123931-40-8

Basic information

• Product Name: (±)11(12)-EET
• Synonyms: 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid ~100 mug/mL in ethanol, >=95%;5,8-Decadienoic acid, 10-[(2S,3R)-3-(2Z)-2-octen-1-yl-2-oxiranyl]-, (5Z,8Z)-
• CAS NO: 123931-40-8
• Molecular Formula: C20H32O3
• Molecular Weight: 320.46628
• EINECS: 200-578-6
• Mol File: 123931-40-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 461.8±33.0 °C(Predicted)
• Flash Point: 9℃
• Appearance: /
• Density: 0.983±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: (±)11(12)-EET(CAS DataBase Reference)
• NIST Chemistry Reference: (±)11(12)-EET(123931-40-8)
• EPA Substance Registry System: (±)11(12)-EET(123931-40-8)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16
• RIDADR: UN1170 - class 3 - PG 2 - Ethanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 123931-40-8(Hazardous Substances Data)

Usage

Description

(±)11(12)-EET is a fully racemic version of the R/S enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. A higher proportion of 11(R),12(S)-EET is produced by the CYP450 isoforms CYP2C23 and CYP2C24 while CYP2B2 produces a higher proportion of 11(S),12(R)-EET. 11(12)-EET has been shown, along with 8(9)-EET , to play a role in the recovery of depleted calcium pools in cultured smooth muscle cells. It also inhibits basolateral 18-pS potassium channels in the renal cortical collecting duct when used at a concentration of 100 nM. 11(12)-EET (50 μg/kg per day) increases adhesion of isolated peripheral blood leukocytes in a chamber coated with P-selectin and ICAM-1 but does not affect choroidal neovascularization size following laser photocoagulation. It also has anti-inflammatory, angiogenic, and cardioprotective properties.

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 73958-09-5 Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide 
• 109296-17-5 7-carbomethoxy hepta-3-(Z)-en-1-ylidenetriphenylphosphorane 
• 90080-08-3 11(S),12(R)-epoxyeicosatrienoic acid methyl ester 

Relevant articles and documents

Analysis of epoxyeicosatrienoic acids by chiral liquid chromatography/ electron capture atmospheric pressure chemical ionization mass spectrometry using [13C]-analog internal standards

The metabolism of arachidonic acid (AA) to epoxyeicosatrienoic acids (EETs) is thought to be mediated primarily by the cytochromes P450 (P450s) from the 2 family (2C9, 2C19, 2D6, and 2J2). In contrast, P450s of the 4 family are primarily involved in omega oxidation of AA (4A11 and 4A22). The ability to determine enantioselective formation of the regioisomeric EETs is important in order to establish their potential biological activities and to asses which P450 isoforms are involved in their formation. It has been extremely difficult to analyze individual EET enantiomers in biological fluids because they are present in only trace amounts and they are extremely difficult to separate from each other. In addition, the deuterium-labeled internal standards that are commonly used for stable isotope dilution liquid chromatography/mass spectrometry (LC/MS) analyses have different LC retention times when compared with the corresponding protium forms. Therefore, quantification by LC/MS-based methodology can be compromised by differential suppression of ionization of the closely eluting isomers. We report the preparation of [13C20]-EET analog internal standards and the use of a validated high-sensitivity chiral LC/electron capture atmospheric pressure chemical ionization (ECAPCI)-MS method for the trace analysis of endogenous EETs as their pentafluorobenzyl (PFB) ester derivatives. The assay was then used to show the exquisite enantioselectivity of P4502C19-, P4502D6-, P4501A1-, and P4501B1-mediated conversion of AA into EETs and to quantify the enantioselective formation of EETs produced by AA metabolism in a mouse epithelial hepatoma (Hepa) cell line. Copyright

Absolute Configuration of Epoxyeicosatrienoic Acids (EETs) Formed during Catalytic Oxygenation of Arachidonic Acid by Purified Rat Liver Microsomal Cytochrome P-450

Incubation of arachidonic acid with a reconstituted enzymatic system containing a purified preparation of the major, phenobarbital-inducible form of rat liver microsomal cytochrome P-450, NADPH, cytochrome b5, and NADPH-cytochrome P-450 reductase affords as the principal products four regioisomeric cis-epoxides: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs).Their absolute configurations were established by conversion to the corresponding hydroxyeicosatetraenoic acid (HETE) methyl esters, derivatization with dehydroabiethylisocyanate, and chromatographic analysis.Except for 5,6-EET, the cytochrome P-450 catalyzed epoxidation is highly enantioselective.