Fumonisin B3-C , CAS No.2819816-90-3

CAS: 2819816-90-3 Cat. No.: F1449334 Formula: ₁₃C₃₄H₅₉NO₁₄ Peso molecolare: 739.58

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Fumonisin B3 - 13 C 34 is the 13 C labeled Fumonisin B3. Fumonisin B3 is a mycotoxin derived from fusarium fungi, a member of fumonisins.

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

739.58

Application Protocols

No item-specific, validated application protocols are provided in the Product Data for SKU F1449334.

General guidance for preparing analytical standards (literature/best practice)

• Stock preparation: Accurately weigh the material (or use the exact mass from the vial label/CoA). Dissolve to a gravimetrically prepared stock in methanol or 50:50 MeOH:H2O containing 0.1% acetic acid.
• Aliquoting: Split into single-use amber vials to avoid repeated freeze–thaw and adsorption losses.
• Working solutions: Prepare serial dilutions in mobile-phase-like solvent (e.g., water with 10–30% MeOH and 0.1% formic acid). Include an internal standard if quantitative analysis is required.
• System suitability: Verify retention time, peak shape, and expected MRM transitions for FB3 prior to analyzing unknowns.
• Recovery checks: For method validation, perform spike-and-recovery and matrix-matched calibration.

If your application involves biochemical assays, validate compatibility of the solvent system (typically ≤10% MeOH in buffer) with your biomolecules and confirm the stability of fumonisin B3 under assay conditions.

Biological Roles

Literature/general background (for research context; not item-specific and not implying medical/clinical use)

• Origin: Fumonisins are secondary metabolites produced by Fusarium species that can contaminate maize and other cereals.
• Biochemical activity: Fumonisin B-series compounds, including B3, are known inhibitors of ceramide synthase (sphinganine N-acyltransferase) in cells. This disrupts sphingolipid biosynthesis, leading to accumulation of sphinganine and altered sphingolipid profiles.
• Structural determinants: The aminopolyol backbone and tricarballylate esters are important for binding to the acyl-CoA-dependent active site of ceramide synthase. Differences between B1, B2, and B3 (regio/ stereochemical hydroxylation patterns) modulate potency and transport.
• Cellular handling: Highly polar, tends to reside in aqueous compartments; may associate with membranes and proteins via ionic/hydrogen-bonding interactions rather than classical hydrophobic partitioning. Transporters and protein binding can influence disposition in biological systems (organism- and matrix-dependent).
• Research use cases: Employed as a tool compound to perturb sphingolipid metabolism in vitro, to develop and validate analytical assays (LC–MS/MS) for exposure studies, and to study structure–activity relationships among fumonisin homologs.

Important notice

• All work must comply with institutional biosafety and chemical safety practices. This material is for research use only and is not intended for diagnostic, therapeutic, or food/feed uses.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare buffer systems. For analytical use, it may be diluted into existing buffers or mobile phases.

Practical guidance (general)

• For LC–MS/MS working solutions, aqueous mobile phases with 0.05–0.2% formic acid or acetic acid and 2–5 mM ammonium formate are commonly used to support positive-ion ESI and consistent retention.
• For biochemical assays (research), if an aqueous buffer is required to maintain biomolecule integrity, start with PBS or HEPES-buffered saline and add ≤10% methanol to aid solubility; verify no hydrolysis or adsorption losses occur.

Note: No specific buffering capacity or pKa profile for buffer design is provided for this item. Refer to your method SOP and validate recovery and stability of fumonisin B3 under chosen buffer conditions.

Green Alternatives

As an analytical standard, fumonisin B3 itself is not replaceable in methods requiring its measurement. However, the surrounding workflow can incorporate greener practices.

Greener choices in sample prep (general)

• Solvent selection: Prefer water-rich mixtures and methanol over acetonitrile where performance allows. Reduce total solvent volumes by miniaturizing extraction protocols.
• Solid-phase extraction: Employ reusable cartridge manifolds and optimize wash/elution to minimize solvent consumption.
• Energy and waste: Consolidate runs, use lower-temperature storage where stability permits (check CoA/SDS), and segregate halogenated from non-halogenated waste.

Comparison (illustrative, general)

| Aspect | Conventional choice | Greener adjustment | Trade-offs | |---|---|---|---| | Extraction | ACN:water (60:40) | MeOH:water (60:40) | May alter protein precipitation and co-extractives; re-optimize cleanup | | Additives | 0.1% TFA | 0.1% formic or acetic acid | Improved MS compatibility; similar acidity | | Cleanup | Single-use SPE | Optimized SPE to reduce cartridges or adopt 96-well formats | Upfront validation effort |

Notes

• Maintain method performance criteria (recoveries, precision, LOQs) when substituting solvents.
• Always document any change to validated methods and re-verify selectivity for FB3 versus FB2.

