L1376

Linoleic acid

≥99%

• Synonym(s): α-Linoleic acid, cis-9,cis-12-Octadecadienoic acid
• Linear Formula: CH₃(CH₂)₄CH=CHCH₂CH=CH(CH₂)₇CO₂H
• CAS Number: 60-33-3
• Molecular Weight: 280.45
• Beilstein/REAXYS Number: 1727101
• EC Number: 200-470-9
• MDL number: MFCD00064241
• UNSPSC Code: 12352211
• PubChem Substance ID: 24896279
• NACRES: NA.25

Properties

• biological source: plant oil (safflower)
• Quality Level: 200
• assay: ≥99%
• form: liquid
• color: colorless
• refractive index: n20/D 1.466 (lit.)
• bp: 229-230 °C/16 mmHg (lit.)
• mp: −5 °C (lit.)
• density: 0.902 g/mL at 25 °C (lit.)
• application(s): life science and biopharma
• functional group: carboxylic acid
• lipid type: omega FAs
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: OC(CCCCCCC/C=C\C/C=C\CCCCC)=O
• InChI: 1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
• InChI key: OYHQOLUKZRVURQ-HZJYTTRNSA-N
• Gene Information: human ... SOAT1(6646) , SOAT2(8435)

Description

General description

Linoleic acid is considered an important dietary omega-6 fatty acid. It contributes to the structural components of cell membranes.

Application

Linoleic acid has been used as a substrate to measure lipoxygenase activity. It has also been used to prepare linoleic acid hydroperoxide samples and study the prooxidant activity of citrate-stabilized CeO2.

Biochem/physiol Actions

Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes .

Linoleic acid is an n-6 polyunsaturated essential fatty acid (PUFA) used as a precursor of arachidonic acid (AA) and various prostaglandins. Linoleic acid may be used to improve the delivery and efficacy of anticancer drugs and in cancer protection. Linoleic acid has a significant influence on the membrane function. This fatty acid serves as a precursor for the bioactive metabolites called eicosanoids, which regulate renal and pulmonary function, vascular tone, and inflammatory responses. Linoleic acid deficiency has been observed in infants with chronic fat malabsorption conditions. Insufficient levels of this fatty acid result in poor growth and development in infants, scaly dermatitis, and an impaired immune response. Linoleic acid maintains the skin’s moisture content, hence it is utilized in topical applications.

Other Notes

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Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves