number, and labeling matches your method.
• Review CoA for: chemical purity, isotopic enrichment, residual solvents, water, and identity confirmation (NMR/HRMS/LC). If any value is not listed above, it is item-specific only when present on the CoA/specification.

Reaction and Applications

Primary use cases for N‑Octyl 4‑hydroxybenzoate‑d center on analytical and mechanistic studies rather than serving as a general reagent.

Analytical applications (literature/good practice):

• Internal standard for LC‑MS/MS quantitation of octyl paraben in environmental, cosmetic, or material extracts. The +1 Da mass shift (mono‑D) enables precise isotope‑dilution quantification with coelution and matched ionization.
• Tracer for hydrolysis kinetics: track enzymatic (esterase) or base‑catalyzed cleavage to 4‑hydroxybenzoic acid (p‑HBA) while distinguishing from native backgrounds.
• NMR studies: Deuterium labeling can simplify 1H spectra near the phenolic region and enable 2H NMR tracking of exchange.

Reactivity studies (literature):

• Base- or enzyme-catalyzed ester hydrolysis to p‑HBA and n‑octanol; isotopic label can probe exchange at the phenolic site and mass balance.
• Oxidation of phenol is possible under harsh conditions; generally avoided in analytical work.

Practical tips:

• For LC‑MS: prepare standards in ACN or MeOH; store aliquots at −20 °C; minimize aqueous exposure to preserve O–D.
• Avoid prolonged exposure to strong base or elevated temperature to limit saponification. If phenolate formation is necessary, anticipate rapid D/H exchange.
• Use amber vials to mitigate potential photodegradation of phenolic aromatics (general precaution).

Reaction Conditions

General, literature-based conditions relevant to studies involving octyl 4‑hydroxybenzoate; not product specifications.

• Base-catalyzed hydrolysis (saponification): • Typical: MeOH/H2O (1:1 to 9:1), NaOH or KOH (0.01–1.0 M).
  • Temperature: 20–60 °C.
  • Time: minutes to a few hours depending on base strength and temperature.
  • Outcome: quantitative conversion to p‑hydroxybenzoate and n‑octanol; monitor by HPLC/LC‑MS. Expect rapid O–D/H exchange in basic media.

• Enzymatic hydrolysis (esterases): • Buffer: phosphate or Tris, pH ~7.4.
  • Enzyme: porcine liver esterase or carboxylesterases (units per mL per supplier guidance).
  • Temperature: 37 °C.
  • Organic cosolvent: keep ≤1–5% MeOH/ACN to maintain solubility without inhibiting enzyme.
  • Monitoring: LC‑MS with deuterated internal standard for accurate kinetics.

• Transesterification (acid-catalyzed, general): • Alcohol solvent (ROH) with catalytic H2SO4 or p‑TsOH; Dean–Stark if using higher alcohols in nonpolar media.
  • Temperature: reflux of chosen alcohol/solvent.
  • Notes: Competes with hydrolysis in the presence of water; remove water to drive equilibrium.

• Oxidation sensitivity (phenol): • Avoid strong oxidants (e.g., peracids, elevated ozone) unless intentionally studying degradation.

Always validate conditions at small scale with your matrix and instrumentation. If isotopic integrity is required, avoid protic and basic conditions that promote O–D exchange.

Safety and Handling

Item-specific hazard classifications are not provided. Always consult the SDS for authoritative safety information.

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

General safety considerations for aryl esters and parabens (literature/good practice):

• Hazards: May cause skin/eye irritation; avoid inhalation of dust/aerosols and contact with skin/eyes. High hydrophobicity can enhance dermal uptake of solvents—use appropriate PPE.
• PPE: Lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). Handle solids/liquids in a fume hood.
• Incompatibilities: Strong bases (saponification/rapid hydrolysis), strong oxidizers, and strong acids under reflux (possible hydrolysis). Avoid prolonged exposure to alkali metal alkoxides.
• Special risks: Phenolic functionality can undergo oxidation in harsh conditions; ester linkage is susceptible to base- or enzyme-catalyzed hydrolysis. Deuterated O–D may exchange with H2O/MeOH; minimize unnecessary protic exposure if isotopic integrity matters.
• First aid (overview; defer to SDS): • Inhalation: Move to fresh air; seek medical attention if symptoms persist. • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice for persistent irritation. • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Combustible organic. Use CO2, dry chemical, or foam. Avoid water jet.
• Spill response: Absorb with inert material; avoid release to drains; collect for disposal per local regulations.

Solvent Selection

N‑Octyl 4‑hydroxybenzoate‑d is highly hydrophobic with a phenolic OD, favoring moderately polar to nonpolar organic solvents.

• Polarity/miscibility (literature): • Highly soluble: methanol, ethanol, isopropanol, acetonitrile, acetone, ethyl acetate, THF, DMSO, DMF, dichloromethane, chloroform, toluene.
  • Poorly soluble: water and aqueous buffers (expect very low solubility at neutral pH). Solubility can increase in basic aqueous media via phenolate formation but will compromise isotopic integrity (O–D/H exchange) and can promote hydrolysis.
• Recommended stock solvents (analytical workflows): • LC‑MS: acetonitrile or methanol (LC‑MS grade); prepare 1–10 mg/mL or 1–100 mM stocks depending on assay range.
  • NMR: CDCl3, CD3OD, or DMSO‑d6; note that CD3OD/D2O will exchange the phenolic deuterium.
• When to choose alternatives: • If water compatibility is essential, formulate as an ACN/H2O or MeOH/H2O co‑solvent with ≤5% organic into aqueous streams, injecting small volumes; consider using a solubilizing carrier (e.g., small % DMSO) if compatible with detection. • For base-sensitive studies (to avoid hydrolysis), avoid strong basic media and high temperatures.

