CALIDAD & PUREZAMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.≥98%~10mg/mL in ethanol
Moligand™, ≥98%, ~10mg/mL in ethanol Moligand™ para flujos de trabajo cromatográficos y analíticos sensibles que requieren una interferencia mínima de la línea base.
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Almacenamiento y envío
Desiccated,Store at -80°C Envío Dry ice packs + Cold packs. Consulte el COA específico del lote para conocer las especificaciones exactas.
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Documentos de calidad
SDS, COA, ficha técnica y hoja de especificaciones disponibles para descargar. COA específico del lote accesible mediante búsqueda por número de lote.
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Prueba documental
Citado en 0 publicaciones revisadas por pares sobre cromatografía, síntesis orgánica y reacciones de acoplamiento cruzado.
Descripción general
Noladin ether (2-Arachidonyl glycerol ether) is a stable analog of the endogenous cannabanoid 2-Arachidonylglycerol (2-AG) with selectivity for CB1 receptors. Noladin ether is a CB1 agonist. The Ki values for CB1 vs CB2 receptors are 21.2 nM and 3 mM, respectively. Noladin ether induces sedation and has modest antinociceptive activity in vivo, and reduces inter ocular pressure after administration in the eye. 2-Arachidonyl glycerol ether (2-AG ether) is supplied as a solution in ethanol. To change the solvent, simply evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice. Solvents such as DMSO and dimethyl formamide purged with an inert gas can be used.
This compound belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.
External Descriptors
Monoacylglycerols
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No vendor-validated protocols are provided for this item. The following are general, non-binding examples to help plan pilot studies; adjust to your system and validate experimentally.
Example A: Stock preparation (cell-based assays)
Dissolve noladin ether at 10–50 mM in anhydrous DMSO under nitrogen. Vortex briefly, sonicate if needed (short, cold). Aliquot 10–50 µL into amber vials, flush with N2, and freeze at −80°C.
Example B: Dosing into culture medium
Thaw one aliquot on ice, dilute into pre-warmed medium to the desired concentration keeping final DMSO at 0.05–0.2% v/v. Optionally include fatty-acid–free BSA (0.1–1%) to enhance dispersion. Prepare matched vehicle controls. Use immediately; avoid storing diluted solutions.
Example C: Membrane binding/biochemical assays
Prepare serial dilutions in assay buffer containing 0.1% BSA and ≤0.1% DMSO. Maintain low-light conditions and nitrogen overlay during setup. Verify compound integrity by LC–MS post-assay.
Note
These are general best practices for hydrophobic lipid ligands. For any quantitative recommendations (e.g., working ranges, incubation times), develop and document system-specific SOPs.
Biological Roles
General background (literature; no therapeutic claims)
Noladin ether (2-O-arachidonyl glycerol ether) is widely used as a research tool in endocannabinoid biology. It is a synthetic/endogenous-like lipid agonist reported to engage cannabinoid receptors (CB1/CB2) in various systems. As an ether analog of 2-arachidonoylglycerol (2-AG), it is comparatively resistant to enzymatic hydrolysis by monoacylglycerol lipase (MAGL), enabling prolonged signaling studies in vitro.
Structural biology relevance: The ether linkage at sn-2 and the polyunsaturated C20 chain confer high membrane affinity and lateral mobility, making noladin ether a useful probe for receptor partitioning within lipid microdomains.
Metabolic considerations: While esters like 2-AG are rapidly turned over by serine hydrolases, ether-linked analogs often exhibit altered metabolic stability, allowing separation of receptor-mediated effects from rapid metabolic clearance in cell-based assays.
Signaling assays: Used to profile GPCR-mediated pathways (e.g., cAMP modulation, Ca2+ mobilization, MAPK phosphorylation) and β-arrestin recruitment in recombinant or native systems.
Caveats
Oxidative degradation of the polyunsaturated chain can yield confounding products. Employ antioxidants/inert handling and verify analyte integrity by LC–MS before and after assays.
