OAG - Moligand™ , Activator of TRPC3;Activator of TRPC6;Activator of TRPC7, CAS No.84746-00-9, Activator of TRPC3;Activator of TRPC6;Activator of TRPC7
OAG - Moligand™ , Activator of TRPC3;Activator of TRPC6;Activator of TRPC7, CAS No.84746-00-9, Activator of TRPC3;Activator of TRPC6;Activator of TRPC7
GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
This compound belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
External Descriptors
Not available
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
Item-specific validated protocols are not provided. The following are general, literature-based guidelines for research use of OAG; adjust to your system and consult primary references.
A. Preparing stock solutions
Dissolve OAG at 10–50 mM in anhydrous DMSO (or 10–25 mM in ethanol). Vortex and, if needed, gently warm to 30–37 °C. Filter (0.22 μm PTFE) if particulate persists.
Aliquot into amber vials or microtubes under inert gas if available; store to minimize headspace oxygen.
B. Cell-based dosing (example framework)
Prepare working dilutions by adding the DMSO stock to pre-warmed culture medium while vortexing to reach 0.5–10 μM final OAG and ≤0.1–0.2% DMSO.
Optional: Include 0.1–0.5% fatty-acid–free BSA to aid dispersion if compatible with the assay.
Dose cells and measure endpoints within minutes to tens of minutes for acute activation (e.g., PKC translocation reporters); include vehicle controls.
C. Membrane/protein assays
Reconstitute purified proteins in detergent micelles or liposomes containing defined mole% OAG (e.g., 1–10 mol% relative to total lipid) or add OAG from DMSO stocks to preformed bilayers with rapid mixing.
For lipid films, deposit OAG with phospholipids from chloroform/ethanol, dry under nitrogen, desiccate, then hydrate and extrude to form vesicles.
D. Termination and cleanup
For reversible assays, wash cells with buffer free of OAG and vehicle. Dispose of DMSO/organic waste per institutional guidelines.
Note: These are general recommendations; not item-specific performance claims.
Biological Roles
Literature overview (not product claims)
Mechanistic role: OAG is a membrane-permeable analog of diacylglycerol (DAG), the endogenous second messenger produced by phospholipase C from phosphatidylinositol 4,5-bisphosphate. DAGs activate conventional and novel protein kinase C (PKC) isoforms by binding to C1 domains; OAG mimics this interaction and promotes PKC translocation to membranes.
Target landscape: In addition to PKC isoforms (α, β, γ, δ, ε, η, θ), C1-domain–containing proteins such as RasGRPs and some chimaerins can be modulated by DAG analogs in a context-dependent manner (literature). OAG may thereby influence downstream signaling pathways (e.g., MAPK cascades) in experimental systems.
Biophysical effects: Incorporation into lipid bilayers alters membrane curvature stress and lateral pressure profiles, which can indirectly modulate the activity of membrane proteins and ion channels (literature).
Cells: ~0.5–20 μM for acute activation with rapid (seconds–minutes) responses.
Membrane/protein assays: ~5–200 μM depending on lipid composition and protein abundance.
Note: Optimal dosing depends on cell type, membrane composition, and readout; titration and vehicle controls are essential.
Kinetics: OAG shows faster cell entry and distribution than many native long-chain DAGs, enabling rapid-onset experiments. Effects are generally reversible upon washout, though signaling cascades may persist.
Use notes
Because OAG is bioactive, treat as a potent research tool. Avoid extrapolating cellular findings to in vivo contexts. No clinical or therapeutic claims are implied.
Buffer Applications
Not typically applicable.
OAG is not a buffering agent and does not form defined buffer systems. For biological delivery, it is commonly dosed into existing buffers (e.g., HEPES- or PBS-based) from DMSO or ethanol stocks.
Practical tip (general): Warm the buffer (e.g., 25–37 °C) and add OAG stock with vigorous mixing to minimize precipitation. Inclusion of carriers such as fatty-acid–free BSA (0.1–1% w/v) or mild nonionic detergents (0.01–0.1%) can improve dispersion when compatible with your assay.
Green Alternatives
Context
OAG is a specific bioactive lipid tool compound; it does not have a direct “green substitute” that preserves both structure and function.
