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Merck

L1012

Sigma-Aldrich

Ácido linoleico

liquid, BioReagent, suitable for cell culture

Sinónimos:

Ácido cis-9,cis-12-octadecadienoico

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About This Item

Fórmula lineal:
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
Número de CAS:
Peso molecular:
280.45
Beilstein/REAXYS Number:
1727101
EC Number:
MDL number:
UNSPSC Code:
12352211
eCl@ss:
32190102
PubChem Substance ID:
NACRES:
NA.75

biological source

plant (Safflower oil)

Quality Level

product line

BioReagent

assay

≥99%

form

liquid

technique(s)

cell culture | mammalian: suitable

refractive index

n20/D 1.466 (lit.)

bp

229-230 °C/16 mmHg (lit.)

mp

−5 °C (lit.)

solubility

NaOH: 1 M
ethanol: soluble

density

0.902 g/mL at 25 °C (lit.)

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 (LA) is the precursor for the synthesis of arachidonic prostaglandins and other eicosanoids. LA is present in vegetable oils and meat.

Application

Fatty acid that is typically bound to a carrier molecule such as BSA or cyclodextrin for use in cell culture.
Linoleic acid has been used as a component of S12 medium for cardiomyocytes differentiation, minimum essential medium α for spermatogonial stem cell culture and for endothelial differentiation of mouse adipose-derived stem cells (mASC).

Biochem/physiol Actions

El ácido linoleico aumenta la proliferación celular y la expresión génica del receptor activado por proliferadores peroxisómicos tipo alfa, PPARα, y sus genes de interés, como el de la acil-CoA oxidasa en hepatocitos primarios de pato .
Linoleic acid (LA) may improve wound healing in diabetic rat. The levels of LA in adipose tissue and platelets are correlated with coronary artery disease. It may induce tumor and apoptosis in colorectal cancer cells. Studies also support their protective effects in lymphocytes. Linoleic acid is typically bound to a carrier molecule such as bovine serum albumin (BSA) or cyclodextrin for use in cell culture.

Packaging

Sealed ampule.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


Certificados de análisis (COA)

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Intramyocardial adipose-derived stem cell transplantation increases pericardial fat with recovery of myocardial function after acute myocardial infarction
Kim JH, et al.
PLoS ONE, 11(6), e0158067-e0158067 (2016)
Enhancement effects of BSA and linoleic acid on hybridoma cell growth and antibody production
Cytotechnology, 112(6), 51-56 (1994)
Differentiation and characterization of rhesus monkey atrial and ventricular cardiomyocytes from induced pluripotent stem cells
Zhang X, et al.
Stem Cell Research, 20(6), 21-29 (2017)
Chemical-defined and albumin-free generation of human atrial and ventricular myocytes from human pluripotent stem cells
Pei F, et al.
Stem Cell Research, 19(6), 94-103 (2017)
Omega-6 vegetable oils as a driver of coronary heart disease: the oxidized linoleic acid hypothesis
DiNicolantonio JJ and O?Keefe JH
Open heart, 5(2), e000898-e000898 (2018)

Protocolos

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Discover our primary human hepatocytes and plating and maintenance media formulations. Explore our protocol for plateable primary hepatocyte cell culture.

Discover our primary human hepatocytes and plating and maintenance media formulations. Explore our protocol for plateable primary hepatocyte cell culture.

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