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Merck
CN

L1012

Linoleic acid

liquid, BioReagent, suitable for cell culture

Synonym(s):

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
NACRES:
NA.75
PubChem Substance ID:
24896270
eCl@ss:
32190102
UNSPSC Code:
12352211
EC Number:
200-470-9
MDL number:
MFCD00064241
Beilstein/REAXYS Number:
1727101

Key Documents

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Product Name

Linoleic acid, liquid, BioReagent, suitable for cell culture

InChI key

OYHQOLUKZRVURQ-HZJYTTRNSA-N

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

biological source

plant (Safflower oil)

product line

BioReagent

assay

≥98%

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

Quality Level

200

Gene Information

human ... SOAT1(6646), SOAT2(8435)

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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

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

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.

Packaging

Sealed ampule.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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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)
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)
Enhancement effects of BSA and linoleic acid on hybridoma cell growth and antibody production
Cytotechnology, 112(6), 51-56 (1994)
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)
An overview of the effect of linoleic and conjugated-linoleic acids on the growth of several human tumor cell lines
Maggiora M, et al.
International Journal of Cancer. Journal International Du Cancer, 112(6), 909-919 (2004)
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