13038-47-6

Usage

Uses

Used in Cosmetic and Personal Care Industry:
(9E,11E)-9,11-Octadecadienoic acid methyl ester is used as an ingredient in the formulation of cosmetic and personal care products for its emollient and moisturizing properties. It helps to maintain the skin's softness and suppleness, providing a smooth and hydrated feel.
Used in Biodiesel Production:
Methyl linoleate is used as a component in the production of biodiesel, a renewable and environmentally friendly alternative to traditional fossil fuels. Its presence in biodiesel contributes to improved fuel properties, such as lubricity and reduced emissions.
Used as a Lubricant:
In the industrial sector, (9E,11E)-9,11-Octadecadienoic acid methyl ester is used as a lubricant due to its ability to reduce friction between moving parts. This application is particularly relevant in the manufacturing processes of various mechanical components and machinery.
Used as a Solvent:
Methyl linoleate is also utilized as a solvent in the chemical and pharmaceutical industries. Its solvent properties enable the dissolution of various substances, facilitating reactions and processes in the production of different products.
Used in Scientific Research:
(9E,11E)-9,11-Octadecadienoic acid methyl ester is employed in scientific research for its potential benefits in human health and nutrition. Studies are conducted to explore its role in various physiological processes and its potential applications in the development of novel therapeutic strategies.

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/h8-11H,3-7,12-18H2,1-2H3/b9-8+,11-10+

Upstream product

• 506-23-0 eleostearic acid 
• 79760-41-1 (E)-12-Methanesulfonyloxy-octadec-9-enoic acid methyl ester 
• 112-62-9 Methyl oleate 
• 67-56-1 methanol 
• 544-70-7 cis-9,trans-11-octadecadienoic acid 
• 2462-85-3 linoleic acid methyl ester 
• 112-63-0 Methyl linoleate 
• 544-70-7 trans-9,trans-11-octadecadienoic acid 
• 23224-20-6 methyl ricinoleate 
• 141-22-0 Ricinoleic acid 
• 141-24-2 methyl ricinoleate 
• 57884-97-6 (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester 
• 67529-83-3 (E)-methyl 12-hydroxy-9-octadecenoate 
• 1072-36-2 trans-10,cis-12-octadecadienoic acid 

Downstream Products

• 2051-25-4 deca-1,3-diene 
• 111-66-0 oct-1-ene 
• 25601-41-6 methyl 9-decenoate 
• 10374-74-0 tetradec-7-ene 
• 256235-74-2 methyl dodeca-9,11-dienoate 
• 13481-97-5 dimethyl 9-octadecen-1,18-dioate 
• 544-70-7 cis-9,trans-11-octadecadienoic acid 
• 56666-45-6 C₂₂H₃₉NO 
• 544-70-7 trans-9,trans-11-octadecadienoic acid 
• 1842-70-2 methyl 9-oxooctadecanoate 
• 112-61-8 Methyl stearate 
• 6114-39-2 methyl 12-hydroxyoctadecanoate 
• 10038-16-1 methyl 8-(5-hexyl-2-furyl)-octanoate 

Relevant academic research and scientific papers

Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid

Production of conjugated linoleic acids (CLA) using castor oil as starting material involves conversion of ricinoleic acid to methyl 12-mesyloxy-octadec-9-enoate (MMOE) followed by dehydration. This process usually uses 1,8-diazabicyclo-(5.4.0)-undec-7-ene (DBU) as an expensive dehydrating reagent. The present study reports that potassium hydroxide (KOH) can serve as a dehydrating reagent in replacement of DBU. The results showed that conversion of MMOE to CLA catalyzed by KOH was an efficient reaction, with a 77% conversion efficiency at 80°C. The CLA isomeric profile produced in KOH-catalyzed dehydration reaction was similar to that catalyzed by DBU. The CLA mixture produced in KOH-catalyzed dehydration of MMOE at 80°C contained 72% 9c,11t-18:2 and 26% 9c,11c-18:2 while in that catalyzed by DBU, 9c,11t-18:2 and 9c,11c-18:2 accounted for 78 and 16%, respectively. It was found that the temperature of dehydration was an important factor in the determination of CLA isomer composition and yield of conversion. Elevating the temperature from 78 to 180°C decreased not only the conversion efficiency but also production of total c,t-18:2 and c,c-18:2 isomers regardless of dehydration catalyzed by either DBU or KOH. It is concluded that KOH may replace DBU as a dehydrating reagent in conversion of MMOE to CLA when the reaction conditions are optimized.

