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Application Protocols
The following are general, non-item-specific protocols commonly used when employing β-tocopherol-d3 as an internal standard. Adjust to your instrumentation and matrix.
LC–MS/MS quantitation of tocopherols in serum/plasma (general)
Prepare stock: dissolve β-tocopherol-d3 at 1–5 mg/mL in ethanol or isopropanol. Aliquot under N2, store −20 °C.
Working IS solution: dilute to 50–500 ng/mL in ethanol.
Sample prep: to 100–200 µL serum, add 10–20 µL IS working solution. Add 400–800 µL ethanol/isopropanol to precipitate proteins. Extract with 1–2 mL n-hexane or MTBE, vortex, centrifuge. Collect organic, evaporate under N2 (room temp, low light). Reconstitute in 100–200 µL methanol/isopropanol (80:20) for LC–MS.
LC–MS: C18 or C30 column; gradient of water (0.1% formic acid) and methanol/isopropanol. Detection by APCI(+) or ESI(+). Monitor transitions for native β-tocopherol and +3 Da for d3.
Food oil analysis by GC–MS (derivatization; general)
Saponify: weigh oil aliquot, add ethanolic KOH; heat gently (avoid extensive exposure to air). Cool, add IS (β-tocopherol-d3), extract with hexane.
Derivatize: evaporate solvent; add BSTFA + 1% TMCS in acetonitrile; heat 60 °C, 30 min.
GC–MS: nonpolar column; SIM mode for native and d3 ions; quantitate by isotope dilution.
Stability check of IS solution
Inject freshly prepared and 1-week stored aliquots to confirm no significant degradation or isotopic exchange; store in amber vials under inert gas.
Note: Concentrations and volumes are illustrative literature practices; validate for your laboratory. For research use only.
Biological Roles
General/literature context (for β-tocopherol, not item-specific claims):
Tocopherols (vitamin E family) are lipid-soluble antioxidants embedded in biological membranes and lipoproteins. β-Tocopherol, like α-, γ-, and δ-isomers, donates a hydrogen atom from its phenolic OH to neutralize lipid peroxyl radicals, interrupting lipid peroxidation chain reactions.
The chromanol ring stabilizes the resulting tocopheroxyl radical via resonance; the phytyl side chain anchors the molecule within lipid bilayers and lipoprotein particles.
Redox cycling: tocopheroxyl radicals can be reduced back to the active form by reductants (e.g., ascorbate, glutathione systems; literature), linking vitamin E to cellular antioxidant networks.
Metabolism (literature): tocopherols undergo ω-oxidation and β-oxidation of the side chain forming carboxyethyl-hydroxychromans (CEHCs) and related metabolites. Isotopically labeled tocopherols are valuable research tools to trace these pathways.
Transport (literature): association with lipoproteins and specific binding/transporter proteins modulates distribution; isoform selectivity differs among tocopherols.
Research use relevance of the d3 label:
Deuterium labeling enables precise mass spectrometric discrimination from endogenous β-tocopherol, facilitating quantitative studies of uptake, stabilization, and oxidative transformation in cells, tissues, oils, and food matrices.
Note: This product is for research use only. No medical or clinical claims are made.
Buffer Applications
β-Tocopherol-d3 is a highly lipophilic small molecule and is not used to formulate aqueous buffer systems. If working in aqueous media is required (e.g., biological assays), prepare concentrated stocks in a water-miscible organic solvent (ethanol or isopropanol) and dilute into buffer with vigorous mixing or use surfactants/lipid carriers. For practical formulation details, see Solvent Selection and Application Protocols.
Green Alternatives
Because β-Tocopherol-d3 is the target analyte rather than a process solvent, “green” considerations primarily concern solvent choices and sample preparation.
Greener solvent options (general guidance):
Prefer ethanol or isopropanol for stock solutions instead of chlorinated solvents.
For liquid–liquid extraction, consider ethyl acetate or MTBE as alternatives to chloroform/DCM when compatible with your method.
Employ minimal solvent volumes via microextraction or supported liquid extraction to reduce waste.
Comparison (literature/general):
Ethanol vs DCM for stock solutions:
Toxicity/environment: Ethanol is benign; DCM is hazardous and regulated.
MS compatibility: Ethanol is fully compatible; DCM can suppress ESI and evaporates rapidly.
Solubility: Both dissolve tocopherols well; ethanol may require gentle warming for viscous concentrates.
MTBE vs chloroform in lipid extraction:
MTBE-based extractions provide phase separation with upper organic phase, easier handling, and reduced toxicity relative to chloroform.
Chloroform (Folch/Bligh–Dyer) gives broad lipid recovery but with higher health/environmental burden.
