Diacetoxyscirpenol - Moligand™, 10 mM in DMSO , CAS No.2270-40-8

CAS: 2270-40-8 Cat. No.: D1499981 Formula: C₁₉H₂₆O₇ Peso molecolare: 366.41 Numero EC: 218-873-3

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Diacetoxyscirpenol (DAS) is a trichothecene mycotoxin, a secondary metabolite product of fungi. Diacetoxyscirpenol (DAS) consumption induces haematological disorders (neutropenia, aplastic anemia) in human and animals.

Specifications

Specifiche e purezza

Moligand™, 10 mM in DMSO

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Moligand™

Nomi e identificatori

• Isomeri SMILES: CC1=C[C@@H]2[C@](CC1)([C@]3([C@@H]([C@H]([C@H]([C@@]34CO4)O2)O)OC(=O)C)C)COC(=O)C
• WGK Germania: 2
• Peso molecolare: 366.41
• Reaxy-Rn: 38538014
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38538014&ln=

Proprietà chimiche e fisiche

• Punto di infiammabilità (°F): 5°C
• Punto di infiammabilità (°C): 5°C
• Punto di fusione (°C): 160°C- 164°C

Riferimenti

1. Mingming Chen, Bihang Su, Huiying Wu, Yawen Dai, Tianwen Chen, Fengfu Fu, Zhenyu Lin, Yongqiang Dong.  (2023)  Hydrogel SERS chip with strong localized surface plasmon resonance for sensitive and rapid detection of T-2 toxin.  TALANTA,      [PMID:37879204] [10.1016/j.talanta.2023.125329]

2. Jiana Lin, Gongke Li, Yuling Hu, Qisheng Zhong.  (2024)  Host-guest mediated recognition and rapid extraction of Fusarium mycotoxins in cereals by nickel ferrite magnetic calix[4]arene-derived covalent organic framework fabricated in room-temperature.  FOOD CHEMISTRY,      [PMID:39522376] [10.1016/j.foodchem.2024.141887]

Application Protocols

No item-specific, tested application protocols are provided in the Product Data for this Moligand™ small molecule. Refer to your institutional SOPs and assay-specific literature.

General guidance (literature/practice; not item specifications)

• Stock preparation: Dissolve in anhydrous DMSO to 10 mM (or concentration suitable for your assay). Vortex and, if needed, briefly sonicate. Filter through 0.22 µm PTFE for sterile applications.
• Cell-based assays: Dilute into pre-warmed media to desired final concentration, keeping final DMSO ≤0.1–0.5% v/v. Include vehicle controls and a dilution series (e.g., half-log steps) to map potency and cytotoxicity.
• Analytical standards: Prepare gravimetric stocks; use Class A glassware. For LC–MS/MS, store working solutions at ≤4 °C for short term and at −20 to −80 °C for long term; verify stability and recovery over time.
• Decontamination: Wipe down tools/surfaces with appropriate solvent (e.g., ethanol) followed by detergent; dispose of wipes as hazardous waste.

Biological Roles

Literature/general overview (no clinical/medical claims)

• Diacetoxyscirpenol (DAS) is a type A trichothecene mycotoxin produced by certain Fusarium and related fungal species. It is a potent inhibitor of eukaryotic protein synthesis by binding within the peptidyl transferase center of the 60S ribosomal subunit, interfering with peptide bond formation.

• Cellular responses and pathways

  • Rapid inhibition of translation leads to activation of integrated stress responses, including eIF2α phosphorylation, altered transcriptional programs, and apoptosis pathways in sensitive cell types.
  • Induces ribotoxic stress signaling involving MAPK cascades (e.g., JNK, p38) as reported for trichothecenes.
  • The epoxide moiety is critical for activity in many trichothecenes; hydrolysis or modification often reduces potency, a common SAR observation.

• Experimental uses in biochemistry/cell biology

  • Tool compound to modulate global translation for studying protein turnover, stress granule dynamics, and quality control pathways (e.g., ubiquitin–proteasome responses).
  • Reference analyte in metabolism studies of trichothecenes (esterase-mediated deacetylation pathways; conjugation reactions) using microsomes or cell lysates.

• Selectivity considerations

  • Primary target is the eukaryotic ribosome; prokaryotic ribosomes are generally less sensitive to trichothecenes. Off-target effects may arise at high concentrations due to membrane perturbation or reactive functional groups—careful dose–response design and orthogonal controls are recommended.

Buffer Applications

Not typically applicable. Diacetoxyscirpenol is not a buffering agent and is not used to prepare pH buffer systems. For experimental work requiring buffers (e.g., cell culture media, assay buffers), prepare standard buffers separately and add DAS as a diluted stock (commonly from DMSO or ethanol) while controlling final cosolvent content and pH.

