This compound belongs to the class of organic compounds known as para cresols. These are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.
External Descriptors
Not available
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.
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Application Protocols
Not applicable as validated bioassay protocols.
No WB/IHC/IF/FC protocols apply. For analytical workflows, users typically prepare internal standard solutions (e.g., 0.1–10 µg/mL) in appropriate solvents and spike into samples prior to extraction. Exact procedures depend on the analytical method (GC–MS, LC–MS) and matrix; consult your method SOPs and validation guidelines.
Item-specific recommended dilutions or methods: Not specified for this item; refer to CoA/Spec Sheet or your laboratory’s validated methods.
Biological Roles
General biological context (literature)
Origin: p-Cresol (4-methylphenol) arises from microbial metabolism of tyrosine and phenylalanine via p-hydroxyphenylacetic acid intermediates. It is encountered in environmental samples, industrial effluents, and biological matrices.
Biochemistry: As a phenolic aromatic, p-cresol can undergo phase II metabolism (glucuronidation, sulfation) in higher organisms, forming conjugates such as p-cresyl sulfate and p-cresyl glucuronide. The deuterated analog can be used as a tracer to study these pathways quantitatively in research settings.
Physicochemical behavior in biology: Moderate hydrophobicity (logP ~2) promotes partitioning into lipid phases while the phenolic group enables ionization at alkaline pH (pKa ~10.2), influencing absorption and transport.
Applications of p-cresol-d8 in biological research
Internal standard for quantitative assays of p-cresol and its conjugates in complex matrices (e.g., wastewater, fermentation broths, model biological fluids) to correct for recovery and matrix effects.
Isotopic tracer to follow microbial transformations, adsorption/desorption in soils and sediments, and phase II conjugation in in vitro enzyme systems.
Notes
All statements here describe biochemistry/analytical research contexts only. No medical or clinical claims are made.
Exchangeable OD: In aqueous biological systems, the phenolic deuteron exchanges rapidly with solvent; for tracing non-exchangeable deuterium, focus on ring/methyl positions (d7 component).
Buffer Applications
Not typically applicable.
p-Cresol-d8 is not used as a buffering agent. While phenols have pKa values near 10.2–10.3 (literature), they are not standard buffer components due to limited aqueous solubility and safety considerations.
For work requiring controlled pH when handling or measuring p-cresol/p-cresol-d8, use established buffer systems in the alkaline range (e.g., carbonate/bicarbonate pH 9–10, borate pH 8–10; literature) and introduce the analyte dissolved in a miscible organic cosolvent as needed.
Note that in buffered aqueous media the phenolic deuteron (OD) will exchange rapidly, converting p-cresol-d8 to p-cresol-d7.
Green Alternatives
Context
p-Cresol-d8 is typically used in small quantities as an analytical internal standard or tracer. Greener considerations focus on solvent choice, derivatization reagents, and waste minimization rather than replacing the analyte.
Greener choices (literature/general)
Solvents: Prefer acetonitrile, ethanol, ethyl acetate, 2-MeTHF, or CPME over chlorinated solvents where feasible. For GC, heptane/ethyl acetate can replace DCM.
Derivatization: If silylation is required, select less hazardous silyl reagents where compatible and minimize excess. Consider direct LC–MS without derivatization to avoid reagent waste.
Workflows: Micro-scale preparations and on-instrument dilutions reduce solvent consumption and analyte loss.
Trade-offs
Avoiding protic solvents preserves the OD label but may force the use of aprotic solvents that have different EHS profiles (e.g., MeCN toxicity). Balance isotopic needs with operator safety and environmental impact.
Ethyl acetate/MeCN: Good solvency with a better green profile; MeCN has toxicity concerns but favorable air fate; EtOAc is biodegradable and low toxicity.
2-MeTHF/CPME: Bio-based or improved safety ethers; useful for extractions and some reactions, immiscible with water (aids separations).
Waste handling
Phenolic wastes should be collected as halogen-free organic waste. Neutralize phenolates before disposal per institutional/Regulatory guidance. Maintain segregation of deuterated waste streams if isotopic tracing is relevant to your facility.
Pharmaceutical Uses
Formulation/manufacturing context (no therapeutic claims)
Role as analytical internal standard: p-Cresol-d8 can serve as a stable-isotope-labeled internal standard for method development and validation in pharmaceutical analytics (e.g., monitoring phenolic impurities or excipient-related phenols), supporting ICH-compliant quantitative assays by LC–MS/GC–MS.
Reference material: Useful in system suitability tests, recovery studies, and cross-laboratory comparisons where phenolic analytes are measured.
Notes and caveats
It is not an excipient, API, or buffer. Any application is limited to research and analytical laboratory use, as indicated by the product’s Research Use Only designation in the Product Data.
