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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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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

Quality Level

200

Gene Information

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

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

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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

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 .

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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Certificates of Analysis (COA)

Lot/Batch Number
0000525764
0000525764
0000525763
0000525765
0000525765

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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)
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)
Linoleic acid: a nutritional quandary
Jandacek RJ
Healthcare (Basel, Switzerland) , 5(2), 25-25 (2017)
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