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:
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-
SMILES string
OC(CCCCCCC/C=C\C/C=C\CCCCC)=O
InChI key
OYHQOLUKZRVURQ-HZJYTTRNSA-N
biological source
plant oil (safflower)
assay
≥98%
form
liquid
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 increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes citation.
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.
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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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
Allison Dilzer et al.
Critical reviews in food science and nutrition, 52(6), 488-513 (2012-03-29)
Conjugated linoleic acid (CLA) has drawn significant attention in the last two decades for its variety of biologically beneficial effects. CLA reduces body fat, cardiovascular diseases and cancer, and modulates immune and inflammatory responses as well as improves bone mass.
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
Yin Ning Chiang et al.
PLoS genetics, 12(6), e1006126-e1006126 (2016-06-23)
Many of the lipids found on the cuticles of insects function as pheromones and communicate information about age, sex, and reproductive status. In Drosophila, the composition of the information-rich lipid profile is dynamic and changes over the lifetime of an
James E Dombrowski et al.
BMC research notes, 7, 807-807 (2014-11-19)
Previously it has been shown that mechanical wounding, salinity and heat activated a 46 kDa and 44 kDa mitogen-activated protein kinases (MAPKs) in forage related grasses. Forage and turf related grasses are utilized in diverse environments where they are routinely subjected to
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