n-Dinonyl Phthalate Acid Ester solution - analytical standard, 136.0ug/ml in Methanol , CAS No.84-76-4

CAS: 84-76-4 Cat. No.: D119858 Formula: C₂₆H₄₂O₄ Peso molecolare: 418.61 Numero EC: 201-560-0

GRADE & PURITY Analytical standard, 136.0ug/ml in Methanol

Synonyms

n-Dinonyl Phthalate Acid Ester in Methanol Certified Reference Material Phthalic Acid Dinonyl Ester

Storage

Room temperature

Shipped In

Normal

Specifications

Sinonimi

n-Dinonyl Phthalate Acid Ester in Methanol Certified Reference Material Phthalic Acid Dinonyl Ester

Specifiche e purezza

analytical standard, 136.0ug/ml in Methanol

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Grado

Standard analitico

Nomi e identificatori

Isomeri SMILES

CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC

RTECS

TI1800000

Peso molecolare

418.61

Reaxy-Rn

1916263

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1916263&ln=

Proprietà chimiche e fisiche

• Sensibilità: light sensitive
• Indice di rifrazione: 1.4825-1.4845
• Punto di infiammabilità (°F): 216℃
• Punto di infiammabilità (°C): 216℃
• Punto di ebollizione (°C): 279-287°C

Application Protocols

No application protocols are specified for this item in the Product Data. As general guidance for analytical use (literature-informed; not product specifications):

• GC-MS/FID calibration:
  • Prepare serial dilutions in high-purity isooctane or hexane using glassware and amber autosampler vials with PTFE-lined caps. Include an internal standard. Verify concentration against CoA.
  • Use splitless or PTV injection; start oven at low temperature and ramp to >300 °C to elute high-boiling phthalates. Employ guard columns/liners dedicated to phthalate analysis.
• LC-MS screening:
  • Dissolve in ACN or MeOH; inject onto C18 with high organic content mobile phase. Prefer APCI source to reduce ion suppression. Use strong needle wash (e.g., IPA/MTBE) to minimize carryover.
• Blanks and QC:
  • Run solvent blanks and system suitability injections to monitor background. Replace plastic consumables with glass to minimize contamination.

Always adapt protocols to your laboratory’s validated methods and the exact standard concentration/solvent specified on the CoA.

Biological Roles

No biological role is assigned to this product; it is sold strictly as a research/analytical standard.

General literature context for dialkyl phthalates (not product-specific, no clinical claims):

• Exposure and fate: Dialkyl phthalates are ubiquitous environmental xenobiotics due to extensive use as plasticizers. They exhibit high logP and preferentially partition into lipids and particulates. Biotransformation typically proceeds via enzymatic hydrolysis to monoesters (e.g., mono-nonyl phthalate, MNP) followed by oxidative chain shortening and conjugation (e.g., glucuronides) to enhance excretion.
• Interactions: The parent diester is relatively inert; biological interactions are more often associated with the monoester metabolites, which possess greater polarity and can interact with proteins and membranes differently than the diester.
• Analytical biomonitoring: Studies often measure urinary monoester metabolites as exposure biomarkers. For DnNP specifically, mono-nonyl phthalate (MNP) and oxidized metabolites may be targeted depending on isomeric composition of the exposure source.
• Environmental microbiology: Certain microbes can hydrolyze and further degrade long-chain phthalates, but rates are slow under many environmental conditions due to poor bioavailability.

These literature notes are provided to contextualize why robust analytical standards for phthalates are important in exposure and migration studies.

Buffer Applications

Not typically applicable. n-Dinonyl phthalate is a highly hydrophobic plasticizer analyte and is essentially insoluble in aqueous buffers. It does not serve as a buffering agent or pH control component. For laboratory work, focus on organic solvent systems and sample preparation methods discussed under Solvent Selection and Reaction & Applications.

