14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid
Basic information
- CAS
197508-62-6- Standard SMILES
CCCCCC1OC1C/C=C\C/C=C\C/C=C\CCCC(=O)O- InChIKey
JBSCUHKPLGKXKH-ILYOTBPNSA-N- Molecular formula
- C20H32O3
- Average molar mass
- 320.5 g/mol
- Monoisotopic mass
- 320.23514488
Overview
14,15-EET is an EET obtained by formal epoxidation of the 14,15-double bond of arachidonic acid. It has a role as a mouse metabolite. It is a conjugate acid of a 14,15-EET(1-).
Names & identifiers
- Preferred name
- 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid
- IUPAC
- (5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid
- English name
- (14(15)-EET MaxSpecStandard
- Molecular formula
- C20H32O3
- Molecular weight
- 320.47
Names & synonyms
14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acidRefChem:105749614,15-Eet(5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid(+/-)14,15-EpETrE14,15-epoxyeicosatrienoic acid81276-03-114,15-EpETrE197508-62-614(15)-EpETrE14(15)-EET(5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoic acid
Show more names
(±)14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acidAnti-IL11 Antibody (X203)(14(15)-EET MaxSpecStandard(±)14(15)-EET Lipid Maps? MS Standard5,8,11-Tridecatrienoic acid, 13-(3-pentyl-2-oxiranyl)-, (5Z,8Z,11Z)-
(5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoic acid(+/-)14,15-EPOXYEICOSA-5Z,8Z,11Z-TRIENOIC ACID( inverted exclamation markA)14,15-Epoxyeicosatrienoic acid14(15)-Epoxy-5Z,8Z,11Z-eicosatrienoic acidBSPBio_001335starbld0008791BML1-D11CHEMBL269319
Database identifiers
- CAS
197508-62-6、81276-03-1
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 49.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 14
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 396
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Epoxyeicosatrienoic acids [FA0308]
Physical DescriptionSolid
Collision Cross Section
185.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]
182.43 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
185.9 Ų [M+Na]+
Physicochemical properties
- Boiling point
- 464.5 · 464.5±33.0 °C(Predicted)
- Density
- 0.983 · 0.983±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 50 mg/ml · DMF: >50 mg/ml (per Rao Maddipati),DMSO: >50 mg/ml (per Rao Maddipati),Ethanol: >50 mg/ml (per Rao Maddipati),
- pka
- 4.75 · 4.75±0.10(Predicted)
- form
- ethanol solution
- color
- Colorless to light yellow
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 1
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H225
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites14,15-EET is a known human metabolite of arachidonic acid.
Cellular LocationsExtracellular
Metabolite PathwaysAcetaminophen Action Pathway
Applications
UsesEpoxyeicosatrienoic Acid (EET) has antihypertensive and anti-inflammatory properties and play a role in the maintenance of renal vascular function. N,N''-dicyclohexylurea (DCU) increased release of 14,15-EET when the cells were stimulated with a calcium ionophore.Also, it is derived from Arachidonic Acid >97% (A765000), which is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.
Additional notes
DefinitionChEBI: 14,15-Epoxy-5,8,11-eicosatrienoic acid is a long-chain fatty acid.
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