Oxacillin-d , CAS No.O1418123

CAS: O1418123 Cat. No.: O1418123 Formula: C₁₉H₁₄D₅N₃O₅S Peso molecolare: 406.47

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Oxacillin-d 5 is the deuterium labeled Oxacillin. Oxacillin is an orally active synthetic penicillin with good bactericidal activity against staphylococci and other gram-positive pathogens.

Specifications

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: 406.47

Application Protocols

Item-specific tested applications, dilutions, or protocols: Not specified for this item.

General procedural guidance (contextual; verify experimentally):

• LC–MS internal standard (if deuterated): prepare a concentrated stock (e.g., 1–10 mM) in DMSO or water, aliquot, and store at −20°C or colder. Spike into samples at a fixed concentration prior to extraction or directly into reconstitution solvent. Optimize MRM transitions based on exact labeling.
• Enzyme assays: prepare fresh aqueous buffer solutions near pH 7.0; pre-chill; initiate reactions by adding enzyme to minimize compound pre-hydrolysis. Monitor progress by LC–MS or spectrophotometry if applicable.
• Stability studies: subject aliquots to controlled stress (acid/base/thermal/oxidative) and analyze by LC–MS to map degradation pathways and validate stability-indicating methods.

Critical reminder: The exact salt form, isotopic labeling pattern, and concentration limits for Oxacillin-d are not specified in the Product Data. Consult the CoA/Spec Sheet and SDS, and perform small-scale pilot experiments to finalize conditions.

Biological Roles

Item-specific biological/biochemical data: Not specified for this item; refer to CoA/Spec Sheet.

General/literature context for oxacillin-class compounds (no clinical claims):

• Mode-of-action context: oxacillin belongs to the isoxazolyl penicillins that bind penicillin-binding proteins (PBPs), interfering with bacterial cell-wall transpeptidation. The isoxazole substituent confers steric protection against many β-lactamases.
• Enzymology and binding: widely used probes to study PBP active sites and β-lactamase-mediated hydrolysis; hydrolyzed products (e.g., penicilloic acids) are informative markers in mechanistic enzymology.
• Metabolic transformations (in vitro/in situ, literature): β-lactam ring opening, isomerization to penillic/penicillenic species, and conjugation reactions can occur depending on conditions.
• Assay relevance: employed as positive controls or standards in bacterial enzyme assays and in analytical quantification workflows.

Caveats:

• Salt form, counterions, and isotopic labeling (if “-d” is deuterated) can influence mass spectral behavior and chromatographic retention. Verify details on the CoA when designing experiments.
• No therapeutic or clinical usage is asserted for this catalog item; it is designated strictly for research and laboratory use.

Buffer Applications

This compound is not a buffer reagent per se. No item-specific buffer system guidance is provided in the Product Data.

General/literature context for handling oxacillin-class compounds in buffers (not item-specific specifications):

• pH window: prepare solutions near neutral pH (approximately pH 6.5–7.5) to balance solubility and β-lactam stability. Avoid strong acid/base.
• Common buffers: phosphate, HEPES, MOPS, or volatile ammonium acetate/formate for LC–MS workflows. Select buffer components that do not catalyze β-lactam hydrolysis and that are compatible with intended detection.
• Ionic strength: moderate ionic strength supports solubility for salt forms while limiting ion-suppression in MS detection.
• Filtration: sterile filtration (0.22 µm) may be used for microbiology-adjacent assays, ensuring minimal hold times at ambient temperature.

Always confirm the salt form and concentration guidance on the CoA/Spec Sheet before preparing buffered solutions.

Green Alternatives

This catalog entry represents a specific small-molecule research chemical rather than a process solvent. “Green alternatives” are therefore considered in terms of analytical and handling practices rather than replacing the molecule itself.

Greener practice suggestions (general/literature):

• Minimize solvent volumes in sample prep; adopt micro-scale LC–MS workflows and plate-based dilutions to reduce DMSO and acetonitrile consumption.
• Prefer aqueous buffers at near-neutral pH when feasible; use volatile, lower-toxicity salts (ammonium formate/acetate) for LC–MS.
• Cold-chain optimization: consolidate shipments and store as aliquots to reduce freeze–thaw cycles and waste.
• Waste reduction: implement stability-informed scheduling so freshly prepared solutions are consumed fully, limiting decomposed waste.
• Safer cleaning: avoid chlorinated solvents for glassware decontamination; use aqueous detergents or alcohols compatible with β-lactam deactivation.

