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Key Documents

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:
Molecular Weight:
292.46
Beilstein:
1728194
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

biological source

plant

Quality Level

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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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
Patrícia Baptista et al.
Analytica chimica acta, 607(2), 153-159 (2008-01-15)
Biodiesel is the main alternative to fossil diesel. The key advantages of its use are the fact that it is a non-toxic renewable resource, which leads to lower emissions of polluting gases. European governments are targeting the incorporation of 20%
Rosario Zamora et al.
Journal of agricultural and food chemistry, 51(16), 4661-4667 (2004-01-07)
The oxidation of methyl linoleate (LMe) and methyl linolenate (LnMe) in the presence of bovine serum albumin (BSA) in the dark at 60 degrees C was studied to analyze the role of the type of fatty acid and the protein/lipid
Saori Okuda et al.
Journal of agricultural and food chemistry, 53(24), 9624-9628 (2005-11-24)
The purpose of this research was to examine the influence of the physical state of lipids on iron-promoted oxidation of methyl linolenate in octadecane oil-in-water emulsions. Octadecane and methyl linolenate oil-in-water emulsions were prepared that contained droplets having the octadecane
Philippe Lesot et al.
Analytical chemistry, 80(8), 2963-2972 (2008-03-11)
The quantitative determination of isotopic (2H/1H)i ratios at natural abundance using the SNIF-NMR protocol is a well-known method for understanding the enzymatic biosynthesis of metabolites. However, this approach is not always successful for analyzing large solutes and, specifically, is inadequate

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