For GMP/GLP environments, verify the certificate of analysis (CoA) for isotopic enrichment, chemical purity, residual solvents, and traceability (lot-specific documentation). If a pharmacopeial reference is required, consult compendial monographs for p-cresol (non-deuterated) and adapt as scientifically justified.
Handling in regulated labs
Maintain segregation of labeled vs unlabeled standards to avoid cross-contamination.
Document stability studies under your storage conditions if the standard is used in validated methods (evaluate potential H/D exchange under the chosen diluent conditions).
Physical Properties
Item-specific specs
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical values (parent compound p-cresol unless noted; deuteration causes only minor shifts)
Physical state: Solid or low-melting liquid near ambient (p-cresol mp ~35–36 °C; literature). Deuteration may shift mp slightly.
Boiling point: ~201–203 °C at 1 atm (p-cresol; literature).
Melting point: ~35–36 °C (p-cresol; literature).
Density: ~1.03 g/mL at 25 °C (p-cresol; literature). Deuterated material may be marginally higher due to isotopic mass.
Refractive index (n20/D, liquid phase above mp): ~1.530 (p-cresol; literature).
Vapor pressure: Low; ~0.05–0.1 mmHg at 25 °C (p-cresol; literature).
Solubility: Sparingly soluble in water (~2–3 g/L at 20–25 °C; p-cresol; literature); freely soluble in ethanol, acetone, ether, chloroform, and most organics.
pKa (phenolic OH): ~10.2–10.3 (aqueous, 25 °C; literature). Isotope effects on pKa are small.
The OD in p-cresol-d8 will readily exchange with H2O/ROH/acid/base, potentially reducing the deuterium count to d7. For analytical applications where exact isotopologue is important, handle under anhydrous conditions.
All numerical values above are literature/general guidance and are not item-specific specifications for this SKU.
Quality and Grades
Item-specific information
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Isotopic enrichment (%D): Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for deuterated small molecules (literature/industry practice)
Isotopic enrichment: Deuterated reference materials are commonly supplied at ≥98 atom % D overall, with specified distributions across ring, methyl, and OD positions. The phenolic OD is exchangeable and may be reported separately (e.g., “non-exchangeable D ≥98%”). Always verify the CoA for exact isotopic assay and distribution.
Analytical grade expectations: Low levels of residual protio analogue (p-cresol-h8/h7) and organic impurities are important for accurate isotope-dilution quantitation. Chromatographic purity is typically established by GC/LC and NMR; residual solvents and water are often reported.
UV/background: For LC-UV work, low UV-absorbing impurities in the 200–300 nm range are desirable. For LC–MS, adduct-formers (Na/K) and non-volatile buffers should be minimized.
What to check on the CoA for this SKU
Isotopic assay (%D total; non-exchangeable %D; OD exchange information)
Chemical purity (% area by GC/LC; residual water/solvents)
Trace metals (if relevant to your application): Not specified for this item; refer to CoA/Spec Sheet.
Recommended analytical methods and acceptance criteria used by QA
Implications for use
For isotope-dilution mass spectrometry, match the analyte and IS closely in structure/retention; p-cresol-d8 typically coelutes with p-cresol and provides a robust internal standard.
Reaction and Applications
Primary application domains (literature/general)
Isotope-dilution standards: p-Cresol-d8 is widely used as an internal standard for quantitative LC–MS/GC–MS analysis of p-cresol in environmental, petrochemical, and biochemical matrices.
Kinetic isotope effects/tracers: The deuterium incorporation enables mechanistic studies involving benzylic hydrogen transfer, electrophilic aromatic substitution patterns, and radical pathways.
Representative workflows and tips
GC–MS quantitation: Extract phenolic fraction (e.g., from wastewater or process streams), optionally derivatize (BSTFA/TMCS to TMS ethers) to improve volatility and chromatographic performance; co-inject p-cresol-d8 as IS. Monitor characteristic m/z shifts (Δm = +8) between analyte and IS.
LC–MS quantitation: Use reversed-phase C18 with aqueous buffer/organic gradient; introduce p-cresol-d8 as IS to correct for matrix effects and ionization variability. Electrospray in negative mode (phenolate) or positive mode (adducts) can be tuned depending on mobile phase.
Derivatization chemistry: Phenolic –OD can be protected/derivatized as ethers (e.g., methylation with MeI/Ag2O or dimethyl sulfate) or esters (acyl chlorides/anhydrides) to modulate volatility and stability. Perform under anhydrous conditions to retain non-exchangeable D labels.