Comparison (contextual):

• DMSO vs water/buffer stocks: water/buffer is greener and often adequate for short-term use if solubility allows; DMSO provides higher solubility but at added environmental and health burdens.
• Acetonitrile vs methanol for HPLC: methanol is less hazardous but may alter selectivity; evaluate with method scouting.

Note: No item-specific composition, stabilizers, or solvent-use requirements are provided for this product; consult the CoA/SDS to ensure selected practices are compatible.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation information is specified for this catalog item. It is supplied strictly for research use only.

General/literature context (not item-specific):

• Oxacillin-class compounds are studied in formulation science for stability profiling, degradation pathways, and compatibility with excipients. Research often evaluates the influence of pH, ionic strength, antioxidants, and lyophilization protocols on β-lactam stability.
• Deuterated analogs (if applicable) serve as internal standards in bioanalytical method validation supporting manufacturing quality control and stability-indicating assays.

Important: No therapeutic, diagnostic, or clinical claims are made for this product listing. For any regulated use, consult applicable guidelines and rely on the batch-specific CoA and SDS.

Physical Properties

Item-specific physical properties (from Product Data):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, pKa, logP, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.

General/literature information for oxacillin (context only; not item-specific specifications):

• Typical physical form: white to off-white solid; sodium salt is common in research use and is hygroscopic.
• Stability considerations: β-lactam ring undergoes hydrolysis under strongly acidic or basic conditions and at elevated temperature; solutions are typically prepared fresh.
• Solubility (literature): oxacillin sodium is water-soluble; solubility increases in aqueous buffers near neutral to slightly basic pH; limited solubility in nonpolar organic solvents.
• pH behavior (literature): aqueous solutions may show gradual degradation outside the near-neutral pH range.
• Spectroscopy (literature): UV absorbance mainly in the far-UV with weak chromophores; analytical detection often by HPLC-UV at short wavelengths or by LC–MS.

Important: Because this catalog entry does not list verified numeric specifications, users should rely on the item’s CoA/Spec Sheet for exact salt form, water content, potency, isotopic enrichment (if deuterated), and solution stability.

Quality and Grades

Item-specific quality information from Product Data:

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretive guidance (general):

• When grade/purity is not specified, consult the CoA for details such as assay (by HPLC), water content (Karl Fischer), residual solvents, and isotopic enrichment if the “-d” denotes deuteration.
• For deuterated analytical standards (if applicable), key quality descriptors include: isotopic purity at labeled positions, total deuterium incorporation, and residual unlabeled analog content. These parameters directly impact quantitative LC–MS workflows and internal standard performance.
• If offered as a screening library member (category indicates small molecules library), purity is often suitable for HTS/phenotypic assays; however, confirm acceptance criteria (e.g., ≥90–98% by LC–MS/UPLC) on the CoA.
• Stabilizers: None are listed for this catalog entry. If a stabilizer is present in a related product, it should be disclosed on the CoA; stabilizers can influence chromatographic background and ionization in MS.

Documentation:

• For regulated work or rigorous quantitation, retain the batch-specific CoA and any spectral data (1H/13C NMR, MS, HRMS, HPLC trace) provided. Request impurity profiles if needed for method development.

Reaction and Applications

Item-specific application notes from Product Data: None provided beyond “For research use only.”

General/literature applications for oxacillin-class molecules (context; not item-specific):

• Reference and internal standards: deuterium-labeled analogs of small molecules are widely used as internal standards for LC–MS quantification. If Oxacillin-d is deuterated, it may support pharmacokinetic or stability-indicating assays; confirm labeling pattern on the CoA.
• Enzymology: substrates/inhibitors in β-lactamase and penicillin-binding protein (PBP) studies; kinetic assays tracking β-lactam ring opening.
• Stability profiling: forced degradation (acid/base, oxidative, thermal, photolysis) to establish degradation pathways and validate stability-indicating methods.
• Derivatization chemistry: β-lactam acylation/hydrolysis studies, nucleophile-promoted opening to penicilloic/penillic acids (analytical characterization by LC–MS/NMR).
• Materials/immobilization: coupling via carboxylate or side-chain handles to solid supports for affinity capture of β-lactam-binding proteins.