Green Alternatives

This section is generally aimed at solvent/process reagents. Diacetoxyscirpenol is a specialized bioactive small molecule (mycotoxin) and does not have a “green substitute” in the conventional sense.

• Context (general)

  • If your objective is to study translation inhibition or ribotoxic stress with a lower-hazard tool, consider alternative mechanistic probes that fit your biosafety and waste profile (e.g., cycloheximide for translation elongation inhibition), acknowledging differences in target site and hazard classification. Such substitutions change biological mechanism and are not strictly interchangeable.

• Greener handling practices

  • Use minimal quantities and micro-scale assays to reduce toxin usage and waste.
  • Choose lower-toxicity solvents (e.g., ethanol, ACN/water) where analytically feasible instead of chlorinated solvents.
  • Implement closed-vial autosampler workflows and pre-aliquoted single-use stocks to minimize exposure and waste generation.

Trade-offs

• Substituting the compound alters biological readouts; validate equivalence carefully. From a green chemistry standpoint, focus on exposure minimization, solvent selection, and efficient experimental design rather than replacement of the analyte itself.

Pharmaceutical Uses

No therapeutic or clinical use is stated or implied for this item. For research use only.

Formulation/analytical roles (literature/general)

• Reference standard: Employed as a calibration/quality-control standard in analytical method development for trichothecene monitoring (e.g., LC–MS/MS assays in research laboratories studying mycotoxins in agricultural matrices).
• Preformulation studies: Researchers may evaluate solubility, stability, and protein binding characteristics in various vehicles to understand exposure and matrix effects in in vitro models.

Regulatory/compendial status

• Pharmacopeial monographs: None known specific to DAS; use is confined to research settings. Always consult institutional and local regulations regarding procurement, storage, and disposal of potent toxins.

Formulation cautions (general)

• Avoid alkaline aqueous vehicles that can hydrolyze acetate esters or open the epoxide ring.
• Adsorptive losses to plastics can occur at low concentrations; prefer low-bind polypropylene or glass vials and include carrier protein or inert surfactant only if validated for your assay.

Physical Properties

Item-specific values

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

Measured/specification values for this item

• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Water/peroxide/metal/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for diacetoxyscirpenol (for context; not item specifications)

• Physical state: typically obtained as a white to off-white solid in purified form (literature reports for DAS standards).
• Solubility: sparingly soluble in water; soluble in polar aprotic and protic organic solvents (DMSO, methanol, ethanol, acetone, ethyl acetate, chloroform) per literature on trichothecenes/DAS; recommended to prepare concentrated DMSO stocks for bioassays.
• Partitioning: trichothecenes are moderately lipophilic due to multiple oxygenated functions and acetate esters; exact logP for DAS varies among sources—consult primary references if a precise value is required.
• Thermal/light stability: trichothecenes can degrade upon prolonged exposure to strong UV, heat, or alkaline conditions; epoxide and ester moieties are susceptible to nucleophilic/alkaline hydrolysis (literature).

Notes

• Use the item’s Certificate of Analysis for any definitive numeric properties (mp, purity, elemental composition). If you require quantitative solubility or logP for method validation, verify with your own pre-study characterization or vendor CoA.

Quality and Grades

Item-specific grade

• Grade/Purity: Moligand™ (as listed in Product Data).

What Moligand™ implies (general explanation)

• Moligand-grade materials are intended for discovery screening and chemical biology applications where target engagement, SAR exploration, and library compatibility are prioritized. Such materials are typically provided with identity confirmation (e.g., NMR/LC–MS) suitable for research use, but not certified for clinical, diagnostic, or GMP manufacturing.

How to use this grade effectively

• Suitable for primary/secondary screening, mechanistic enzymology, cell-based assays (with appropriate containment and toxin handling), and as a reference standard in analytical methods.
• If your application requires ultra-trace impurity control (e.g., quantitative toxicology, regulatory submissions), request and review the CoA/Spec Sheet and consider additional in-house QC (chiral purity if relevant, water content by KF, residual solvents, endotoxin for sensitive bioassays).

Stabilizers/other additives

• Stabilizers or additives: Not specified for this item; refer to CoA/Spec Sheet.

Documentation and traceability

• Always match lot-specific CoA to your study records. Verify identity by LC–MS and retention time against a reference when building screening collections or analytical methods.

Reaction and Applications

This product is primarily used as a bioactive reference small molecule rather than as a synthetic reagent. Nevertheless, several research application domains are common:

• Biological/chemical biology applications (literature/general)

  • Probe of eukaryotic translation: DAS binds the ribosomal peptidyl transferase center, inhibiting protein synthesis; used to dissect stress responses, translation control, and cytotoxic pathways in model systems.
  • Positive control/toxin standard in mycotoxin method development for LC–MS/MS (food/feed safety research) and in vitro toxicology.
  • Structure–activity relationship (SAR) studies across trichothecenes; DAS often serves as a scaffold for semi-synthetic modifications (e.g., deacetylation, etherification) to interrogate epoxide/ester roles.

