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Application Protocols
No manufacturer‑verified application protocols are provided for this item. Typical research uses include the following general workflows (non‑validated examples; adjust to your SOP):
GC‑MS internal standard preparation:
Prepare a 1.0 mg/mL stock in isooctane; store at −20 °C in silanized glass vials.
Spike samples to achieve 10–500 ng on‑column equivalent, depending on method sensitivity.
HS‑SPME headspace analysis:
Add Nonanal‑d to matrix at known concentration; equilibrate 30–45 min at 40–60 °C; extract with PDMS or DVB/Carboxen/PDMS fiber; desorb in GC inlet.
DNPH derivatization (carbonyl quantitation):
React sample containing nonanal with excess DNPH in acidic ACN/H2O; analyze hydrazone by LC‑UV or LC‑MS. Include Nonanal‑d as internal standard to correct for derivatization efficiency.
These are general, literature‑style examples and not item‑specific recommendations. Validate conditions in your laboratory.
Biological Roles
Context (general literature for the non‑labeled analogue, nonanal):
Origin: Nonanal is a common volatile aldehyde arising from lipid peroxidation of polyunsaturated fatty acids (notably linoleic acid) in plants, foods, and biological tissues.
Occurrence: Detected in plant headspace volatiles, food aromas (citrus, green, fatty notes), and in exhaled breath or biofluids during oxidative stress.
Biotransformation: In vivo, aliphatic aldehydes are typically oxidized by aldehyde dehydrogenases to the corresponding carboxylic acids (nonanoic acid) or reduced by aldo‑keto reductases to nonanol; further β‑oxidation shortens the chain.
Biophysical effects: As a hydrophobic carbonyl, nonanal can form adducts with nucleophiles (e.g., primary amines) yielding imines/Schiff bases; protein adduction is less pronounced than with α,β‑unsaturated aldehydes but can occur under certain conditions.
Role of the deuterated analogue (research use):
Stable‑isotope tracing: Nonanal‑d enables measurement of aldehyde metabolism, compartmentalization, and turnover by MS without perturbing pathways significantly.
Quantitative biomarker analysis: Serves as an internal standard for isotope‑dilution assays of nonanal in complex biological matrices (breath, plasma extracts, tissue headspace), improving accuracy and precision.
Note: This product is for research use only. No clinical or diagnostic claims are made or implied.
Buffer Applications
Nonanal‑d is a hydrophobic volatile aldehyde and does not function as a buffering agent. It is not typically used to prepare buffer systems or to control pH.
Practical note (analytical):
If spiking aqueous buffers or biological media for recovery studies, use water‑miscible co‑solvents (e.g., ACN or ethanol at ≤1–5% v/v) or emulsions, and add immediately before analysis to minimize volatilization and adsorption losses.
For derivatization workflows (e.g., DNPH), the buffer/acid composition is dictated by the derivatization chemistry; follow your validated method.
Green Alternatives
For this compound (a labeled analytical standard rather than a process solvent or reagent), “green alternatives” are best considered in terms of greener workflows rather than replacement of the analyte itself.
Greener considerations (general):
Alternative isotopes: 13C‑labeled nonanal offers a non‑exchangeable label that avoids potential H/D exchange; however, synthesis may have a higher resource footprint and cost.
Solvent selection for standards: prefer heptane/isooctane over chlorinated solvents (e.g., DCM) for GC‑MS stock solutions to reduce halogenated waste.
Miniaturization: employ HS‑SPME or solventless microextraction to minimize solvent usage in volatile aldehyde analysis.
Derivatization choice: opt for less hazardous carbonyl reagents when feasible (e.g., O‑alkylhydroxylamines) and avoid excessive acid catalysts.
Illustrative comparison (general):
Deuterated vs 13C‑labeled nonanal
Exchange stability: D (potentially exchangeable at certain sites) vs 13C (non‑exchangeable)
Mass shift: typically +1 for mono‑D vs +1 for mono‑13C; multi‑labeling tunable
Cost/availability: D‑labeled often more accessible; 13C may be pricier
Environmental impact: both are used at trace levels; solvent and waste choices dominate the footprint
Note: This product is a research analytical standard; selection should prioritize method performance and data quality, while adopting greener sample prep and solvent practices.
Pharmaceutical Uses
Nonanal‑d is not an excipient or an approved pharmaceutical ingredient. It is used in pharmaceutical research and quality laboratories as an analytical standard.
