11,12-DiHETrE-d - ≥99% , CAS No.D1440061

CAS: D1440061 Cat. No.: D1440061 Summenformel: C₂₀H₂₃D₁₁O₄ Molekulargewicht: 349.55

QUALITÄT & REINHEIT ≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

11,12-DiHETrE-d 11 is the deuterium labeled 11,12-DiHETrE.

Spezifikationen

Spezifikationen & Reinheit

≥99%

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥99%

Namen und Kennungen

Molekulargewicht

349.55

Application Protocols

No manufacturer-validated application protocols were provided for this item. The following are general research protocols for this compound class; adapt and validate for your system.

1. Preparation of stock solutions (general)

• Warm to room temperature briefly. Under N2/Ar, dissolve to 1–10 mM in anhydrous DMSO or ethanol. Optionally add 0.01% BHT. Aliquot into amber vials, purge headspace, and store at −20 °C.

2. LC–MS/MS quantitation in plasma/tissue (general)

• Spike samples with an internal standard (use a deuterated 11,12‑DiHETrE if applicable) prior to extraction.
• Protein precipitation with 3–4 volumes of cold acetonitrile containing 0.1% acetic acid; vortex, chill, and centrifuge.
• SPE (optional): Condition C18 cartridge; load supernatant; wash with water; elute with methanol. Evaporate under N2 at ≤30 °C; reconstitute in 50:50 water:methanol for LC–MS.
• Chromatography: C18, water/methanol gradient with 0.01–0.1% formic acid or ammonium acetate. Detect in negative ESI using validated MRM transitions.

3. sEH enzyme assay (general)

• Incubate enzyme with 11,12‑EET substrate in HEPES buffer (pH ~7.4) at 37 °C; quench at time points with cold acetonitrile; quantify 11,12‑DiHETrE formation by LC–MS with an internal standard.

Notes

• Adsorption losses can be significant; use low-bind or silanized glassware, and pre-rinse with standard solution.
• Validate linearity, recovery, and matrix effects per your laboratory’s SOPs. Adjust protocols if your lot is a salt or formulated solution.

Biological Roles

Background (literature/general)

• 11,12‑DiHETrE is a diol metabolite derived from the hydrolysis of 11,12‑epoxyeicosatrienoic acid (11,12‑EET), a cytochrome P450 epoxygenase product of arachidonic acid. Soluble epoxide hydrolase (sEH; EPHX2) catalyzes this conversion in many tissues.
• As a member of the oxylipin/eicosanoid family, 11,12‑DiHETrE participates in complex signaling networks influencing ion transport, vascular tone, inflammation pathways, and cellular proliferation in model systems (research context).
• The molecule’s amphiphilicity and vicinal diol functionality influence membrane interactions and enzymatic recognition.

Research significance

• Used as a standard to track flux through the EET–DiHETrE axis, enabling assessment of sEH activity and P450 epoxygenase function in tissue extracts.
• Incorporated into in vitro assays probing transporter interactions and metabolic stability (e.g., β‑oxidation, conjugation to glucuronides/sulfates).
• When isotopically labeled ("-d"), serves as an internal standard to normalize extraction efficiency and matrix effects in quantitative bioanalysis.

Caveats

• Biological effects are highly context-dependent; avoid extrapolating in vitro findings to clinical claims. Binding partners, receptor targets, and downstream responses can differ by species, cell type, and experimental conditions.

Note

• No item-specific biological testing data are provided for this lot. Users should validate concentration ranges, exposure times, and carriers appropriate to their model system.

Buffer Applications

This compound is not a conventional buffering agent. It does not provide defined pH buffering capacity in the typical laboratory pH range.

Practical handling in aqueous buffers (general guidance)

• To introduce 11,12‑DiHETrE into aqueous systems, prepare a concentrated stock in DMSO or ethanol and dilute into the target buffer while vortexing. Keep the final organic percentage low (e.g., ≤1% v/v) to avoid perturbing the system.
• For improved dispersion and reduced adsorption, include fatty‑acid–free BSA (0.1–1% w/v) or a minimal amount of nonionic surfactant if compatible with your assay.
• Maintain cold, oxygen-reduced conditions to limit autoxidation; protect from light.

