(10E,12Z)-octadeca-10,12-dienoic acid

Base Information

• Chemical Name: (10E,12Z)-octadeca-10,12-dienoic acid
• CAS No.: 2420-56-6
• Molecular Formula: C₁₈H₃₂O₂
• Molecular Weight: 280.451
• Hs Code.: 2916150000
• European Community (EC) Number: 607-342-5
• UNII: N151ZM4M27
• DSSTox Substance ID: DTXSID0040628
• Nikkaji Number: J604.212K
• Wikidata: Q419936
• Metabolomics Workbench ID: 558
• ChEMBL ID: CHEMBL1093743
• Mol file: 2420-56-6.mol

Synonyms:10E12Z-CLA;t10,c12 CLA;trans-10, trans-12 conjugated linoleic acid;trans-10,cis-12-conjugated linoleic acid;trans-12,cis-10-conjugated linoleic acid;trans10cis12-conjugated linoleic acid

Chemical Property of (10E,12Z)-octadeca-10,12-dienoic acid

Chemical Property:

• Vapor Pressure: 9.54E-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

10-trans,12-cis-LinoleicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CCCCCCCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C=C\CCCCCCCCC(=O)O
• Description: Conjugated linoleic acid (CLA) refers to a family of 8 geometric isomers of linoleic acid in which the two double bonds are contiguous. (The predominant form of linoleic acid in nature, 18:ω6, has double bonds at 9 and 12, interrupted by a methylene carbon.) CLA is found in both meat and dairy products, but it is not found to any significant degree in plants. The predominant isomer of CLA in animal tissue is 9Z,11E; smaller amounts of 10E,12Z also occur. Various antioxidant and antitumor activities have been attributed to CLA or its downstream metabolites. Reported health benefits of dietary supplementation with CLA have been attributed variously to competitive inhibition of Δ6-desaturase and/or PPARγ activation. [Matreya, LLC. Catalog No. 1249]
• Uses: 10-trans,12-cis-Linoleic Acid?is an isomer of Linoleic Acid (L467495). Linoleic Acid is a dietary unsaturated fatty acid, which increases the expression of adhesion molecules and attenuates Endothelial cell function. Linoleic Acid is anti-inflammatory, acne reductive, and moisture retentive when applied topically on the skin. It is popular in the beauty products industry because of its beneficial properties on the skin.

Technology Process of (10E,12Z)-octadeca-10,12-dienoic acid

There total 28 articles about (10E,12Z)-octadeca-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: 22.0%

Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8) → 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) + trans-10,cis-12-octadecadienoic acid (1072-36-2,2420-44-2,2420-56-6,7307-45-1,22880-03-1) + 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) + 10E,12E-octadecadienoic acid (1072-36-2) + (R,Z)-13-hexyloxacyclotridec-10-en-2-one (59744-10-4,62272-86-0,68399-13-3,69651-29-2,127062-51-5,127062-52-6,127062-54-8)

Guidance literature:

With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hydroxide; In ethylene glycol; at 180 ℃; for 0.5h; Microwave irradiation;

DOI:10.1039/c2gc35792e

Reference yield: 14.0%

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) + trans-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9) + trans-10,cis-12-octadecadienoic acid (1072-36-2,2420-44-2,2420-56-6,7307-45-1,22880-03-1)

Guidance literature:

With ruthenium grafted Ru-MgAl₄₅₀ composite oxide; In decane; at 180 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/c5ra00417a

Reference yield: 5.0%

Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8) → 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) + trans-10,cis-12-octadecadienoic acid (1072-36-2,2420-44-2,2420-56-6,7307-45-1,22880-03-1) + 10E,12E-octadecadienoic acid (1072-36-2) + (R,Z)-13-hexyloxacyclotridec-10-en-2-one (59744-10-4,62272-86-0,68399-13-3,69651-29-2,127062-51-5,127062-52-6,127062-54-8)

Guidance literature:

With 1-hexyl-3-methyl-1-imidazolium bromide; potassium hydroxide; In ethylene glycol; at 180 ℃; for 0.5h; Microwave irradiation;

DOI:10.1039/c2gc35792e

upstream raw materials:

linoleic acid methyl ester

tetrachloromethane

linoleic acid

diethylene glycol

Downstream raw materials:

12-oxo-(10E)-dodecan-10-oic acid

ω-oxydecanocarboxylic acid

(9Z,11E)-methyl octadeca-9,11-dienoate

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

Refernces

• 1、 Chen, Jiebo,Chen, Xinxiang,Zheng, Ying,Li, Qinglu. "Synergetic effect of ruthenium and basicity sites in the Ru-MgAl catalyst for hydrogen-free production of conjugated linoleic acids". . p. 20248 - 20255. Retrieved 2015/03/18.
• 2、 -. "Method For The Production Of Conjugated Polyunsaturated Fatty Acids With Heterogenous Catalysts". Paragraph 0105. . Retrieved 2013/09/26.