Mono(2-hydroxyisobutyl)phthalate-d , CAS No.2119597-90-7

CAS: 2119597-90-7 Cat. No.: M1445388 Formula: C₁₂H₁₀D₄O₅ Peso molecolare: 242.26

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Mono(2-hydroxyisobutyl)phthalate-d 4 is the deuterium labeled Mono(2-hydroxyisobutyl)phthalate.

Specifiche

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

242.26

Application Protocols

No immunoassay or bioassay protocols (WB, IHC, IF, FC) are applicable to this small-molecule reference standard.

Analytical handling suggestions (general) • Prepare a primary stock in LC–MS grade methanol or acetonitrile at a gravimetrically verified concentration (e.g., 1–10 mg/mL). Record exact mass and purity from the CoA to calculate the molarity; adjust for isotopic enrichment if required for IDMS. • Aliquot into low-binding, amber vials; flush headspace with inert gas if long-term storage is needed. Store at −20°C per product guidance. • For calibration, prepare serial dilutions in solvent-matched matrix or surrogate matrix; include the unlabeled analyte as the quantifier and the deuterated compound as the internal standard. • Assess matrix effects using post-extraction spiking and evaluate recovery by pre-extraction spikes.

Biological Roles

This product is an isotope-labeled synthetic organic compound provided for research and analytical purposes. It is not a natural metabolite or biomacromolecule.

General considerations (informational only) • Functional groups: carboxylic acid, aromatic ring, and ester typical of phthalate monoesters. Such structures can bind nonspecifically to proteins or lipids in complex matrices, which is relevant for extraction recoveries in bioanalytical methods. • Isotopic labeling: The deuterium label enables mass spectrometric discrimination from endogenous or contaminant unlabeled analogues, supporting accurate quantitation in biological fluids or tissue extracts. • Metabolic context: In biotransformation studies (in vitro), monoester phthalates can undergo hydrolysis to phthalic acid and oxidation at side chains (literature, compound-general). The deuterium label can assist in pathway elucidation, provided that labeled positions are not exchanged during incubation.

No medical/clinical claims are made. For any biological matrix work (plasma, urine, tissue homogenates), ensure appropriate ethical approvals and follow institutional biosafety procedures.

Buffer Applications

This compound is not a buffering reagent. It lacks a suitable conjugate acid/base pair in the physiological pH range for maintaining constant pH.

Practical note • If dissolved in aqueous buffers for analytical purposes, buffer choice is driven by compatibility with detection (e.g., volatile ammonium acetate/formate for LC–MS). Avoid high-pH buffers if ester hydrolysis would be problematic. • For sample preparation in aqueous systems, maintain pH to control ionization of the carboxyl group (acidic pH to keep neutral for extraction; basic pH to retain in aqueous phase), but do not expect significant buffering capacity from the analyte itself.

Green Alternatives

Context: This is a specialty, isotope-labeled reference material used at trace levels. Green chemistry considerations focus on solvent and workflow choices rather than replacing the analyte.

Greener practice recommendations • Solvent selection: Prefer methanol, ethanol, ethyl acetate, and water where compatible. Minimize use of chlorinated solvents (e.g., DCM) and high-toxicity ethers. For LC–MS, MeOH and ACN are typical; reduce ACN volumes by optimizing gradients or using MeOH-based methods when sensitivity allows. • Miniaturization: Scale down extraction volumes and use microelution SPE to cut solvent consumption for calibration and sample prep. • Waste reduction: Consolidate isotope-labeled waste streams for appropriate disposal; keep volumes small to reduce environmental footprint. • Energy: Store at the recommended −20°C but avoid unnecessary freeze–thaw by preparing aliquots, which reduces repeated cooling cycles.

Comparison table (general) • Conventional approach: Large-volume LLE with DCM/hexanes; multiple evaporations. • Greener alternative: SPE with aqueous MeOH/EtOAc elution; single gentle evaporation under N2; aqueous-compatible LC mobile phases.

Note: Because this compound is a target analyte/internal standard, substitution with a “greener” chemical is not applicable. Focus on greener methods around its use.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item; it is sold for research use only.