Absorption Kinetics of the Main Conjugated Linoleic Acid Isomers in Commercial-Rich Oil after Oral Administration in Rats

This study aimed to assess the oral absorption and plasma kinetics of two main isomers contained in commercial conjugated linoleic acid (CLA)-rich oil (Tonalin TG-80), rumenic acid (RA), and C18:2 trans-10, cis-12. The isomer plasma disposition after the single oral dose of 3000 mg of Tonalin TG-80/kg, containing 1200 mg/kg of each isomer, was studied in rats. The isomer plasma concentrations were determined by gas chromatography with flame ionization detection. The plasma kinetics showed rapid oral absorption of RA and C18:2 trans-10, cis-12 (t1/2a 0.34 ± 0.09 and 0.53 ± 0.01 h) and slow elimination (t1/2β 25.68 ± 3.29 and 18.12 ± 1.71 h); the maximal isomer plasma concentrations (Cmax) of 8.48 ± 0.98 and 7.67 ± 0.80 μg mL-1, respectively, were estimated at 2.08 ± 0.14 and 2.26 ± 0.11 h. Our results from a preclinical kinetic study in rats help to design future studies in humans for evaluating the CLA isomer dose-response.

Transformation of Methyl Linoleate to its Conjugated Derivatives with Simple Pd(OAc)2/Lewis Acid Catalyst

With the rapid depletion of fossil resources, the exploitation of biomass to partly replace fossil resources as the source of carbon in the chemical industry constitutes a promising alternative for the near future. This work introduces catalytic transformation of vegetable oil, i.e., methyl linoleate, to its conjugated esters by a simple Pd(OAc)2/Sc(OTf)3 catalyst, which has extensive applications in industry. It was found that adding non-redox metal ions like Sc(III) to a simple Pd(OAc)2 catalyst can effectively improve its isomerization activity in toluene/t-BuOH solvent, whereas Pd(OAc)2 alone is inactive. Preliminary mechanistic investigations together with previous studies suggested that the in situ-generated heterobimetallic Pd(II)/Sc(III) dimer serves as the key species for methyl linoleate isomerization, and the reaction proceeds by [1,3]-hydrogen shift mechanism involving a formal Pd(II)/Pd(IV) cycle.

Dissociation of proton-bound complexes reveals geometry and arrangement of double bonds in unsaturated lipids

Double bond position and stereochemistry in unsaturated lipids can have profound impact on biological properties and activities but the assignment of these features by mass spectrometry is frequently challenging. Conventional techniques for lipid identification rely on collision-induced dissociation (CID) and are most often unable to differentiate between lipid isomers, particularly those involving double bond position and geometry (i.e., cis and trans). In this study, CID performed on proton-bound complexes of fatty acid methyl esters and iodoaniline (and related reagents) reveals unusual fragmentation patterns. CID products are shown to result from proton transfer and are associated with specific structures of the unsaturated lipids. Notably, CID of these complexes can not only distinguish cis- and trans-fatty acid methyl esters, but also differentiate conjugated double bond arrangements from non-conjugated analogs. Herein, the mechanisms underpinning this unique CID behavior are investigated by stable isotope labeling and are proposed to involve both carbene and free radical intermediates.

Sustainable and efficient methodology for CLA synthesis and identification

Microwave-assisted organic synthesis and continuous-flow techniques have been successfully employed for the preparation of conjugated linoleic acids (CLA), compounds with high health beneficial effects. A good production rate of CLA was obtained. A sustainable methodology for the differentiation of both positional and geometrical CLA isomers (diene), based on the analysis by NMR spectroscopy of the resulting Diels-Alder cycloadducts with an appropriate dienophile, was developed.