Off-targets typical of hydrophobic lipids (e.g., membrane perturbation) should be controlled with vehicle and negative lipid controls.
This section summarizes literature knowledge only; consult primary sources for specific potency/efficacy data.
Buffer Applications
This compound is a hydrophobic research ligand, not a buffering agent. It does not form conventional buffer systems.
Practical note (general)
When dosing into aqueous buffers, prepare concentrated DMSO or ethanol stocks and dilute immediately before use. To aid dispersion, include fatty-acid–free BSA (0.1–1%) or a low level of nonionic surfactant (e.g., 0.01–0.05% Tween-80), verifying compatibility with your assay.
Maintain final organic cosolvent at minimal levels (often 0.05–0.2% v/v) and include matched vehicle controls.
Green Alternatives
Context
Noladin ether is a specialized research ligand, not a commodity solvent or reagent. “Green alternative” considerations therefore focus on handling solvents and assay media rather than replacing the compound itself.
Greener handling choices (general guidance)
Prefer ethanol or isopropanol for stock or intermediate solutions when compatible with your assay, instead of chlorinated solvents.
Use minimal DMSO percentages (≤0.1–0.2% v/v in final assay) while maintaining solubility and performance.
Prepare lipid films with ethyl acetate or ethanol where feasible, instead of dichloromethane/chloroform; confirm residue and film homogeneity.
Employ micro-aliquoting to reduce waste and avoid repeated thaw–freeze cycles that lead to degradation and disposal.
Illustrative comparison (general)
DMSO vs Ethanol: DMSO provides higher solvency but may perturb some biological systems at modest percentages; ethanol is more benign environmentally and biologically but may limit achievable concentrations.
CHCl3/DCM vs Ethyl acetate/EtOH: chlorinated solvents excel in lipid solubilization and rapid evaporation but carry higher environmental/health burdens; ethyl acetate and ethanol offer safer profiles at potential cost of slower evaporation and slightly reduced solvency.
Note
There is no direct “green substitute” for noladin ether’s biological activity profile. If your study allows, endogenous lipids such as 2-AG or anandamide may be considered as comparators; select solvents and protocols that minimize environmental impact.
Pharmaceutical Uses
No pharmacopoeial or excipient role is specified for this item; it is sold strictly for research use only.
General research/formulation context (non-clinical, literature)
Utilized as a reference or probe compound in preclinical discovery assays focused on lipid–receptor interactions and endocannabinoid pathway characterization.
Formulated as concentrated stocks in DMSO or ethanol for in vitro studies. For in vivo exploratory research (outside the scope of this catalog’s use terms), investigators typically employ solubilization systems such as PEG derivatives, cyclodextrins, or lipid carriers; such applications must follow institutional approvals and are not endorsed here.
Compliance note
This product is not intended for human or veterinary use, diagnostic procedures, or as a drug substance/excipient. For any regulated application, obtain appropriate regulatory-grade materials and documentation.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general characteristics of noladin ether and similar long-chain polyunsaturated glycerol ethers
Physical state: oily, highly hydrophobic lipid at ambient temperature (literature).
Color: typically colorless to pale yellow oils when fresh; may darken upon oxidation (literature).
Solubility: insoluble in water; soluble in organic solvents such as ethanol, methanol (limited), isopropanol, acetone, ethyl acetate, chloroform, dichloromethane, and DMSO (literature). For biological work, typically prepared in DMSO or ethanol and diluted into aqueous media with carriers (e.g., BSA, surfactants).
Partitioning: expected high logP due to C20 polyunsaturated chain and ether linkage (literature; quantitative value not provided here).
Volatility: non-volatile, high-boiling lipid; handled as solutions/films rather than distilled (literature).
Refractive index/density: typical of long-chain lipids; item-specific values not established here.
Not provided for this item (refer to CoA/Spec Sheet)
Exact melting point, boiling point, density, refractive index, pKa, logP, UV cutoff.
