Eprinomectin - ≥91% , CAS No.123997-26-2

CAS: 123997-26-2 Cat. No.: E131865 Fórmula: B1a：C₅₀H₇₅NO₁₄（R=C₂H₅ ） B1b：C₄₉H₇₃NO₁₄（ R=CH₃ ） Peso molecular: B1a：914.14 ;B1b：900.11 Número CE: 602-966-4 PubChem CID: 254759630

GRADE & PURITY ≥91%

Synonyms

Eprinex | (4′’R)-4″-(Acetylamino)-4″-deoxy-avermectin B1

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Visão geral

Eprinomectin is a mixture of Eprinomectin B1a and B1b that is commonly used as a topical anthelmintic.
A mixture of Eprinomectin B1a and B1b showing anti-anthelintic activity

Specifications

Sinónimos

Eprinex | (4′’R)-4″-(Acetylamino)-4″-deoxy-avermectin B1

Especificações e pureza

≥91%

Condições de armazenamento de armazenamento

Store at -20°C,Argon charged

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Pureza

≥91%

Nomes e identificadores

• Pubchem Sid: 504773779
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773779
• PubChem CID: 254759630
• Peso molecular: B1a：914.14 ;B1b：900.11

Propriedades químicas e físicas

• Solubilidade: Soluble in methanol.
• Ponto de fusão (°C): 163.3-165.7° C

Referências

1. Jiawen Ji, Siyue Zhu, Xinping Hu, Jianhui Zhu, Sen Pang, Yongqiang Ma, Xuefeng Li.  (2025)  Enhanced residual risk of abamectin induced by 6PPD: in water, soil, and vegetables.  Environmental Science-Processes & Impacts,      [PMID:40099488] [10.1039/D5EM00053J]

Application Protocols

Only item-specific, tested application protocols (e.g., WB, IHC, IF, FC for antibodies) may be listed here; none were provided in the Product Data for SKU E131865.

General handling protocol (non-validated suggestion; verify in your lab)

• Stock preparation: Dissolve the compound in anhydrous DMSO under inert gas to a convenient concentration that remains fully soluble. Vortex and, if necessary, sonicate briefly. Filter sterilize (0.2 µm PTFE) for cell-free assays.
• Working solutions: Dilute the DMSO stock into assay medium/buffer with vigorous mixing to avoid precipitation; keep final DMSO low (≤0.5–1%). Prepare fresh just before use or validate short-term stability by LC.
• Storage of stocks: Aliquot and store at −20 °C under inert gas and desiccation. Avoid repeated freeze–thaw.

These are generic best practices, not validated protocols for this specific product.

Biological Roles

General literature context (non-clinical; no therapeutic claims)

• Target class: Macrocyclic lactone that modulates invertebrate ligand-gated chloride channels—principally glutamate-gated Cl− channels—leading to hyperpolarization in susceptible organisms. It may also interact with other Cys-loop receptors in invertebrates at higher concentrations.
• Mechanistic notes: Binding enhances chloride conductance, stabilizing the open channel state. Structure–activity relationships implicate the disaccharide and macrocyclic diene region in receptor interactions; N-acylamino substitution in eprinomectin influences lipophilicity and bioavailability traits compared with parent avermectins.
• ADME considerations in research models: Highly lipophilic, with strong plasma/serum protein binding in many systems; tends to accumulate in lipid-rich matrices. Poor intrinsic aqueous solubility necessitates formulation with organic cosolvents or carriers for in vitro assays.
• Biodegradation and ecotoxicology (qualitative): Avermectin-like compounds can show persistence and high toxicity to aquatic invertebrates; handle and dispose with environmental stewardship.

Use in the lab

• Acts as a positive control/ligand in invertebrate neurobiology assays (e.g., electrophysiology on glutamate-gated Cl− channels) and as an analytical reference in chromatographic method development.

All roles above are literature/general background and are not specifications or endorsed uses for this specific item.