Research/manufacturing lab contexts (general):
Process and stability studies: Isotope‑dilution internal standard for monitoring nonanal as a degradant or impurity arising from lipid oxidation in formulations and excipients (e.g., polysorbates, lipids).
Method development/validation: System suitability and recovery standard for HS‑GC‑MS or derivatization‑LC methods targeting carbonyl impurities.
Extractables/leachables investigations: Surrogate/internal standard in volatile profiling to correct for sampling and analytical variability.
Regulatory note:
There is no pharmacopeial monograph specific to Nonanal‑d. Use is restricted to research and non‑clinical quality control applications unless otherwise justified by internal procedures. Always document standards traceability and maintain current CoA records.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values for the unlabeled analogue (nonanal, C9H18O), provided for context (deuteration typically has negligible impact on bulk properties):
Typical boiling point: ~191–193 °C (literature)
Typical melting point: ~−18 °C (literature)
Density (20–25 °C): ~0.83 g/mL (literature)
Refractive index n20 D: ~1.436 (literature)
Aqueous solubility: very low (order of a few mg/L at ambient temperature; literature); readily soluble in nonpolar organic solvents (hexane, diethyl ether) and moderately soluble in acetonitrile and alcohols (literature)
LogP (octanol/water): ~3.5–3.8 (literature)
Vapor pressure: low at ambient temperature; increases significantly with warming (literature)
General physicochemical commentary (general knowledge):
The terminal aldehyde strongly absorbs in IR near ~1725 cm−1; CHO C–H stretch near ~2720–2820 cm−1. Incorporation of deuterium slightly shifts the associated vibrational frequencies (isotopic shift).
In NMR, aldehydic 1H at ~9.4–10.0 ppm (for non‑D at formyl); deuteration at the labeled position suppresses the corresponding 1H signal and introduces a 2H resonance near the analogous chemical shift in 2H NMR.
GC behavior: elutes later than octanal and before decanal on nonpolar columns; suitable for HS‑SPME/GC‑MS quantitation of volatile aldehydes (general observation).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and best practices (general guidance for deuterated small molecules):
Isotopic enrichment: Deuterated analytical standards are commonly specified by atom% D and labeling position(s). Higher enrichment (e.g., ≥98 atom% D at the specified site) minimizes isotopic cross‑talk in MS quantitation. Verify the atom% D and labeling site on the CoA.
Chemical purity: For quantitative work (GC‑MS/LC‑MS), purity ≥95% is typical; low levels of isomeric or oxidative impurities (e.g., nonanoic acid) are important. Review chromatographic purity and residual solvent limits on the CoA.
Low‑oxygen handling: Aldehydes can oxidize in storage. If your application is trace‑level quantitation, consider purging the container headspace with inert gas upon first opening and storing aliquots to reduce formation of acid impurities over time.
What “life science catalog” positioning implies: material is suitable for research use, including metabolomics and volatile profiling. It is not certified for clinical/diagnostic use unless explicitly stated (it is not for human or animal administration).
Documentation: Request the latest CoA/batch record for:
Exact isotopologue description (position of D), atom% D
GC/LC purity, residual solvents, water
Any stabilizer present (e.g., BHT) and its implications for your method’s blanks and MS background
Reaction and Applications
Primary use cases (research/analytical; general guidance):
Internal standard for GC‑MS or HS‑SPME‑GC‑MS quantitation of nonanal in food aroma, environmental air, and biological samples. Isotopic labeling corrects for matrix effects and volatility losses.
Isotopic tracer in lipid peroxidation studies: nonanal arises from cleavage/oxidation of linoleic‑acid–derived hydroperoxides; the D‑label assists in pathway elucidation and kinetic isotope effect (KIE) evaluations.
Carbonyl derivatization analytics: forms hydrazones/oximes (e.g., DNPH hydrazone, PFBHA oxime) for LC/GC analyses; the D‑label preserves mass offset through derivatization for accurate isotope‑dilution quantitation.
Reactivity highlights (general for aliphatic aldehydes):
Nucleophilic addition: Grignard/organolithium reagents yield secondary alcohols after workup.
Condensation: Wittig/Horner–Wadsworth–Emmons to give terminal alkenes; aldol reactions under base or Lewis acids.
Redox: readily reduced to nonanol (NaBH4, catalytic hydrogenation) or oxidized to nonanoic acid (TEMPO/bleach, Jones, O2/catalyst).
Practical tips:
Oxidative stability: purge headspace with N2/Ar; add antioxidant only if compatible with your detection (not item‑specified).