Practical notes
Susceptible to autoxidation (allylic positions) and light/air degradation; protect from air, light, and heat. Use antioxidants (e.g., BHT) only if consistent with your assay, and document use.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Moligand™
What Moligand™ typically implies (general explanation)
Moligand™ designates materials intended for ligand screening, target engagement, and chemical biology workflows where batch-to-batch identity and integrity are prioritized. While exact acceptance criteria are product-specific, Moligand™ offerings are generally supported by analytical identity testing (e.g., NMR/MS/HPLC) suitable for discovery assays.
How to use this information in practice
Spectral transparency: For optical or fluorescence-based assays, verify background absorbance/fluorescence of the lot using your assay buffer and wavelength window.
Stability: For polyunsaturated lipids like noladin ether, confirm inhibitor/agonist integrity by quick LC-MS before and after assay runs, particularly if solutions are kept at room temperature.
Additives/stabilizers: None are specified for this item; refer to CoA/Spec Sheet. If your workflow tolerates it, you may add inert antioxidants (e.g., BHT, 50–100 ppm) to bulk stocks in aprotic solvents; document and validate for your assay.
Documentation and traceability
For regulatory or high-throughput screening environments, retain CoA/SDS and record storage, handling temperatures, and freeze–thaw cycles for each lot to ensure reproducibility.
Reaction and Applications
This product is primarily used as a research ligand rather than a bulk reaction solvent or reagent. Accordingly, synthetic reaction applications are limited. Relevant use-cases include (literature/general):
Chemical biology/pharmacology: Employed as a tool compound in studies of endocannabinoid system signaling, receptor activation, and lipid–protein interactions. Typical use in binding or functional assays (e.g., GPCR activation) requires careful solvent control and light/oxygen protection.
Membrane/lipid research: Serves as a model polyunsaturated ether lipid for investigating membrane partitioning, raft association, and lipid oxidation kinetics.
Derivatization chemistry: The remaining primary/secondary alcohols on the glycerol moiety allow selective protection/derivatization (e.g., silylation, acylation, carbonate formation) to prepare analytical probes or stability-modified analogs.
Oxidation/hydrogenation studies: The arachidonyl chain’s conjugated diene segments undergo epoxidation, dihydroxylation, or partial hydrogenation to generate structure–activity series; reactions are typically run under inert gas at low temperatures with light exclusion.
Surface/film preparation: Thin films can be cast from volatile organic solvents (e.g., CHCl3/MeOH) for Langmuir–Blodgett or supported bilayer studies; anneal under inert atmosphere.
Note: For general organic reactions on noladin ether, pre-dry solvents, degas, and operate under nitrogen/argon. Monitor reactions by LC–MS with soft ionization to minimize in-source oxidation artifacts.
Reaction Conditions
Because noladin ether is typically used as a ligand, not a general reagent, there are no standardized “reaction conditions” for its use. The following are literature-style guidelines for common transformations on related polyunsaturated glycerol ethers; adapt as needed and validate experimentally.
Representative transformations (literature, general ranges)
Selective acylation of primary glycerol OH: Ac2O/pyridine or acyl chloride/DMAP, 0–25°C, 0.5–4 h; monitor to avoid overacylation.
Silyl protection of secondary OH: TBSCl/imidazole in DMF or DCM, 0–25°C, 1–12 h; inert atmosphere, dry solvents.
Epoxidation of double bonds: mCPBA (≤1.0 eq per C=C) in DCM, 0–5°C to RT, 0.5–3 h; quench carefully; light exclusion.
Dihydroxylation: OsO4 (cat.)/NMO in t-BuOH:H2O (or acetone:H2O), 0–25°C; protect glycerol OH groups to control regioselectivity.
Carbonate formation (label installation): p-NPC (p-nitrophenyl chloroformate)/base in DCM, 0–5°C to RT; subsequent coupling to amines/fluorophores.