Green Alternatives

While n-dinonyl phthalate is a widely used plasticizer analyte, its environmental persistence and high hydrophobicity warrant consideration of greener choices in both solvent selection and reference materials where study goals permit.

Greener solvent choices for handling/analysis (general guidance):

• Prefer ethyl acetate, isopropanol, or cyclopentyl methyl ether (CPME) over chlorinated solvents (DCM/CHCl3) when chromatographic performance allows.
• For GC standards/dilutions, isooctane or heptane may be preferable to hexane from a health perspective (reduced n-hexane neurotoxicity risk), though not strictly “green.”

Alternative plasticizer analytes (context-dependent):

• Citrates (e.g., triethyl citrate, acetyl tributyl citrate) and adipates (e.g., di-2-ethylhexyl adipate) are commonly studied as lower-toxicity plasticizer substitutes. If the research question targets overall plasticizer migration rather than specific phthalates, these may be suitable model compounds.

Concise comparison (literature-based, qualitative):

• n-Dinonyl phthalate (DnNP): High hydrophobicity, very low volatility, strong adsorption; robust GC amenability; environmental persistence.
• Adipates/citrates: Generally better toxicological profiles; may be more biodegradable; sometimes lower hydrophobicity (facilitating cleanup), but analytical responses and retention times differ—method revalidation is required.

Trade-offs:

• Replacing DnNP with alternatives changes physicochemical behavior and may not represent legacy phthalate contamination. For regulatory or historical comparability, retain DnNP but optimize greener sample prep solvents and minimize waste.

Pharmaceutical Uses

No pharmaceutical or therapeutic use is claimed for this catalog item; it is for research use only.

General formulation context (literature, not item-specific):

• Some phthalate esters have historically been used in excipient roles (e.g., plasticizers in coatings). However, n-dinonyl phthalate is not a common pharmacopeial excipient, and regulatory scrutiny on phthalates in drug products is high.
• If analytical work involves excipient screening or extractables/leachables from elastomers and polymeric components, n-dinonyl phthalate may be included in target analyte lists as a representative hydrophobic phthalate.

Practical analytical notes for pharma quality labs:

• Employ low-bleed consumables and phthalate-free solvents; establish stringent system and method blanks.
• Use matrix-matched calibration and, where possible, isotopically labeled internal standards to correct for recovery and adsorption.

Consult relevant pharmacopeial chapters and regulatory guidances for limits and method verification requirements when phthalates are part of extractables/leachables assessments.

Physical Properties

Item-specific values for this solution (concentration, solvent system, exact density/refractive index) are Not specified for this item; refer to CoA/Spec Sheet.

Literature properties for neat n-dinonyl phthalate (DnNP; for reference only, not product specs):

• Physical state/appearance: Colorless to pale yellow, oily liquid (literature).
• Boiling behavior: High-boiling plasticizer; reported distillation typically only under reduced pressure. Typical bp >350 °C at 1 atm (literature, varies by source); exact value depends on isomeric purity and measurement method.
• Melting point: Typically remains liquid at room temperature; mp often below −20 °C (literature).
• Density: ~0.97–0.98 g/mL at 20–25 °C (literature range for long-chain dialkyl phthalates).
• Refractive index (nD20): ~1.485–1.490 (literature, approximate for C9–C10 dialkyl phthalates).
• Vapor pressure: Very low at ambient temperature (literature; contributes to low volatility and persistence on surfaces).
• Solubility: Practically insoluble in water; miscible with nonpolar and moderately polar organic solvents (e.g., hexane, toluene, DCM, THF, acetone) (literature). Partitions strongly into hydrophobic phases (high logP).
• LogP (octanol/water): Expected high, typically >7 for C9–C10 phthalates (literature estimates).
• UV characteristics: Aromatic ester exhibits modest absorbance in near-UV due to benzene chromophore; exact UV cutoff/epsilon Not specified for this item; refer to CoA/Spec Sheet.

Always verify method-critical physical constants (e.g., density for gravimetric dilutions, refractive index) against the item’s CoA before use.

