9(Z),11(E)-OCTADECADIENOIC ACID

Base Information

• Chemical Name: 9(Z),11(E)-OCTADECADIENOIC ACID
• CAS No.: 2540-56-9
• Deprecated CAS: 1839-11-8
• Molecular Formula: C₁₈H₃₂O₂
• Molecular Weight: 280.451
• UNII: 46JZW3MR59
• ChEMBL ID: CHEMBL4303722
• DSSTox Substance ID: DTXSID1041003
• Metabolomics Workbench ID: 551
• Nikkaji Number: J604.211B
• Wikidata: Q284757
• Wikipedia: Rumenic_acid
• Mol file: 2540-56-9.mol

Synonyms:9,11-Octadecadienoicacid, (E,Z)- (8CI);(9Z,11E)-9,11-Octadecadienoic acid;Bovinicacid;9Z,11E-Octadecadienoic acid;9-cis,11-trans-Octadecadienoic acid;9-cis,11-trans-Linoleicacid;cis-9,trans-11 Conjugated linoleic acid;cis-9,trans-11-Octadecadienoic acid;trans-11-cis-9-Octadecadienoic acid;Rumenic acid;(9Z,11E)-Octadeca-9,11-dienoic acid;

Chemical Property of 9(Z),11(E)-OCTADECADIENOIC ACID

Chemical Property:

• Vapor Pressure: 7.01E-07mmHg at 25°C
• Refractive Index: 1.478
• Boiling Point: 381.6 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 278.5 °C
• PSA: 37.30000
• Density: 0.911 g/cm³
• LogP: 5.88450
• Storage Temp.: −20°C
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 280.240230259
• Heavy Atom Count: 20
• Complexity: 267

Purity/Quality:

99% ^*data from raw suppliers

RumenicAcid(~80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 24-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCC=CC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCC/C=C/C=C\CCCCCCCC(=O)O
• Uses: Rumenic Acid is a trans fatty acid that may potentially reduce the risk of cancer and cardiovascular diseases.?It may also prevent disease processes that lead to chronic inflammation, atherosclerosis, and diabetes.

Technology Process of 9(Z),11(E)-OCTADECADIENOIC ACID

There total 64 articles about 9(Z),11(E)-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: 72.6%

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) → cis-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9)

Guidance literature:

With ruthenium-MgAlP₁₁; at 180 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c7ra10457j

Reference yield: 54.0%

(E)-2-Nonenal (18829-56-6) + (8-carboxyoctyl)triphenylphosphonium bromide (88462-46-8) → cis-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9) + trans-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9)

Guidance literature:

(8-carboxyoctyl)triphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 2h;

(E)-2-Nonenal; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 12h;

DOI:10.1016/j.tet.2006.03.006

Reference yield: 54.0%

(E)-2-Nonenal (18829-56-6) + (8-carboxyoctyl)triphenylphosphonium bromide (88462-46-8) → cis-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9) + trans-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9)

Guidance literature:

(8-carboxyoctyl)triphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 2h;

(E)-2-Nonenal; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 12h;

DOI:10.1016/j.tet.2006.03.006

upstream raw materials:

trans-ximenynic acid

linoleic acid methyl ester

tetrachloromethane

linoleic acid

Downstream raw materials:

8-[7-hexyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisobenzofuran-4-yl]octanoic acid

trans-9,trans-11-octadecadienoic acid

9r_F,10t_F,11r'_F,12t'_F-tetrahydroxy-octadecanoic acid

8-(4-hexyl-9,10-dioxo-9,10-dihydro-[1]anthryl)-octanoic acid

Refernces

• 1、 Fan, Ye,Fang, Yun,Ma, Lin,Jiang, Hang. "Investigation of Micellization and Vesiculation of Conjugated Linoleic Acid by Means of Self-Assembling and Self-Crosslinking". . p. 179 - 188. Retrieved 2015/07/27.
• 2、 Niezgoda, Natalia,Mitula, Pawel,Kempinska, Katarzyna,Wietrzyk, Joanna,Wawrzenczyk, Czeslaw. "Synthesis of phosphatidylcholine with conjugated linoleic acid and studies on its cytotoxic activity". . p. 354 - 361. Retrieved 2013/05/22.