Buffer Applications

This compound is a neutral, highly lipophilic macrocyclic lactone and is not used as a buffering agent. It has no defined acid/base buffering range applicable to aqueous systems.

Practical guidance

• For aqueous assays, prepare a concentrated stock in DMSO or another suitable organic solvent and dilute into the target buffer (e.g., PBS, HBSS) to a low final organic percentage, ensuring the compound remains in solution (use surfactants or carriers if necessary).
• Filter solutions if precipitation occurs; consider cyclodextrin complexation to enhance apparent solubility when strictly aqueous vehicles are required.

Green Alternatives

Greener handling focuses on solvent and process choices, as the active itself is a complex macrocycle not readily replaced.

Greener solvent choices (general guidance)

• Replace dichloromethane with EtOAc or 2-MeTHF where solubility allows.
• Prefer ethanol or isopropanol over acetonitrile/methanol for preparative work if the compound remains soluble and stable.
• For extractions/purifications, cyclopentyl methyl ether (CPME) or 2-MeTHF can reduce environmental burden versus chlorinated solvents.

Illustrative comparison (general; not item-specific specs)

• Dichloromethane: Excellent solubility, but high environmental/health concerns.
• Ethyl acetate: Biodegradable, lower toxicity; may require larger volumes due to solubility limits.
• 2-MeTHF/CPME: Good solvency for lipophilic macrocycles; water immiscible; lower peroxide formation than ethers like THF; derived partly from renewable feedstocks (2-MeTHF).

Operational tips

• Evaluate mixed-solvent systems (EtOAc with small DMSO/MeOH co-solvent) to balance solubility and greenness.
• Minimize DMSO volumes for downstream waste reduction; consider high-concentration stocks followed by microdosing into aqueous media.
• Implement light protection and inert handling to extend solution shelf life, reducing the need for repeated preparations and waste generation.

Pharmaceutical Uses

No clinical or therapeutic claims are made. For research and laboratory use only (Product Data: Research Use Note).

Non-clinical/formulation-related contexts (literature/general)

• Reference standard: Employed as a calibration/quantitation standard in LC–MS/LC–UV methods for macrocyclic lactones in matrices relevant to residue and stability studies.
• Preformulation research: Used to explore solubilization strategies for highly lipophilic macrocycles (e.g., cyclodextrin inclusion, lipid-based carriers) and to evaluate stability under stress conditions (light, oxygen, heat).
• Impurity profiling: Acts as a comparator for process- or degradation-related impurities within the avermectin class.

Regulatory/compendial status

• Pharmacopeial monographs and specific pharmacopeial quality criteria are not provided here. Any such status, if applicable, should be confirmed from primary pharmacopeial sources and the product CoA/Spec Sheet.

Note: All information above is for laboratory research, analytical development, or process understanding only and does not imply suitability for human or veterinary therapeutic use.

Physical Properties

Item-specific physical specifications

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

Literature/General properties (typical for eprinomectin and related avermectins; not item specifications)

• Physical state: Typically an off-white to pale solid at ambient conditions.
• Solubility profile: Practically insoluble in water; soluble in polar aprotic and moderately polar organic solvents (DMSO, DMF), and in many organic solvents such as acetone, ethyl acetate, dichloromethane, and to varying degrees in ethanol/methanol. A stock in anhydrous DMSO is commonly used for bioassays and analytics.
• Lipophilicity: Highly lipophilic macrocyclic lactone; logP is high for avermectins, consistent with poor aqueous solubility (qualitative literature expectation).
• UV/Vis: Avermectin chromophores display UV absorbance in the 240–250 nm region due to conjugated diene; additional bands may appear at shorter wavelengths (literature, qualitative).
• Thermal behavior: Macrocyclic lactones may soften before melting and can decompose with extended heating; avoid unnecessary thermal stress.

