L1376

Sigma-Aldrich

Linoleic acid

≥99%

Synonym(s):
Telfairic acid, 9-cis,12-cis-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:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

biological source

plant oil (safflower)

assay

≥99%

form

liquid

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.)

functional group

carboxylic acid

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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Related Categories

Packaging

1, 5, 10, 25 g in ampule
10, 500 mg in ampule

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

> 113 °C - closed cup

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....
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...
Laurent L'homme et al.
Journal of lipid research, 54(11), 2998-3008 (2013-09-06)
The NLRP3 inflammasome is involved in many obesity-associated diseases, such as type 2 diabetes, atherosclerosis, and gouty arthritis, through its ability to induce interleukin (IL)-1β release. The molecular link between obesity and inflammasome activation is still unclear, but free fatty...
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...
Articles
Importance and uses of linoleic acid in serum-free eukaryotic, including hybridoma and Chinese Hamster Ovary (CHO) cell, cultures
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The potential for the prevention and treatment of cardiovascular disease through increased dietary intake of omega-3 (w-3) fish oils is not a recent scientific discovery.
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Protocols
Lipoprotein lipase (LPL) hydrolyzes triglycerides associated with VLDL.
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Separation of Palmitic acid; Linoleic acid; Palmitelaidic acid; Linolelaidic acid; Stearic acid; Oleic acid; Elaidic acid; Methyl palmitoleate.
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