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L1376

Sigma-Aldrich

Linoleic acid

≥99%

Synonym(s):

α-Linoleic acid, cis-9,cis-12-Octadecadienoic acid

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About This Item

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

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)

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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

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Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Introduction: the role of fats in human diet
Sanders, Thomas AB
Functional Dietary Lipids (2016)
Céline Robo et al.
Acta biomaterialia, 72, 362-370 (2018-03-22)
Poly(methyl methacrylate) (PMMA) is the most commonly used material for the treatment of osteoporosis-induced vertebral compression fractures. However, its high stiffness may introduce an increased risk of adjacent vertebral fractures post-surgery. One alternative in overcoming this concern is the use
Fatty acids: Omega-6 polyunsaturated
Benjamin Caballero
Encyclopedia of Human Nutrition, 232-238 (2013)
Inactivation of soybean lipoxygenase in soymilk by pulsed electric fields
Li YQ, et al.
Food Chemistry, 109(2) (2008)
Philong Ta et al.
Journal of bacteriology, 193(8), 1981-1990 (2011-02-22)
The mshA::Tn5 mutant of Mycobacterium smegmatis does not produce mycothiol (MSH) and was found to markedly overproduce both ergothioneine and an ~15-kDa protein determined to be organic hydroperoxide resistance protein (Ohr). An mshA(G32D) mutant lacking MSH overproduced ergothioneine but not
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Articles

Linoleic acid in Cell Culture

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

Protocols

LPL Activity Assay Protocol

Lipoprotein lipase (LPL) hydrolyzes triglycerides associated with VLDL.

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