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 long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
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Application Protocols
No manufacturer-validated application protocols are provided for this item.
General starting points (literature/good practice)
LC–MS/MS stock: Prepare 1–10 mM in LC–MS grade ethanol or DMSO under nitrogen; store in amber vials. Dilute to 1–1000 nM in mobile phase immediately before injection.
Cell-free biochemical assays: Prepare ≤100 mM DMSO stocks; final assay DMSO typically ≤0.5% v/v. Include a vehicle control at the same solvent concentration.
Hydrolysis to free acid: For generating RvD1 in situ, add 0.1–0.5 equiv LiOH in MeOH/H2O (9:1) at 0–4°C for minutes, monitor by LC–MS, and immediately neutralize.
GC–MS (derivatized): Convert hydroxyls to TMS ethers (BSTFA) and analyze with a low-oxygen carrier and deactivated liners/columns to minimize on-column oxidation.
Item-specific recommended dilutions, positive controls, or instrument parameters are Not specified for this item; refer to CoA/Spec Sheet and validate within your laboratory.
Biological Roles
General/literature context (no medical/clinical claims)
Resolvin D1 (RvD1) is a specialized pro-resolving mediator (SPM) biosynthesized from docosahexaenoic acid (DHA, ω-3) via lipoxygenase pathways. It features multiple hydroxylations and defined double-bond geometry/stereochemistry.
The methyl ester (RvD1-ME) is a chemically modified form where the carboxylic acid is esterified to a methyl group. This increases hydrophobicity and can aid stability/handling relative to the free acid. In biological systems, methyl esters can be hydrolyzed by esterases to release the parent acid; hydrolysis kinetics depend on the system and should be empirically verified.
Research utility: Used to probe SPM-related biochemical pathways, receptor interactions, and enzymatic conversions in vitro. Also used as a calibration/identification aid in lipid mediator omics workflows.
Structural implications: The trihydroxylated, highly unsaturated skeleton enables multiple hydrogen-bonding interactions while anchoring in lipid bilayers due to the long aliphatic chain—considerations relevant to membrane protein binding studies.
Item-specific biological data (target receptors, EC50/IC50, pathway activation): Not specified for this item; refer to CoA/Spec Sheet and primary literature. All uses are for research only.
Buffer Applications
Not typically applicable. RvD1-ME is a hydrophobic small molecule, not a buffering agent.
Practical notes
For aqueous assays, prepare concentrated stocks in DMSO or ethanol and dilute into buffered media with vigorous mixing; maintain final organic co-solvent at a low percentage compatible with your system (commonly 0.1–1% v/v).
To improve dispersion, consider carriers such as fatty-acid free BSA or nonionic surfactants at minimal levels validated for your assay.
Buffer recipes, pKa values, and buffering ranges are not relevant to this compound.
Green Alternatives
Context: RvD1-ME is a target analyte/research reagent, not a process solvent. “Green alternatives” therefore focus on greener handling solvents and workflows rather than replacing the compound itself.
Greener handling options (literature/general)
Prefer bio-derived solvents where possible: Ethyl acetate (bio-based), ethanol (fermentation-derived) in place of halogenated solvents.
Replace diethyl ether/THF: Use MTBE or CPME as less peroxide-prone ethers; however, all ethers can form peroxides—monitor accordingly.
Minimize solvent volume: Prepare concentrated stock solutions (e.g., 10–50 mM in DMSO/EtOH) and dilute at point of use to reduce waste.
Low-temperature, inert handling reduces byproduct formation, improving atom economy in protection/deprotection sequences.
Illustrative comparison (general)
Ethyl acetate vs DCM for extractions: Comparable partitioning for lipids; EtOAc is less toxic and has better environmental profile.
Heptane vs hexane: Heptane offers lower neurotoxicity concerns and similar nonpolar solvency.
Trade-offs
Ethanol and ethyl acetate can accelerate ester hydrolysis under basic conditions—control pH and exposure time.
CPME/MTBE have higher boiling points than diethyl ether, potentially lengthening solvent removal.
Item-specific environmental metrics (e.g., PMI, solvent selection guide scores): Not specified for this item; refer to CoA/Spec Sheet.
