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L1376

Sigma-Aldrich

Linoleic acid

≥99%

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

biological source

plant oil (safflower)

Quality Level

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

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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

For additional information on our range of Biochemicals, please complete this form.

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves


Certificates of Analysis (COA)

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Articles

Importance and uses of linoleic acid in serum-free eukaryotic, including hybridoma and Chinese Hamster Ovary (CHO) cell, cultures

Protocols

Lipoprotein lipase (LPL) hydrolyzes triglycerides associated with VLDL.

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