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Sigma-Aldrich

Linolenic acid

~70% (GC)

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Synonym(s):
α-Lnn, cis,cis,cis-9,12,15-Octadecatrienoic acid
Linear Formula:
CH3(CH2CH=CH)3(CH2)7CO2H
CAS Number:
463-40-1
Molecular Weight:
278.43
Beilstein/REAXYS Number:
1727693
EC Number:
207-334-8
MDL number:
MFCD00065720
UNSPSC Code:
12352211
PubChem Substance ID:
57651877
NACRES:
NA.77

assay

~70% (GC)

Quality Level

200

impurities

~25% linoleic acid
~5% oleic acid

refractive index

n20/D 1.477
n20/D 1.480 (lit.)

bp

230-232 °C/1 mmHg (lit.)

mp

-11 °C (lit.)

density

0.914 g/mL at 25 °C (lit.)

lipid type

omega FAs

storage temp.

2-8°C

SMILES string

CC/C=C\C/C=C\C/C=C\CCCCCCCC(O)=O

InChI

1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-

InChI key

DTOSIQBPPRVQHS-PDBXOOCHSA-N

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Biochem/physiol Actions

An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.

wgk_germany

WGK 1

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves

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An Pan et al.
The American journal of clinical nutrition, 96(6), 1262-1273 (2012-10-19)
Prior studies of α-linolenic acid (ALA), a plant-derived omega-3 (n-3) fatty acid, and cardiovascular disease (CVD) risk have generated inconsistent results. We conducted a meta-analysis to summarize the evidence regarding the relation of ALA and CVD risk. We searched multiple
Gwendolyn Barceló-Coblijn et al.
Progress in lipid research, 48(6), 355-374 (2009-07-22)
There is little doubt regarding the essential nature of alpha-linolenic acid (ALA), yet the capacity of dietary ALA to maintain adequate tissue levels of long chain n-3 fatty acids remains quite controversial. This simple point remains highly debated despite evidence
Eoin Barrett et al.
PloS one, 7(11), e48159-e48159 (2012-11-28)
The aim of this study was to compare the impact of dietary supplementation with a Bifidobacterium breve strain together with linoleic acid & α-linolenic acid, for 7 weeks, on colonic sensitivity and fatty acid metabolism in rats. Maternally separated and
C Mapiye et al.
Meat science, 95(1), 98-109 (2013-05-15)
Yearling steers were fed 70:30 forage:concentrate diets for 205 d, with either grass hay (GH) or red clover silage (RC) as the forage source, and concentrates containing either sunflower-seed (SS) or flaxseed (FS), each providing 5.4% oil to diets. Feeding
Takayoshi Suzuki et al.
Journal of medicinal chemistry, 51(23), 7640-7644 (2008-11-15)
A weak, nonselective G protein-coupled receptor 120 (GPR120) agonist 10 was found by screening a series of carboxylic acids derived from the peroxisome proliferator-activated receptor gamma (PPARgamma) agonist 3. Modification based on the homology model of GPR120 led to the
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