Pharmaceutical Uses
Scope: No therapeutic claims. Discussion limited to formulation/manufacturing context and analytical use.
General/literature context
Reference standard: RvD1-ME can serve as an analytical standard in method development and quality control for lipid mediator profiling by LC–MS/MS or GC–MS (after derivatization), aiding specificity and retention time assignment.
Formulation studies: As a lipophilic methyl ester, it may be used in preformulation screening to assess solubilization strategies (lipid vehicles, mixed micelles) or esterase-mediated conversion to the free acid, strictly in research settings.
Impurity/Degradation tracking: Useful as a comparator for monitoring autoxidation products (hydroperoxides, epoxides, isomers) in stress studies of ω-3 derived materials.
Regulatory/compendial status
Pharmacopeial monographs or excipient listings for RvD1-ME: Not specified for this item; refer to CoA/Spec Sheet.
Residual solvents, elemental impurities, and other GMP-related controls: Not specified for this item; not intended for human or veterinary use.
Note
This product is for research use only. Any application in manufacturing or clinical development requires appropriate qualification and regulatory assessment beyond the scope of this listing.
Physical Properties
Item-specific
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Moligand™ (see Quality & Grades tab).
Physical state: Typically an oily liquid or viscous oil at ambient temperature due to long-chain unsaturation.
Solubility: Practically insoluble in water; soluble in organic solvents (e.g., ethanol, methanol, acetonitrile, ethyl acetate, hexanes, toluene, DCM). High solubility in nonpolar and moderately polar aprotic media; dissolves readily in DMSO for biochemical assays.
Partitioning: Expected high logP (lipophilic) typical of long-chain polyunsaturated methyl esters.
Volatility: Low; not amenable to routine distillation without degradation; GC analysis often feasible for methyl esters but may require derivatization and careful temperature programs.
Stability: Susceptible to autoxidation and isomerization under light/air/heat due to multiple double bonds; stabilized by inert atmosphere, low temperature, and antioxidants.
Not specified for this item; refer to CoA/Spec Sheet.
Practical notes
Prepare solutions fresh, protect from light (amber glass), and minimize headspace oxygen to limit peroxide/hydroperoxide formation.
Quality and Grades
Item-specific
Grade/Purity: Moligand™.
Interpretation and implications
Moligand™ (general description): A screening/ligand-discovery oriented quality designation used for small-molecule libraries and chemical probes. Materials are typically suitable for target screening, binding assays, and exploratory medicinal chemistry. This grade emphasizes identity and utility in ligand-focused applications rather than ultra-trace impurity control needed for, e.g., environmental quantitation.
Documentation: For exact purity, residual solvent, stereochemical integrity, and assay method, Not specified for this item; refer to CoA/Spec Sheet.
UV/Fluorescence background: Not specified for this item; refer to CoA/Spec Sheet.
What this means for RvD1-ME
Appropriate for discovery workflows (e.g., biochemical assays, receptor profiling, lipid mediator research) where reliable identity and typical research purity are required.
If your application demands quantitative analytical standards (isotope dilution LC–MS) or pharmacopeial conformance, request a detailed CoA/Spec Sheet and consider analytical standard grade with certified assay/uncertainty.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If none are present, users may add antioxidant (e.g., 0.01% BHT) to working solutions as a laboratory practice; verify compatibility with your assay first.
Reaction and Applications
Research/application contexts (literature)
Analytical standard: RvD1-ME is commonly used as a reference standard in lipidomics (LC–MS/MS) to aid identification/quantitation of resolvin species; methyl ester can be a process control for derivatization or hydrolysis workflows.
Pro-resolving mediator research: Suitable as a chemical probe in receptor-binding/biochemical studies exploring specialized pro-resolving mediator (SPM) pathways. Avoid biological/clinical extrapolations without proper validation.
Hydrolysis to acid: The methyl ester is a convenient, more handleable form; base- or enzyme-catalyzed hydrolysis affords the corresponding free acid (RvD1), which is often the biologically relevant form.
Derivatization: The secondary alcohols enable esterification, carbonate/carbamate formation, or silylation (e.g., TMS ethers) for GC–MS volatility enhancement and protection during multistep synthesis.