Quality and Grades

• Item-specific grade: Analytical standard (from Product Data).

  • Meaning (general): “Analytical standard” denotes material or solution intended for calibration/quantitation in analytical methods (e.g., GC-FID/MS, LC-UV/MS). These standards typically have tightly controlled identity, purity/assay, and uncertainty, and are accompanied by a Certificate of Analysis (CoA) specifying concentration (if a solution), solvent, traceability, and permissible uncertainty.
  • Implications for use: Suitable for preparing calibration curves, system suitability tests, matrix spikes, and proficiency assessments in phthalate monitoring (plastics, environmental, food-contact migration studies), subject to the exact analyte and solvent/concentration stated on the CoA.

• Appearance, purity assay, stabilizers, and certified concentration: Not specified for this item; refer to CoA/Spec Sheet.

• Best practices with analytical standards:

  • Verify concentration by mass balance or independent check standard where required by QA systems.
  • Minimize adsorption or loss: Use amber glass vials with PTFE-lined caps; avoid plastic disposables that may either leach background phthalates or adsorb analyte.
  • Record lot number, open date, and storage conditions. Follow stated shelf life and uncertainty budget on the CoA.

• Regulatory/traceability notes (general): When applicable, choose lots with traceability to SI units or accredited reference materials. For phthalate analysis, low-background solvents and consumables are critical to maintaining method blanks.

Reaction and Applications

This catalog item is intended as an analytical standard; no specific synthetic application is claimed in the Product Data.

Analytical applications (general; literature-informed):

• Method calibration/validation for phthalate contamination monitoring in polymers, food-contact materials, indoor dust/air particulates, and environmental extracts (water/soil following SPE or LLE).
• GC-FID/MS quantitation with nonpolar columns (e.g., 5% phenyl polysiloxane). Temperature programming to elute high-boiling plasticizers; on-column or PTV injection minimizes thermal degradation and discrimination.
• LC-UV or LC-MS screening when GC is unsuitable; expect strong hydrophobic retention and potential ion suppression—use APCI for better desolvation of nonpolar esters.
• Recovery studies in sample prep workflows: Soxhlet, UAE/MAE, QuEChERS-like dispersive SPE, polymer migration simulants (e.g., isooctane, 95% ethanol). Employ isotopically labeled surrogates to quantify losses.

Chemical reactivity considerations (general):

• Ester stability: Resistant under neutral conditions; slow hydrolysis under strong acid/base, accelerated by heat and water content; yields mono-nonyl phthalate and phthalic acid.
• Transesterification: Possible with alcohols under acid or base catalysis.
• Oxidative degradation: Strong oxidants can cleave alkyl chains; photolysis minimal without sensitizers.

Practical tips:

• Minimize adsorption to plastics and silica. Pre-rinse autosampler paths and vials with working solvent containing low levels of the analyte.
• Control blank levels rigorously; phthalates are ubiquitous laboratory contaminants.

Reaction Conditions

No item-specific reaction conditions are provided, as this product is intended as an analytical standard. The following general, literature-based conditions describe transformations of dialkyl phthalates and are provided for reference only (not product specifications):

• Hydrolysis to monoester/acid:
  • Base-catalyzed: Aqueous NaOH or KOH in alcohol/water (e.g., MeOH/H2O), 25–60 °C to reflux; hours to completion depending on phase transfer. Acidify to isolate phthalic acid or neutralize to obtain monoester after partial hydrolysis. Use phase-transfer catalysts to accelerate in biphasic systems.
  • Acid-catalyzed: Mineral acid (H2SO4) in alcohol/water or neat alcohol, reflux; slower than base; control time to avoid complete saponification.
• Transesterification:
  • Acidic: p-TsOH or H2SO4 (0.5–5 mol%), excess ROH, reflux with Dean–Stark or continuous removal of ROH byproduct; hours.
  • Basic: Alkoxide (RO−) in dry ROH, 0–25 °C to reflux; monitor to avoid saponification.
• Oxidation of alkyl chains (for metabolite analogs):
  • KMnO4 or catalytic systems (e.g., RuO4 generated in situ) under controlled, dilute conditions; yields can be modest; protective measures to preserve ester linkages required.