Greener handling strategies (general guidance)
Solvent choice: Prefer ethanol or isopropanol over chlorinated solvents where compatible with your assay. Use the minimum DMSO concentration required for solubility.
Process minimization: Prepare concentrated stocks to reduce solvent volumes; use micro-scale assay formats and sealed microplates to limit emissions.
Waste reduction: Pool organic waste streams appropriately; employ solvent recovery where feasible.
Comparison of delivery approaches (general)
Direct DMSO dilution: Operationally simple; minimal volatile organic solvents; potential DMSO cytotoxicity at higher percentages.
Lipid film hydration: Uses volatile solvents (e.g., chloroform) but affords more uniform bilayer incorporation; mitigate by using ethanol-based thin films when compatible.
Bottom line
Because OAG’s utility is structure-specific, “green alternative” means optimizing formulation and workflow for lower solvent hazard and volume, rather than replacing the molecule itself.
Pharmaceutical Uses
Not a therapeutic or excipient claim.
Role: OAG is widely used as a research tool compound in preclinical discovery and chemical biology to probe DAG-responsive signaling. It is not described as a pharmacopeial excipient.
Formulation research context (literature/general): When used in vitro or ex vivo, OAG is typically formulated as concentrated stocks in DMSO or ethanol and delivered into aqueous systems with carriers (e.g., BSA, cyclodextrins). Such practices are for research assays and method development rather than human or veterinary use.
Regulatory status: For research use only (per Product Data). No clinical, diagnostic, or therapeutic applications are claimed or supported.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature and general reference values (not item specifications)
Physical state: Typically a colorless to pale yellow, viscous oil at ambient temperature; strongly amphiphilic with pronounced hydrophobic character.
Melting point: Often below room temperature; reported as liquid at 20–25 °C (literature).
Boiling point: Not ordinarily distilled due to thermal lability; decomposition may occur before boiling under ambient pressure (literature). Vacuum purification, if needed, is usually by flash chromatography rather than distillation.
Density: Reported for similar DAGs ~0.95–0.99 g/mL at 20–25 °C (literature, indicative only).
Calculated partitioning: High lipophilicity; cLogP typically >6 for mono-unsaturated DAG analogs (literature/computed trends).
Poorly soluble: Water and aqueous buffers; may be dispersed with surfactants, cyclodextrins, or carrier proteins (e.g., BSA) (literature).
Refractive index: Similar long-chain esters typically nD20 ~1.46–1.48 (literature for class).
Notes for use (general)
Prepare concentrated stocks in dry DMSO or ethanol; dilute into assay buffers with vigorous mixing to minimize aggregation.
Avoid prolonged exposure to elevated temperatures or strong light to limit acyl migration and oxidation of the olefin (literature). Always confirm with your lab’s method validation.
Quality and Grades
Item-specific
Grade/Purity: Moligand™ (as provided by Aladdin Scientific for screening-library small molecules and ligands).
What Moligand™ implies (general guidance)
Intended use: Research-use-only grade suitable for discovery biology, target validation, and chemical biology where a well-characterized small-molecule ligand is required.
Documentation: For exact purity, residual solvents, identity confirmation (NMR/LC–MS/HRMS), and related substances, refer to the item’s CoA/Spec Sheet. Do not infer HPLC area% or UV-cutoff in the absence of explicit data.
Performance considerations: Moligand™ items are typically selected/curated for bioactivity or tool-compound utility rather than for chromatographic solvent specifications. Low non-volatile residue or UV absorbance is not implied unless explicitly stated.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. If antioxidants or acidifiers are present in some lots of lipidic materials, they will be declared on the CoA.
Practical notes for lipidic tool compounds (general)
Isomeric purity: DAG analogs can isomerize (acyl migration). Reanalyze by LC–MS or 1H/13C NMR if your application is sensitive to regioisomers.
Water content/peroxides/metals: Not specified for this item; refer to CoA/Spec Sheet. If working at low micromolar concentrations, trace impurities may influence assays—consider running vehicle controls and orthogonal confirmation assays.
Reaction and Applications
This compound is primarily a biochemical tool rather than a general-purpose synthetic reagent.
Applicable uses (literature/general; expand on catalog intent “small molecule and compound library”)
Cell signaling studies: Acute activation of DAG-sensitive pathways in intact cells, membranes, or purified protein systems, with OAG serving as a permeable analog (e.g., PKC translocation/activation assays, reporter assays).
