(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

Base Information

• Chemical Name: (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
• CAS No.: 73543-67-6
• Molecular Formula: C18H32 O3
• Molecular Weight: 296.45
• European Community (EC) Number: 804-144-2
• UNII: 42KE04U9BM
• DSSTox Substance ID: DTXSID901017275
• Wikipedia: 9-Hydroxyoctadecadienoic_acid
• Wikidata: Q27074045
• Pharos Ligand ID: 932DB7DWA2GG
• Metabolomics Workbench ID: 2224
• ChEMBL ID: CHEMBL1230670
• Mol file: 73543-67-6.mol

Synonyms:9-hydroxyoctadecadienoic acid;9S-HOD acid

Chemical Property of (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

Chemical Property:

• Vapor Pressure: 1.15E-08mmHg at 25°C
• Refractive Index: 1.492
• Boiling Point: 416.1°C at 760 mmHg
• Flash Point: 219.6°C
• PSA: 57.53000
• Density: 0.97g/cm³
• LogP: 4.85530
• Storage Temp.: ?20°C
• 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% ^*data from raw suppliers

9(S)-HODE ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CC(CCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C=C\[C@H](CCCCCCCC(=O)O)O
• Description: 9(S)-HODE is produced by the lipoxygenation of linoleic acid in both plants and animals. It has been detected in atherosclerotic plaques, as an esterified component of membrane phospholipids and in oxidized LDL particles.

Technology Process of (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

There total 22 articles about (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic 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 (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → azelaic acid (123-99-9,26776-28-3) + (3Z)-dodecene-1,12-dioic acid (189034-80-8) + 9-hydroxynonanoic acid (3788-56-5) + (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid (5503-03-7,70144-92-2,26369-27-7) + 13-hydroxy-12-oxo-octadeca-cis-9-enoic acid (5502-89-6) + (9Z)-11-hydroxy-12,13-epoxy-9-octadecenoic acid + (4Z)-2-pentyl-4-tridecene-1,13-dioic acid + (2’Z)-2-(2’-octenyl)-decane-1,10-dioic acid + (2’Z,5’Z)-2-(2’,5’-octadienyl)-decane-1,10-dioic acid + (12Z)-10-oxo-11-hydroxy-12-octadecenoic acid + (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (29623-28-7) + (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (73543-67-6)

Guidance literature:

With oxygen; for 0.5h; Enzymatic reaction;

DOI:10.1002/open.201800045

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

upstream raw materials:

linoleic acid

dilinoleolylphosphatidylcholine

lecithin

(R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate

Downstream raw materials:

9-hydroxy-(10E,12Z)-octadecadien-1-oic acid methyl ester

9‐oxo‐10E,12Z‐octadecanoic acid

(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid methyl ester

Octadeca-8t,10t,12c-triensaeure

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