13-keto-9Z,11E-octadecadienoic acid

Base Information

• Chemical Name: 13-keto-9Z,11E-octadecadienoic acid
• CAS No.: 54739-30-9
• Molecular Formula: C18H30O3
• Molecular Weight: 294.434
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID101296867
• Wikidata: Q27104960
• Metabolomics Workbench ID: 2058
• ChEMBL ID: CHEMBL1378466
• Mol file: 54739-30-9.mol

Synonyms:13-keto-9,11,-octadecadienoic acid;13-KODDA;13-oxo-9,11-octadecadienoic acid;13-OXO-ODE;13-oxooctadecadienoic acid

Chemical Property of 13-keto-9Z,11E-octadecadienoic acid

Chemical Property:

• Vapor Pressure: 1.98E-08mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 425.5 °C at 760 mmHg
• Flash Point: 225.2 °C
• PSA: 54.37000
• Density: 0.966 g/cm³
• LogP: 5.06350
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 294.21949481
• Heavy Atom Count: 21
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

13-OxoODE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C=CC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCC(=O)/C=C/C=C\CCCCCCCC(=O)O
• Uses: 13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa. 13-OxoODE stimulates cell proliferation when instilled intrarectally in rats. 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO. 13-OxoODE is a stimulator of cell proliferation. 13-OxoODE is an activator of PPAR α(peroxisome proliferator-activated receptor α).

Technology Process of 13-keto-9Z,11E-octadecadienoic acid

There total 27 articles about 13-keto-9Z,11E-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: 88.0%

(13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (29623-28-7) → 13-oxo-9Z,11E-octadecadienoic acid (54739-30-9)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; at 85 ℃; for 1.5h;

DOI:10.1016/j.chemphyslip.2005.01.005

Reference yield: 85.0%

13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester (79790-32-2) → 13-oxo-9Z,11E-octadecadienoic acid (54739-30-9)

Guidance literature:

With sodium hydroxide; In methanol; water; for 6h; Ambient temperature;

DOI:10.1271/bbb.62.1771

Reference yield: 75.0%

(13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (29623-28-7) → 13-oxo-9Z,11E/Z-octadecadienoic acid (29623-29-8,31385-09-8,54739-30-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0009-3084(03)00087-2

upstream raw materials:

(13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid

linoleic acid

(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid

13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester

Downstream raw materials:

13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester

methyl coriolate

Methyl-13-hydroxystearat

(R,S)-coriolic acid

Refernces

• 1、 Belyaeva, Olga V.,Boeglin, William E.,Brash, Alan R.,Goggans, Kelli R.,Karki, Suman,Kedishvili, Natalia Y.,Popov, Kirill M.,Wendell, Stacy G.,Wirth, Samuel E.. "Dehydrogenase reductase 9 (SDR9C4) and related homologs recognize a broad spectrum of lipid mediator oxylipins as substrates". . . Retrieved 2022/01/31.
• 2、 -. "Macamides compound and synthetic method and application thereof". Paragraph 0070; 0071; 0072; 0084; 0088. . Retrieved 2017/12/09.