Handling conditions (general)
Strictly anhydrous, oxygen-free solvents; nitrogen/argon blanket; amber glassware. Use BHT (trace) if compatible. Maintain ≤5°C for sensitive oxidations; avoid strong bases and prolonged heating which can induce isomerization/oxidation.
Safety and Handling
Item-specific (from Product Data)
Storage: Desiccated, Store at -80°C. Shipped on dry ice + cold packs.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
General safety guidance (defer to SDS for authoritative instructions)
Hazards: Lipidic, non-volatile material; not expected to be acutely volatile-toxic by inhalation. Polyunsaturated moieties can form peroxides/oxidation products on air/light exposure; handle under inert atmosphere where feasible.
PPE: laboratory coat, safety glasses, and nitrile gloves as a minimum. Use chemical fume hood when weighing, dissolving, or aliquoting organic solutions.
Incompatibilities: strong oxidizers; radical initiators; prolonged exposure to air/oxygen, light, and elevated temperatures that promote autoxidation.
Handling tips: Work quickly on ice or at room temperature with pre-chilled, dry, oxygen-reduced solvents. Purge vials with nitrogen/argon after use. Minimize headspace and light exposure (use amber glass/aluminum foil wrap).
First aid (general): If on skin—wash with soap/water. If in eyes—rinse with water for several minutes. If inhaled (from aerosols/solvent vapors)—move to fresh air. If ingested—rinse mouth. Seek medical attention if symptoms persist. Provide the SDS to responders.
Waste: Collect solutions and contaminated disposables as halogenated or non-halogenated organic waste per your solvent system and institutional EHS guidance.
Note: Always consult the product’s SDS and your institutional EHS policies before use.
Solvent Selection
General guidance for noladin ether (literature-based)
Recommended stock solvents: anhydrous DMSO or ethanol (EtOH). DMSO often enables higher concentrations (e.g., 10–50 mM) with good stability when kept cold, dry, and protected from light.
Alternative solvents: isopropanol, methanol (limited), acetone, acetonitrile (limited), ethyl acetate, dichloromethane, chloroform, toluene, and hexanes for synthetic/analytical work. For biological dosing, stick to DMSO or EtOH as cosolvents.
Aqueous work: prepare concentrated DMSO/EtOH stocks and dilute into buffered media immediately before use (final organic 0.05–0.5% v/v). Use carriers such as fatty-acid–free BSA (0.1–1%) or mild nonionic surfactants (e.g., 0.01–0.05% Tween-80) to improve dispersion; verify assay compatibility.
Avoid: prolonged residence in basic aqueous media (can promote oxidative degradation of polyunsaturated chains); repeated freeze–thaw of dilute aqueous dispersions.
Quick comparison (general)
DMSO: maximal solvency, good glass compatibility, low volatility; may affect certain channels/enzymes at >0.5% v/v.
Ethanol: biocompatible at ≤0.1–0.5% v/v in many systems; lower solvency than DMSO.
Chlorinated solvents (DCM/CHCl3): excellent solvency for film formation and analytics; not suitable for live-cell exposure.
Note: Optimize solvent choice to your assay constraints and confirm by small-scale pilot tests.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Desiccated, Store at -80°C.
Shipping: Dry ice packs + Cold packs.
General best practices for this compound class
Light/oxygen sensitivity: Store under inert gas (N2/Ar) in amber vials. Minimize headspace and avoid repeated freeze–thaw cycles.
Aliquoting: Upon receipt, allow the sealed container to equilibrate to room temperature under desiccation before opening to prevent moisture condensation. Immediately prepare small, single-use aliquots.
Reconstitution: Dissolve in anhydrous DMSO or ethanol to prepare concentrated stocks (e.g., 10–50 mM). Vortex gently and, if necessary, briefly sonicate in a cold bath. After preparation, purge headspace with nitrogen, cap tightly, and return to −80°C.
