112-63-0

Basic information

• Product Name: Methyl cis,cis-9,12-octadecadienoate
• Synonyms: 9,12-Octadecadienoicacid (Z,Z)-, methyl ester;Linoleic acid, methyl ester (6CI,8CI);(9Z,12Z)-9,12-Octadecadienoic acid methyl ester;(9Z,12Z)-Octadecadienoic acidmethyl ester;Methyl (9Z,12Z)-octadecadienoate;Methyl(Z,Z)-9,12-octadecadienoate;Methyl 9-cis,12-cis-octadecadienoate;Methylcis,cis-9,12-octadecadienoate;Methyl cis-9,cis-12 linoleate;Methyl cis-9,cis-12-octadecadienoate;Methyl linoleate;Methyl octadec-9,12-dienoate;Radia 7062
• CAS NO: 112-63-0
• Molecular Formula: C₁₉H₃₄O₂
• Molecular Weight: 294.4721
• EINECS: 203-993-0
• Mol File: 112-63-0.mol
• Article Data: 60

Chemical Properties

• Boiling Point: 373.3 °C at 760 mmHg
• Flash Point: 97 °C
• Appearance: Clear pale to dark yellow liquid
• Density: 0.884 g/cm³
• Vapor Pressure: 9.04E-06mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: Methyl cis,cis-9,12-octadecadienoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl cis,cis-9,12-octadecadienoate(112-63-0)
• EPA Substance Registry System: Methyl cis,cis-9,12-octadecadienoate(112-63-0)

Safety Data

• Hazardous Substances Data: 112-63-0(Hazardous Substances Data)

Usage

General Description

Methyl cis,cis-9,12-octadecadienoate, also known as methyl linoleate, is a chemical compound that belongs to the class of organic compounds known as fatty acid esters. It is a methyl ester derivative of linoleic acid, which is an essential polyunsaturated omega-6 fatty acid found in many vegetable oils. Methyl cis,cis-9,12-octadecadienoate is commonly used in the synthesis of various organic compounds and is also found naturally in plant oils, such as safflower oil and sunflower oil. It is used in the production of cosmetics, surfactants, and lubricants due to its moisturizing and emollient properties. Additionally, it is often used as a flavoring agent in food products and as a fragrance ingredient in perfumes and personal care products.

InChI:InChI=1/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-

Upstream product

• 67-56-1 methanol 
• 8001-25-0 olive oil 
• 8001-22-7 soybean oil 
• 8001-30-7 corn oil 
• 60-33-3 linoleic acid 
• 79760-41-1 (E)-12-Methanesulfonyloxy-octadec-9-enoic acid methyl ester 
• 186581-53-3 diazomethane 
• 1103509-91-6 (2S)-1-O-palmitoyl-2-O-linolenoyl-3-O-[α-D-galactopyranosyl-(1''->6')-(3''-O-linoleoyl)-β-D-galactopyranosyl]glycerol 
• 124-41-4 sodium methylate 
• 1103509-93-8 (2S)-1-O-palmitoyl-2-O-linoleoyl-3-O-[α-D-galactopyranosyl-(1''->6')-(3''-O-palmitoyl)-β-D-galactopyranosyl]glycerol 
• 1037300-77-8 11,11-dideutero-cis,cis-octadeca-9,12-dienoic acid methyl ester 
• 684-93-5 1-methyl-1-nitrosourea 
• 13019-22-2 9-Decen-1-ol 
• 111-12-6 methyl 2-octynoate 

Downstream Products

• 553-90-2 Dimethyl oxalate 
• 627-93-0 hexanedioic acid dimethyl ester 
• 1732-10-1 Dimethyl azelate 
• 1119-40-0 Dimethyl glutarate 
• 1732-09-8 dimethyl subarate 
• 106-65-0 Dimethyl succinate 
• 7424-91-1 methyl 3,3-dimethoxypropionate 
• 1599-47-9 1,1-dimethoxyhexane 
• 1599-48-0 9,9-bis(methoxy)nonanoic acid methyl ester 
• 38433-95-3 propyl linoleate 
• 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 

Relevant articles and documents

Two new glyceroglycolipids from the fruits of Cucurbita moschata

Aphytochemical study of Cucurbita moschata resulted in the characterisation of two new glyceroglycolipids, 1-O-(9Z, 12Z,15Z-octadecatrienoyl)-3-0-[β- D-galactopyranosyl-(1-6)-0-p-D-galactopyranosyl-(1?6)-O-p-D-galactopyranosyl] glycerol (1) and 1-0-(9Z,12

A Facile Method for Activation of Carboxylic Acids

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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.