Common buffer systems used alongside this analyte (assay context)

• Enzyme assays: HEPES or phosphate-buffered saline (pH 7.2–7.5) with Mg2+ or cofactors as required by the enzyme system (e.g., sEH assays). Specific recipes vary by protocol and are not item-specific.

Note: No item-specific buffer formulations or pKa data are provided; tailor buffer selection to the biological system and analytical method.

Green Alternatives

Solvent and process choices offer the main opportunity for greener handling of lipidic standards.

Greener choices (general guidance)

• Prefer ethanol or isopropanol over chlorinated solvents where feasible for stock preparation and cleaning.
• Use acetonitrile in place of methylene chloride for extractions when compatible with your method; combine with MTBE or ethyl acetate for phase transfer.
• For LC, aqueous mobile phases with methanol can substitute for acetonitrile in some methods, though selectivity may differ.

Comparison (literature/practice)

• Ethanol vs DMSO: Ethanol is biorenewable and lower hazard but offers lower solubilizing power; DMSO provides higher solubility and stability but is less volatile and can complicate some bioassays.
• Ethyl acetate vs DCM: Ethyl acetate is biodegradable and less toxic; however, it may extract more matrix components and has higher water miscibility.

Operational improvements

• Minimize solvent volume by preparing concentrated stocks and using low-dead-volume glassware.
• Implement inert-atmosphere handling to extend shelf-life, reducing waste from degraded material.
• Use amber glass and cold-chain logistics to avoid product loss and repeated shipments.

Note

• No changes to the compound itself are proposed; green optimization focuses on solvent selection and workflow. Verify that greener solvents do not compromise analyte recovery, ionization efficiency, or chromatographic resolution for your validated methods.

Pharmaceutical Uses

This product is supplied for research use only. No clinical or therapeutic uses are claimed or supported.

Relevant roles in pharmaceutical R&D (general)

• Bioanalytical standard: 11,12‑DiHETrE (and isotopically labeled analogs denoted by “-d” where applicable) are employed as reference standards and internal standards in LC–MS/MS methods for nonclinical PK/PD, tissue distribution, and metabolism studies of the epoxide hydrolase pathway.
• Method development: Used to optimize extraction, chromatographic separation, and MRM transitions for oxylipin panels; assists in system suitability testing and assay calibration.
• Stability studies: Probe compound for evaluating sample stabilization strategies (antioxidants, chelators, temperature control) during preanalytical handling of lipid mediators.

Formulation/excipient context

• Not used as an excipient. The compound’s propensity for oxidation and adsorption makes it unsuitable for general formulation roles.

Compliance and documentation

• For regulated studies, use lots with fully traceable CoA documentation including purity, isomeric composition, and (if applicable) isotopic enrichment. Establish and document reference standard qualification per your QA procedures.

Note: No pharmacopeial monograph or item-specific regulatory status is provided; confirm suitability with your quality unit before use in GLP/GMP contexts.

Physical Properties

Item-specific specifications

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

Typical physical properties (literature/general for 11,12‑DiHETrE class; not item specifications)

• Phase at ambient: Viscous oil or low-melting solid; many eicosanoid diols are oils at room temperature.
• Solubility: Practically insoluble in water; soluble in polar organic solvents (methanol, ethanol, acetonitrile) and highly soluble in aprotic solvents (DMSO, DMF, dichloromethane, ethyl acetate). Often formulated as ethanol or DMSO stock solutions for bioassays.
• pKa: Carboxylic acid pKa typically ~4.5–5.0 for long-chain fatty acids; vicinal diol hydroxyls are much less acidic (literature).
• LogP: High lipophilicity expected (logP > 4) due to C20 chain (literature).
• Density, refractive index, BP/MP: Not widely tabulated for specific DiHETrE regioisomers; values depend on isomeric purity and counterion/salt state.

Handling implications (general)

• Amphiphilic character leads to adsorption losses on plastic; glass vials with silanized inserts can improve recovery.
• The vicinal diol and polyunsaturation can undergo oxidation; minimize exposure to air, light, and elevated temperature; consider including an antioxidant (e.g., 0.01% BHT) in organic stock solutions for stability during use (literature practice).

