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Usage

Uses

Used in Pharmaceutical Industry:
METHYL LINOLENATE is used as a cytotoxic agent for human lung carcinoma cell lines, making it a potential candidate for cancer treatment.
Used in Food Industry:
METHYL LINOLENATE is used as a natural flavoring agent and essential oil component in various food products due to its presence in fruits and vegetables.
Used in Cosmetic Industry:
METHYL LINOLENATE can be used as a natural ingredient in cosmetic products due to its essential oil properties and potential health benefits.
Used in Research:
METHYL LINOLENATE can be used in scientific research to study its potential applications and effects on human health and disease.

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.

InChI:InChI=1/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-

Upstream product

• 186581-53-3 diazomethane 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 145937-22-0 (2S)-3-O-[α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl]-1-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 90121-04-3 <(Z,Z)-nona-3,6-dien-1-yl>triphenylphosphonium bromide 
• 68254-41-1 MethPrep I 
• 67-56-1 methanol 
• 1403471-58-8 C₄₇H₈₂O₁₀ 
• 1352455-08-3 C₅₁H₉₀O₁₅ 
• 121124-30-9 C₄₅H₇₆O₁₀ 
• 63180-02-9 (2S)-3-O-β-D-galactopyranosyl-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol 
• 87584-96-1 (2S)-1-O-(9Z,12Z,15Z-octadecyltrienoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(β-D-galactopyranose-6-1-α-D-galactopyranose)-sn-glycerol 

Downstream Products

• 20257-95-8 8-hydroxyoctanoic acid methyl ester 
• 627-93-0 hexanedioic acid dimethyl ester 
• 1732-10-1 Dimethyl azelate 
• 1732-08-7 dimethyl 1,7-heptanedioate 
• 1732-09-8 dimethyl subarate 
• 14565-11-8 methyl 7-hydroxyheptanoate 
• 7424-91-1 methyl 3,3-dimethoxypropionate 
• 4744-10-9 dimethoxypropane 
• 1599-48-0 9,9-bis(methoxy)nonanoic acid methyl ester 
• 10601-80-6 ethyl 3,3-diethoxypropanoate 
• 51503-33-4 Methyl ethyl nonanedioate 
• 129082-98-0 Methyl 9,9-diethoxynonanoate 
• 105-53-3 diethyl malonate 
• 112-61-8 Methyl stearate 

Relevant academic research and scientific papers

Epoxy-acetogenins and other polyketide epoxy derivatives as inhibitors of the mitochondrial respiratory chain complex I

Annonaceous acetogenins (ACG), an extensive group of cytotoxic natural products, are antitumor agents whose main mode of action is inhibition of the mammalian mitochondrial complex I. Herein we describe the importance of the different chemical groups along the alkyl chain for optimal inhibitory potency, discussing the structurally relevant factors present in these compounds. For this purpose, a series of epoxide derivatives from α- linolenic acid were prepared and their activity compared with that of epoxy- acetogenins and tetrahydrofuranic (THF) acetogenins isolated from Rollinia membranacea.

Chemical constituents and antibacterial activity of Melastoma malabathricum L.

The aqueous methanolic extracts of Melastoma malabathricum L. exhibited antibacterial activity when assayed against seven microorganisms by the agar diffusion method. Solvent fractionation afforded active chloroform and ethyl acetate fractions from the leaves and the flowers, respectively. A phytochemical study resulted in the identification of ursolic acid (1), 2α- hydroxyursolic acid (2), asiatic acid (3), β-sitosterol 3-O-β-D-glucopyranoside (4) and the glycolipid glycerol 1,2-dilinolenyl-3-O-β-D-galactopyanoside (5) from the chloroform fraction. Kaempferol (6), kaempferol 3-O-α-L-rhamnopyranoside (7), kaempferol 3-O-β-D-glucopyranoside (8), kaempferol 3-O-β-D-galactopyranoside (9), kaempferol 3-O-(2 ,6 -di-O-E-p-coumaryl)-β-D-galactopyranoside (10), quercetin (11) and ellagic acid (12) were found in the ethyl acetate fraction. The structures of these compounds were determined by chemical and spectral analyses. Compounds 1-4, the flavonols (6 and 11) and ellagic acid (12) were found to be active against some of the tested microorganisms, while the kaempferol 3-O-glycosides (7-9) did not show any activity, indicating the role of the free 3-OH for antibacterial activity. Addition of p-coumaryl groups results in mild activity for 10 against Staphylococcus aureus and Bacillus cereus. Compounds 2-5, 7 and 9-12 are reported for the first time from M. malabathricum. Compound 10 is rare, being reported only once before from a plant, without assignment of the double bond geometry in the p-coumaryl moiety.

