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L1012

Sigma-Aldrich

Linoleic acid

liquid, BioReagent, suitable for cell culture

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Synonym(s):
cis-9,cis-12-Octadecadienoic acid
Linear Formula:
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
CAS Number:
60-33-3
Molecular Weight:
280.45
Beilstein:
1727101
EC Number:
200-470-9
MDL number:
MFCD00064241
UNSPSC Code:
12352211
eCl@ss:
32190102
PubChem Substance ID:
24896270
NACRES:
NA.75

biological source

plant (Safflower oil)

Quality Level

200

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

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

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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.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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