(±)11(12)-EET methyl ester - A solution in ethanol , CAS No.73799-06-1

CAS: 73799-06-1 Cat. No.: E342849 분자식: C₂₁H₃₄O₃ 분자량: 334.5

GRADE & PURITY A solution in ethanol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

개요

Biosynthesized in rat and rabbit liver microsomes by CYP450. Has been shown, along with (±)8(9)-EET, to play a role in the recovery of depleted Ca|2+|pools in cultured smooth muscle cells. It can be readily hydrolyzed to the free acid as needed.

Specifications

사양 및 순도

A solution in ethanol

보관 조건

Store at -20°C

배송

Ice chest + Ice pads

이 제품은 콜드 체인 배송이 필요합니다.지상 및 기타 경제 서비스는 사용할 수 없습니다.

이름과 식별자

• 정식 스마일: CCCCCC=CCC1C(O1)CC=CCC=CCCCC(=O)OC
• IUPAC Name: methyl (5Z,8Z)-10-[3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoate
• InChIKey: DHUPCTVGLDZJCY-VYHOSFGSSA-N
• INCHI: 1S/C21H34O3/c1-3-4-5-6-10-13-16-19-20(24-19)17-14-11-8-7-9-12-15-18-21(22)23-2/h7,9-11,13-14,19-20H,3-6,8,12,15-18H2,1-2H3/b9-7-,13-10-,14-11-
• 이성체 SMILES: CCCCC/C=C\CC1C(O1)C/C=C\C/C=C\CCCC(=O)OC
• 분자량: 334.5
• Reaxy-Rn: 5288798
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5288798&ln=

Application Protocols

No vendor-validated application protocols are provided for this item. General practices used by researchers working with EET methyl esters include (literature/general):

• Stock preparation: Dissolve in anhydrous ethanol or DMSO to prepare concentrated stocks (e.g., 1–50 mM depending on solubility). Vortex and, if needed, warm gently to room temperature. Filter through PTFE syringe filters for particulate removal.
• Dosing into aqueous systems: Add stock dropwise with vigorous mixing to pre-warmed buffer or media; final solvent typically kept ≤0.1–0.5% v/v. Include carrier proteins (e.g., 0.1–1% BSA) when appropriate to reduce adsorption and improve dispersion.
• Enzymatic assays (e.g., sEH): Pre-equilibrate enzyme and substrate; maintain pH 7.4, 25–37°C; terminate reactions with cold ACN/MeOH and analyze by LC–MS/MS.
• Sample stability: Work under low light and inert atmosphere; minimize time at ambient temperature; add antioxidant if compatible with downstream detection.

These are non-binding suggestions for research use only. Optimize conditions for your specific system.

Biological Roles

EETs (epoxyeicosatrienoic acids) are endogenous cytochrome P450 epoxygenase metabolites of arachidonic acid (literature). The methyl ester is a non-ionizable, membrane-permeable analog commonly used for research.

• Origin and metabolism (literature/general):
  • 11,12-EET is produced by CYP2C/CYP2J family epoxygenases from arachidonic acid. It is further metabolized by soluble epoxide hydrolase (sEH) to 11,12-dihydroxyeicosatrienoic acid (11,12-DHET).
  • Esterification to the methyl ester does not occur in vivo; it is a research tool that mimics hydrophobicity and improves handling.
• Biochemical activities (literature/general, no clinical claims):
  • EETs act as lipid mediators influencing ion channels, GPCR-like targets, and intracellular signaling; they can modulate vascular tone, cell proliferation/migration, and inflammation pathways in model systems.
  • The epoxide functionality is central to recognition and metabolism by sEH; blocking hydrolysis (e.g., by inhibitors) alters signaling lifetimes.
• Experimental utility:
  • The methyl ester increases stability against non-enzymatic hydrolysis, facilitates incorporation into membranes or delivery vehicles, and simplifies LC–MS quantitation.