Notes

• For precise numeric data applicable to this lot (e.g., exact MW for any isotopic labeling), consult the CoA/Spec Sheet.

Quality and Grades

Item-specific quality details

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for purity, isomeric composition, and any isotopic labeling pattern.

Context for this compound class (general guidance)

• Research-use eicosanoid standards are commonly supplied at high chemical purity with defined regioisomer content. If deuterated ("-d"), the CoA typically reports isotopic enrichment (atom% D) and mass shift (e.g., d4, d8). Confirm labeling site(s) and enrichment for accurate LC–MS quantitation.
• Stabilizers: Some lots include trace antioxidants (e.g., BHT) or are formulated in ethanol. Presence/absence of stabilizers affects UV background and MS performance; consult the CoA.
• Analytical characterization: Suppliers often provide HPLC/UPLC purity, NMR identity, and HRMS. For quantitative work, obtain the exact concentration for solution-formulated standards (gravimetric or ampouled calibrant).

Practical implications

• For LC–MS bioanalytical assays, isotopically labeled analogs serve as internal standards to correct matrix effects and recovery variability. Match the analyte’s retention and ionization behavior as closely as possible. If this listing is unlabeled, consider ordering the labeled counterpart; if labeled, confirm it is the correct regioisomer (11,12- vs 14,15-).

Documentation

• Always defer to the lot-specific CoA/SDS for acceptance criteria, impurity profiles, water content, and recommended analytical methods. Do not assume specifications without verification.

Reaction and Applications

Research applications (general for 11,12‑DiHETrE)

• Biochemical studies: Substrate/product in cytochrome P450 epoxygenase/sEH pathways; used to investigate arachidonic acid metabolism, signaling, and enzyme kinetics in cell-free systems.
• Analytical standard: Applied as a reference or internal standard in LC–MS/MS quantitation of eicosanoids in biological matrices. If the "-d" indicates deuteration, it can serve as an isotopically labeled internal standard to correct for matrix effects and process losses.
• Receptor/pharmacology probes: Utilized to study DiHETrE actions on ion channels and vascular tone in ex vivo systems (literature; research context only).

Chemical reactivity/derivatization (general)

• Esterification: Conversion to methyl or pentafluorobenzyl (PFB) esters enhances GC–MS volatility and sensitivity; typical reagents include diazomethane (caution) or BF3–MeOH for methyl esters; PFBBr for PFB esters.
• Silylation: Diol and acid can be protected as TMS ethers/esters (e.g., BSTFA + 1% TMCS) to improve GC behavior.
• Oxidation/dehydration: Periodate cleaves vicinal diols; acid-catalyzed dehydration can form epoxides or allylic rearrangements; these are generally avoided during handling.

Practical tips

• Work cold and under inert atmosphere; include antioxidant when appropriate.
• Use glass syringes/vials to minimize adsorption; pre-rinse surfaces with a small amount of concentrated standard.
• For enzymology with sEH, monitor conversion to DiHETrE by LC–MS using MRM transitions validated for the specific regioisomer; include a labeled internal standard when available.

Note: No manufacturer application text was provided; the above reflects common research uses for this compound class.

Reaction Conditions

General conditions drawn from literature/practice for handling and derivatizing 11,12‑DiHETrE (not item-specific specifications):

• Esterification (methyl ester): BF3–MeOH (10–14% w/w in MeOH), 0–50 °C, 10–60 min; or diazomethane in ether at 0–25 °C (caution). Quench and extract into hexane/ethyl acetate for GC.
• PFB ester formation: PFBBr (5–20 eq) with DIPEA or K2CO3 in acetonitrile/DMF, RT–50 °C, 30–120 min; work up under low light and inert atmosphere.
• Silylation for GC: BSTFA + 1% TMCS (or MSTFA), 60–70 °C for 30–60 min in anhydrous acetonitrile or pyridine.
• LC–MS analysis: Reverse-phase C18; water/MeOH or water/ACN with 0.01–0.1% acetic or formic acid (or ammonium acetate 2–5 mM) to aid ionization; column temp 30–45 °C. Monitor [M−H]− in negative ESI for free acid; collision energies tuned empirically.
• Enzyme assays (sEH): Tris or HEPES buffer, pH ~7.4, 25–37 °C; substrate micromolar range; quantify formation of DiHETrE from EETs (or vice versa when testing reverse chemistry) by LC–MS. Include appropriate controls and internal standards.

