(15S)-15-hydroxyicosa-8,11,13-trienoic acid

Base Information

• Chemical Name: (15S)-15-hydroxyicosa-8,11,13-trienoic acid
• CAS No.: 92693-02-2
• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.488
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID40390598
• Mol file: 92693-02-2.mol

Synonyms:(15S)-15-hydroxyicosa-8,11,13-trienoic acid;Bio1_001037;92693-02-2;CBiol_001773;DTXSID40390598;Bio1_000059;Bio1_000548;15-(s)-hydroxy-8,11,13-eicosatrienoic acid

Chemical Property of (15S)-15-hydroxyicosa-8,11,13-trienoic acid

Chemical Property:

• Boiling Point: 487.4±40.0°C at 760 mmHg
• Flash Point: 262.7±23.8°C
• PSA: 57.53000
• Density: 1.0±0.1g/cm3
• LogP: 5.41310
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 322.25079494
• Heavy Atom Count: 23
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

15(S)-HETrE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](C=CC=CCC=CCCCCCCC(=O)O)O

Technology Process of (15S)-15-hydroxyicosa-8,11,13-trienoic acid

There total 20 articles about (15S)-15-hydroxyicosa-8,11,13-trienoic acid 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: 60.0%

15-benzyloxy-(8Z,11Z,13E,15S)-8,11,13-eicosatrienoic acid (600180-04-9) → 15(S)-hydroxyeicosatrienoic acid (92693-02-2,15384-21-1)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; for 2h; cooling;

DOI:10.1016/S0957-4166(03)00369-0

Reference yield:

cis-8,11,14-eicosatrienoic acid (7324-41-6,68820-40-6,133939-47-6,133939-49-8,1783-84-2) → 15(S)-hydroxyeicosatrienoic acid (92693-02-2,15384-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 50percent (NH₄)2SO₄ / soybean lipoxygenase

2: NaBH₄

With ammonium sulfate; sodium tetrahydroborate;

DOI:10.1021/jm00385a005

Reference yield:

(8Z,11Z,13E)-(S)-15-Hydroperoxy-icosa-8,11,13-trienoic acid → 15(S)-hydroxyeicosatrienoic acid (92693-02-2,15384-21-1)

Guidance literature:

With sodium tetrahydroborate; Yield given;

DOI:10.1021/jm00385a005

upstream raw materials:

15-benzyloxy-(8Z,11Z,13E,15S)-8,11,13-eicosatrienoic acid

8-(tetrahydro-2H-pyran-2-yloxy)octan-1-ol

8-tetrahydropyranyloxyoctanal

1,8-Octanediol

Refernces

• 1、 Nanda,Yadav. "Asymmetric synthesis of unnatural (Z,Z,E)-octadecatrienoid and eicosatrienoid by lipoxygenase-catalyzed oxygenation". . p. 1799 - 1806. Retrieved 2007/10/03.