Laboratory reactions (adapted from p-cresol chemistry)
Williamson ether synthesis: Phenoxide generated with base (e.g., K2CO3/DMF; NaH/THF) reacts with alkyl halides to afford aryl ethers—useful for labeled standards of p-cresyl ethers.
Electrophilic substitution: Nitration, sulfonylation, and Friedel–Crafts reactions proceed at activated ortho sites; regioselectivity resembles p-cresol.
Note: All conditions above are general literature guidance; optimize for your system.
Reaction Conditions
General conditions (literature guidance, adapted from p-cresol chemistry)
O-Alkylation (Williamson ether): Base (K2CO3, Cs2CO3) in DMF/acetone; or NaH in THF/DMF. Typical 20–80 °C, 1–16 h. Alkyl halides or sulfonates as electrophiles. For minimal H/D exchange, exclude water/alcohols.
O-Acylation: Acyl chlorides/anhydrides with base (pyridine, triethylamine) in DCM/THF, 0–25 °C, 0.5–4 h. Catalytic DMAP accelerates; monitor to avoid over-acylation.
Silylation (analytical derivatization): BSTFA (or MSTFA) with 1% TMCS, 60–70 °C, 15–30 min, neat or in anhydrous acetonitrile; yields TMS ether suitable for GC–MS.
Electrophilic substitution (nitration): Mild mixed-acid or acetyl nitrate at 0–25 °C affords ortho-nitrated products; control temperature to manage regioselectivity.
Metalation/direct arylation: Strong bases (e.g., BuLi) at −78 to 0 °C can effect ortho-lithiation of protected phenol derivatives; subsequent trapping with electrophiles. Use protecting groups (e.g., silyl ethers) to prevent proton/deuteron exchange.
Analytical preparation
LC–MS stock solutions: 0.1–1.0 mg/mL in dry MeCN; store cold and dry when OD label integrity matters. For routine IS use where OD exchange is acceptable, aqueous-organic mixtures are common.
GC–MS: 0.1–1.0 mg/mL in toluene/hexane; derivatize as needed.
Expected performance
Yields and conversions are substrate-/condition-dependent; for simple O-alkylations and acylations, isolated yields of 70–95% are typical in literature for p-cresol derivatives. Isotopic integrity should be confirmed by MS/2H NMR post-reaction.
Safety and Handling
Item-specific hazard data
Signal word: Not specified for this item; refer to SDS.
H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
General safety considerations for p-cresol and deuterated analogs (literature/generic)
Hazard profile: Phenolic compounds are typically corrosive/irritating to skin and eyes, with potential for systemic absorption through skin. Vapors may irritate respiratory tract. Avoid inhalation and contact.
Flammability: Combustible organic compound; keep away from ignition sources. Use grounding/bonding when transferring liquids above mp.
Peroxide formation: Not prone to peroxide formation (unlike ethers).
Incompatibilities: Strong oxidizers (risk of exotherm), strong bases/acids (promote H/D exchange and may accelerate corrosion), acylating/alkylating agents (react with phenolic OH).
PPE and engineering controls
Wear lab coat, safety goggles/face shield, and chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and avoid inhalation.
First-aid overview (consult SDS for authoritative instructions)
Skin/eye contact: Immediately flush with water for ≥15 minutes; remove contaminated clothing. Seek medical attention.
Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Isotopic integrity handling tip
To preserve the OD label, avoid contact with moisture and protic reagents; store and handle under dry, inert conditions when isotopologue purity matters.
Always consult the product SDS for complete, current hazard and handling information.
Solvent Selection
Applicability
p-Cresol-d8 is a moderately polar phenolic aromatic. Solvent choice depends on whether it is used as a reaction substrate, an analytical standard, or an NMR/MS internal standard.
Polarity and miscibility (literature/general)
Polarity: Moderate; capable of hydrogen bonding as donor (OD) and acceptor (phenoxide when deprotonated).
Water: Sparingly soluble at neutral pH; solubility increases markedly upon deprotonation (phenolate salts are water-miscible).
Organic solvents: Freely soluble in polar protic (MeOH, EtOH; may cause H/D exchange) and polar aprotic (MeCN, DMSO, DMF) as well as in less polar solvents (EtOAc, dichloromethane, toluene).
Selection tips by application
Isotope-dilution LC–MS: Prepare stocks in dry acetonitrile or methanol; note that methanol/water will exchange the OD label to OH (yielding d7). If maintaining OD is not critical, MeOH/H2O (1:1) with 0.1% formic acid or ammonium buffer is common.
GC–MS: Dissolve in non-protic organic solvents (hexane, toluene, ethyl acetate). For derivatization (e.g., silylation), use anhydrous solvents.
Synthetic use: Choice parallels p-cresol—ethers (THF), DMF/DMSO, or hydrocarbons depending on base/nucleophile and electrophile.