Pharmaceutical Uses

No excipient or formulation role is specified for this item. Fumonisin B3 is a mycotoxin standard supplied strictly for research use only; it is not intended for pharmaceutical, diagnostic, therapeutic, or food/feed applications.

Manufacturing/analytical context (general)

• Can serve as an analytical reference standard in quality-control laboratories developing or validating methods to detect fumonisin contaminants in raw materials derived from agricultural sources.
• Employed in instrument qualification (system suitability, calibration verification) for LC–MS/MS platforms analyzing mycotoxins.

Regulatory note

• This product is not accompanied by pharmacopeial monographs (USP/EP/JP) for excipient or API use. Any analytical use in regulated environments should be supported by appropriate reference standard qualification, traceability documentation (CoA), and method validation records.

Physical Properties

Item-specific properties (from Product Data)

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

Literature/typical properties for fumonisin B3 (for reference; not item specifications)

• Physical state: typically isolated as a white to off-white amorphous solid or lyophilizate; frequently handled as methanolic or aqueous-organic solutions for analytics.
• Solubility: highly polar; soluble in water, methanol, acetonitrile–water mixtures; poorly soluble in nonpolar solvents (hexane, toluene). Solubility improves with small amounts of acid (e.g., 0.1% formic/acetic) due to protonation of the amine.
• LogP (estimated, literature): strongly negative to near-zero for the protonated form; overall behaves as a polar amphiphile.
• pKa (literature): primary amine pKa typically ~8–9; multiple carboxylates (as part of TCA esters) affect ionization of hydrolyzed forms; intact diester is less acidic but can bear partial negative charge depending on medium.
• UV absorbance: lacks strong chromophores; weak end-absorbance in the deep UV; LC-MS/MS (ESI) detection preferred.
• Thermal behavior: decomposes on extended heating; drying typically performed under mild vacuum at ≤40 °C.

Practical notes (general)

• Prepare analytical stocks in MeOH or 50:50 MeOH:H2O with 0.1% HOAc to aid dissolution and reduce surface adsorption.
• Avoid basic conditions that can hydrolyze tricarballylate esters.

Quality and Grades

Item-specific quality information

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

Guidance on typical quality attributes for fumonisin analytical standards (general)

• Purity: Analytical/reference standards are commonly supplied at high chemical purity (often ≥95% by HPLC/UPLC). Verify the exact assay method (UV, ELSD, MS, or CAD) and solvent content on the CoA.
• Identity confirmation: Vendors typically confirm by LC–MS/MS (characteristic transitions), HRMS, and 1H/13C NMR when feasible. Optical rotation may be reported for stereochemical consistency.
• Water/solvent content: Lyophilized or amorphous solids may include residual water or counter-ions. Karl Fischer moisture or residual solvent profiles may be provided; if not, assume small amounts can be present.
• Counter-ions/salt form: Fumonisins may be provided as free acids, partial salts, or as solutions in MeOH/H2O. Confirm exact form to compute accurate concentration and prepare calibrants.
• Stabilizers: Generally not required; some lots may be formulated in slightly acidic solvent to minimize adsorption and hydrolysis. If a stabilizer is present, it will be listed on the CoA.

Practical recommendations

• For quantitative work (e.g., LC–MS calibration), verify potency on arrival using the CoA value (e.g., mg of analyte per vial or % purity × net mass). Prepare gravimetric stock solutions to minimize uncertainty.
• Record lot numbers and retain CoAs to ensure traceability.

Reaction and Applications

This product is primarily an analytical/research standard rather than a synthetic reagent. The most relevant applications are in analytical chemistry and exposure/biochemistry studies (research-use only). No medical or clinical uses are implied.

Analytical applications (literature/general)

• LC–MS/MS calibration: Use as a native standard to build external calibration curves for fumonisin B3. Often paired with isotopically labeled internal standards (if available) to correct matrix effects.
• Method validation: Spike-and-recovery, linearity, LOD/LOQ, accuracy, and precision assessments in grains, feeds, and biological matrices.
• QC/Proficiency: Positive controls for proficiency testing and inter-laboratory comparisons.

Sample preparation contexts

• Food/feed matrices: QuEChERS-like extractions with MeOH:water or ACN:water, sometimes with 0.1% FA; cleanup with SPE (e.g., SAX or mixed-mode) for fumonisins.
• Biological matrices (research): protein precipitation (ACN or MeOH), followed by dilution into LC mobile phase and SPE as needed.