Operational practices:
Use amber vials and inert gas headspace to extend solution lifetime, reducing remakes and waste.
Batch-prepare aliquots at validated concentrations to minimize repeated solvation and disposal.
Where possible, adopt solid-phase extraction (SPE) methods to cut down on halogenated solvent use.
Pharmaceutical Uses
Item-specific pharmacopeial/grade information: Not specified for this item; refer to CoA/Spec Sheet.
General/literature context (non-clinical):
Tocopherols are used in pharmaceutical manufacturing as antioxidant excipients to protect oxidation-sensitive actives and lipids. However, deuterated analogs like β-tocopherol-d3 are primarily research tools and analytical standards rather than routine excipients.
Analytical control: Deuterated tocopherols are employed as system-suitability and internal standards in QC/QA workflows for nutritional products, oils, and dosage forms containing vitamin E, supporting method validation (accuracy, precision, recovery) by isotope-dilution LC–MS or GC–MS.
Formulation studies: In preformulation research, labeled tocopherols can assist in tracking partitioning into lipid vehicles and monitoring oxidative stability pathways under stress testing.
Compliance notes:
No pharmacopeial monograph or therapeutic use is implied for β-tocopherol-d3 in this listing. Use is limited to research and analytical applications.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values for β-tocopherol (non-deuterated; deuterated analogs are typically similar):
Physical state: viscous, pale yellow to colorless oil; low volatility.
Melting point: typically below room temperature (α-tocopherol ~ −27 °C; β is similar; literature).
Boiling point: decomposes before boiling at ambient pressure (literature).
Density: ~0.94–0.98 g/mL at 20–25 °C (literature range for tocopherols).
Solubility: practically insoluble in water; soluble in nonpolar and moderately polar organic solvents (hexanes, toluene, chloroform, dichloromethane, ethyl acetate, ethanol; literature). Solubility increases in the presence of surfactants or lipids.
Partitioning: very hydrophobic; high logP (reported >7 for tocopherols; literature).
UV/Vis: chromanol absorption with weak bands in UV; ε varies with solvent (literature). Not specified for this item.
Refractive index: values around nD 1.49–1.50 reported for tocopherols (literature).
Practical notes:
Solutions are air-/light-sensitive; phenolic OH can undergo oxidation to tocopheroxy radicals and quinones. Protect from light and oxygen.
Viscosity hampers accurate pipetting at low temperature; warm gently to ambient (cap closed, protected from light) before aliquoting.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for exact assay, isotopic enrichment (%D), and residual solvent levels.
How to interpret common parameters for deuterated small molecules (general guidance):
Isotopic enrichment (%D at labeled positions): Indicates the fraction of molecules with deuterium at the specified sites. High enrichment (typically ≥98 atom %D at labeled positions; literature expectation) is preferred for quantitative LC–MS internal standards to minimize isotopic overlap.
Chemical purity (HPLC/GC area %): Determines background interferences and suitability for quantitative analysis.
Residual solvents and volatiles: Relevant for trace analysis; may appear as additional MS peaks.
Water/peroxides/UV cutoff/metal content: Not specified for this item; refer to CoA/Spec Sheet if applicable.
Stabilization and packaging (general):
Tocopherols are light/air sensitive as solutions; suppliers often package under inert gas in amber vials. If provided as solution or with stabilizers, follow label instructions. For this listing, no stabilizer is specified.
Fit-for-purpose guidance:
Analytical standard use (lipidomics, food/oil analysis): prioritize high isotopic enrichment and low impurity profile; verify exact labeling pattern from CoA to model MRM transitions accurately.
Synthetic use: if employing in derivatization (e.g., succinate formation), confirm absence of inhibitors or stabilizers that may interfere.
Reaction and Applications
Primary application domain (research/analytical):
Isotope-dilution mass spectrometry (IDMS): β-Tocopherol-d3 serves as an isotopically labeled internal standard for quantifying native β-tocopherol in biological fluids, foods, and oils by LC–MS/MS or GC–MS (after derivatization). The +3 Da mass shift enables selective MRM transitions with minimal isotopic overlap (literature).
Lipidomics and redox biology: used to normalize extraction recovery and matrix effects in studies of vitamin E status and lipid peroxidation products.
Stable-isotope tracer experiments: permits qualitative assessment of uptake, distribution, and oxidative transformation of tocopherols in model systems (cells, microsomes, liposomes) under research settings.
Analytical tips (general):
Spike strategy: add β-tocopherol-d3 early (pre-extraction) to correct for losses. Typical spike levels are chosen to bracket expected endogenous concentrations; verify linearity.