Best practices

• Degas and inert‑gas blanket reaction vials; use amber glassware. Limit oxygen and light exposure to reduce autoxidation.
• Validate recovery by spiking matrix with a labeled internal standard (if “-d” denotes deuteration) prior to extraction.

Note: Specific yields and kinetics depend on isomer, stereochemistry, and method; optimize for your system.

Safety and Handling

Authoritative safety information for this product has not been specified in the provided data. Always consult the product SDS before handling.

Item-specific safety fields

• 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 for lipidic carboxylic acids (informational)

• PPE: Use lab coat, safety glasses, and appropriate disposable gloves (nitrile). Avoid inhalation of aerosols and skin contact.
• Engineering controls: Handle solutions in a chemical fume hood; avoid generating mists. Use amber or foil-wrapped glassware to limit light exposure.
• Incompatibilities: Strong oxidizers can degrade polyunsaturated chains; strong bases can cause saponification; dehydrating agents/strong acids may dehydrate diols.
• Stability risks: Polyunsaturated lipids are susceptible to autoxidation; work under inert atmosphere (N2/Ar) when preparing concentrated stocks; keep cold and protected from light.
• First aid overview: In case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth and seek medical attention. Follow SDS guidance.
• Waste disposal: Collect organic solutions as halogen-free organic waste unless halogenated solvents are used. Dispose according to institutional and regulatory requirements.

Shipping/storage

• Shipped cold: Ice chest + ice pads (per Product Data).
• Storage: Store at −20 °C (per Product Data).

Solvent Selection

Solubility and solvent choice (general for 11,12‑DiHETrE analogs)

• Water: Very low intrinsic solubility; use co-solvents or carrier proteins for aqueous work.
• Alcohols: Methanol and ethanol dissolve the acid and are LC–MS compatible. Ethanol (≤1% v/v final) is commonly used for cell-free assays.
• Aprotic polar: DMSO and DMF provide high solubility; DMSO stocks (1–50 mM) are typical for small-volume dosing.
• Moderately polar aprotic: Acetonitrile and ethyl acetate are good for sample prep and chromatography.
• Nonpolar: Hexanes/toluene dissolve the hydrocarbon chain but may be less suitable for handling the free acid without a small polar co-solvent.

Formulation tips (literature/practice)

• Prepare concentrated stocks in DMSO or ethanol under inert gas. Aliquot in amber vials to minimize freeze–thaw and photodegradation.
• For aqueous buffers, dissolve in a small volume of DMSO/ethanol, then dilute into buffer containing 0.1–1% fatty-acid–free BSA or 0.05–0.1% nonionic surfactant (e.g., Tween‑20) if compatible with the assay.

Choosing among alternatives

• For LC–MS sample workup, acetonitrile protein precipitation and SPE elution with methanol/MTBE are common for eicosanoids; select based on downstream detection.
• If oxidation is a concern, use oxygen-free solvents (sparged with N2/Ar) and include trace antioxidant in working stocks; avoid peroxide-containing ethers.

Note: No item-specific solvent specs are provided; tailor solvent systems to your method validation.

Storage and Reconstitution

Item-specific storage conditions

• Storage: Store at −20 °C (per Product Data).
• Shipping: Ice chest + ice pads (per Product Data).

General best practices for this compound class

• Light/oxygen sensitivity: Protect from light; purge vials with inert gas (N2/Ar) after opening. Minimize headspace and avoid repeated freeze–thaw cycles by aliquoting upon first thaw.
• Container choice: Use amber glass vials with PTFE-lined caps. Avoid prolonged contact with plastics to reduce adsorption.
• Reconstitution: For neat material, allow vial to equilibrate to room temperature in a desiccated environment. Dissolve in anhydrous DMSO, ethanol, or methanol to prepare concentrated stocks (e.g., 1–10 mM). Filter through PTFE (0.2 µm) only if necessary; adsorption may occur.
• Stability in solution: Keep working solutions cold and under inert atmosphere. For extended storage (>1–2 weeks), maintain at −20 °C or below; consider adding a trace antioxidant (e.g., 0.01% BHT) if compatible with downstream assays.
• Documentation: Record preparation date, solvent, concentration, and any stabilizers on the vial.