Practical considerations:

• Maintain near-neutral pH and low temperature to limit ring hydrolysis during experiments.
• For LC–MS: use volatile buffers (ammonium formate/acetate, pH ~3–6) to balance ionization efficiency with acceptable stability; minimize autosampler dwell at ambient temperature.
• Validate carryover and adsorption; penicillins can adsorb to stainless steel or glass—use silanized/glass vials and low-adsorption plastics where suitable.

Reaction Conditions

Item-specific reaction condition guidance: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for oxacillin-class chemistry (context; not item-specific):

• Hydrolysis kinetics: β-lactam hydrolysis is accelerated by strong acids/bases and higher temperatures; maintain pH near neutrality and keep solutions cold to enhance stability.
• Solution preparation: prepare fresh aqueous or DMSO stock solutions; filter if needed; store aliquots at ≤−20°C to reduce degradation. Avoid repeated freeze–thaw cycles.
• Analytical methods: LC–MS or HPLC-UV with volatile buffers (e.g., 5–20 mM ammonium formate/acetate) at pH 3–6; column temperatures 25–40°C; minimize autosampler time at room temperature.
• Coupling/derivatization: for conjugation via carboxylate, use mild coupling reagents (e.g., EDC/NHS) at low temperatures; brief reaction times (minutes to low hours) help preserve the β-lactam.
• Expected outcomes (literature): clean conversion in mild acylation/coupling is feasible; harsh conditions lead to mixtures of penicilloic/penillic/penicillenic derivatives detectable by LC–MS.

Note: Select conditions must be validated experimentally for the exact salt form and isotopic label (if present). Always verify compatibility on small scale.

Safety and Handling

Item-specific hazard data provided in Product Data:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety guidance (literature; not item-specific):

• β-Lactam compounds are potential respiratory/skin sensitizers. Use appropriate containment (glove box or fume hood) to minimize exposure, especially for personnel with known penicillin sensitivity.
• Recommended PPE: lab coat, nitrile gloves, splash goggles; avoid aerosol/dust formation. Wash thoroughly after handling.
• Incompatibilities: strong acids/bases (promote β-lactam hydrolysis), strong oxidizers, and prolonged exposure to elevated temperatures or moisture.
• First aid (overview; defer to SDS): in case of skin contact, wash with soap and water; for eye exposure, rinse cautiously with water for several minutes; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention as appropriate.
• Spill response: avoid dust, collect with inert absorbent, and dispose of as hazardous chemical waste per institutional and local regulations.
• Thermal/photolysis: avoid unnecessary heat and light; prepare solutions fresh and keep chilled if stability is a concern.

Always consult the product-specific SDS for authoritative hazard classification, exposure limits, and emergency procedures.

Solvent Selection

Item-specific solubility/solvent compatibility: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for oxacillin-class penicillins (context only):

• Polarity and ionization: penicillins are amphoteric; salts (e.g., sodium) are typically water-soluble. Free acids have lower aqueous solubility and may require co-solvents.
• Aqueous media: dissolve readily in water or isotonic buffers at near-neutral to slightly basic pH. Minimize residence time at extreme pH to reduce β-lactam hydrolysis.
• Organic media: limited solubility in nonpolar solvents; miscibility improves in polar aprotic solvents (DMSO) for stock solutions used in screening assays. Dilute DMSO stocks promptly into buffered aqueous media to limit degradation.
• Comparison (context):
  • Water/buffer: best for biological assays; gentle on β-lactam stability near pH 6.5–7.5.
  • DMSO: convenient for concentrated stocks; may accelerate degradation on prolonged storage at room temperature—store frozen aliquots.
  • MeOH/EtOH: possible for short-term handling; avoid acidic alcohols or prolonged heating.