Bioactive tigliane diterpenoids from the latex of Euphorbia fischeriana

Latex is a type of sticky endogenous fluids derived from diverse plants including Euphorbia fischeriana, and is of great scientific and commercial values. In the current study, it was demonstrated that the latex extracted from E. fischeriana strongly respelled the growth of cotton bollworm, Helicoverpa armigera. Using spectroscopic methods, HPLC, and GC-MS analyses, six aliphatic tigliane diterpenoids were isolated from the latex of E. fischeriana, among which three compounds (2, 3, and 5) were new. Two major compounds (1 and 4) exhibited remarkable antifeedant activity against H. armigera, with EC50 values at 2.59 and 15.32 μg/cm2, respectively. In addition, the quantification analysis of diterpenoids in different organs indicated that 4 was the most abundant constituent and was highly accumulated in the latex. Collectively, the current study highlighted that the diterpenoids in latex of E. fischeriana had a considerable antifeedant function against H. armigera, which might be employed for the future development of natural insecticides for organic farming.

Novel synthesized microporous ionic polymer applications in transesterification of Jatropha curcas seed oil with short Chain alcohol

New suites of sulfonic acid-functionalized microporous ionic polymers (PIPs) catalysts were synthesized with polymer, alkyl bromides, and 1, 3-propane sultone via a two-step procedure. The synthesized microporous PIP catalysts were characterized using FT-IR, SEM-Mapping, XPS, N2 adsorption–desorption isotherms, solid NMR spectroscopy, and element analysis. Esterification of several fatty acids with ethanol, which was used as a model reaction in the stabilization of Jatropha curcas seed oil, was checked over functionalized PIP. We tested the catalytic performance of PIP-C8 on the synthesis of fatty acid esters via the transesterification of J. curcas seed oil with a mixture of short-chain alcohols such as ethanol, ethanol–to–diethyl carbonate (1;1 molar ratio), and ethanol–to–dimethyl carbonate (1:1 molar ratio) with 170 mg of PIP-C8 at reflux temperature with agitation. The PIP-C8 catalyst was particularly effective, having achieved yields of 85%, 94%, and 70% for J. curcas seed oil with ethanol, J. curcas seed oil with ethanol–to–DEC, and J. curcas seed oil with ethanol–to–DMC, respectively, under the optimized reaction conditions. The catalyst could be recycled more than five times without significant deactivation. Kinetic studies performed at different temperatures revealed that the conversion of oleic acid to an ethyl ester follows a first-order reaction. The best catalysts with microporous structure (average pore diameter: 1.7–1.9 nm, pore volume: 0.23–0.33 cm3 g–1) and –SO3H density (0.70–0.84 mmol/gcat) were obtained by 1, 3-propane sultone of the chemically activated. The results indicate that the site activity of functionalized microporous ionic polymer materials shows promising approach for the development of environmentally friendly technology.

Highly ordered mesoporous functionalized pyridinium protic ionic liquids framework as efficient system in esterification reactions for biofuels production

Polysiloxane acidic ionic liquids containing pyridinium trifluoroacetate salts (PMO-Py-IL) were synthesized from pyridine containing organosilane precursors. Characterization by SEM, XRD, TGA, and nitrogen porosimetry confirmed that both pyridinium cation and trifluoroacetate anion were successfully incorporated within the organosilica network. The resulting organic-inorganic hybrid nanomaterial (PMO-Py-IL) was studied as nanocatalyst in free fatty acids esterification into biodiesel-like compounds. Remarkably, the synergistic hydrophilic/hydrophobic effect of pyridinium and trifluoroacetate ionic liquid in the well-ordered channels of PMO-Py-IL nanomaterial enhanced the activity toward sustainable biodiesel-like esters production. More importantly, PMO-Py-IL nanocatalyst also exhibited an exceptional activity and stability. The catalyst could be easily separated to reuse at least in ten reactions runs preserving almost intact its catalytic activity under otherwise identical conditions to those employed for the fresh catalysts.