Notes

• Appearance, exact solubility, and concentration of any provided solution formulations are not specified for this item; refer to the CoA/Spec Sheet.
• Research use only; not for human or veterinary use.

Structure and Identity

Brief overview: 11,12-DiHETrE is the 11,12-dihydroxyeicosatrienoic acid regioisomer formed by hydrolysis of 11,12-EET (an arachidonic acid epoxide). The suffix "-d" in the catalog name often denotes an isotopically labeled (deuterated) analog; verify exact labeling on the CoA.

Item-specific identifiers

• 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.
• CAS: D1440061 (catalog placeholder; not a CAS RN)

Structural features (literature/general)

• Core scaffold: C20 polyunsaturated fatty acid bearing a terminal carboxylic acid and a vicinal diol at C11–C12.
• Unsaturation: Three remaining double bonds (trienoic) typical of the arachidonate backbone after epoxide hydrolysis; double-bond configurations in natural material are commonly cis (Z) (literature).
• Functional groups: Carboxylic acid (–CO2H), vicinal 1,2-diol (–CHOH–CHOH–), isolated C=C bonds.
• Stereochemistry: Diol centers may be formed with defined relative/absolute configuration depending on biosynthesis or synthesis route; standards may be racemic or enantioenriched (literature—confirm with CoA if stereochemistry is specified).

2D structure in words

• A 20‑carbon chain terminating in a carboxylate at C1; internal double bonds distributed along the chain; at positions 11 and 12 the epoxide-derived carbons are hydrated to give vicinal secondary alcohols (–CH(OH)–CH(OH)–), producing a flexible amphiphilic lipid with a polar head (CO2H + diol) and hydrophobic tail.

Synthetic Utility

As a functionalized long-chain lipid, 11,12‑DiHETrE offers several handles for derivatization and method development (general/literature):

Functional group transformations

• Carboxylic acid: Esterification (Me, Et, PFB) for GC–MS; amide coupling to generate probes or immobilized analogs; formation of stable isotope-labeled esters for tracer studies.
• Vicinal diol: Protection as acetonide or silyl ethers; selective oxidation (e.g., periodic acid cleavage) for structural elucidation; formation of cyclic carbonates.
• Alkenes: Epoxidation (mCPBA) or dihydroxylation (OsO4) to map double-bond positions; hydrogenation to saturated analogs for control experiments.

Analytical derivatization

• Trimethylsilylation (BSTFA + 1% TMCS, 60–70 °C, 30–60 min) commonly enhances GC volatility and stability of hydroxy and acid functionalities.
• PFB ester formation (PFBBr/DIPEA, room temperature to 50 °C) boosts negative‑ion GC–MS and LC–MS sensitivity for eicosanoids.

Retrosynthetic value

• Serves as a reference for the regiochemical outcome of hydrolysis of 11,12‑EET; helpful in validating synthetic routes to specific DiHETrE stereoisomers via Sharpless epoxidation/hydrolysis or SN2′ strategies on allylic precursors.

Caveats

• Avoid strong acids/bases during workup to prevent dehydration, isomerization, or saponification. Conduct transformations under inert atmosphere with antioxidant when feasible.

Note: No item-specific synthetic grade or impurity profile is provided; verify suitability before use in synthesis.

Target Specificity

Not applicable to this product type. This listing is a small-molecule lipid standard, not a biological macromolecule or antibody. No antigen, clone, isotype, or species reactivity data apply.

Research context (general)

• In biochemical studies, 11,12‑DiHETrE is often examined as a product of soluble epoxide hydrolase (EPHX2) acting on 11,12‑EET; however, this reflects pathway context, not target binding specificity in the immunochemical sense.

For any binding assays or receptor studies, users should establish target engagement independently and not infer specificity from this catalog entry.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is D1440061, the molecular formula is C20H23D11O4, and the molecular weight is 349.55 g/mol.

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.