Complementary analytes

• Frequently analyzed alongside fumonisins B1 and B2; method selectivity must distinguish isobaric/isomeric species (FB2 vs FB3) via chromatographic separation or MS/MS transitions.

Practical tips

• Use glass vials with low-adsorption inserts; plastics can cause losses.
• Include 0.05–0.2% formic/acetic acid in diluents to reduce adsorption and improve peak shape.
• Verify identity by characteristic MRM transitions and retention time relative to standards.

Note: No synthetic reaction use is typical for this compound.

Reaction Conditions

As an analytical standard, Fumonisin B3-C is not intended for use in chemical synthesis. However, typical conditions for its instrumental analysis (literature/general) are provided for convenience. Optimize for your lab and refer to validated methods.

LC–MS/MS (illustrative, general)

• Column: C18, 2.1 × 100 mm, 1.7–3 µm or equivalent.
• Mobile phase A: water + 0.1% formic acid (± 2–5 mM ammonium formate).
• Mobile phase B: methanol or acetonitrile + 0.1% formic acid.
• Gradient: start 10–20% B, ramp to 90–100% B over 6–12 min; re-equilibrate.
• Flow: 0.2–0.4 mL/min; temp 30–40 °C.
• Detection: ESI+, MRM transitions specific to FB3; optimize declustering and collision energies per instrument.

Stability during analysis (general)

• Keep autosampler at 4–10 °C. Use amber vials to limit photolysis.
• Include 0.05–0.2% FA or HOAc in diluents to reduce adsorption; glass inserts minimize losses.

Hydrolysis (if preparing hydrolyzed fumonisin for method development)

• Mild alkaline hydrolysis (e.g., 2 M KOH, 60–70 °C, minutes) can cleave TCA esters, forming HFB analogs. Carefully quench and neutralize; confirm identity by MS. Note: Do not apply to the catalog material unless your protocol calls for this transformation and you have appropriate approvals.

Note: No item-specific reaction parameters are provided in the Product Data.

Safety and Handling

Authoritative safety information must be taken from the product SDS. The following are general considerations for fumonisin mycotoxin standards and do not replace the SDS.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.

General hazard profile (literature/general for fumonisins)

• Fumonisins are mycotoxins produced by Fusarium species. Handle as acutely toxic research chemicals; avoid inhalation, ingestion, and skin contact.
• Potential hazards include organ toxicity upon exposure; they disrupt sphingolipid metabolism in cells (research context). No medical use; for research only.

Laboratory controls

• Work in a certified chemical fume hood or containment enclosure when weighing or making stock solutions to control aerosols/particles.
• PPE: lab coat, nitrile gloves (double-gloving recommended for neat solid), splash goggles; change gloves frequently when handling concentrated solutions.
• Use dedicated, labeled glassware and avoid mouth pipetting. Decontaminate surfaces with appropriate solvent (e.g., 70% MeOH or MeOH:H2O with small % acid), followed by detergent and water.

Incompatibilities and stability (general)

• Strong bases and prolonged high pH can promote ester hydrolysis. Strong oxidants may degrade the molecule.
• Protect from light and heat; avoid repeated freeze–thaw.

First-aid overview (consult SDS for details)

• Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention.
• Inhalation: move to fresh air; seek medical attention.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention immediately.

Waste disposal

• Collect residues and contaminated disposables as hazardous chemical waste per institutional and regulatory requirements.

Solvent Selection

Context: Fumonisin B3 is a highly polar, amphiphilic mycotoxin standard. Solvent choice affects dissolution, stability, adsorption losses, and LC–MS performance.

• Polarity/miscibility (literature/general)

  • Polar protic and mixed aqueous-organic solvents are preferred: methanol (MeOH), water, and MeOH:H2O mixtures.
  • Also soluble in acetonitrile:water; addition of 0.05–0.2% formic or acetic acid improves peak shape and reduces adsorption.
  • Poorly soluble in nonpolar solvents (hexane, toluene, CPME). Avoid neat ACN for initial dissolution if adsorption is observed; a small fraction of water often helps.

• Recommended use scenarios

  • Stock solutions: 0.5–2 mg/mL in MeOH or 50:50 MeOH:H2O with 0.1% HOAc; store cold and protected from light.
  • Working standards for LC–MS/MS: dilute into mobile phase-like matrices (e.g., 10–30% organic in water with 0.1% FA) to match sample composition and reduce matrix effects.
  • Immunoassay prep (if applicable in your lab): aqueous buffers with small % MeOH (≤10%) can aid solubility without denaturing proteins.