Secondary metabolites of Astragalus danicus Retz. and A. inopinatus Boriss

The chemical composition of the above-ground parts of Astragalus danicus and A. inopinatus collected in the Baikal region (Eastern Siberia) was studied for the first time. From A. danicus, pentacyclic triterpene saponins were isolated and identified, viz., 3-O-(β-glucuronopyranosyl)-3β,22β,24-trihydroxyolean-12-ene, 3-O-[O-(β-D-xylopyranosyl)-(1→2)-(β-glucuronopyranosyl)]-3β, 22β,24-trihydroxyolean-12-ene, 3-O-[O-(β-D-glucopyranosyl)-(1→2)-(β-glucuronopyranosyl)]-3β ,22β,24-trihydroxyolean-12-ene, 3-O-[O-(α-L-rhamnopyranosyl)-(1→2)-O-(β-D-xylopyranosyl) -(1→2)-(β-glucuronopyranosyl)]-3β,22β,24-trihydroxyolean-12-ene, 3-O-[O-(α-L-rhamnopyranosyl)-(1→2)-O-(β-D-glucopyranosyl)-(l-2)-(β-glucuronopyranosyl)]-3β,22β,24-trihydroxyolean-12-ene, 3-O-methyl-D-chiro-inositol, and linolenic acid. In A. inopinatus, the same saponins were identified as well as tricosan-1-ol and tetracosan-1-ol, 5,7,4′-trihydroxyflavon (apigenin), and atetracyclic triterpenoid, 20(R),24(S)-epoxycyclolanost-9(11)-ene-3β,6α, 16β, 25-tetrol (cycloastragenol). All reported compounds from the both genus of Astragalus were isolated for the first time. Methanolic extracts of A. danicus and A. inopinatus exhibited low inhibitory activity with respect to the growth of HeLa cells. The chloroform fraction of A. danicus showed a strong antimicrobial activity against Staphylococcus aureus and a strong cytotoxic activity against HeLa cells.

Linoleic acid, α-linolenic acid, and monolinolenins as antibacterial substances in the heat-processed soybean fermented with Rhizopus oligosporus

Antibacterial activities against Staphylococcus aureus and Bacillus subtilis were found in an ethanol fraction of tempe, an Indonesian fermented soybean produced using Rhizopus oligosporus. The ethanol fraction contained free fatty acids, monoglycerides, and fatty acid ethyl esters. Among these substances, linoleic acid and α-linolenic acid exhibited antibacterial activities against S. aureus and B. subtilis, whereas 1-monolinolenin and 2-monolinolenin exhibited antibacterial activity against B. subtilis. The other free fatty acids, 1-monoolein, monolinoleins, ethyl linoleate, and ethyl linolenate did not exhibit bactericidal activities. These results revealed that R. oligosporus produced the long-chain polyunsaturated fatty acids and monolinolenins as antibacterial substances against the Gram-positive bacteria during the fungal growth and fermentation of heat-processed soybean.

Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves

Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linoli

Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions

A catalytic method for the preparation of a series of fatty acid derived biocarbonates has been developed using a binary Al-complex/PPNCl catalyst. This catalyst system allows conversion of fatty acid derived epoxides under comparatively mild reaction conditions (70-85 °C, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios of up to 97:3 in the products. The comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components show that the presence of the Al-complex is crucial for the retention of the original stereochemistry.

Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water

A copper catalytic system was established for the stereoselective hydrodefluorination of gem-difluoroalkenes through C?F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good-functional group compatibility, accepting a range of carbonyls as precursors to the gem-difluoroalkenes, including aliphatic, aromatic, and α,β-unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late-stage modification of complex compounds.

Methanolysis of Jatropha curcas oil using K2CO3/CaO as a solid base catalyst

Biodiesel, fatty acid methyl ester produced by the transesterification of vegetable oil with methanol, is a promising alternative to petroleum-based diesel fuel. In the present study, the methanolysis of high free fatty acid (FFA) Jatropha curcas oil in a transesterification reaction using K 2 CO 3 /CaO solid base catalyst was studied. The various reaction parameters in the transesterification reaction were also discussed. The catalyst was characterized by means of Fourier transform infrared, X-ray diffraction, temperature programmed desorption of CO 2, scanning electron microscopy, particle size analyzer, true density, and surface area analyzer. The optimum conversion of jatropha oil was 92% when the transesterification reaction was carried out at 70? C with 10:1 molar ratio of methanol to oil at reaction time of 3 h and catalyst amount of 6 wt%. The efficiency of catalysts in the methanolysis of jatropha oil was also investigated.

GC-FID analysis of fatty acids and biological activity of Zanthoxylum rhetsa (Roxb.) DC seed oil

The Fatty acid content and composition of fixed oil from Zanthoxylum rhetsa seeds was determined. The seeds were found to contain about ～19.5% of crude fixed oil on a dry weight basis. Fatty acids were converted into methyl esters and analyzed by GC-FID. Ten fatty acids were identified using GC-FID. The major monounsaturated and saturated fatty acids were oleic acid (41.6 - 43.5%) and palmitic acid (26.8-30.2%) respectively, whereas the α-linolenic acid (12.1 - 12.5%) and linoleic acid (10.0%) were polyunsaturated fatty acid. Stearic acid (5.2 - 6.0%), myristic acid (0.1%), traces of pentadecanoic, heptadecanoic and arachidic acid were also identified. These fatty acids have not been reported earlier from the oil of Z. rhetsa. Fixed oil exhibited significant free radical scavenging activity which was measured using DPPH, and is also known to inhibit the gastrointestinal motility significantly.

Plasticizer and surfactant formation from food-waste- and algal biomass-derived lipids

The potential of lipids derived from food-waste and algal biomass (produced from food-waste hydrolysate) for the formation of plasticizers and surfactants is investigated herein. Plasticizers were formed by epoxidation of double bonds of methylated unsaturated fatty acids with in situ generated peroxoformic acid. Assuming that all unsaturated fatty acids are convertible, 0.35 and 0.40 g of plasticizer can be obtained from 1 g of crude algae- or food-waste-derived lipids, respectively. Surfactants were formed by transesterification of saturated and epoxidized fatty acid methyl esters (FAMEs) with polyglycerol. The addition of polyglycerol would result in a complete conversion of saturated and epoxidized FAMEs to fatty acid polyglycerol esters. This study successfully demonstrates the conversion of food-waste into value-added chemicals using simple and conventional chemical reactions.