Membrane biophysics: Incorporation into lipid bilayers or micelles to probe lipid–protein interactions, DAG-dependent curvature, and phase behavior.
Assay development: Positive control ligand in kinase activity assays, high-content imaging of translocation biosensors (e.g., C1-domain GFP fusions), or electrophysiology experiments where DAG elevation modulates channel activity.
Less typical as a reaction reagent
OAG is not commonly used as a stoichiometric reagent or catalyst in synthetic organic transformations. If derivatized, it is usually within lipid chemistry workflows (e.g., tagging, click-derivatization after introducing azide/alkyne handles), not as a general building block.
Practical tips (general)
Prepare fresh working solutions; minimize time in aqueous media to reduce hydrolysis/acyl migration.
Validate activity in your system with dose–response curves and appropriate vehicle controls.
For surface or bilayer incorporation, deposit from volatile organic solvent onto a substrate, dry to form a thin film, then hydrate under controlled conditions.
Reaction Conditions
Not typically used as a reagent in named organic reactions; therefore, standard “reaction conditions” are not applicable.
General handling conditions for assay preparation (literature guidance)
Stock solutions: 10–50 mM in anhydrous DMSO or 10–25 mM in ethanol; store aliquots protected from light. Verify solubility visually and by test dilution.
Working concentrations: Commonly 0.5–20 μM for cellular assays; 5–200 μM for membrane/protein assays, depending on system sensitivity.
Temperature: Prepare and dilute at ambient temperature or slightly warmed (25–37 °C) to aid solubilization; avoid prolonged heating.
Atmosphere: Normal laboratory atmosphere is acceptable, but minimize air exposure to limit oxidation of the olefinic chain; optional nitrogen blanket for long handling steps.
Time: Use promptly after dilution into aqueous media to limit hydrolysis and acyl migration; many labs dose within minutes of preparation.
Yield/kinetics: Not applicable to synthetic conversions. For biological readouts, expect rapid responses (seconds–minutes) in systems expressing DAG-responsive proteins (literature). Always optimize empirically for your assay.
Safety and Handling
Item-specific hazard information
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance (literature/standard practice)
PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a chemical fume hood when handling powders/aerosols or preparing volatile organic solutions.
Handling: OAG is a bioactive lipid tool compound; avoid ingestion, inhalation, and skin contact. Prevent aerosol formation. Use dedicated, labeled containers for stock solutions.
Incompatibilities: Strong oxidizers and strong bases/acids can promote degradation (hydrolysis, oxidation). Unsaturated chains are susceptible to autoxidation; minimize exposure to air and light.
Stability considerations: Diacylglycerol analogs can undergo acyl migration under basic conditions or heat, giving isomeric mixtures. Store neutral to slightly acidic and avoid strong bases. Antioxidants (e.g., BHT) are sometimes used in lipid research stocks; follow your protocol and regulatory guidance.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical advice if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect organic solvent wastes per institutional and local regulations. Decontaminate glassware with suitable organic solvents followed by detergent wash.
Always consult the product SDS for authoritative, item-specific safety information.
Solvent Selection
Solvent behavior (literature/general)
Polarity class: Amphiphilic but predominantly hydrophobic due to the C18:1 oleoyl chain; behaves as a nonpolar–weakly polar lipid in practice.
Preferred stock solvents: Dry DMSO (common for cell-based assays), ethanol or isopropanol (biochemical assays), and chlorinated or aromatic solvents for synthetic handling (e.g., CH2Cl2, CHCl3, toluene).
Aqueous delivery: Poor intrinsic water solubility. For biological assays, dilute DMSO stocks into warm buffer with rapid mixing; final DMSO ≤0.1–0.5% v/v is typical (literature). Alternatively, use carriers: fatty-acid–free BSA (e.g., 0.1–1% w/v), cyclodextrins, or mild nonionic detergents (e.g., 0.01–0.1% Triton X-100 or Tween 20) as your protocol allows.
Comparison (general guidance)
DMSO vs ethanol: DMSO provides superior solvating power and stability for concentrated stocks (10–50 mM common). Ethanol may be preferable when minimizing DMSO in sensitive cell systems but can precipitate upon cold dilution.
