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62240

Sigma-Aldrich

Linoleic acid

technical, 58-74% (GC)

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:
Molecular Weight:
280.45
Beilstein/REAXYS Number:
1727101
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical

Quality Level

form

liquid

concentration

58-74% (GC)

impurities

18-32% oleic acid

color

clear

refractive index

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

bp

229-230 °C/16 mmHg (lit.)

mp

−5 °C (lit.)

density

0.902 g/mL at 25 °C (lit.)

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 can give rise to a class of geometric, positional and conjugated dienoic isomers called conjugated linoleic acids(CLA),mostly found in animal products, which can act like a cancer preventive agent in animals.

Application

  • Alginate Spheres With Urea and Linoleic Acid: A biological nitrification inhibitor proposal utilizing alginate spheres to encapsulate urea and linoleic acid for agricultural benefits (Avendaño-Morales et al., 2024).

Biochem/physiol Actions

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

Caution

partially crystallizes on storage at 0-4°C

wgk_germany

WGK 1

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves


Certificates of Analysis (COA)

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"Conjugated linoleic acid supplementation reduces adipose tissue by apoptosis and develops lipodystrophy in mice"
Tsuboyama-Kasaoka N, et al.
Diabetes, 49(09), 1534-1542 (2000)
"Dietary trans-10, cis-12 conjugated linoleic acid induces hyperinsulinemia and fatty liver in the mouse"
Clement L, et al.
Journal of Lipid Research, 43(09), 1400-1409 (2002)
"Dietary fatty acid sources affect conjugated linoleic acid concentrations in milk from lactating dairy cows"
Kelly.LM, et al.
The Journal of Nutrition, 128(05), 881-885 (1998)
"Conjugated linoleic acid?enriched butter fat alters mammary gland morphogenesis and reduces cancer risk in rats"
Ip C, et al.
The Journal of Nutrition, 129(12), 2135-2142 (1999)
Saman Lashkari et al.
Food science & nutrition, 8(1), 79-87 (2020-01-30)
Manipulation of rumen biohydrogenation (BH) is of great importance, since decreased BH of linolenic acid (LNA) and linoleic acid (LA) is linked to increased content of the beneficial polyunsaturated fatty acids (PUFA) in dairy products and decreased content of trans fatty

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