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
• General Description: **Null** (Neither of the provided abstracts focuses on describing linoleic acid itself; they mention it only in the context of assays or peroxidation studies without detailing its properties or functions.)

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:

9-hydroxynonanoic acid

(R,S)-coriolic acid

8-(3-((3-pentyloxiran-2-yl)methyl)oxiran-2-yl)octanoic acid

octadec-9-enoic acid methyl ester

Refernces

Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering

10.1002/jlcr.3504

The study focuses on the synthesis and characterization of specific deuterated derivatives of long-chain ceramides [EOS] and [EOP] found in the stratum corneum lipids, which are essential components of the skin's barrier function. The researchers replaced linoleic acid with a palmitic acid branched with a methyl group and introduced deuteration in the branched and terminal methyl groups to create these derivatives. The synthesized ceramides were then prepared for neutron scattering investigations. The chemicals used in the study included various fatty acids, deuterated compounds, and ceramide precursors, such as 6-bromohexanoic acid ethyl ester, malonic acid ethyl ester, and lithium aluminum deuteride. These chemicals served the purpose of creating the branched and deuterated fatty acids, which were then used to synthesize the ceramides [EOS] and [EOP]. The synthesized deuterated ceramides are valuable tools for investigating the influence of these long-chain ceramide species on the nanostructure of stratum corneum lipid model membranes, as they can be detected in the lipid model membranes and help to understand their structural role in the skin's barrier.

Facile synthesis of oxo-/thioxopyrimidines and tetrazoles C-C linked to sugars as novel non-toxic antioxidant acetylcholinesterase inhibitors

10.1016/j.carres.2011.11.006

The research aims to synthesize novel compounds that are linked to sugars and possess both antioxidant properties and the ability to inhibit acetylcholinesterase, an enzyme associated with Alzheimer's disease. The study compares the efficiency of conventional heating methods with microwave-assisted synthesis for the creation of these compounds, which include oxo-/thioxopyrimidines and tetrazoles linked to furanoses with D-xylo and D-ribo configurations, and to a D-galacto pyranose. The chemicals used in the synthesis process involve dialdofuranoses and dialdopyranoses, β-keto esters, urea or thiourea, hydroxylamine hydrochloride, copper sulfate, triethylamine, dicyclohexylcarbodiimide, and sodium azide. The research concludes that microwave irradiation is a more efficient method, yielding the target molecules in high yield and in a significantly shorter time (10 minutes) compared to conventional heating. The synthesized compounds showed acetylcholinesterase inhibition ranging from 20% to 80% at a concentration of 100 μg/mL and exhibited antioxidant activity in the β-carotene/linoleic acid assay, with some compounds showing IC50 values comparable to gallic acid. Importantly, the bioactive compounds did not exhibit cytotoxic effects on human lymphocytes nor genotoxicity, indicating their potential as non-toxic therapeutic agents for the control of Alzheimer's disease symptoms.

Catalytic chain-breaking pyridinol antioxidants

10.1021/jo902226t

The study focuses on the synthesis and evaluation of 3-pyridinols, which are compounds carrying alkyltelluro, alkylseleno, and alkylthio groups, as potent antioxidant agents. These pyridinols were tested for their ability to inhibit azo-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system and in a homogeneous phase. The chemicals used in the study include various 3-pyridinols with different substituents, N-acetylcysteine (NAC) as a water-soluble co-antioxidant, and N-tert-butoxycarbonyl cysteine methyl ester (LipCys), a lipid-soluble analogue of NAC. The purpose of these chemicals was to assess their antioxidant activity, specifically their capacity to quench peroxyl radicals, regenerate through reduction by thiol reducing agents, and their potential catalytic antioxidant behavior. The study aimed to understand the kinetic, thermodynamic, and mechanistic aspects of these antioxidants' activities and to identify the structural features that contribute to their high reactivity and effectiveness.