Adsorption: low‑polarity aldehydes can adsorb to glass/plastics at ng/mL levels. Use silanized glassware or consistent vessel types when working at trace levels.
Carryover in GC: bake out inlets/liners; maintain splitless times judiciously to avoid tailing and memory effects.
If the D label is at an exchange‑prone position (e.g., formyl‑D), avoid protic media and elevated temperatures to limit H/D exchange.
Reaction Conditions
The following are general literature guidelines for reactions of saturated aliphatic aldehydes; adapt to maintain isotopic integrity of Nonanal‑d and consult primary sources.
Nucleophilic additions (Grignard):
Reagents: RMgX (1.1–1.5 eq), anhydrous ether/THF
Temperature: 0 °C to rt; workup with NH4Cl(aq)
Notes: strictly anhydrous; if D is at an exchange‑sensitive position, avoid protic/acidic quench until necessary; consider CD3OD quench if tracking label.
Wittig olefination:
Reagents: Ph3P=CHR (1.2–1.5 eq), THF or toluene
Temperature: 0 °C to reflux; typical times 2–12 h
Outcome: terminal alkene; E/Z depends on ylide stability; yields often 60–90% (literature ranges)
Oxime/hydrazone formation (derivatization for analysis):
Reagents: PFBHA or DNPH in buffered aqueous/ACN, mild acid catalysis
Temperature: rt; 10–60 min typical
Notes: maintain cold, minimize exposure to light/oxygen; D‑label mass shift is retained.
Reduction to alcohol:
Reagents: NaBH4 (1.2–2 eq) in MeOH/EtOH or THF/H2O
Temperature: 0 °C to rt; 0.5–2 h
Caution: protic solvents can exchange D if label is at an exchangeable site.
Oxidation to acid:
Reagents: TEMPO (0.05 eq), NaOCl/NaBr, pH ~9–10 (biphasic)
Temperature: 0–10 °C to control over‑oxidation of other functionalities
These conditions are illustrative (literature); they are not item‑specific specifications.
Safety and Handling
Hazard classification and statements: Not specified for this item; refer to SDS for definitive GHS classification, signal word, pictograms, and H‑statements.
General aldehyde safety considerations (general guidance; defer to SDS):
Likely hazards: flammable liquid/ vapor and skin/eye/respiratory irritant are common for short‑chain aliphatic aldehydes. Avoid inhalation and skin contact; use in a fume hood.
Personal protective equipment (PPE): lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). For bulk handling, consider face shield and local exhaust ventilation.
Handling: minimize headspace exposure to air/oxygen; aldehydes can oxidize to the corresponding carboxylic acids. Work under inert gas for sensitive applications. Avoid bases that can promote self‑aldol reactions; keep away from strong oxidizers and reducing agents.
Storage incompatibilities: oxidizing agents, strong bases, amines (can form imines/Schiff bases), and strong acids (can catalyze side reactions). Keep containers tightly closed to limit volatilization and oxidation.
First aid (overview; follow institutional procedures):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire fighting: use alcohol‑resistant foam, dry chemical, or CO2. Combustion may produce CO/CO2 and irritant fumes.
Waste: collect as halogen‑free organic waste unless otherwise directed by your EHS program.
Solvent Selection
Nonanal‑d is a low‑polarity, hydrophobic aldehyde. Solvent choice is driven by volatility control, matrix compatibility, and analytical method.
General solvent behavior (literature/general knowledge):
Polarity/miscibility: insoluble to sparingly soluble in water; readily soluble in nonpolar organics (n‑hexane, isooctane, toluene) and compatible with moderately polar solvents (diethyl ether, dichloromethane, acetonitrile, ethanol).
Dielectric context: prefers solvents with low to moderate dielectric constants to maintain non‑specific interactions and to mimic lipid environments.
Selection guidance by application:
GC‑MS calibration stocks: prepare at 0.1–10 mg/mL in isooctane or n‑hexane to minimize adsorption and promote GC injector compatibility. For HS‑SPME workflows, dilute further into matched matrices or salt solutions.
LC‑MS (if derivatized): acetonitrile or methanol are appropriate; ensure compatibility with derivatization reagents (e.g., DNPH, PFBHA) if using carbonyl tagging.
NMR: CDCl3 or C6D6 for 1H/13C; 2H observation at the labeled site requires a 2H‑compatible probe; avoid protic solvents that may exchange with labile D if the label is at an exchange‑prone position.