Expected yields: Reaction-dependent; hydrolysis and transesterification typically high-yielding under optimized conditions. Always confirm identity/purity by GC/MS or NMR, mindful of isomerization/side reactions.

Caution: For quantitative analytical work, obtain certified reference materials of transformation products rather than preparing in-house when traceability is required.

Safety and Handling

Item-specific hazard classification (GHS signal word, pictograms, H-statements) is Not specified for this item; refer to SDS.

General safety information for dialkyl phthalate plasticizers and analytical standards (literature/good practice; not specific to this item):

• Hazards: Many phthalate esters are hydrophobic substances with low acute toxicity but potential for environmental persistence and bioaccumulation. Certain phthalates (e.g., DEHP) carry reproductive toxicity classifications; do not extrapolate—consult SDS for this specific substance/mixture.
• Handling: Work in a well-ventilated area or fume hood to avoid aerosol/mist. Prevent skin contact and contamination of porous labware. Avoid heating to decomposition; thermal breakdown can release irritating fumes.
• PPE: Safety glasses, lab coat, and suitable chemical-resistant gloves (e.g., nitrile). For bulk handling or spraying operations, consider splash protection and respiratory protection per risk assessment.
• Incompatibilities: Strong oxidizers. Hydrolyzes slowly under strong alkaline or acidic conditions to the monoester and phthalic acid; avoid prolonged exposure to strong bases/acids, especially at elevated temperature.
• Spill/cleanup: Absorb with inert material (diatomite, vermiculite), transfer to waste. Because of high hydrophobicity, detergent and organic solvent rinses may be needed for decontamination.
• First aid (overview): Skin—wash with soap/water. Eyes—rinse with water for several minutes. Ingestion/Inhalation—seek medical advice; move to fresh air. Always follow institutional emergency procedures.
• Waste: Collect as halogen-free organic waste unless local regulations dictate otherwise. Prevent release to the environment.

Authoritative information: Defer to the product SDS for definitive hazard, exposure limits, and emergency guidance.

Solvent Selection

As supplied, this product is an “Acid Ester solution,” but the solvent and concentration are Not specified for this item; refer to CoA/Spec Sheet.

General solvent compatibility for n-dinonyl phthalate (literature/good practice):

• Polarity class: Very nonpolar/hydrophobic analyte with limited polarity from two ester groups.
• Miscibility/solubility (qualitative):
  • Highly soluble in nonpolar/aprotic media: hexane, isooctane, cyclohexane, toluene, xylene.
  • Soluble in moderately polar solvents: dichloromethane, chloroform, THF, acetone, MTBE, ethyl acetate, acetonitrile (moderate).
  • Practically insoluble in water; forms films on glassware and plastics.
• Analytical uses:
  • GC-FID/MS: Nonpolar hydrocarbon solvents (hexane, isooctane) preferred to minimize column bleed interactions and improve injection reproducibility. Add internal standards where needed (e.g., deuterated analogs) to correct for adsorption losses.
  • LC-UV/MS: Retains strongly on C18; requires high-organic mobile phase (e.g., MeOH/ACN with modifiers). Beware of carryover; use strong wash solvents (IPA/MTBE) and low-bleed tubing.

When to choose alternatives:

• If elevated background of phthalates is observed, replace plastic consumables and consider glass syringes/vials. For greener method development, ethyl acetate or cyclopentyl methyl ether (CPME) may substitute for chlorinated solvents while maintaining solubility (tradeoffs in volatility and UV transparency apply).

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipment: Shipped under normal conditions (from Product Data).
• Matrix/concentration: Not specified for this item; refer to CoA/Spec Sheet.

