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Key Documents

L2376

Sigma-Aldrich

Linolenic acid

≥99%

Synonym(s):

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

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500 MG
$104.00
5 G
$623.00
10 G
$1,120.00

$104.00


Estimated to ship onMarch 29, 2025


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500 MG
$104.00
5 G
$623.00
10 G
$1,120.00

About This Item

Linear Formula:
CH3(CH2CH=CH)3(CH2)7CO2H
CAS Number:
Molecular Weight:
278.43
Beilstein/REAXYS Number:
1727693
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

$104.00


Estimated to ship onMarch 29, 2025


Request a Bulk Order

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.)

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.[1]

Application

Linolenic acid has been used:
  • to assess the total antioxidative activity of serum[2] and bacteria[3]
  • in palleroni chamber assay[4]
  • to prepare free fatty acid mixture[5]

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.[1] It plays an important role in brain development and prostaglandin synthesis. Deficiency of essential fatty acid is related to skin disorders and growth retardation.[6]
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_germany

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)

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Two antioxidative lactobacilli strains as promising probiotics
Kullisaar T, et al.
International Journal of Food Microbiology, 72(3), 215-224 (2002)
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)

Articles

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

Lipid Induced Insulin Resistance

Discover Bioactive Small Molecules for Lipid Signaling Research

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Questions

1–4 of 4 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. Is it suitable for cell culture assays?

    1 answer
    1. This product has not been tested specifically for cell culture applications or the presence of endotoxin. However, the following article indicates that this material has been used successfully in cell culture studies. Please see the link below :
      https://www.sigmaaldrich.com/technical-documents/technical-article/cell-culture-and-cell-culture-analysis/mammalian-cell-culture/linolenic-acid

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  4. What is the biological source of this reagent?

    1 answer
    1. The biological source of this is plant source; linseed/flax seed oil. Please check the Certificate of Origin (lot specific) for more information.

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