Caveats

• Stereochemistry can affect biological interactions; this item is racemic (±) at the epoxide center(s). If enantioselectivity matters, consider enantiopure materials.
• Vehicle effects (EtOH/DMSO) and protein binding (e.g., albumin) significantly impact apparent potency and distribution; control for these in experimental design.

This section summarizes general biological roles of EETs; it does not imply therapeutic use.

Buffer Applications

This compound is a hydrophobic lipid ester and is not used to prepare classical aqueous buffer systems. For biochemical assays, it may be dosed into buffers via a co-solvent (e.g., EtOH or DMSO) and delivered with carriers such as BSA or cyclodextrins to improve dispersion (general guidance). For practical handling in aqueous media, see Solvent Selection and Storage & Reconstitution.

Green Alternatives

While the substance itself is the target analyte/reagent, greener choices can be made around solvents and workup (literature/general):

Comparison of common media for handling/transforming EET methyl esters:

• Ethyl acetate vs dichloromethane
  • Greener option: Ethyl acetate (renewable origins possible, biodegradable, lower toxicity)
  • Tradeoffs: Slightly higher polarity; may co-elute impurities differently on silica; higher boiling point can aid or hinder concentration depending on setup.
• 2-MeTHF vs THF/Et2O
  • Greener option: 2-MeTHF (bio-based, better safety profile, forms fewer peroxides than Et2O)
  • Tradeoffs: Different solvation may affect epoxide-opening selectivity and rates; water content must be controlled for hydrolysis-sensitive operations.
• Supercritical CO2 for extractions vs hexane
  • Greener option: scCO2
  • Tradeoffs: Requires specialized equipment; may not solubilize strongly polar additives.

Good practices

• Use micro-scale reactions and high-concentration stocks to reduce solvent volumes.
• Employ inert-atmosphere storage and amberware to reduce need for stabilizers/antioxidants.
• Optimize chromatography to shorter columns and greener eluents (heptane/EtOAc) instead of halogenated solvents.

Note: These are general sustainability guidelines surrounding the handling and synthesis involving lipid epoxides; the molecule itself has no “alternative” if it is your study target.

Pharmaceutical Uses

No pharmacopeial grade or excipient role is specified for this item. The product is labeled for research use only.

General formulation context (literature/general):

• EET methyl esters are sometimes used as research tools in preformulation or delivery studies to probe lipid mediator stability, permeability, and metabolism. Vehicles can include ethanol/PEG mixtures, lipid emulsions, or liposomes for in vitro/in vivo model work.
• Due to susceptibility to oxidation and isomerization, formulations often incorporate antioxidants, inert headspace, and light protection during preparation and storage.

Item-specific regulatory/compendial status, residual solvent limits, or excipient monographs: Not specified for this item; refer to CoA/Spec Sheet. No therapeutic claims are made or implied.

Physical Properties

Item-specific specifications are not provided for this listing; consult the CoA/Spec Sheet for authoritative values. The following are literature/general characteristics of EET methyl esters and closely related eicosanoid methyl esters.

• Physical state: typically a colorless to pale yellow, viscous oil (literature, lipid methyl esters)
• Molecular weight: ~334.49 g/mol (C21H34O3; literature/computed)
• Boiling point: high; prone to thermal decomposition before true boiling under ambient pressure (literature). Distillation, if necessary, is performed under high vacuum at low bath temperature.
• Melting point: often liquid at room temperature due to multiple unsaturations (literature).
• Density: ~0.9–0.95 g/mL at 20–25°C (typical for long-chain unsaturated methyl esters; literature/general).
• Refractive index: elevated (nD ~1.47–1.49) typical for PUFA methyl esters (literature/general).
• Solubility: insoluble in water; soluble in nonpolar and moderately polar organic solvents (hexane, dichloromethane, ethyl acetate, toluene) and miscible with polar organics like ethanol, acetonitrile, and DMSO (literature).
• Lipophilicity: high; expected clogP > 5 (literature/computational expectation for C21 ester with three C=C and an epoxide).
• pKa: not applicable (no titratable groups in the methyl ester form).