Working solutions: Prepare fresh dilutions into assay buffer immediately before use; maintain final organic cosolvent at minimal levels. Discard unused dilutions rather than refreezing.
Stability checks: Periodically verify stock integrity by LC–MS or HPLC-UV (look for oxidative byproducts). Replace stocks that show significant degradation or color change.
Not specified for this item; refer to CoA/Spec Sheet
Exact shelf life, retest date, and any stabilizers or additives, if present.
Structure and Identity
Item-specific (from Product Data)
SKU: N276283
Product name: Noladin ether
Grade/Purity: Moligand™
Storage conditions: Desiccated, Store at -80°C
Shipped in: Dry ice packs + Cold packs
CAS: 222723-55-9
CID: 6483057
Structural identifiers (SMILES, InChIKey): 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 structural description (literature)
Noladin ether is commonly described as 2-O-arachidonyl glycerol ether (2-AGE): a glycerol backbone in which the secondary (sn-2) hydroxyl is ether-linked to an arachidonyl (C20:4, n-6) polyunsaturated aliphatic chain.
Functional groups/features: one primary alcohol and one secondary alcohol remain free on glycerol; one ether linkage at sn-2; the arachidonyl chain contains four cis-alkene units (typical Δ5,8,11,14 positions in literature), making it highly lipophilic and oxidation-prone.
2D description: a three-carbon glycerol scaffold with two terminal –OH groups; at C2, an –O–(CH2–(CH=CH–CH2)4–(CH2)n–CH3) substituent representing the arachidonyl ether.
Notes
This product is provided for research use only. For definitive identity attributes of this lot (e.g., exact stereochemistry confirmation, analytical data), refer to the item’s CoA/SDS.
Synthetic Utility
General chemical reactivity (literature)
Functional handles: two free glycerol hydroxyl groups (primary and secondary) enable selective protection (e.g., TBDMS, TBS, TIPS), acylation (acetates/carbonates), and labeling (e.g., fluorescent carbamates/carbonates) to create analytical probes.
Ether stability: The sn-2 ether resists nucleophilic/acyl transfer hydrolysis that rapidly degrades 2-AG; thus, noladin ether is a more stable scaffold for SAR where receptor engagement is to be decoupled from rapid ester cleavage.
Polyunsaturated chain chemistry: Four cis-alkenes facilitate transformations such as epoxidation (mCPBA), dihydroxylation (OsO4/NMO), ozonolysis, radical additions, and partial hydrogenation (H2/Pd-C) to tune conformation and lipophilicity.
Late-stage diversification: Mitsunobu-type coupling on glycerol OH (with caution to avoid elimination), carbonate/urethanation for reporter installation, and click-compatible handles via pre-installation on glycerol then etherification with arachidonyl analogs.
Analytical considerations
Monitor by LC–MS (APCI/ESI) and by 1H NMR in CDCl3 or CD3OD; avoid prolonged acquisition under ambient oxygen to limit in-tube oxidation. Add small amounts of antioxidant to NMR samples if compatible.
Workflow tip
For targeted probe synthesis, plan protecting group strategies that survive mild oxidation/reduction conditions and allow final global deprotection without isomerizing the polyunsaturated chain.
Target Specificity
Item-specific, tested biological targets or binding data are not provided for this product.
Literature/general context
Noladin ether is widely used as a research agonist for cannabinoid receptors (CB1/CB2). Quantitative potency/efficacy parameters vary by system and are not specified for this item. Users should determine receptor selectivity and activity in their specific assay format and species background.
For authoritative, product-specific target data (e.g., EC50/IC50, selectivity panels), consult the primary literature and perform in-house validation with appropriate positive/negative controls.
Preguntas frecuentes
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
What is Moligand??
Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.
How should this product be stored?
Store at ?80 °C, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.
How is this product shipped?
This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 222723-55-9, the molecular formula is C23H40O3, and the molecular weight is 364.6 g/mol. InChIKey CUJUUWXZAQHCNC-DOFZRALJSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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