General analytical relevance (non-clinical) • May serve as a stable-isotope internal standard in quality-control analytics or extractables/leachables assessments where phthalate-related species are monitored. • Not intended for human or veterinary use, drug substance, or excipient applications. No USP/EP/JP monograph applicability is implied.

Documentation • For any GMP-adjacent analytical work, obtain and retain the lot-specific CoA (purity, isotopic enrichment, residual solvents), SDS, and any impurity profiles. Validate methods per ICH Q2 where applicable.

Physical Properties

Item-specific properties • Appearance: Not specified for this item; refer to CoA/Spec Sheet. • Purity/grade: Not specified for this item; refer to CoA/Spec Sheet. • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. • Refractive index / UV cut-off / residual water or metals: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for related mono-phthalate monoesters (informational only) • Physical state: often low-melting solids or viscous oils depending on side-chain length and substitution. • Solubility: sparingly soluble in water due to hydrophobic aromatic/ester content; soluble in common organic solvents (e.g., MeOH, EtOH, acetone, acetonitrile, DCM, ethyl acetate) — specific solubilities not determined for this item. • Acid–base: one acidic carboxyl (typical pKa for phthalic monoacids ~2–3, literature, compound-specific value not determined); tertiary alcohol typically pKa > 15 (literature), essentially unionized in neutral aqueous media. • Partitioning: aromatic monoesters often exhibit moderate hydrophobicity; exact logP/logD not established for this item.

Important note • Use the product CoA/Spec Sheet for definitive, item-specific physicochemical data needed for method development or quantitation. Where assay sensitivity depends on extinction coefficients or exact isotopic composition, consult the Certificate of Analysis.

Quality and Grades

Item-specific quality details (grade, purity, stabilizers, residual solvents, isotopic enrichment) are Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting typical listings for isotope-labeled organics (general knowledge) • Research grade vs. analytical/isotopic standard grade: Isotope-labeled materials may be offered as research grade (suitable for qualitative work) or as analytical standard grade with certified isotopic enrichment and impurity profiles for quantitative LC–MS/GC–MS. Certification usually includes:

• Isotopic enrichment (%D at designated sites)
• Chemical purity by HPLC/GC and NMR
• Residual solvents and water content
• Identity confirmation (NMR, HRMS) • Implications of stabilizers: Not commonly required for phthalate monoesters, but if present (e.g., trace acid or antioxidant), they can affect LC–MS baselines or derivatization yields. Always check the CoA. • Trace contamination: For isotope-dilution analyses, even low-level unlabeled analogue can bias quantitation. Verify the % unlabeled (protium) impurity and isotopologue distribution. • Documentation: Retain CoA, isotopic labeling map, and lot-specific spectral data in your analytical records; include them in method validation files (linearity, matrix effects, carryover). • Regulatory note: This product is for research use only and is not intended for diagnostic or therapeutic applications.

Reaction and Applications

This compound is an isotopically labeled monoester derivative of phthalic acid. Its primary value is as a stable-isotope internal standard or tracer rather than as a bulk synthetic intermediate. Nevertheless, several application domains are relevant:

Analytical applications (primary) • LC–MS/GC–MS internal standard: The deuterium label provides a mass shift relative to the unlabeled mono(2-hydroxyisobutyl)phthalate, enabling isotope-dilution quantitation in environmental, material, or metabolomic matrices. Verify that the label is non-exchangeable under analytical conditions. • Recovery tracking: Spike-and-recover experiments through extraction and cleanup workflows to quantify matrix losses and ion-suppression.

Chemical applications (secondary, general chemistry) • Ester hydrolysis studies: Benchmark rates of base- or acid-catalyzed hydrolysis of an aryl monoester versus dialkyl phthalates; isotope label aids product tracing. • Derivatization chemistry: Formation of silyl or acyl derivatives of the tertiary alcohol for GC methods (e.g., MSTFA), while monitoring isotopologue integrity. • Salt formation and speciation: Carboxylic acid can form ammonium/amine salts; useful for volatilization control or solubility modulation.

Practical tips • Avoid strong acids/bases or protic deuterated solvents if they can exchange deuterium at labile positions. Confirm labeling map on the CoA and adapt pH and temperature accordingly. • For quantitative work, prepare standards gravimetrically, use amber glass to minimize any photolysis, and include bracketing calibration with the unlabeled analyte.

