L1376
α-Linoleic acid
≥98%
Synonym(s):
Linoleic acid
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About This Item
Linear Formula:
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
CAS Number:
Molecular Weight:
280.45
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
EC Number:
200-470-9
Beilstein/REAXYS Number:
1727101
MDL number:
assay
≥98%
form
liquid
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
SMILES string
OC(CCCCCCC/C=C\C/C=C\CCCCC)=O
biological source
plant oil (safflower)
Quality Level
Gene Information
human ... SOAT1(6646), SOAT2(8435)
color
colorless
refractive index
n20/D 1.466
bp
229-230 °C/16 mmHg
mp
−5 °C
application(s)
life science and biopharma
functional group
carboxylic acid
lipid type
omega FAs
shipped in
ambient
storage temp.
−20°C
Related Categories
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 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.
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes citation.
General description
Linoleic acid is considered an important dietary omega-6 fatty acid. It contributes to the structural components of cell membranes.
Other Notes
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Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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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)
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
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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