Practical tips
Minimize oxidation: Work under nitrogen/argon; add 0.01% antioxidant to volatile solvents when compatible. Use amber vials and pre-chilled solutions for transfers.
LC–MS practice: Use metal-free flow paths when possible (PUFAs can adsorb to active metal sites). Add 0.1% formic acid for positive-mode adduct control; consider ammonium acetate for negative mode.
Work-up: Avoid strong bases, elevated temperature, and prolonged silica exposure to limit double-bond isomerization and dehydration.
Item-specific performance claims are not provided; consult primary literature and your method validation for conditions and expected outcomes.
Reaction Conditions
General laboratory conditions (literature guidance; not item-specific specifications)
Hydrolysis (methyl ester → free acid):
Basic: LiOH/NaOH/K2CO3 (1–2 equiv) in MeOH/H2O or THF/H2O at 0–25°C, minutes to hours; quench at low temperature, acidify to pH ~3, extract under inert atmosphere.
Enzymatic: Porcine liver esterase or lipases in buffered aqueous/organic biphasic systems at ambient temperature for milder conditions and stereochemical preservation.
Protection of triols: TBSCl/imidazole in DMF or pyridine at 0–25°C; or TBDPSCl for enhanced stability. Deprotection with TBAF (≤1 equiv portions, 0–10°C) to avoid elimination.
Silylation for GC–MS: BSTFA + 1% TMCS in anhydrous acetonitrile, 60–70°C, 15–30 min; protect from air/light.
Oxidation avoidance: Perform reactions under nitrogen/argon; include 50–200 ppm BHT in volatile solvents when compatible; use degassed, anhydrous solvents.
Chromatography: Silica gel pre-treated with 0.1–0.5% triethylamine can reduce acid-catalyzed isomerization; elute with hexanes/EtOAc mixtures at low light exposure.
Expected outcomes
Yields vary widely (50–90% typical for careful ester hydrolysis and protection steps in the lipid mediator class). Validate on small scale first.
Note
Numeric conditions are general literature ranges for polyunsaturated methyl ester triols; optimize for your setup and verify by LC–MS/NMR.
Safety and Handling
Item-specific hazard data
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations (literature/good practice)
Likely hazards: Long-chain polyunsaturated methyl esters are generally considered low acute toxicity but may cause skin/eye irritation. Autoxidation can generate peroxides/hydroperoxides that are irritants and may present additional hazards.
PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when handling powders/aerosols or volatile solvents.
Handling: Minimize exposure to air and light; keep containers tightly closed. Consider purging headspace with nitrogen/argon after opening.
First aid (overview; defer to SDS): Skin—wash with soap/water. Eyes—rinse with water for several minutes and seek medical attention if irritation persists. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Combustible organic liquid; avoid high heat sources.
Stability: Due to multiple double bonds, product is prone to peroxidation; test aged solutions for peroxides if relevant and discard if rancid odor/discoloration appears.
Always consult the product SDS for authoritative hazard, exposure limits, and response guidance.
Solvent Selection
Applicability: RvD1-ME is a highly lipophilic, polyunsaturated methyl ester. Solvent choice governs stability and assay performance.
General solvent guidance (literature)
Stock solutions: DMSO, ethanol, or isopropanol are convenient for assay stocks; ensure final solvent concentration is compatible with the bioassay or biochemical system.
Nonpolar media: Hexanes, heptane, cyclohexane, toluene are suitable for preparative handling or normal-phase chromatography.
Mid-polar aprotics: Ethyl acetate, MTBE, MTBE/hexane blends support extraction and silica chromatography while limiting peroxide exposure relative to ethers like THF.
Aqueous workup: Use co-solvents (e.g., 1–5% ethanol, 0.1–1% DMSO, or carrier proteins/detergents) to aid dispersion; avoid strong bases or acids unless hydrolysis is intended.
Polarity/miscibility (literature, qualitative)
Water: Immiscible, negligible solubility.
Alcohols: Miscible at typical stock concentrations; ethanol and methanol are common.