Practical notes

• Because of the high oxygen content, hygroscopic uptake of moisture in amorphous material can occur; handle quickly in dry atmosphere.
• Prepare concentrated stock solutions using dry, oxygen-free solvent; filter if particulate is present.

For exact numerical values (mp, bp, density, refractive index, pKa/logP, UV cutoff) for this specific lot, refer to the product CoA/Spec Sheet or SDS.

Quality and Grades

Item-specific grade/purity

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

What the grade typically signifies (general guidance)

• Research/analytical grade: Intended for laboratory research use, impurity limits tailored for chemical/biological assay reliability rather than clinical use.
• Reference standard suitability: When offered at high assay purity with tight residual solvent/impurity profiles, eprinomectin can serve as a reference material for analytical methods (e.g., LC–UV/LC–MS) in stability and residue studies. Verify with the CoA.

Quality considerations specific to this class

• Isomeric composition: Avermectin-derived materials can be mixtures of B1a/B1b components. The relative ratio and any minor congeners should be characterized by HPLC/LC–MS where relevant to your application.
• Photostability: Macrocyclic lactones can be light sensitive; packaging under inert gas (Product Data: argon charged) mitigates oxidative/photo-degradation.
• Residual solvents/water/peroxides/metals/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Recommended verifications (best practice)

• Identity: Confirm by HRMS and 1H/13C NMR (characteristic sugar and macrocycle resonances), and by HPLC purity profiling.
• Potency/stability in solution: Verify by time-course LC at intended storage temperature/solvent to establish your in-house retest period.

Reaction and Applications

Manufacturer Applications (verbatim)

• Not provided in the Product Data.

Research applications (literature/general; not item-specific claims)

• Analytical standard: Used as a system suitability/reference material in LC–UV/LC–MS methods for macrocyclic lactones and residue/stability studies.
• Chemical biology tool: Serves as a potent modulator of ligand-gated chloride channels in invertebrates (glutamate-gated Cl− channels), enabling mechanistic studies of ion channel pharmacology and neurobiology in non-clinical models.

Chemical reactivity and derivatization (general for avermectins)

• Selective acylation/alkylation: Hydroxyl groups on the sugars and macrocycle can be differentially protected and derivatized (e.g., carbonate/ester formation) to fine-tune lipophilicity and receptor interactions.
• Glycosidic chemistry: Modifications at the 4″-position on the sugar (where eprinomectin bears an amino-acyl substituent) are common for SAR exploration.
• Oxidation sensitivity: Conjugated diene can undergo addition/oxidation; reactions are typically run under inert atmosphere at low temperature.

Practical notes

• Conduct reactions in dry, oxygen-free solvents (e.g., CH2Cl2, THF, DMF) under argon/nitrogen. Protect from light to minimize side reactions.
• Purification by flash chromatography may require gradient elution with EtOAc/hexanes or MeOH/CH2Cl2, sometimes with 0.1% TEA to suppress tailing.

Reaction Conditions

General conditions for common manipulations on avermectin-type macrocycles (literature guidance; not specifications for this item)

• Esterification/acylation of hydroxyls:
  • Typical reagents: Acid anhydrides or acyl chlorides with stoichiometric base (pyridine, DMAP catalysts) in CH2Cl2, THF, or DMF.
  • Temperature: 0–25 °C; monitor carefully to avoid over-acylation.
  • Workup: Quench with aqueous bicarbonate; purify by silica gel using EtOAc/hexanes/MeOH gradients (add 0.1% TEA if tailing).
• Carbamate formation (for tagging):
  • Reagents: Chloroformates or CDI-activated carbonates in dry CH2Cl2/THF; catalytic DMAP.
  • Temperature: 0–23 °C; inert atmosphere, protect from light.
• Amide editing at the N-acylamino site:
  • Couplings: HATU/EDC-mediated amide formation with amines under mildly basic conditions (DIPEA) in DMF.
  • Temperature: 0–25 °C; monitor by LC–MS.
• Hydrogenation/olefin manipulation:
  • Conditions: Very mild catalytic hydrogenation (e.g., Pd/C) can reduce the conjugated diene but risks over-reduction or degradation; evaluate on milligram scale first.