• Derivatization chemistry (literature/general)

  • Selective hydrolysis of acetate esters affords corresponding diols for further functionalization (e.g., carbonate/ether formation); care is required to preserve the sensitive epoxide.
  • Mild acylations can regenerate acetate or introduce isotopically labeled acyl groups for tracer studies.

• Practical tips

  • Handle under low moisture/basicity when intact acetate pattern is required; epoxide opening can occur with strong nucleophiles or bases.
  • For analytical applications, include antioxidant-free, neutral pH diluents; minimize dwell time at elevated temperatures in autosamplers.

Note: If you seek a general reagent for coupling or catalysis, this compound is not typically used as such. Consider appropriate building blocks or catalysts instead.

Reaction Conditions

Not typically applicable as a reagent. However, for researchers performing derivatization or analytical handling of diacetoxyscirpenol, the following literature-based guidance may be useful (general, not item specifications):

• Hydrolysis/deprotection

  • Mild basic conditions (e.g., Na2CO3 or NH3 in methanol, 0–5 °C) can effect partial deacetylation; stronger base increases risk of epoxide opening and decomposition.
  • Acidic methanol can lead to transesterification; control acidity and temperature to limit side reactions.

• Epoxide sensitivity

  • Nucleophilic ring opening is promoted by strong bases/nucleophiles and elevated temperature; to preserve the epoxide, perform reactions at low temperature, neutral to slightly acidic conditions, and minimal reaction times.

• Analytical stability

  • In LC–MS, acidic mobile phases (e.g., 0.1% formic acid) at ambient autosampler temperatures improve peak shape and stability; avoid prolonged residence at >25 °C.

• Typical solvents

  • DMSO, MeOH, EtOH, ACN, and EtOAc are commonly used. Minimize water content for transformations intended to retain acetates.

Always confirm conditions on micro-scale first and monitor by LC–MS/NMR. If you need robust yields or specific selectivity, consult primary literature on trichothecene semi-synthesis.

Safety and Handling

Item-specific hazard information

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

General safety profile (literature/general)

• Diacetoxyscirpenol (DAS) is a trichothecene mycotoxin and a potent inhibitor of eukaryotic protein synthesis via the ribosomal peptidyl transferase center. It is highly bioactive and should be treated as acutely toxic. Avoid any exposure by ingestion, inhalation, or skin contact.

Recommended PPE and engineering controls

• Work in a chemical fume hood or certified biosafety cabinet when weighing or preparing solutions to prevent aerosol exposure.
• Wear lab coat, double nitrile gloves, and eye protection (safety glasses or face shield when handling powders/stock solutions). Change outer gloves frequently.
• Use closed-cap microtubes and wipe down work surfaces with suitable decontaminants after use.

Handling and incompatibilities (general)

• Avoid strong bases and nucleophiles that may hydrolyze acetate esters/epoxide; avoid strong acids that may cause degradation.
• Prevent aerosolization and dust formation; use antistatic measures when handling dry solid.
• Segregate from food-contact areas; dedicated tools/containers recommended for toxin handling.

First aid (overview; defer to SDS)

• Skin/eye contact: Immediately flush with water for ≥15 min; remove contaminated clothing.
• Inhalation: Move to fresh air; seek medical attention.
• Ingestion: Rinse mouth; do not induce vomiting; seek urgent medical attention.

Waste

• Collect contaminated disposables as hazardous chemical waste; incineration via licensed contractor is recommended. Consult institutional EHS for local regulations.

Solvent Selection

Context: Diacetoxyscirpenol is a non-volatile, polyoxygenated small molecule (trichothecene). Solvent choice primarily concerns preparing concentrated stock solutions for bioassays or analytical standards.

• Polarity/miscibility profile (literature/general)

  • Readily soluble in DMSO; good solubility in methanol and ethanol; soluble in acetone, acetonitrile, ethyl acetate, and chlorinated solvents (e.g., chloroform). Poorly soluble in water and nonpolar alkanes.
  • For aqueous systems, prepare DMSO or ethanol stocks and dilute into buffered media, keeping final organic cosolvent typically ≤0.1–0.5% v/v for cell-based assays (optimize per assay tolerance).

• Practical recommendations

  • Preferred stock solvent: DMSO (anhydrous) at 5–50 mM, aliquoted to minimize freeze–thaw.
  • For LC–MS quantitation, ACN:water with 0.1% formic acid often provides robust chromatography; avoid strong base in mobile phases to minimize epoxide/ester hydrolysis.
  • Avoid prolonged exposure to strong alkaline buffers or high-temperature aqueous media which can cause degradation.