Practical tips:

• Filter through 0.22 µm for sterile applications if compatible.
• Prepare fresh solutions; keep on ice during use when feasible.
• Verify salt form and intended solvent on the CoA before protocol finalization.

Storage and Reconstitution

Item-specific instructions from Product Data:

• Storage Conditions: Store at −20°C.
• Shipped In: Ice chest + Ice pads.

Additional item-specific details (appearance, solvent, stabilizer, reconstitution): Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance (not item-specific):

• Keep tightly closed in the original container, protected from light and moisture. Consider storing under inert atmosphere for hygroscopic salts.
• For working solutions: prepare freshly in water, buffer, or suitable solvent (e.g., DMSO) depending on salt form and intended use. Filter if sterility is required and compatible.
• Aliquoting: to avoid repeated freeze–thaw cycles, dispense single-use aliquots and store at ≤−20°C; for extended stability, −80°C may be preferred.
• Thawing: thaw on ice; mix gently to avoid foaming. Discard solutions showing discoloration or precipitate inconsistent with expected behavior.
• Stability notes: β-lactams can degrade in solution; verify stability by LC–MS/HPLC before critical experiments. Avoid prolonged exposure at room temperature and extremes of pH.

Always defer to the batch-specific CoA and SDS for definitive storage, handling, and reconstitution instructions for Oxacillin-d.

Structure and Identity

Item-specific identifiers provided in Product Data:

• SKU: O1418123
• Product Name: Oxacillin-d
• CAS: O1418123 (catalog reference; CAS not specified)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• 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.

General/literature context (for orientation; not item-specific):

• Oxacillin is a semisynthetic isoxazolyl penicillin bearing a β-lactam (azetidin-2-one) fused to a thiazolidine ring with an acyl side chain containing an isoxazole moiety. The most common research form is the sodium salt.
• Key structural features (oxacillin, literature): β-lactam amide (highly strained, electrophilic), thiazolidine sulfur, carboxylate (often present as sodium salt), and an isoxazole ring that imparts steric hindrance to resist many β-lactamases.
• Stereochemistry (literature): Penam core typically has defined stereocenters at C-5 and C-6 of the thiazolidine/β-lactam framework.

Notes on the “-d” designation:

• The “-d” suffix commonly denotes deuterium labeling in analytical standards; however, the exact labeling pattern, isotopic enrichment, and salt form for this catalog item are not specified. Consult the item’s CoA/Spec Sheet for definitive structural and isotopic details.

Synthetic Utility

Item-specific synthetic roles: Not specified for this item; refer to CoA/Spec Sheet.

General/literature synthetic context for oxacillin-type molecules (not item-specific):

• Functional group reactivity: the β-lactam carbonyl is electrophilic and undergoes nucleophile-induced ring opening to penicilloates; the carboxylate (or acid) enables salt formation or coupling; the isoxazole ring is relatively inert under mild conditions.
• Derivatization: selective protection strategies can be used on the carboxylate to enable side-chain modifications or affinity tagging. C-3 carboxylate activation can allow conjugation to solid supports or reporter groups.
• Isotopic standards: deuterated variants are valuable for mechanistic isotope effect studies and as LC–MS internal standards; precise labeling supports accurate quantitation by correcting for matrix effects and sample loss.
• Retrosynthetic considerations: access typically involves acylation of 6-aminopenicillanic acid (6-APA) with the appropriate isoxazolyl acyl chloride under conditions that preserve the β-lactam.

Handling implications for synthesis:

• Avoid strong base/acid and elevated temperatures that compromise the β-lactam. Utilize low-temperature, anhydrous conditions for acylation or coupling steps.
• Monitor reactions by LC–MS or HPLC to minimize overexposure to conditions that cause ring opening.

Target Specificity

Item-specific target/binding details: Not specified for this item.

General/literature context (not item-specific):

• Oxacillin-class molecules interact with penicillin-binding proteins (PBPs) by acylation of the active-site serine, and are substrates for various β-lactamases. Specific PBP isoform selectivity varies by organism and experimental conditions.

Because this product listing provides no validated target, epitope, or binding parameters, users should consult the primary literature or develop in-house assays to establish specificity in their system of interest.