Small comparison (literature trends):

• vs butyl paraben: Octyl is more hydrophobic, less water soluble; better for hydrophobic phase studies and shows longer RT in RP‑LC.
• vs methyl paraben: Octyl requires stronger organic eluent for elution; provides broader separation window for long‑chain parabens.

Storage and Reconstitution

Item-specific storage and shipping:

• Storage: Store at −20 °C.
• Shipped: Ice chest + ice pads.

Reconstitution and handling (general best practice for this class):

• Solvents: Dissolve in acetonitrile, methanol, ethanol, acetone, ethyl acetate, DMSO, or chloroform. Use LC‑MS grade solvents for analytical work.
• Concentrated stocks: Prepare 1–10 mg/mL (or 10–100 mM) master stocks; aliquot into amber vials to avoid repeated freeze–thaw cycles.
• Thawing: Allow vials to warm to room temperature before opening to prevent condensation ingress. Reseal promptly; purge headspace with inert gas if long-term storage is planned.
• Light/moisture: Store in amber containers, tightly sealed. Minimize exposure to ambient humidity; water promotes hydrolysis and O–D/H exchange at the phenolic site.
• Aqueous solutions: Prepare immediately before use. Avoid basic pH and elevated temperature if preserving isotopic integrity; discard after session.

Stability notes:

• Long-term stability is matrix- and temperature-dependent; verify by periodic LC‑MS or HPLC purity checks.
• Any appearance, purity, or isotopic enrichment specifications not listed here are item-specific only when provided on the CoA/Spec Sheet.

Research use only: Not for human or veterinary use.

Structure and Identity

N-Octyl 4-hydroxybenzoate-d is the deuterium-labeled analog of n‑octyl 4‑hydroxybenzoate (octyl paraben), featuring a para‑phenolic OD group.

• SKU: N1446018
• Product name: N-Octyl 4-hydroxybenzoate-d
• CAS: 2708282-26-0
• Category: Life Science (research use only)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Representative literature/deuterated SMILES (for reference only): CCCCCCCCOC(=O)c1ccc(O[2H])cc1
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Typical (non-deuterated) octyl 4-hydroxybenzoate formula (literature): C15H22O3
  • Deuterated analog often bears one D at the phenolic position (literature), giving C15H21DO3
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Calculated MW (literature): non-deuterated ≈ 250.33 g/mol; mono‑deuterated ≈ 251.33 g/mol

Structural features (descriptive, literature):

• Aromatic para‑hydroxybenzoate core: a benzene ring bearing a para‑phenolic OD and an ester at the para position.
• Ester linkage: benzoate carbonyl (–C(=O)O–) connected to a linear n‑octyl chain (C8H17–O–).
• Functional groups: phenolic OD (acidic hydrogen replaced by deuterium), aryl ester (electrophilic at the carbonyl), hydrophobic alkyl chain conferring high lipophilicity.
• 2D description: a para‑substituted phenyl ring with opposite substituents; one is OD, the other is –C(=O)O–(CH2)7CH3.

Notes: Identity fields not listed above are item-specific only when present on the CoA/specification; use those as primary reference.

Synthetic Utility

While primarily an analytical standard, N‑Octyl 4‑hydroxybenzoate‑d can function as a substrate or probe in synthetic and mechanistic experiments.

Reactivity features (literature):

• Aryl ester: Electrophilic carbonyl susceptible to nucleophilic acyl substitution under basic or catalytic conditions, yielding p‑hydroxybenzoate derivatives or the parent acid/alcohol upon hydrolysis.
• Phenolic OD: The phenolic proton (here deuteron) is weakly acidic; forms phenolate under basic conditions, enabling further functionalization on the aromatic ring via electrophilic substitution or O‑acylation/alkylation (though such transformations typically start from p‑HBA rather than the octyl ester).
• Hydrophobic tail: The n‑octyl group influences phase behavior, micellization, and can be leveraged in partition‑controlled catalysis studies.

Use cases:

• Hydrolysis kinetics and isotope effects: Compare rates vs. non‑deuterated analog to assess any secondary isotope effects on phenolic participation or H‑bonding in transition states.
• Transesterification models: Exchange of the octyl moiety with other alcohols using acid or base catalysis; useful in teaching/lab demonstrations of ester equilibria (research context).
• Oxidative stability probes: Evaluate phenol oxidation pathways (e.g., with peroxyl radicals) while tracking products by LC‑MS using the isotopic tag for internal standardization.

Note: For most synthetic elaborations of 4‑hydroxybenzoate chemistry, starting from p‑hydroxybenzoic acid or its activated derivatives is more practical.

Target Specificity

This product is a small-molecule standard and does not target biological epitopes.

• Antigen/epitope, species reactivity, clone, isotype: Not applicable.
• No item-specific immunoassay specificity data are provided for this molecule.