DMSO/DMF: Readily soluble; DMSO preferred for biotesting due to lower reactivity.
Comparisons
DMSO vs ethanol: DMSO maximizes solubility and minimizes volatility; ethanol may better mimic lipid environments and is easier to remove.
Hexanes vs toluene: Hexanes favor low-temperature, oxygen-limited handling; toluene offers higher solvating power but retains unsaturated compounds longer at elevated temps—risking oxidation.
Specifications (solubility numbers, dielectric constants) for this item are Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Item-specific
Storage Conditions: Room temperature (as listed).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/best practice)
Light/air sensitivity: Store in amber, airtight containers. After opening, consider purging headspace with nitrogen/argon. While the labeled storage is room temperature, many laboratories keep polyunsaturated lipids at 2–8°C or below for extended stability; assess according to your use horizon.
Working solutions: Prepare fresh, keep cold and protected from light during use. Avoid repeated freeze–thaw; aliquot stocks to single-use vials.
Solvent recommendations: DMSO or ethanol for concentrated stocks; ensure compatibility with downstream assays. Avoid basic aqueous media unless hydrolysis is intended.
If supplied neat: Dissolve to desired concentration using anhydrous solvent under inert gas.
If supplied in solution: Use as provided; verify solvent composition on the label/CoA.
Always consult the product label and CoA/Spec Sheet for definitive storage and handling instructions.
Research Use Note: For research use only.
Structure and Identity
Item-specific (from Product Data)
SKU: R613338
Product Name: RvD1-ME
CAS: R613338 (as listed)
CID: 71519431
InChIKey: 408366 (as listed)
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.
General/literature description (non-spec)
RvD1-ME commonly denotes the methyl ester of Resolvin D1, a polyunsaturated lipid mediator derived from docosahexaenoic acid (DHA).
Structural features (literature): C22 polyunsaturated backbone (six Z/E-configured double bonds) bearing multiple secondary alcohols (trihydroxylated) and a terminal methyl-esterified carboxylate. Stereochemistry at several centers (e.g., 7S,8R,17S in canonical RvD1) is typically defined in the natural mediator; methyl ester retains the configuration.
2D structure (verbal): An extended ω-3 fatty acyl chain containing conjugated/nonconjugated diene/triene segments, with three hydroxyl substituents along the chain and a methyl ester at the carboxylate terminus; overall highly unsaturated and amphiphilic (lipophilic chain with polar OH groups).
Notes
Exact stereochemical assignment, SMILES, and InChIKey for this catalog item are Not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
General synthetic perspectives (literature)
Protecting group strategies: The three secondary alcohols can be transiently masked as silyl ethers (TMS/TBS/TIPS) or carbonate esters to enable selective transformations on the polyunsaturated backbone.
Functional group interconversions: The methyl ester provides a handle for hydrolysis (to free acid), transesterification (e.g., ethyl, benzyl), or activation (mixed anhydride/acid chloride) under mild conditions compatible with sensitive alkenes.
Stereochemical integrity: Double-bond geometry and chiral centers are prone to isomerization under acid/base and heat; reactions should be conducted at low temperature with non-nucleophilic bases and short residence times.
Oxidation chemistry: Allylic oxidations or epoxidations can generate higher-order mediators (e.g., diols/triols/epoxides) but must be controlled to avoid overoxidation; oxygen-free solvents and antioxidants help maintain selectivity.
Analytical derivatization: Silylation (BSTFA, MSTFA) of hydroxyls enhances GC–MS volatility; picolinyl ester formation (after deprotection) can aid tandem MS structural elucidation.
Utility in retrosynthesis
RvD1 frameworks are assembled from DHA or shorter ω-3 building blocks via regio- and stereoselective oxygenation and coupling strategies; having the methyl ester simplifies purification and storage of advanced intermediates.
Target Specificity
Not applicable to this product class. RvD1-ME is a small molecule reagent, not an antibody or affinity reagent with defined antigen/epitope or isotype characteristics.
Any receptor-binding or target engagement data for this specific item are Not specified for this item; refer to CoA/Spec Sheet and primary literature.
For biochemical assays, determine target selectivity empirically using appropriate controls and orthogonal readouts.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
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