Item-specific values (water content, peroxide value, UV cutoff, metal limits): Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

Context and implications (general guidance for lipid mediators):

• Research-use materials: This product is labeled for research use only. It is intended for analytical standards, biochemical assays, receptor/pharmacology exploration, or synthetic transformations, not for human or veterinary use.
• Purity metrics: For eicosanoid methyl esters, purity is commonly established by GC-FID/GC–MS and/or HPLC-UV/MS. If optical/stereochemical purity is relevant, chiral/positional isomer analysis may be reported. For this racemic listing, enantiomeric excess is not applicable.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. In general, unsaturated lipids may be supplied under inert gas in amber vials; trace antioxidant may be used in some catalogs. Users should verify compatibility with their assays.
• UV background: Not specified for this item. Polyunsaturated chains absorb weakly above 200–220 nm; epoxide does not add strong chromophores (literature/general). For LC-UV applications, MS or derivatization may offer improved sensitivity.

Documentation

• For exact specifications (assay method, impurity profile, residual solvents, stabilizers, water/peroxide indexes), consult the item’s CoA/Spec Sheet.

Reaction and Applications

Use domains for (±)11(12)-EET methyl ester span chemical biology, lipidomics, and synthetic organic chemistry.

• Chemical biology/biochemistry (literature/general):
  • Serves as a stable, membrane-permeable analog of 11,12-EET for receptor and signaling studies; racemate avoids stereochemical bias when chirality is not central.
  • Employed as an internal or external standard in LC–MS lipidomics after appropriate calibration.
  • Useful for probing metabolic conversions (e.g., soluble epoxide hydrolase, sEH) to vicinal diols (11,12-DHET methyl ester) in vitro.
• Synthetic applications (literature/general):
  • Epoxide reactivity: nucleophilic ring opening to give regio-/stereodefined diols; Lewis acid or base catalysis enables selective transformations.
  • Hydrolysis: conversion to the corresponding free acid (11,12-EET) under mild basic or enzymatic conditions for downstream coupling (amide/ester formation).
  • Functionalization: selective hydrogenation of C=C, epoxide rearrangements, or tagging (e.g., fluorophores/biotin) after partial reduction/derivatization.

Practical tips:

• Minimize oxygen, light, and heat to prevent autoxidation/isomerization.
• For sEH assays, control pH and co-solvent composition; monitor conversion by LC–MS using multiple reaction monitoring of characteristic fragments (general guidance).
• When performing epoxide opening, consider neighboring double bonds: soft nucleophiles and lower temperatures favor better selectivity; quench carefully to avoid transesterification.

Reaction Conditions

General literature conditions for typical transformations of 11,12-EET methyl ester and related lipid epoxides (users should optimize for scale and selectivity):

• Hydrolysis to free acid:
  • Conditions: MeOH/H2O with LiOH or NaOH (0.05–0.2 M base), 0–25°C, 0.5–2 h; monitor by LC–MS or TLC. Acidify to pH ~3 and extract. Avoid strong base or elevated temperatures to prevent epoxide opening/isomerization.
• Epoxide ring opening to 11,12-diol (DHET methyl ester):
  • Acid-catalyzed: Catalytic BF3·OEt2 or p-TsOH in dry CH2Cl2/MeOH at 0–25°C yields trans- or cis-diols depending on conditions; quench promptly.
  • Nucleophilic: Primary amines/thiols/alcohols with catalytic Lewis acid (Ti(OiPr)4) in toluene or CH2Cl2 at 0–25°C; 1–6 h.
  • Aqueous/biological: sEH-catalyzed hydrolysis in buffered media (pH 7.4) at 25–37°C; rate depends on enzyme prep and co-solvent.
• Selective hydrogenation of C=C:
  • Pd/C (1–10 wt%), H2 (1 atm), EtOAc/EtOH at 0–25°C; minutes to hours. Protect epoxide by low temperature and short exposure; alternative catalysts (Rh/Al2O3) can improve selectivity.
• Derivatization/tagging (after saponification):
  • Amide formation with HATU/DIPEA in DMF or EDC/NHS in DMF/DCM at 0–25°C; 1–12 h.