• Comparison (general)

  • MeOH vs ACN: MeOH often yields better dissolution for fumonisins; ACN provides stronger protein precipitation in sample prep but may exacerbate adsorption to plastics. Blends mitigate issues.
  • Additives: 0.1% formic acid improves ESI+ response and suppresses tailing; ammonium formate (2–5 mM) can stabilize retention in LC.

Note: These are general best practices; optimize for your instrument and method.

Storage and Reconstitution

Item-specific storage and shipping

• Storage Conditions: Store at -20°C (per Product Data).
• Shipped In: Ice chest + Ice pads.

General guidance (complementary to item-specific instructions; verify with CoA/SDS)

• Protection: Store in amber, tightly sealed containers to protect from light and moisture. Use desiccant if storing as a solid.
• Temperature: -20 °C is suitable for long-term storage. For frequent access, maintain a working aliquot at 2–8 °C for up to several days to minimize freeze–thaw.
• Reconstitution solvent: For initial dissolution, use methanol or 50:50 MeOH:H2O with 0.1% acetic or formic acid to enhance solubility and reduce adsorption to surfaces.
• Aliquoting: Prepare single-use aliquots immediately after first opening to avoid concentration drift from adsorption or evaporation.
• Stability (general): Avoid strong bases or prolonged exposure to high pH, which can hydrolyze tricarballylate esters. Minimize exposure to elevated temperatures during drying or solvent removal (≤40 °C under vacuum if needed).
• Freeze–thaw: Avoid repeated cycles; if unavoidable, assess by LC–MS for degradation or loss.

Labeling and documentation

• Record lot number, preparation date, concentration, solvent, and storage conditions on each aliquot. Retain CoA for potency calculations.

Note: If the product is supplied as a solution (check label/CoA), store as instructed and adjust aliquoting accordingly.

Structure and Identity

Brief overview: Fumonisin B3-C is supplied for research use as a life-science standard related to the fumonisin B-series mycotoxins. Item-specific identifiers for this SKU are limited in the Product Data; consult the CoA/SDS for definitive structural identifiers.

• Item-specific identifiers (from Product Data)

  • CAS: 2819816-90-3
  • 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.

• Literature/general identity (fumonisin B3, for reference only; not item-specific)

  • Fumonisin family: aminopolyol mycotoxins bearing two tricarballylic acid (TCA) ester side chains.
  • Typical formula (literature, FB3): ~C34H59NO14
  • Typical molecular weight (literature, FB3): ~705.8 g/mol
  • Core features: a long-chain 2-aminopentol backbone with multiple secondary hydroxyl groups; two TCA esters; one primary amine (often protonated near neutral pH); no aromatic rings; multiple stereocenters (isomeric configuration depends on producing strain and purification history).

• 2D structural description (literature, qualitative)

  • Linear aliphatic chain (~20–22 carbons equivalent when counting substituents) decorated by hydroxyls at several positions.
  • A single primary amino group on the polyol backbone (giving cationic character at physiological pH) and two distal tricarballylate diesters (imparting polyanionic character when hydrolyzed or deprotonated).

Note: “-C” in the name often denotes a catalog/lot or certification descriptor; confirm exact meaning on the CoA for SKU F1449334.

Synthetic Utility

This product is not typically used as a synthetic building block or reagent. Its complex, highly functionalized structure (aminopolyol with multiple stereocenters and tricarballylate esters) limits routine use in preparative organic synthesis.

Research-relevant considerations (general)

• Derivatization for analytics: Pre-column derivatization (e.g., with o-phthalaldehyde for fluorescence) has been explored historically for fumonisins, though LC–MS/MS is now preferred. Such derivatizations are analytical rather than synthetic transformations.
• Hydrolysis products: Base- or acid-mediated hydrolysis yields partially or fully de-esterified fumonisin derivatives (e.g., hydrolyzed fumonisin B, HFB). These can be used as reference materials for method development but require careful control to avoid degradation artifacts.
• Isotopic labeling: Researchers may use isotopically labeled internal standards for quantitative LC–MS/MS; if using unlabeled FB3, pair with an appropriate labeled analog for best quantitation.

Bottom line: View Fumonisin B3-C as an analyte standard. If your work entails chemical modification, treat any transformed products as distinct analytes and re-validate methods accordingly.

Target Specificity

Not applicable. This product is a small-molecule mycotoxin standard and is not an antibody, enzyme, nucleic acid, or affinity reagent with defined biological target specificity in the immunoassay sense.

For analytical workflows, “specificity” refers to chromatographic and mass-spectrometric selectivity distinguishing fumonisin B3 from related homologs (e.g., B2) and matrix interferences. Achieve this via adequate chromatographic resolution and compound-specific MS/MS transitions.