17(18)-EpETE

Base Information

• Chemical Name: 17(18)-EpETE
• CAS No.: 131339-23-6
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• ChEMBL ID: CHEMBL1802674
• Metabolomics Workbench ID: 2360
• Nikkaji Number: J2.308.588G
• Wikidata: Q27140189
• Mol file: 131339-23-6.mol

Synonyms:17,18-EETeTr;17,18-EpETE;17,18-epoxy-5,8,11,14-eicosatetraenoic acid;17,18-epoxyeicosatetraenoic acid

Chemical Property of 17(18)-EpETE

Chemical Property:

• Vapor Pressure: 6.42E-10mmHg at 25°C
• Boiling Point: 464.6°Cat760mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 156.7°C
• PSA: 49.83000
• Density: 0.996g/cm³
• LogP: 5.20390
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(O1)CC=CCC=CCC=CCC=CCCCC(=O)O
• Isomeric SMILES: CCC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

Technology Process of 17(18)-EpETE

There total 33 articles about 17(18)-EpETE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4) → 17,18-Epoxyeicosatetraenoic acid (1283063-45-5,131339-23-6)

Guidance literature:

With human recombinant cytochrome P₄₅₀ 1A₁; stereoselective reaction; Enzymatic reaction;

DOI:10.1194/jlr.M003061

Reference yield: 91.0%

methyl (5Z,8Z,11Z,14Z)-16-((2R,3S)-3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoate (421593-74-0) → (5Z,8Z,11Z,14Z)-16-((2R,3S)-3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid (725246-18-4,131339-23-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h;

DOI:10.1039/c7ob02291c

Reference yield: 76.0%

all cis-5,8,11,14,17-eicosapentaenoic acid (10417-94-4) → 11,12-Epoxyeicosaquatraenoic acid + (±)-8,9-epoxy-5Z,11Z,14Z,17Z-eicosatetraenoic acid (851378-93-3) + 14,15-epoxyeicosatetraenoic acid (851378-94-4) + (5Z,8Z,11Z,14Z)-16-((2R,3S)-3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid (725246-18-4,131339-23-6)

Guidance literature:

With human recombinant cytochrome P₄₅₀ 1A₂; stereoselective reaction; Enzymatic reaction;

DOI:10.1194/jlr.M003061

upstream raw materials:

all cis-5,8,11,14,17-eicosapentaenoic acid

(E)-1-(trimethylsilyl)pent-1-en-3-ol

(R)-1-((2R,3R)-3- (trimethylsilyl)oxiran-2-yl)propan-1-ol

(S,E)-1-(trimethylsilyl)pent-1-en-3-ol

Refernces

• 1、 -. "DERIVATIVES OF EPA ENDOCANNABINOID EPOXIDES AS ANTI-INFLAMMATORY, ANTI-CANCEROUS, ANTI-ANGIOGENC AND ANTIPLATELET AGGREGATION COMPOUNDS". Paragraph 00123. . Retrieved 2019/04/16.
• 2、 Nanba, Yutaro,Shinohara, Riku,Morita, Masao,Kobayashi, Yuichi. "Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium". . p. 8614 - 8626. Retrieved 2017/10/27.