13-Hydroxy-6,9,11-octadecatrienoic acid

Base Information

• Chemical Name: 13-Hydroxy-6,9,11-octadecatrienoic acid
• CAS No.: 74784-20-6
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.434
• DSSTox Substance ID: DTXSID401345712
• Nikkaji Number: J1.919.249K
• Wikidata: Q63408693
• Metabolomics Workbench ID: 2209
• Mol file: 74784-20-6.mol

Synonyms:13-HODTA;13-hydroxy-6,9,11-octadecatrienoic acid

Chemical Property of 13-Hydroxy-6,9,11-octadecatrienoic acid

Chemical Property:

• Vapor Pressure: 1.89E-09mmHg at 25°C
• Boiling Point: 436.5°C at 760 mmHg
• Flash Point: 231.9°C
• PSA: 57.53000
• Density: 0.984g/cm³
• LogP: 4.63130
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 294.21949481
• Heavy Atom Count: 21
• Complexity: 329

Purity/Quality:

98%Min ^*data from raw suppliers

13(S)-HOTrE(γ) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 13-Hydroxy-6,9,11-octadecatrienoic acid

There total 21 articles about 13-Hydroxy-6,9,11-octadecatrienoic 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%

13-benzyloxy-(6Z,9Z,11E,13S)-6,9,11-octadecatrienoic acid (600180-02-7) → (13S,6Z,9Z,11E)-hydroxyoctadeca-6,9,11-trienoic acid (74784-20-6)

Guidance literature:

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

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

Reference yield:

all-cis-6,9,12-octadecatrienoic acid (506-26-3,34615-07-1) → (13S,6Z,9Z,11E)-hydroxyoctadeca-6,9,11-trienoic acid (74784-20-6)

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:

13S-hydroperoxy-6Z,9Z,11E-octadecatrienoic acid (121107-97-9) → (13S,6Z,9Z,11E)-hydroxyoctadeca-6,9,11-trienoic acid (74784-20-6)

Guidance literature:

With sodium tetrahydroborate; Yield given;

DOI:10.1021/jm00385a005

upstream raw materials:

13S-hydroperoxy-6Z,9Z,11E-octadecatrienoic acid

13-benzyloxy-(6Z,9Z,11E,13S)-6,9,11-octadecatrienoic acid

6-(tetrahydro-2H-pyranyloxy)hexan-1-ol

1,6-hexanediol

Refernces

• 1、 An, Jung-Ung,Hong, Seung-Hye,Oh, Deok-Kun. "Regiospecificity of a novel bacterial lipoxygenase from Myxococcus xanthus for polyunsaturated fatty acids". . p. 823 - 833. Retrieved 2018/05/14.
• 2、 Haviv,Ratajczyk,DeNet,Martin,Dyer,Carter. "Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues". . p. 254 - 263. Retrieved 2007/10/02.