Linoleic Acid

Base Information

• Chemical Name: Linoleic Acid
• CAS No.: 60-33-3
• Deprecated CAS: 8024-22-4,949900-18-9,949900-18-9
• Molecular Formula: C18H32O2
• Molecular Weight: 280.451
• Hs Code.: 2916150000
• European Community (EC) Number: 200-470-9,606-872-4,617-024-8
• UNII: 9KJL21T0QJ
• ChEMBL ID: CHEMBL267476
• DSSTox Substance ID: DTXSID2025505
• Metabolomics Workbench ID: 553
• NCI Thesaurus Code: C615
• Nikkaji Number: J4.801A
• NSC Number: 281243
• Pharos Ligand ID: 441TNZQ7HKW4
• RXCUI: 6400
• Wikidata: Q407426
• Wikipedia: Linoleic acid,Linoleic_acid
• Mol file: 60-33-3.mol

Synonyms:9 trans,12 trans Octadecadienoic Acid;9,12 Octadecadienoic Acid;9,12-Octadecadienoic Acid;9-trans,12-trans-Octadecadienoic Acid;Acid, 9,12-Octadecadienoic;cis,cis-9,12-Octadecadienoic Acid;Linoelaidic Acid;Linoelaidic Acid, (E,Z)-Isomer;Linoleate;Linoleic Acid;Linoleic Acid, (E,E)-Isomer;Linoleic Acid, (Z,E)-Isomer;Linoleic Acid, (Z,Z)-Isomer;Linoleic Acid, (Z,Z)-Isomer, 14C-Labeled;Linoleic Acid, Ammonium Salt, (Z,Z)-Isomer;Linoleic Acid, Calcium Salt, (Z,Z)-Isomer;Linoleic Acid, Potassium Salt, (Z,Z)-Isomer;Linoleic Acid, Sodium Salt, (E,E)-Isomer;Linoleic Acid, Sodium Salt, (Z,Z)-Isomer;Linolelaidic Acid;trans,trans-9,12-Octadecadienoic Acid

Chemical Property of Linoleic Acid

Chemical Property:

• Appearance/Colour: Colorless to straw colored liquid
• Vapor Pressure: 3.54E-06mmHg at 25°C
• Melting Point: -5 °C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 360.552 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 272.976 °C
• PSA: 37.30000
• Density: 0.912 g/cm³
• LogP: 5.88450
• Water Solubility.: INSOLUBLE
• XLogP3: 6.8
• 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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids,Biological Agents -> Fatty Acids and Fats
• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
• Recent ClinicalTrials: Dietary Essential Fatty Acid Regulation of Omega-3 HUFA Metabolism; Satiety and Body Composition
• Recent NIPH Clinical Trials: Evaluation of the effect of continuous intake of nuts on the functional components in blood and feces

Technology Process of Linoleic Acid

There total 65 articles about Linoleic 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: 81.0%

linoleic nitrile (19836-71-6) → 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)

Guidance literature:

With sodium hydroxide; In ethanol; water; Heating;

DOI:10.1016/S0040-4039(00)92696-0

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: 5.39%

soybean oil, refined, bleached and deodorized → trans fatty acid; mixture of + cis-Octadecenoic acid (112-80-1,2027-47-6) + 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) + (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) + stearic acid (57-11-4)

Guidance literature:

With hydrogen; mineral malachite; at 165 ℃; for 4h; under 3102.97 Torr; Conversion of starting material;

upstream raw materials:

linoleic acid methyl ester

9,12-octadecadiynoic acid

Methyl linoleate

linoleic nitrile

Downstream raw materials:

linoleyl chloride

(+/-)-manno-9,10;12,13-diepoxy-octadecanoic acid

octadeca-9,12-dienoic acid ethyl ester

linoleic acid

Refernces

• 1、 Bao, Li,Chen, Baosong,Han, Junjie,Liu, Hongwei,Ma, Ke,Wang, Wenzhao. "Identification and α -Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus". . p. 571 - 578. Retrieved 2020/06/03.
• 2、 Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.. "Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids". . p. 4115 - 4131. Retrieved 2018/10/02.