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L1012

Sigma-Aldrich

Linoleic acid

liquid, BioReagent, suitable for cell culture

Synonym(s):
9-cis,12-cis-Linoleic acid, cis-9,cis-12-Octadecadienoic acid, Telfairic acid
Linear Formula:
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
CAS Number:
Molecular Weight:
280.45
Beilstein:
1727101
EC Number:
MDL number:
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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This Item
62240W80007562230
Linoleic acid liquid, BioReagent, suitable for cell culture

Sigma-Aldrich

L1012

Linoleic acid

Linoleic acid technical, 58-74% (GC)

Sigma-Aldrich

62240

Linoleic acid

Linoleic acid natural (US), ≥95%, FG

Sigma-Aldrich

W800075

Linoleic acid

Linoleic acid analytical standard

Supelco

62230

Linoleic acid

assay

≥99%

assay

-

assay

≥95%

assay

≥98.0% (GC)

form

liquid

form

liquid

form

-

form

-

technique(s)

cell culture | mammalian: suitable

technique(s)

-

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

refractive index

n20/D 1.466 (lit.)

refractive index

n20/D 1.466 (lit.)

refractive index

n20/D 1.466 (lit.)

refractive index

n20/D 1.466 (lit.), n20/D 1.470

bp

229-230 °C/16 mmHg (lit.)

bp

229-230 °C/16 mmHg (lit.)

bp

229-230 °C/16 mmHg (lit.)

bp

229-230 °C/16 mmHg (lit.)

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 Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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25G
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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)
Chemical-defined and albumin-free generation of human atrial and ventricular myocytes from human pluripotent stem cells
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Linoleic acid: a nutritional quandary
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