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Sigma-Aldrich

Linoleic acid

technical, 58-74% (GC)

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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
PubChem Substance ID:
57651878
NACRES:
NA.22

grade

technical

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

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

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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.

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

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

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