• Comparison to alternatives

  • If DMSO is incompatible with your assay, methanol stocks can be used with rapid dilution; however, methanol may be less tolerated by some cells and can extract plastics—validate matrix effects.
  • Cyclodextrin complexation or serum albumin carriers may increase apparent aqueous solubility for biological assays (literature approaches), but can alter free concentration; quantify unbound fraction as needed.

Storage and Reconstitution

Item-specific instructions (from Product Data)

• Storage Conditions: Store at −80 °C.
• Shipped In: Dry ice packs + Cold packs.

Additional handling guidance (general best practice; not item specifications)

• Light/moisture protection: Store in amber, tightly sealed vials under dry, inert atmosphere if possible. Allow vials to equilibrate to room temperature while sealed to avoid condensation before opening.
• Aliquoting: Upon first receipt, subdivide into single-use aliquots to minimize freeze–thaw cycles and headspace exposure.

Reconstitution (general)

• Solvents: DMSO is recommended for primary stock solutions; methanol or ethanol are alternatives. Target 5–50 mM stocks depending on assay needs and solubility.
• Dilution: For aqueous use, dilute stocks into buffer/media with vigorous mixing; maintain final organic cosolvent at the lowest level compatible with your system.

Stability notes (literature/general)

• Avoid prolonged exposure to elevated temperatures or alkaline pH, which can hydrolyze acetate esters and compromise the epoxide.
• For long-term storage of solutions, keep at −80 °C in sealed, low-bind containers. Periodically verify integrity by LC–MS or HPLC.

Documentation

• Record lot number, preparation date, solvent, and concentration on each aliquot. Consult the CoA and SDS for definitive guidance and any lot-specific precautions.

Research Use

• For research use only. Not for human or animal therapeutic or diagnostic use.

Structure and Identity

Brief description: Diacetoxyscirpenol (often abbreviated DAS; also known in literature as anguidine) is a sesquiterpenoid trichothecene mycotoxin featuring the characteristic 12,13‑epoxytrichothec-9-ene core with two acetate ester substituents.

• Item-specific identifiers (from Product Data)

  • SKU: D1499981
  • CAS: 2270-40-8
  • Category: Small molecules and compound library (Moligand)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Composition

  • 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 (literature/general)

  • Core scaffold: tricyclic 12,13‑epoxytrichothec-9-ene sesquiterpene.
  • Functional groups: an epoxide bridge (12,13‑epoxy), an exocyclic double bond (C9–C10), multiple secondary/tertiary alcohol stereocenters in the trichothecane ring system, and two acetate esters (diacetate, commonly at C-3 and C-4 positions in reported structures).
  • Stereochemistry: multiple defined chiral centers inherent to the trichothecene framework (exact absolute configuration as reported in the literature for DAS; consult primary references/CoA for definitive stereochemical notation for this item).

• 2D structure in words (literature/general)

  • A fused polycyclic hydrocarbon backbone bearing a constrained epoxide across one ring junction, with pendant acetate groups replacing two hydroxyls. The molecule is compact, highly functionalized, and rigid, consistent with ribosomal-binding trichothecenes.

Synthetic Utility

Diacetoxyscirpenol is a complex, highly functionalized natural product and is not generally deployed as a general-purpose synthetic reagent. However, from a synthetic chemistry perspective, it offers a platform for semi-synthesis and SAR development (literature/general):

• Functional group handles

  • Two acetate esters amenable to selective or global deprotection, enabling access to diols for further derivatization (carbonate, carbamate, ether formation) while preserving the trichothecane core.
  • An epoxide that can undergo regioselective ring opening under carefully controlled, mild conditions—though retaining the epoxide is often desired for biological potency.
  • Allylic positions adjacent to the exocyclic double bond that can be targets for mild oxidation or conjugate additions under constrained conditions.

• Semi-synthetic modifications

  • Preparation of labeled analogs (e.g., 13C/2H-acetyl groups) for metabolic tracing and quantitative MS.
  • Prodrug approaches: transient masking of hydroxyls with more hydrolytically robust groups to modulate stability for specific in vitro paradigms (recognizing altered activity).

• Retrosynthetic value

  • The molecule serves as a benchmark for methods capable of stereocontrolled polyoxygenated sesquiterpene construction. Total syntheses reported in the literature inform strategies for late-stage oxidation and protective group choreography relevant to other trichothecenes.

Note: If you require a building block for general coupling chemistry, consider simpler alcohols/epoxides/esters rather than this specialized scaffold.

Target Specificity

Not applicable to this product category. Target specificity metadata (antigen, clone, isotype, species reactivity) is provided for antibodies or affinity reagents. This listing is a small-molecule standard; no antibody target information is available in the Product Data.