Typical outcomes (literature): good to excellent conversions if oxygen/light are excluded and silica exposure is minimized. Always validate regio-/stereochemistry by NMR and MS.

Safety and Handling

Hazard classification for this specific item is not provided; always consult the product SDS for authoritative safety information.

General safety considerations for epoxide-bearing, polyunsaturated lipid esters (literature/general):

• Potential hazards: May cause skin/eye irritation; hydrocarbon-like narcotic effects possible upon inhalation of concentrated vapors/aerosols. Epoxide moiety is electrophilic and can react with nucleophiles; handle to minimize exposure.
• GHS information: Not specified for this item; refer to SDS.
• Pictograms/H-statements: Not specified for this item; refer to SDS.

Handling

• Work in a fume hood; avoid aerosol formation. Use inert atmosphere (N2/Ar) and subdued light; polyunsaturated lipids are prone to autoxidation.
• PPE: lab coat, nitrile gloves (change frequently when handling organic solutions), safety glasses or goggles.
• Incompatibilities: Strong oxidizers, strong acids/bases (promote epoxide opening/ester hydrolysis), radical initiators, and prolonged exposure to air/light.
• Special risks: Autoxidation and peroxidation can occur in unsaturated lipids; consider adding trace antioxidant in working solutions if appropriate for your application, and use amber vials.

First aid (general)

• Skin/eye contact: rinse with water for several minutes; remove contaminated clothing.
• Inhalation: move to fresh air.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Waste

• Collect organic waste in appropriate containers; do not discharge to drains.

Solvent Selection

This compound is a hydrophobic lipid methyl ester with high lipophilicity and an internal epoxide.

• Polarity/miscibility (literature/general):
  • Water: insoluble.
  • Alcohols (MeOH, EtOH, i-PrOH): soluble; EtOH is commonly used for biochemical stocks.
  • Polar aprotics (DMSO, DMF, ACN): soluble; DMSO is frequently used for high-concentration stocks.
  • Nonpolar/medium polarity (hexane, toluene, MTBE, EtOAc, DCM): readily soluble.
• Practical selection:
  • Biochemical assays/cell studies: prepare concentrated stocks in EtOH or DMSO, then dilute into buffered media with carrier proteins (e.g., BSA) or dispersants as appropriate to minimize precipitation (general guidance; validate for your system).
  • Synthetic operations: use anhydrous, oxygen-poor solvents; Et2O, THF, toluene, DCM, or EtOAc are typical depending on transformation (epoxide opening, hydrolysis, oxidations/reductions).
• Adsorption/handling: Lipidic materials can adsorb to plastics; use silanized glassware or low-bind plastics and include small amounts of co-solvent (e.g., 0.1–1% EtOH/DMSO) in aqueous buffers if needed.

Comparison notes (literature/general):

• DMSO vs EtOH: DMSO affords higher solubility and stability but may interfere in bioassays; EtOH is more volatile and often preferred for quick dilutions.
• Hexane/DCM for workup and chromatography provide good mobility; avoid prolonged exposure to acidic silica to limit epoxide opening.

Storage and Reconstitution

• Storage conditions (item-specific): Store at -20°C (as provided). Keep tightly closed, under inert gas if possible, protected from light (amber vial), and minimize headspace.
• Shipping (item-specific): Shipped in ice chest with ice pads to maintain cold chain.