Typical timelines and yields

• Reaction times commonly range from 0.5–24 h depending on transformation and steric demands. Yields vary widely (30–85%) due to chemoselectivity and purification challenges.

Stability precautions

• Use an inert atmosphere (argon/nitrogen), dry solvents, and minimal light exposure. Maintain temperatures below ~40 °C during processing to limit decomposition.

Safety and Handling

Item-specific hazard data

• Signal word, H-statements, GHS classification, pictograms: Not specified for this item; consult the SDS for authoritative information.

General laboratory safety guidance (literature-informed; not item-specific)

• Likely hazards: Macrocyclic lactones of the avermectin class may be harmful if swallowed and may cause eye/skin irritation. Avoid inhalation of dust or aerosols. Handle as a substance of unknown acute toxicity.
• Environmental considerations: Compounds in this class are toxic to aquatic organisms; prevent release to the environment. Dispose of in accordance with institutional and local regulations.
• PPE: Lab coat, nitrile gloves (change regularly), safety glasses. Use a chemical fume hood when weighing or preparing solutions.
• Incompatibilities: Strong oxidizing agents. Avoid prolonged exposure to air/oxygen and moisture if long-term stability is critical; Product Data specifies argon-blanketed storage.
• First aid (overview; follow SDS): If inhaled—move to fresh air. If on skin—wash with soap and water. If in eyes—rinse cautiously with water for several minutes; remove contact lenses if present. If swallowed—rinse mouth; seek medical attention.
• Fire safety: Use CO2, dry chemical, or foam. Combustible organic solid; thermal decomposition may produce irritating fumes.

Always defer to the Aladdin Scientific SDS for Eprinomectin (SKU E131865) for complete hazard, toxicological, and ecological information.

Solvent Selection

Compound-type driven guidance (macrocyclic, highly lipophilic, low aqueous solubility)

• Primary solvents for stock solutions: Anhydrous DMSO or DMF (excellent solubilization), acetone, acetonitrile, ethyl acetate, dichloromethane. Ethanol or methanol may dissolve at moderate concentrations; water is ineffective without cosolvents or carriers.
• Cosolvent strategies: For biological assays, prepare a concentrated DMSO stock (e.g., 10–50 mg/mL as solubility permits) and dilute into buffer to low final DMSO percentages (≤0.5–1%) to minimize assay interference. Use solubilizing excipients (e.g., cyclodextrins) where needed.
• Polarity/miscibility: Neutral, nonionic; dissolves in organic media across a range of polarities but poorly in hydrocarbons at room temperature. DMSO is miscible with water and aids microdosing into aqueous systems.

Comparison (general)

• DMSO vs ethanol: DMSO provides higher maximum solubility and better stability under inert atmosphere; ethanol offers faster evaporation but lower solubility and potentially more precipitation upon aqueous dilution.
• Acetonitrile vs acetone: Both support LC compatibility; acetonitrile offers lower UV background and better chromatographic behavior for LC methods.

Practical tips

• Warm gently (≤40 °C) and sonicate to assist dissolution; avoid prolonged heating. Pre-inert and dry solvents to align with the argon-blanketed storage recommendation in Product Data.
• Filter 0.2 µm before critical assays or LC quantitation to remove undissolved particulates.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data)

• Storage conditions: Store at −20 °C, argon charged.
• Shipping: Ice chest + ice pads.