Chromatography: reverse-phase LC (C18, C30) with methanol/isopropanol mobile phases; APCI or ESI in positive mode are commonly used for tocopherols. For GC–MS, derivatize phenolic OH (e.g., TMS ethers) to improve volatility.
Ionization: APCI often gives robust response for nonpolar analytes like tocopherols; deuteration slightly shifts fragment ions (+3) without altering fragmentation pathways significantly (literature).
Chemical reactivity (general):
Phenolic antioxidant: undergoes hydrogen-atom transfer to peroxyl radicals; oxidized to tocopheroxyl radical and further to quinone derivatives (literature). Deuteration can modestly affect kinetic isotope effects in mechanistic studies.
Derivatization: formation of esters (e.g., succinate) for conjugation or to modulate polarity; O-alkylation/acylation under standard conditions.
Reaction Conditions
General literature guidance for common manipulations of tocopherols (applicable to β-tocopherol-d3; item-specific conditions not specified):
O-Acylation (ester formation):
Typical reagents: acyl chlorides or anhydrides; bases such as pyridine, triethylamine; catalysts like DMAP.
Solvents: dichloromethane, toluene, THF, or acetonitrile.
Temperature: 0 °C to room temperature; reaction times from 0.5–12 h depending on acyl donor.
Notes: Exclude moisture; monitor by TLC/LC–MS. Preserve isotopic labels by avoiding prolonged basic methanolysis.
Silylation for GC–MS (derivatization):
Reagents: BSTFA or MSTFA (±1% TMCS) or TBDMS-Cl/imidazole.
Solvents: acetonitrile or pyridine.
Conditions: room temperature to 60 °C for 15–60 min.
Outcome: increased volatility and thermal stability; mass shift accounts for both silyl group and d3 label.
Controlled oxidation (mechanistic studies):
Radical generation: AIBN/AMVN with linoleate in chlorinated/aromatic solvents at 37–60 °C to probe peroxyl scavenging (literature).
Electrochemical oxidation: anodic oxidation in aprotic media to generate chromanoxyl species; monitor by UV–Vis/ESR/MS.
Stock solution preparation:
Concentrations: commonly 0.1–10 mg/mL in ethanol or isopropanol for LC–MS usage.
Storage: aliquot under inert gas in amber vials at −20 °C; verify stability by periodic QC injections.
Expected yields: Reaction yields are system- and substrate-dependent; consult primary literature for the specific derivative of interest. These are general conditions, not item-specific specifications.
Safety and Handling
Authoritative safety classification for this item: Not specified for this item; consult the product SDS for definitive GHS signal word, hazard statements, pictograms, and first-aid measures.
General laboratory guidance (good practice; not a substitute for SDS):
PPE: wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile) when handling solids and organic solutions.
Ventilation: handle in a fume hood when preparing organic solutions or using volatile/chlorinated solvents.
Incompatibilities: strong oxidizers (can oxidize the phenolic moiety); strong bases in air may accelerate oxidation; avoid prolonged exposure to light and oxygen which can promote autoxidation.
Special risks: although tocopherols are antioxidants, they can form oxidation products upon air/light exposure, especially in dilute organic solution. Use amber glassware, inert gas blanket (N2/Ar), and antioxidant-free solvents to avoid background signals in MS.
First aid (general):
Skin: wash with soap and water. Remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing. Seek medical attention if irritation persists.
Ingestion/Inhalation: move to fresh air; rinse mouth; obtain medical advice.
Spill/cleanup: absorb small spills with inert material (vermiculite), collect in compatible waste. Avoid release to drains.
Fire: use CO2, dry chemical, or foam. Combustible organic compound.
Storage per Product Data: Store at −20 °C. Protect from light and moisture. Keep tightly closed under inert atmosphere if possible. Shipped in ice chest with ice pads.
Solvent Selection
Compound class and polarity: β-Tocopherol-d3 is a highly hydrophobic phenolic chromanol with a long isoprenoid side chain; it behaves as a lipophilic neutral compound (weakly acidic phenol) with very low water solubility (literature).
Polar protic: ethanol, isopropanol (good), methanol (moderate). Solubility in alcohols is typically sufficient for preparing analytical stock solutions.
Aqueous systems: insoluble; requires co-solvents (≤1–2% v/v of DMSO/EtOH/PEG) or surfactants/micelles for dispersion. For LC–MS spiking into aqueous matrices, prepare concentrated stocks in ethanol or isopropanol and dilute into sample with vigorous mixing.
Selection notes:
LC–MS internal standard work: ethanol or isopropanol stocks (1–10 mg/mL) are commonly used to avoid chlorinated solvents; ensure compatibility with your extraction and chromatographic method.