CH2Cl2/CHCl3: Useful for film-deposition methods (lipid film hydration, liposome incorporation); not suitable for direct biological exposure.
When to choose OAG vs alternatives (use-case driven)
OAG is chosen when a membrane-permeable DAG mimetic is needed for acute activation of DAG-responsive pathways (e.g., protein kinase C) with faster uptake than native DAGs (literature). For slower, sustained signaling, endogenous DAGs or short-chain DAGs (e.g., 1,2-dioctanoyl-sn-glycerol) may be used instead.
Item-specific solvent specifications: Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Item-specific (from Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General recommendations (literature/practice; align with room-temperature storage unless your CoA specifies otherwise)
Protection: Store tightly closed in a dry place, protected from light to limit oxidation of the unsaturated chain and from heat to minimize acyl migration.
Atmosphere: If feasible, blanket partially used containers with inert gas (e.g., nitrogen or argon) before reclosing to reduce oxidative degradation.
Reconstitution: For biological use, prepare concentrated stock solutions in anhydrous DMSO or ethanol. Dispense single-use aliquots in amber vials/microtubes to avoid repeated opening and moisture ingress.
Freeze–thaw: Avoid repeated freeze–thaw of stock solutions. If freezing is used for long-term storage of solutions, aliquot to single-use volumes and keep protected from light; thaw at room temperature and mix thoroughly before use.
Stability monitoring: Inspect visually for discoloration or precipitation. For sensitive studies, verify integrity by LC–MS or NMR at intervals.
Research Use Note
For research use only (per Product Data). Consult the CoA/Spec Sheet and SDS for authoritative, lot-specific guidance on stability, packaging, and storage.
Structure and Identity
Overview: OAG is widely recognized in the literature as 1-oleoyl-2-acetyl-sn-glycerol, a membrane-permeable diacylglycerol (DAG) analog used as a biochemical tool compound.
Item-specific (from Product Data)
Product Name: OAG (SKU: O612450)
CAS: 84746-00-9
PubChem CID: 5353264
InChIKey: 288985 (as provided; appears truncated—refer to CoA/Spec Sheet for full identifier)
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 identity (for reference; not item specification)
Common chemical name: 1-oleoyl-2-acetyl-sn-glycerol (OAG)
Core scaffold: Glycerol backbone esterified at sn-1 with an oleoyl chain (C18:1, cis-Δ9) and at sn-2 with an acetyl group; sn-3 typically free hydroxyl (in many depictions), though positional notation follows the sn stereochemistry of glycerol.
Functional groups: Two ester linkages (acyloxy substituents), one secondary alcohol (if sn-3 free), one long-chain cis-alkenyl substituent.
2D description: A three-carbon glycerol backbone bearing at C1 a long hydrophobic oleoyl ester, at C2 a short acetyl ester, and at C3 a hydroxyl group; amphiphilic overall with a dominant hydrophobic tail.
Synthetic Utility
Limited as a general synthetic reagent.
Chemical reactivity (general): As a diacylglycerol analog, OAG contains two ester linkages and (typically) one free hydroxyl group. The molecule can participate in transesterification or acyl migration under basic or thermal conditions, but these are usually degradation pathways rather than productive synthetic transformations.
Niche applications: In lipid chemistry, OAG or related DAGs may be derivatized for probe development (e.g., fluorescent tags, photoaffinity groups) after introducing suitable handles via selective protection/activation strategies. Such derivatization is specialized and beyond routine synthetic workflows.
Retrosynthetic note: OAG is commonly prepared (literature) by regioselective acylation of protected glycerol derivatives, coupling oleoyl chloride or activated oleoyl esters at sn-1 and acetylation at sn-2, followed by deprotection to furnish the sn-defined product while minimizing acyl migration.
Bottom line: Choose OAG for biological assay utility rather than as a stoichiometric reagent or building block in general organic synthesis.
Target Specificity
Item-specific, from Product Data
No target, epitope, or biological binding specificity is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.
General literature context (not an item guarantee)
OAG is commonly used as a broad DAG mimetic engaging C1-domain–containing proteins, notably conventional and novel PKC isoforms. Specific isoform selectivity is typically modest and context dependent; membrane composition and local concentration strongly influence apparent selectivity.
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