Quick comparison (general):
Hexane/isooctane: optimal for GC; lowest polarity, minimal background.
DCM/Et2O: better solvation, faster evaporation; more volatile/regulated.
ACN/MeOH: useful for LC‑MS or derivatization; may accelerate oxidation—use cold/inert handling.
Note: Item‑specific solubilities are not specified; consult your method SOP and CoA.
Storage and Reconstitution
Storage conditions (item‑specific): Store at −20 °C.
Shipped in (item‑specific): Ice chest + ice pads.
Research use note (item‑specific): For research use only.
General handling and aliquoting (recommended best practices for aldehydes; not item‑specific specifications):
Upon receipt: allow the sealed container to equilibrate to room temperature before opening to avoid moisture condensation. Open in a fume hood.
Aliquoting: divide into small, inert‑gas–purged vials to minimize headspace oxygen and repeated freeze‑thaw cycles.
Light/oxygen: protect from light and air to reduce oxidation to nonanoic acid; consider storing under nitrogen/argon.
Solvents: prepare concentrated stocks in isooctane, n‑hexane, or acetonitrile, depending on the analytical method. Use dry, oxygen‑reduced solvents for long‑term stability.
Working solutions: prepare fresh daily or weekly as method dictates; store cold (e.g., 2–8 °C) and discard if oxidation is detected (e.g., acid/oxime impurities).
Container compatibility:
Use amber, PTFE‑lined, crimp‑cap or screw‑cap glass vials. Silanized glass can reduce adsorption for low‑ng/mL levels.
Refer to the product’s CoA/SDS for any additional, lot‑specific storage or stability information.
Structure and Identity
Brief: Nonanal‑d is a deuterium-labeled analogue of nonanal (a C9 saturated aliphatic aldehyde), used predominantly as an isotopic internal standard and tracer in analytical and mechanistic studies.
SKU: N1449241
Product name: Nonanal-d
CAS: 1466552-36-2
CID: 72735673
InChIKey (as provided): 114725
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):
Core scaffold: a straight, saturated nine‑carbon chain terminating in an aldehyde group (–CHO). The carbonyl carbon is sp2-hybridized; remaining carbons sp3.
Isotopic label: one hydrogen in the molecule is replaced by deuterium (2H, D). The exact labeling position may vary by product definition; consult the CoA for position-specific labeling (e.g., formyl‑D, α‑D, etc.).
Functional groups: terminal aldehyde (susceptible to oxidation, nucleophilic addition, imine/oxime formation), long hydrophobic alkyl tail conferring low polarity.
2D description in words: an n‑nonyl chain (CH3–(CH2)7–) attached to a terminal formyl carbonyl (–CHO), with a single 2H atom located at a defined site in the structure (position‑specific per batch documentation).
Notes:
For exact isotopologue identity (site of deuteration, atom% D), refer to the item’s Certificate of Analysis (CoA).
Synthetic Utility
Although purchased primarily as a labeled standard, Nonanal‑d retains the reactivity of an aliphatic aldehyde and can be used as an isotopically labeled building block.
Transformations (general):
Nucleophilic additions: Grignard/organolithium reagents furnish 2° alcohols after aqueous workup; the D label may be retained or scrambled depending on its position and reaction conditions.
Carbonyl olefinations: Wittig, Horner–Wadsworth–Emmons, Julia–Kocienski to access terminal nonenes or substituted alkenes with predictable E/Z outcomes.
Condensations: Aldol/Tishchenko reactions under base or Lewis acids; imine/oxime/hydrazone formation with amines, hydroxylamines, hydrazines (useful for labeled derivatives).
Redox chemistry: Reduction to nonanol‑d (NaBH4, catalytic H2) or oxidation to nonanoic acid‑d (TEMPO/bleach, O2 with catalysts). Oxidation state manipulations enable incorporation of D into derivative libraries for mechanistic probes.
Retrosynthetic value:
As a terminal aldehyde, it is a convergent handle for chain‑extension (e.g., homologations via cyanohydrin formation/reduction or via Wittig and subsequent functionalization), while preserving an isotopic tag for kinetic isotope effect studies or tracer experiments.
Caution:
If the deuterium is at an exchangeable site (e.g., formyl), avoid protic/acidic conditions that can promote H/D exchange and loss of isotopic integrity.
Target Specificity
Not applicable. This product is a small‑molecule isotopically labeled aldehyde and is not an antibody, probe, or affinity reagent. There are no antigen/epitope targets, species reactivity, or clone/isotype data associated with this item.
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