General reconstitution guidance (literature-informed; verify in your lab)

• Solvent choice: Use anhydrous, oxygen-free DMSO or DMF for primary stocks. Alternative solvents (acetone, acetonitrile, ethyl acetate, methanol/ethanol) may be used depending on intended application and solubility.
• Technique: Allow the sealed container to equilibrate to room temperature before opening to avoid moisture condensation. Backfill with argon or nitrogen after use. Weigh quickly in a dry box or under a dry nitrogen stream if feasible.
• Concentration: Choose a stock concentration that ensures complete dissolution and compatibility with your downstream dilution vehicle; confirm by visual inspection and analytical check (HPLC/LC–MS).
• Aliquoting: Prepare small, single-use aliquots to minimize headspace oxygen and freeze–thaw cycles. Store aliquots tightly sealed under inert gas at −20 °C, protected from light and moisture.
• Stability: In-solution stability depends strongly on solvent, temperature, oxygen, and light exposure. Establish an in-house retest period by periodic LC analysis of stored stocks.

Notes

• Appearance, purity, water/peroxide/metal limits, and exact solubility values: Not specified for this item; refer to CoA/Spec Sheet.
• For research use only (Product Data).

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: E131865
• CAS: 123997-26-2
• Category: Small molecules and compound library (小分子和化合物库)
• Storage (as supplied): Store at −20°C, argon charged (Product Data)

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

Literature/General structural information (for context; not item-specific specs)

• Compound class: Macrocyclic lactone of the avermectin family; semisynthetic derivative (contains one nitrogen due to an amino substituent introduced onto the disaccharide).
• Typical architecture: A ~16-membered macrocyclic lactone core bearing multiple olefinic and hydroxyl functionalities, and a disaccharide (two L-oleandrose units) at C13. Eprinomectin is commonly described as a mixture of closely related B1 components differing by a minor alkyl substitution on the macrocycle side chain.
• Functional groups: Macrocyclic ester (lactone), secondary/tertiary alcohols, ether linkages, acetal/spiroketal motifs within the sugar moieties, conjugated diene on the macrocycle, and an N-acylamino substituent on the sugar (responsible for the single nitrogen atom in the molecule).
• Stereochemistry: Multiple defined stereocenters across the macrocyclic core and the two deoxy sugars; the commercial material is a well-defined stereochemical ensemble characteristic of avermectins.

2D structure (verbal description)

• A large, oxygen-rich ring (lactone) with a diene side chain; two deoxy-sugars are glycosidically linked to the macrocycle. Numerous hydroxyls decorate both the macrocycle and sugars; one sugar bears an amino-acyl substituent.

Synthetic Utility

General synthetic perspective (literature; not item-specific)

• Eprinomectin is a densely functionalized macrocycle with multiple hydroxyls and glycosidic linkages, serving as a platform for semisynthetic diversification. Typical transformations include:
  • Site-selective acylation or carbonate formation at secondary alcohols on the sugars or macrocycle to modulate physicochemical properties.
  • Derivatization at the N-acylamino substituent (e.g., amide exchange or further acyl elaboration) to probe SAR.
  • Temporary protection (silyl ethers, carbonate protections) enabling downstream oxidation/reduction or cross-coupling on suitably activated positions.
• Retrosynthetic value: While not a small building block, its rich functionality allows convergent introduction of reporter groups (e.g., fluorescent tags) via carbamate/ester linkages for probe development.
• Chemoselectivity challenges: The presence of multiple alcohols with similar reactivity necessitates careful use of selective protecting groups and mild, orthogonal conditions. Reactions are commonly run under inert atmosphere to limit oxidative processes at the conjugated diene.

Analytical support

• Monitoring by LC–MS with soft ionization (ESI/APCI) and UV detection near 245 nm (typical avermectin chromophore) aids in mapping reaction progress and impurity formation.

Note: For any derivatization campaign, confirm identity/purity by NMR (distinctive sugar anomeric and macrocycle signals) and HRMS.

Target Specificity

Only item-specific target data from Product Data may be listed here. No such data were provided for SKU E131865.

Statement of applicability

• This product is a small-molecule macrocyclic lactone, not an antibody or protein reagent. Target specificity parameters such as antigen, epitope, clone, isotype, and species reactivity are not applicable.