9-hydroxy-10E,12Z-octadecadienoic acid

Base Information

• Chemical Name: 9-hydroxy-10E,12Z-octadecadienoic acid
• CAS No.: 98524-19-7
• Molecular Formula: C₁₈H₃₂O₃
• Molecular Weight: 296.45
• UNII: XL87KT7C6Z
• DSSTox Substance ID: DTXSID101249404
• Nikkaji Number: J365.920H
• Wikidata: Q50318263
• Metabolomics Workbench ID: 2187
• ChEMBL ID: CHEMBL1077284
• Mol file: 98524-19-7.mol

Synonyms:9-HODE;9-hydroxy-10,12-octadecadienoic acid;9-hydroxy-10,12-octadecadienoic acid, (E,E)-(+-)-isomer;9-hydroxy-10,12-octadecadienoic acid, (E,E)-isomer;9-hydroxy-10,12-octadecadienoic acid, (E,Z)-(+-)-isomer;9-hydroxy-10,12-octadecadienoic acid, (E,Z)-isomer;9-hydroxy-10,12-octadecadienoic acid, (R-(E,Z))-isomer;9-hydroxy-10,12-octadecadienoic acid, (S-(E,Z))-isomer;9-hydroxylinoleic acid;9-OH-18:2delta(10t,12t);dimorphecolic acid

Chemical Property of 9-hydroxy-10E,12Z-octadecadienoic acid

Chemical Property:

• PSA: 57.53000
• LogP: 4.85530
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 296.23514488
• Heavy Atom Count: 21
• Complexity: 295

Purity/Quality:

98%Min ^*data from raw suppliers

(+/-)9-HODE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CC(CCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C=C\C(CCCCCCCC(=O)O)O
• Description: (±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.
• Uses: (±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs. (+/-)9-HODE is a distinct product of non-enzymatic linoleic acid oxidation.Also, it is one of the component in rice koji extract (RKE), which activates peroxisome proliferator-activated receptor alpha (PPARα).It is derived from Methyl Linoleate (M265190), which is a common methyl ester produced from soybean or canola oil and methanol. Methyl Linoleate is classified as a biodiesel due to its long methyl chain and is used as a fuel in standard diesel engines.

Technology Process of 9-hydroxy-10E,12Z-octadecadienoic acid

There total 8 articles about 9-hydroxy-10E,12Z-octadecadienoic 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: 83.0%

(R)-9-hydroxy-(10E,12Z)-10,12-octadecadienoic acid methyl ester (6084-82-8,6114-34-7,6157-02-4,10075-07-7,23324-71-2,65700-62-1,96393-36-1,98524-18-6,114297-06-2,69257-16-5) → (9R,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (15514-85-9,18104-44-4,73543-67-6,96745-45-8,98524-19-7,109281-79-0,115185-06-3,127911-30-2,127911-31-3,133397-72-5,133397-73-6,10075-11-3)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1039/c39910001197

Reference yield:

linoleic acid (2420-55-5,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (29623-28-7) + (9R,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (15514-85-9,18104-44-4,73543-67-6,96745-45-8,98524-19-7,109281-79-0,115185-06-3,127911-30-2,127911-31-3,133397-72-5,133397-73-6,10075-11-3)

Guidance literature:

With oxygen; In methanol; at 25 ℃; for 0.333333h; pH=7.5; Temperature; pH-value; stereospecific reaction; Enzymatic reaction;

DOI:10.1016/j.molcatb.2014.03.009

Reference yield:

1-Heptyne (628-71-7) → (9R,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (15514-85-9,18104-44-4,73543-67-6,96745-45-8,98524-19-7,109281-79-0,115185-06-3,127911-30-2,127911-31-3,133397-72-5,133397-73-6,10075-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / Pd(PPh₃)4, CuI, n-PrNH₂

2: 65 percent / H₂ / Pd/BaCO₃

3: 83 percent / K₂CO₃ / methanol

With propylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; potassium carbonate; palladium-barium carbonate; In methanol;

DOI:10.1039/c39910001197

upstream raw materials:

(R)-9-hydroxy-(10E,12Z)-10,12-octadecadienoic acid methyl ester

1-Heptyne

(E)-(R)-11-Bromo-9-hydroxy-undec-10-enoic acid

Heleninolsaeure-methylester

Refernces

• 1、 Hornung, Ellen,Kunze, Susan,Liavonchanka, Alena,Zimmermann, Grit,Kuehn, Diana,Fritsche, Kathrin,Renz, Andreas,Kuehn, Hartmut,Feussner, Ivo. "Identification of an amino acid determinant of pH regiospecificity in a seed lipoxygenase from Momordica charantia". scheme or table. p. 2774 - 2780. Retrieved 2009/04/10.