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Merck
CN

L2376

Linolenic acid

≥99%

Synonym(s):

α-Lnn, cis,cis,cis-9,12,15-Octadecatrienoic acid

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About This Item

Linear Formula:
CH3(CH2CH=CH)3(CH2)7CO2H
CAS Number:
463-40-1
Molecular Weight:
278.43
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
24896311
EC Number:
207-334-8
Beilstein/REAXYS Number:
1727693
MDL number:
MFCD00065720
Assay:
≥99%
Quality level:
200

Key Documents

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Quality Level

200

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.)

lipid type

omega FAs

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

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.

Packaging

Sealed ampule

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000545332
0000529413
0000529410
0000529415
0000533538

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Sabiston Textbook of Surgery E-Book, 144-144 (2012)
Rennie & Roberton's Textbook of Neonatology E-Book, 285-285 (2012)
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)
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)
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
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Linolenic Acid in Cell Culture

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

脂质诱导的胰岛素耐受性

脂肪组织中的胰岛素耐受性减少了循环游离脂肪酸的摄入，并增加了脂肪酶对储存甘油三酯的水解。了解与胰岛素耐受性相关的激素、细胞因子和脂肪因子。

Global Trade Item Number

SKUGTIN
L2376-10G04061833949979
L2376-5G04061835516124
L2376-500MG04061835506385

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