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L2626

Sigma-Aldrich

Methyl linolenate

≥99% (GC)

Synonym(s):

Linolenic acid methyl ester, Methyl cis,cis,cis-9,12,15-octadecatrienoate

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About This Item

Linear Formula:
CH3(CH2CH=CH)3(CH2)7COOCH3
CAS Number:
301-00-8
Molecular Weight:
292.46
Beilstein:
1728194
EC Number:
206-102-3
MDL number:
MFCD00135851
UNSPSC Code:
12352211
PubChem Substance ID:
24896319
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

plant

Quality Level

200

Assay

≥99% (GC)

form

liquid

refractive index

n20/D 1.470 (lit.)

bp

182 °C/3 mmHg (lit.)

density

0.895 g/mL at 25 °C (lit.)

functional group

ester

lipid type

unsaturated FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

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

InChI

1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h4-5,7-8,10-11H,3,6,9,12-18H2,1-2H3/b5-4-,8-7-,11-10-

InChI key

DVWSXZIHSUZZKJ-YSTUJMKBSA-N

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Application


  • Exogenous Jasmonic Acid Alleviates Blast Resistance Reduction Caused by LOX3 Knockout in Rice.: The research explores the role of jasmonic acid, associated with methyl linolenate, in enhancing blast resistance in rice. The findings show that external application of jasmonic acid can compensate for the resistance loss due to LOX3 knockout, providing insights into plant disease management strategies (Su et al., 2023).

  • Effects of (13)C isotope-labeled allelochemicals on the growth of the invasive plant Alternanthera philoxeroides.: This study uses (13)C-labeled methyl linolenate to trace allelochemical effects on invasive plant species. The results indicate a significant impact on plant growth, suggesting potential applications in controlling invasive species (Hua et al., 2023).

Biochem/physiol Actions

Methyl linolenate, a polyunsaturated fattly acid (PUFA), is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids. Methyl linolenate is being studied as a possible skin whitening agent with anti-melanogenesis activity.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000407570
0000407569
0000407569
0000407571
0000407570

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Kevin Huvaere et al.
The journal of physical chemistry. B, 114(16), 5583-5593 (2010-04-10)
Triplet-excited riboflavin ((3)RF*) was found by laser flash photolysis to be quenched by polyunsaturated fatty acid methyl esters in tert-butanol/water (7:3, v/v) in a second-order reaction with k approximately 3.0 x 10(5) L mol(-1) s(-1) at 25 degrees C for
G M Huber et al.
Journal of food science, 74(9), C693-C700 (2010-05-25)
Lipid oxidation, especially the oxidation of polyunsaturated fatty acids, is a significant issue in the food industry impacting both food quality and health of consumers. Apple skin was investigated as a source of natural antioxidants. The phenolic compound composition and
Photoaddition of angelicin to linolenic acid methyl ester.
S Caffieri et al.
Journal of photochemistry and photobiology. B, Biology, 2(4), 515-521 (1988-12-01)
Caroline P Baron et al.
Free radical research, 39(7), 777-785 (2005-07-23)
Protection against protein oxidation by lipophilic and hydrophilic antioxidants in model systems using bovine serum albumin (BSA) in solution alone, or in an emulsion with linolenic acid methyl ester (LnMe) was found to be strongly dependent on the oxidation initiator.
A A Gallon et al.
Lipids, 28(2), 125-133 (1993-02-01)
The autoxidation of polyunsaturated fatty acids is initiated both in vivo and in vitro by nitrogen dioxide. The mechanism of the initiation process is believed to involve both addition reactions and hydrogen atom abstraction reactions, with hydrogen abstraction predominating at
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Questions

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  1. 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

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  2. 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

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