Good-practice guidance for analytical standard solutions (general):

• Keep tightly capped in amber glass with PTFE-lined closure to minimize adsorption and photodegradation. Store in a clean cabinet away from reactive chemicals (acids/bases/oxidizers).
• Minimize headspace and avoid repeated opening. For frequent use, consider preparing single-use aliquots in pre-cleaned amber vials.
• If a concentrate requires reconstitution or dilution, use high-purity, phthalate-free solvents (e.g., pesticide-grade isooctane/hexane or LC-MS grade ACN/MeOH). Rinse receiving vials with a small portion of solvent containing trace analyte to condition surfaces before final dilution.
• Avoid plastic labware when possible; use glass syringes and pipettes with PTFE tips to reduce background contamination and adsorption.
• Stability: Dialkyl phthalates are generally stable at ambient temperature; avoid prolonged exposure to strong light and elevated heat. Adhere to the lot-specific expiry and uncertainty provided on the CoA.

For any uncertainty about solvent composition, concentration, or stabilizers, consult the item’s CoA and SDS prior to use.

Structure and Identity

n-Dinonyl phthalate (commonly abbreviated DnNP) is a dialkyl phthalate plasticizer comprising a phthalic acid core esterified with two linear n-nonyl chains.

• Item-specific identifiers (from Product Data):
  • SKU: D119858
  • CAS: 84-76-4
  • Grade: Analytical standard
  • Product format: “Acid Ester solution” (exact solvent, concentration: Not specified for this item; refer to CoA/Spec Sheet.)
• Literature/computed identifiers (for reference only; not item specifications):
  • Molecular formula (literature, DnNP): C26H42O4
  • Molecular weight (literature): ~418.61 g/mol
  • SMILES (literature, one possible canonical): O=C(OCCCCCCCCC)c1ccccc1C(=O)OCCCCCCCCC
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general chemistry description):
  • Aromatic benzene ring bearing two para- to ortho-positioned carboxylate esters (o‑phthalate diester framework).
  • Two identical, linear, saturated C9 alkoxy chains (n-nonyl) attached via ester linkages.
  • No stereocenters; conformational flexibility in the alkyl chains; overall highly hydrophobic, nonpolar character with polarizable aromatic core and two ester carbonyls.
  • Functional groups: two aryl esters (–COOR), aromatic ring; no heteroatoms beyond the ester oxygens.

Note: The above structural/literature details are provided to aid method development and qualitative understanding. Consult the CoA for the exact identity details of this catalog item’s solution preparation (e.g., concentration, solvent, stabilizers, and any assigned reference value).

Synthetic Utility

As a dialkyl phthalate, n-dinonyl phthalate is chemically robust and not commonly employed as a synthetic reagent. Its value in the laboratory is primarily as an analytical standard. Nonetheless, understanding its functional groups can inform limited transformations and method development (literature/general chemistry):

• Functional group profile: Two aryl ester moieties on a benzene ring; long linear alkyl chains (C9) confer hydrophobicity and steric bulk.
• Transformations:
  • Hydrolysis (acidic or basic, often with heating) affords mono-nonyl phthalate and phthalic acid; careful control allows preparation of monoester standards.
  • Transesterification with shorter/longer alcohols under acid catalysis to access other dialkyl phthalates for comparative studies.
  • Mild oxidative processes on the alkyl chains can generate oxidized metabolites (e.g., ω- or (ω−1)-hydroxy/oxo derivatives) for analytical reference, though these typically require dedicated synthesis.
• Retrosynthetic value: Limited; the compound is a synthetic endpoint in plasticizer manufacture via esterification of phthalic anhydride with n-nonanol.

Analytical/synthetic interface:

• Due to its nonvolatility and adsorption tendency, DnNP serves as a useful system for evaluating recovery in SPE/LLE and cleanup protocols in trace analysis, simulating worst-case behavior of hydrophobic extractables.

Target Specificity

Not applicable. This product is a small-molecule analytical standard, not a biological affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.