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L2376

Sigma-Aldrich

Linolenic acid

≥99%

Synonym(s):
α-Lnn, cis,cis,cis-9,12,15-Octadecatrienoic acid
Linear Formula:
CH3(CH2CH=CH)3(CH2)7CO2H
CAS Number:
Molecular Weight:
278.43
Beilstein:
1727693
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥99%

refractive index

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.)

storage temp.

−20°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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General description

Linolenic acid is an essential fatty acid, which is not produced in the body. Plants and fishes are rich sources of linolenic acid.

Application

Linolenic acid has been used:
  • to assess the total antioxidative activity of serum and bacteria
  • in palleroni chamber assay
  • to prepare free fatty acid mixture

Packaging

500 mg in ampule
5, 10 g in ampule
Sealed ampule

Biochem/physiol Actions

Linolenic acid is involved in the formation of highly unsaturated fatty acid. It is essential for the development of skin, blood and neural cells. Linolenic acid is also associated with the organization of lipid membranes of neural synapses, pigment epithelial cells of retina and myocardial cells. It plays an important role in brain development and prostaglandin synthesis. Deficiency of essential fatty acid is related to skin disorders and growth retardation.
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.

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Rennie & Roberton's Textbook of Neonatology E-Book, 285-285 (2012)
Sabiston Textbook of Surgery E-Book, 144-144 (2012)
Bacterial chemoattraction towards jasmonate plays a role in the entry of Dickeya dadantii through wounded tissues
Antunez-Lamas M, et al.
Molecular Microbiology, 74(3), 662-671 (2009)
Culture of rodent spermatogonial stem cells, male germline stem cells of the postnatal animal
Kubota Hiroshi and Brinster Ralph L
Methods in Cell Biology, 86, 59-84 (2008)
Two antioxidative lactobacilli strains as promising probiotics
Kullisaar T, et al.
International Journal of Food Microbiology, 72(3), 215-224 (2002)

Articles

Linolenic Acid in Cell Culture

Importance and uses of linolenic acid in serum-free eukaryotic, including hybridoma and Chinese Hamster Ovary (CHO) cell, cultures

Omega-3 Fatty Acids and Heart Disease

The potential for the prevention and treatment of cardiovascular disease through increased dietary intake of omega-3 (w-3) fish oils is not a recent scientific discovery.

Lipid-induced Insulin Resistance

Lipid Induced Insulin Resistance

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