Working solution guidance (general/literature):

• Reconstitution: Dissolve in anhydrous ethanol or DMSO to make concentrated stocks. Alternatively, dissolve in nonpolar solvents (e.g., hexane, DCM) for synthetic use.
• Aliquoting: Prepare single-use aliquots to avoid repeated freeze–thaw and headspace oxygen ingress.
• Freeze–thaw: Avoid multiple cycles; thaw at room temperature briefly, mix gently, and promptly return unused material to -20°C or colder. For long-term storage of sensitive lipids, -80°C is often employed (user’s discretion).
• Stability: Polyunsaturated, epoxide-bearing lipids are susceptible to oxidation and isomerization. Use inert atmosphere, low light, and consider antioxidants if compatible. Monitor integrity by LC–MS or 1H NMR over time.

Shelf-life and item-specific stabilizers, water/peroxide specifications: Not specified for this item; refer to CoA/Spec Sheet.

Research Use Only: Not for human or veterinary use.

Structure and Identity

(±)11(12)-EET methyl ester is the methyl ester of the epoxygenated arachidonic acid metabolite 11,12-epoxyeicosatrienoic acid (EET). It contains a 20-carbon polyunsaturated chain bearing an internal 11,12-epoxide and three remaining C=C double bonds, terminated by a methyl ester.

• SKU: E342849
• Product name: (±)11(12)-EET methyl ester
• CAS: 73799-06-1
• PubChem CID: 71684442 (external identifier; literature)
• InChIKey: 63851 (as provided; appears truncated — full identifier not specified for this item; refer to CoA/Spec Sheet)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C21H34O3 (literature/computed for EET methyl esters)
• Molecular weight: ~334.49 g/mol (literature/computed)

Structural features (descriptive, literature):

• Carbon skeleton: C20 eicosanoid backbone with a terminal methyl ester (–CO2Me).
• Functional groups: internal epoxide at C11–C12; three cis-configured double bonds elsewhere in the chain; methyl ester at C1.
• Stereochemistry: listed as racemic (±) at the epoxide center(s); double-bond geometries typically Z in natural EETs, but stereochemistry for this catalog item is not specified; refer to CoA/Spec Sheet.
• 2D description: a linear polyunsaturated chain bearing an epoxide ring roughly mid-chain, terminating in a methyl ester. No rings besides the three-membered epoxide.

Synthetic Utility

As a functionalized polyunsaturated methyl ester bearing an internal epoxide, (±)11(12)-EET methyl ester is a versatile intermediate and probe (literature/general):

• Epoxide chemistry:
  • Regioselective nucleophilic ring opening affords 11,12-vicinal diols (DHET methyl esters) with control using Lewis acids (BF3·OEt2, Ti(OiPr)4) or bases (alkoxides, amines). Neighboring alkene geometry can influence regiochemistry and stereochemical outcome.
  • Reductive opening (e.g., with LiAlH4 variants) or thiol additions enable diversification for probe synthesis.
• Carboxylate handle (as methyl ester):
  • Saponification provides the free acid for amide coupling (HATU/EDC) or ester exchange to install reporter tags (fluorophores, biotin) via linker chemistry.
• Polyene transformations:
  • Selective hydrogenation/isomerization of the remaining double bonds to map structure–activity relationships.
  • Epoxidation of other double bonds allows access to alternative EET regioisomers for comparative studies.
• Analytical utility:
  • Serves as a calibration standard in GC/LC–MS after appropriate derivatization (e.g., trimethylsilylation of diols or PFBBr esterification for electron capture; general lipidomics practice).

Note: Control temperature, acidity/basicity, and oxygen exposure to preserve the native epoxide and double-bond geometry during manipulations.

Target Specificity

This product is a small-molecule lipid and not an antibody, enzyme, or oligonucleotide. No target specificity data (e.g., antigen, clone, isotype, species reactivity) applies. For biological context, see Biological Roles and Reaction & Applications.