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62240

Sigma-Aldrich

Linoleic acid

technical, 58-74% (GC)

Synonym(s):
Telfairic acid, 9-cis,12-cis-Linoleic acid, cis-9,cis-12-Octadecadienoic acid
Linear Formula:
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
CAS Number:
Molecular Weight:
280.45
Beilstein:
1727101
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

technical

assay

58-74% (GC)

form

liquid (clear)

impurities

18-32% oleic acid

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.

Packaging

1 L in glass bottle
250 mL in glass bottle

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

Storage Class Code

10 - Combustible liquids

WGK Germany

WGK 1

Flash Point F

235.4 °F - closed cup

Flash Point C

> 113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

"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)
"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)
"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 supplementation reduces adipose tissue by apoptosis and develops lipodystrophy in mice"
Tsuboyama-Kasaoka N, et al.
Diabetes, 49(09), 1534-1542 (2000)
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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