Reaction Conditions

Typical conditions relevant to this compound are those used for derivatization or controlled hydrolysis in analytical workflows (general literature guidance; not item-specific):

• Acid-catalyzed hydrolysis: Aqueous HCl or H2SO4 (0.1–2 M), 40–80°C, 0.5–4 h; converts the ester to phthalic acid. Monitor for potential H/D exchange if deuterium is on labile positions. • Base-catalyzed hydrolysis (saponification): Aqueous NaOH/KOH (0.05–1 M), 20–60°C, minutes to hours depending on conditions; proceed under N2 to limit oxidative side reactions. Neutralize carefully before LC–MS. • Alcohol derivatization (acylation): Acetic anhydride or benzoyl chloride with pyridine/DMAP, 0–25°C, 0.5–2 h; useful to cap the tertiary hydroxyl for GC methods. • Silylation: MSTFA, BSTFA, or TBDMS-Cl with imidazole, 50–70°C, 15–60 min; enhances GC volatility and MS response. Verify that derivatization does not induce H/D scrambling. • Salt formation: Dissolve in minimal MeOH, add equimolar volatile amine (e.g., NH4OH, TEA) at 0–25°C to form soluble salts; remove solvent under gentle N2 stream.

Operational notes • Use anhydrous solvents (MeCN, acetone, EtOAc) and low moisture glassware for reproducibility. • Confirm labeling integrity by LC–HRMS before and after treatment. Include procedural blanks and bracketing standards.

Safety and Handling

Authoritative safety data must be taken from the product SDS.

GHS information (item-specific) • Signal word: Not specified for this item; refer to SDS. • Hazard statements (H-codes): Not specified for this item; refer to SDS. • GHS classification/pictograms: Not specified for this item; refer to SDS.

General safety guidance for aromatic monoesters/organic acids (informational only) • Hazards: May cause skin/eye irritation; ingestion/inhalation of dusts/aerosols should be avoided. Some phthalate esters are harmful to the environment. Treat as hazardous until SDS is reviewed. • PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to minimize inhalation exposure, especially during weighing or solvent evaporation. • Storage incompatibilities: Keep away from strong bases (can cause hydrolysis), strong acids (can promote hydrolysis/esterification), strong oxidizers, and reactive acylating agents. Avoid moisture ingress for best stability. • Handling tips: Dispense quickly at room temperature to limit atmospheric moisture uptake; recap tightly. For LC–MS applications, use high-purity solvents and glassware dedicated to isotope-labeled standards to avoid cross-contamination. • First aid (overview): In case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth. Seek medical attention as appropriate. Always follow institutional safety procedures. • Waste: Collect organic waste and contaminated materials according to local regulations; avoid environmental release.

Solvent Selection

Without item-specific solubility data, select solvents based on functional groups: an aromatic monoester with one free carboxyl and a tertiary alcohol side chain typically dissolves well in polar aprotic and moderately polar protic solvents.

Recommendations (general guidance) • LC–MS sample prep: Methanol, acetonitrile, or their water mixtures (0.1% formic acid or ammonium formate/acetate for ionization as needed). For negative ESI, mild ammonium acetate buffers aid deprotonation of the carboxyl. • NMR: CDCl3 or DMSO‑d6; if poor solubility in CDCl3, use DMSO‑d6 or CD3OD. Deuterated solvent choice should avoid isotope exchange at labeled positions; verify labeling stability under chosen conditions. • Workup/extraction: Ethyl acetate or MTBE from mildly acidic aqueous phases (pH ~2–3) often extracts carboxylic acids in their neutral form. At basic pH, the carboxylate partitions to water; avoid if you need to extract into organics. • Chromatography: Normal-phase silica may cause tailing due to the acid; consider adding 0.1–1% acetic acid to eluent or use reversed-phase C18 with aqueous-organic gradients.

Comparison notes • Versus nonpolar solvents (hexanes/toluene): substantially better solubility is expected in EtOAc, acetone, MeOH, MeCN, and DMSO. • Water: likely low intrinsic solubility; improve by cosolvent or pH control (salt formation at high pH increases aqueous solubility but may compromise LC–MS if not neutralized).