Quick comparison (literature)
MeCN (aprotic, LC–MS friendly): preserves deuterium better than MeOH/H2O.
Methanol/Water: convenient for bioanalytical workflows but will exchange OD to OH.
Toluene: excellent for nonpolar extractions and EAS reactions; minimizes H/D exchange.
Always ensure solvent dryness when isotopic integrity (especially OD) must be preserved.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature
Shipped in: Normal
General best practices for this compound class
Container: Store in amber glass with PTFE-lined cap to minimize light exposure and sorption. Keep tightly closed.
Atmosphere: For maximal retention of OD labeling, store under dry inert gas (argon/nitrogen). Exposure to moisture/protic media will exchange the phenolic deuteron (converting d8 to d7).
Stability: Phenolic compounds are generally stable at ambient conditions when dry and protected from strong oxidants. Avoid prolonged exposure to air/heat to limit slow oxidation or discoloration.
Reconstitution/preparation of stock solutions
Solvents: Dry acetonitrile, toluene, or ethyl acetate are recommended when preserving OD. If OD exchange is acceptable, methanol or water-containing mixtures can be used.
Concentration: Common analytical stock concentrations are 0.1–1 mg/mL; prepare working solutions fresh as needed.
Freeze–thaw: Not typically required; if refrigerated or frozen for long-term stability studies, avoid repeated freeze–thaw by aliquoting.
Label integrity note
Track isotopic content over time for critical applications. Verify by LC–MS (exact mass shift) or 2H NMR, especially after storage in protic solvents.
For definitive storage, stability, and reconstitution instructions, refer to the lot-specific CoA and SDS.
Structure and Identity
Item-specific (from Product Data)
SKU: P345444
Product name: p-Cresol-d8 (4-methylphenol-d8)
CAS: 190780-66-6
Storage conditions: Room temperature
Shipped in: Normal
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature identity (for the fully deuterated isotopologue)
Molecular formula (idealized): C7D8O (literature; corresponds to d8 isotopologue)
Molecular weight: ~116.19 g/mol (literature; based on C7D8O)
Synonyms: 4-methylphenol-d8; p-tolyl alcohol-d8 (phenol); 4-tolyl-d8 phenol (OD form)
Structural features (general chemistry description)
Core scaffold: A benzene ring with a para-disposed methyl group (–CD3 in d-labelled material) and a phenolic group (–OD in the d8 isotopologue; the OD is exchangeable).
Substitution pattern: 1,4-disubstituted benzene (para). The ring has two ortho positions relative to the phenol and two relative to the methyl; electrophilic substitution is directed/activated by both groups.
2D description: A six-membered aromatic ring bearing –OD at position 1 and –CD3 at position 4; remaining ring positions carry deuterium atoms in the d8 idealization.
Notes on isotopic labeling
The phenolic deuteron (OD) is labile and can exchange with protic media, whereas aromatic and methyl deuteriums are substantially non-exchangeable under neutral conditions. Preserve isotopic integrity by avoiding water/alcohols/acids/bases when the OD label is critical.
Synthetic Utility
General reactivity (modeled on p-cresol; literature)
Nucleophilicity of phenoxide: Deprotonation (or deuteron removal) of the phenolic OD with base (e.g., K2CO3, NaH) generates a strong nucleophile for O-alkylation (Williamson ether synthesis), O-acylation (esters, carbonates), and silylation.
Electrophilic aromatic substitution (EAS): The phenolic group and para-methyl are ortho/para directors; with para already substituted, reactions tend to occur at the two ortho positions relative to the phenol or the methyl, following typical activation patterns.
Benzylic chemistry: The methyl group can participate in side-chain halogenation/oxidation; deuteration at the benzylic positions enables kinetic isotope effect studies on radical or cationic pathways.
Applications specific to labeled materials
Isotopologue-defined derivatives: Preparation of labeled ethers, esters, and sulfonate esters provides internal standards mirroring analyte derivatives (e.g., TMS ethers for GC–MS).
Tracing transformations: Track oxygen versus ring substitution pathways by monitoring retention of deuterium in products via MS/NMR.
Practical considerations
Preserve non-exchangeable D: Conduct reactions in aprotic, anhydrous media; avoid strong acids/bases that might promote H/D scrambling at benzylic positions under harsh conditions.
Monitoring: 2H NMR and HRMS are powerful for verifying isotopologue integrity post-synthesis; include controls for OD exchange.
This section provides general synthetic insight; consult primary literature for substrate- and condition-specific optimization.
Target Specificity
Not applicable.
This product is a small-molecule chemical standard (p-cresol-d8), not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular target specificity). No antigen/epitope, clone, or species reactivity data apply.
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