Oxidation control: avoid prolonged dissolution in oxygenated solvents; degas or sparge solvents when preparing long-lived standards; store aliquots under inert gas in amber vials.
Comparison (general):
Ethanol vs DCM: Ethanol is greener and MS-compatible; DCM offers faster dissolution but is less desirable environmentally and for ESI sources.
Hexane vs isopropanol: Hexane maximizes solubility in nonpolar workflows (e.g., GC sample prep); isopropanol balances solubility with miscibility into aqueous phases for LC–MS.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data):
Storage Conditions: Store at −20 °C.
Shipped In: Ice chest + Ice pads.
General handling and reconstitution guidance for tocopherols:
Protection: Store in amber, tightly sealed containers to protect from light and air. If possible, keep under inert gas (N2/Ar), especially for solutions.
Solid/oil handling: Allow vial to equilibrate to room temperature before opening to prevent moisture condensation. The material may be a viscous oil.
Reconstitution solvents: ethanol or isopropanol are preferred for LC–MS applications; hexane, toluene, or DCM for nonpolar workflows. Use anhydrous solvents for long-term standards.
Stock solutions: prepare 0.1–10 mg/mL stocks depending on intended use. Filter through PTFE syringe filter if particulate is present.
Aliquoting: divide into single-use amber microvials to minimize freeze–thaw and headspace oxygen. Label with concentration, solvent, preparation date.
Stability: Not specified for this item; refer to CoA/Spec Sheet. As general practice, store solutions at −20 °C and use within weeks; verify by periodic QC injections (no new peaks, consistent response).
Thawing: Warm to room temperature briefly before use; mix gently. Avoid repeated freeze–thaw cycles by using aliquots.
Disposal: Treat as organic chemical waste; follow institutional and local regulations.
For research use only.
Structure and Identity
Brief description: β-Tocopherol-d3 is the deuterium-labeled isotopologue of β-tocopherol (a vitamin E isomer) bearing three deuterium atoms for use as an internal standard and tracer in analytical workflows.
Item-specific identifiers (from Product Data):
SKU: T355573
Product Name: β-Tocopherol-d3
CAS: 936230-75-0
PubChem CID: 71752598
InChIKey: 398083 (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 description of β-tocopherol core):
Contains a chromanol (6-chromanol) ring system with a phenolic OH at C6, fused to a heterocyclic oxygen in the benzopyran framework.
A long, branched phytyl-like aliphatic side chain (isoprenoid) at the 2-position of the chromanol imparts strong hydrophobic character.
β-Tocopherol differs from α/γ/δ isomers by the methylation pattern on the chromanol ring (β: dimethyl at 5- and 8-positions, unmethylated at 7-position; literature).
“d3” denotes three deuterium atoms incorporated at defined methyl positions (supplier-dependent; literature note). Isotopic labeling does not change connectivity, only isotopic composition.
2D structure in words (literature): phenolic chromanol ring with two ring methyl substituents, an isoprenoid side chain at C2, and a benzylic stereocenter in the chroman; typically isolated as a single natural configuration at the benzylic center. Deuteriums replace hydrogens at specific methyl sites used to generate a mass shift (+3 Da) for mass spectrometry.
Synthetic Utility
While β-tocopherol-d3 is most commonly used as an analytical standard, the molecule retains the chemical reactivity of a phenolic chromanol and can participate in transformations useful for method development and probe preparation (general/literature):
Phenolic derivatization:
O-acylation (e.g., with acyl chlorides/anhydrides) to form esters, including hemisuccinate derivatives for conjugation to carriers or to adjust polarity for chromatographic separation.
Silylation (TMS, TBDMS) to enhance GC volatility and thermal stability for GC–MS workflows.
Oxidation chemistry:
Controlled oxidation to tocopheroxyl radicals and quinone forms for mechanistic redox studies; electrochemical or peroxyl radical-generating systems are commonly used.
Isotope-probe roles:
The d3 label provides mass separation for reaction monitoring by MS, allowing concurrent tracking of labeled and unlabeled species in complex matrices.
Retrosynthetic/value considerations:
The intact chromanol core with an isoprenoid tail is not generally a modular synthon for diversity-oriented synthesis, but selective functionalization at the phenolic OH or side-chain terminal positions enables preparation of conjugates, pro-derivatives, or immobilized standards for solid supports.
Note: For any synthetic transformation, verify that isotopic enrichment is preserved at the labeled positions (avoid H/D exchange conditions such as strong base/alcohol at elevated temperature).
Target Specificity
Not applicable. This product is a small-molecule isotopically labeled standard, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies.
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