Storage and Reconstitution

Item-specific conditions • Storage temperature: Store at −20°C (per Product Data). • Shipping: Shipped in ice chest + ice pads. • Appearance: Not specified for this item; refer to CoA/Spec Sheet. • Reconstitution solvent: Not specified for this item; refer to CoA/Spec Sheet. Common choices for similar standards include LC–MS grade methanol or acetonitrile.

Good practice for isotope-labeled small molecules (general guidance) • Upon receipt: Allow the sealed container to equilibrate to room temperature before opening to prevent condensation. Inspect for integrity. • Stock solutions: Prepare concentrated stock (e.g., 1–10 mg/mL) in dry MeOH or MeCN. If water solubility is required, dissolve in minimal organic solvent then dilute with water or buffer immediately before use. • Aliquoting: Divide into single-use aliquots in amber vials to minimize freeze–thaw cycles and photodegradation. Label with lot number, concentration, solvent, and preparation date. • Stability: Keep tightly closed under inert atmosphere (N2/Ar) when possible. Avoid prolonged exposure to moisture, strong light, or elevated temperature. Monitor by LC–MS for signs of ester hydrolysis or isotopic scrambling during storage. • Shelf life: For definitive stability and retest date, consult the CoA/Spec Sheet and follow your lab’s stability program. • Research use only: Not for human or veterinary use.

Structure and Identity

• Item name: Mono(2-hydroxyisobutyl)phthalate-d (isotopically labeled monoester of phthalic acid) • CAS: 2119597-90-7 • Isotopic note: “-d” indicates deuterium labeling; exact labeling pattern and D-incorporation level are 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. • SMILES: Not specified for this item; refer to CoA/Spec Sheet. • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general chemistry knowledge): • Core scaffold: phthalate (benzene-1,2-dicarboxylate) bearing one free carboxyl and one 2-hydroxyisobutyl ester substituent (monoester). The benzene ring is ortho-disubstituted by carboxyl-derived groups. • Functional groups: aromatic ring; one carboxylic acid (–CO2H); one ester (–CO2–R); one pendant tertiary alcohol within the 2-hydroxyisobutyl group [HO–C(CH3)2–CH2–]. The deuterated variant replaces one or more hydrogens with deuterium. • Ionization: the carboxyl group is acidic; the phenyl ester is neutral; the tertiary alcohol is weakly acidic and typically non-ionized in neutral media. • 2D description in words: a benzene ring with adjacent (ortho) substituents—one is a free carboxyl group, the other is an ester linking to a branched side chain that contains a tertiary hydroxyl and two methyl groups. Deuterium atoms occupy specific sites depending on the labeling scheme (not provided here).

Synthetic Utility

As a deuterium-labeled monoester of phthalic acid, this material is primarily an analytical standard. However, its functional groups provide avenues for derivatization and method development (general chemistry guidance):

• Carboxylic acid: Can form salts (e.g., ammonium, tertiary amines) to tune solubility; can be converted to acyl chlorides or activated esters (e.g., via SOCl2, DCC) if derivatization is needed for specialized analytics. Exercise caution to preserve deuterium labeling. • Ester moiety: Susceptible to hydrolysis (acid/base, enzymatic) generating phthalic acid (and the corresponding labeled alcohol fragment if labeling resides there). Useful for kinetic isotope studies of hydrolysis and for confirming analyte identity by generated fragments in MS. • Tertiary alcohol (in the 2-hydroxyisobutyl side chain): Can undergo silylation (TMS, TBDMS) or acylation to increase volatility for GC analysis; can form carbonate derivatives for alternative detection strategies. • Aromatic ring: Amenable to electrophilic substitution only if appropriately directed; typically inert under mild conditions used in sample prep.

For synthetic manipulations beyond analytical derivatization, consider the risk of H/D exchange at acidic or benzylic positions; maintain neutral, anhydrous conditions and low temperatures where feasible.

Target Specificity

Not an antibody or affinity reagent. No target specificity parameters (antigen, clone, isotype, species reactivity) apply to this small-molecule standard.