Design of ru-zeolites for hydrogen-free production of conjugated linoleic acids

While conjugated vegetable oils are currently used as additives in the drying agents of oils and paints, they are also attractive molecules for making bio-plastics. Moreover, conjugated oils will soon be accepted as nutritional additives for "functional food" products. While current manufacture of conjugated vegetable oils or conjugated linoleic acids (CLAs) uses a homogeneous base as isomerisation catalyst, a heterogeneous alternative is not available today. This contribution presents the direct production of CLAs over Ru supported on different zeolites, varying in topology (ZSM-5, BETA, Y), Si/Al ratio and countercation (H+, Na+, Cs+). Ru/Cs-USY, with a Si/Al ratio of 40, was identified as the most active and selective catalyst for isomerisation of methyl linoleate (cis-9,cis-12 (C18:2)) to CLA at 165 °C. Interestingly, no hydrogen pre-treatment of the catalyst or addition of hydrogen donors is required to achieve industrially relevant isomerisation productivities, namely, 0.7 g of CLA per litre of solvent per minute. Moreover, the biologically most active CLA isomers, namely, cis-9,trans-11, trans-10,cis-12 and trans-9,trans-11, were the main products, especially at low catalyst concentrations. Ex situ physicochemical characterisation with CO chemisorption, extended X-ray absorption fine structure measurements, transmission electron microscopy analysis, and temperature-programmed oxidation reveals the presence of highly dispersed RuO2 species in Ru/Cs-USY(40). Copyright

Superior anticarcinogenic activity of trans, trans-conjugated linoleic acid in N-methyl-N-nitrosourea-induced rat mammary tumorigenesis

The anticarcinogenic activity of a mixture of trans,trans-conjugated linoleic acid (trans,trans-CLA) was investigated in rat mammary tumorigenesis induced by N-methyl-N-nitrosourea (MNU), with references to cis-9,trans-11-CLA and trans-10,cis-12-CLA isomers. Female, 7-week-old Sprague-Dawley rats were intraperitoneally injected with MNU (50 mg/kg of body weight) and then subjected to one of five diets (control, 1% trans,trans-CLA, 1% cis-9,trans-11-CLA, 1% trans-10,cis-12-CLA, and 1% linoleic acid; 8 rats/group) for 16 weeks. Food and water were made available ad libitum. trans,trans-CLA significantly (p 0.05) reduced tumor incidence, number, multiplicity, and size and significantly (p 0.05) increased apoptosis, relative to cis-9,trans-11-CLA and trans-10,cis-12-CLA. The molecular mechanism of trans,trans-CLA was elucidated by measuring apoptosis-related gene products and fatty acid composition in tumors. trans,trans-CLA led to increases in the p53 protein and Bax protein levels but suppressed the expression of Bcl-2 protein. The activation of caspase-3 led to the cleavage of poly(ADP-ribose) polymerase, which resulted in the execution of apoptosis. In addition, trans,trans-CLA reduced cytosolic phospholipase A2, cyclooxygenease-2, and peroxisome proliferator-activated receptor γ protein levels. These results suggest that the trans,trans-CLA inhibits MNU-induced rat mammary tumorigenesis through the induction of apoptosis in conjunction with the reduction of arachidonic acid metabolites and that the efficacy of trans,trans-CLA is superior to cis-9,trans-11-CLA and trans-10,cis-12-CLA.

PROCESS FOR PREPARING CONJUGATED LINOLEIC ACID AND DERIVATIVES THEREOF FROM RICINOLEIC ACID

A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.

Method for Making Industrial Chemicals

A process for producing industrially important chemicals from renewable resources is disclosed. This “biobased” process employs readily available, renewable resources comprising fatty acids rather than exploiting fossil sources, such as coal and petroleum. In one embodiment of the process 1-octene, along with methyl-9-decenoate and butadiene, is produced from linoleic acid via an enzymemediated isomerization reaction, followed by a metathesis reaction with ethylene. Linoleic acid can be isolated from vegetable oils, such as soybean oil.

Elucidation of structural isomers from the homogeneous rhodium-catalyzed isomerization of vegetable oils

The structural isomers formed by the homogeneous rhodium-catalyzed isomerization of several vegetable oils have been elucidated. A detailed study of the isomerization of the model compound methyl linoleate has been performed to correlate the distribution of conjugated isomers, the reaction kinetics, and the mechanism of the reaction. It has been shown that [RhCl(C8H 8)2]2 is a highly efficient and selective isomerization catalyst for the production of highly conjugated vegetable oils with a high conjugated linoleic acid (CLA) content, which is highly desirable in the food industry. The combined fraction of the two major CLA isomers [(9Z,11E)-CLA and (10E,12Z)-CLA] in the overall CLA mixture is in the range from 76.2% to 93.4%. The high efficiency and selectivity of this isomerization method along with the straightforward purification process render this approach highly promising for the preparation of conjugated oils and CLA. Proposed improvements in catalyst recovery and reusability will only make this method more appealing to the food, paint, coating, and polymer industries in the future.