868364-06-1

Basic information

• Product Name: 9-10-monoepoxy-12-octadecenoic acid
• CAS NO: 868364-06-1
• Molecular Weight: 296.45
• Mol File: 868364-06-1.mol

Chemical Properties

• CAS DataBase Reference: 9-10-monoepoxy-12-octadecenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-10-monoepoxy-12-octadecenoic acid(868364-06-1)
• EPA Substance Registry System: 9-10-monoepoxy-12-octadecenoic acid(868364-06-1)

Safety Data

• Hazardous Substances Data: 868364-06-1(Hazardous Substances Data)

Upstream product

• 60-33-3 linoleic acid 
• 112-63-0 Methyl linoleate 
• 186792-27-8 9,10-epoxy-(12Z)-octadecen-1-oic acid methyl ester 

Downstream Products

• 99530-30-0 methyl 9-benzoyloxylinoleate 
• 10075-07-7 (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid methyl ester 
• 403619-52-3 Benzoic acid (2E,4Z)-(R)-1-(7-methoxycarbonyl-heptyl)-deca-2,4-dienyl ester 
• 6084-82-8 (R)-9-hydroxy-(10E,12Z)-10,12-octadecadienoic acid methyl ester 
• 98442-95-6 benzoate of 9-hydroxy-(E)-10-(Z)-12-octadecadienoic acid methy ester 
• 147848-81-5 8-[((Z)-3-Oct-2-enyl)-oxiranyl]-octanoic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester 
• 6084-82-8 9-hydroxy-(10E,12Z)-octadecadien-1-oic acid methyl ester 

Relevant articles and documents

Identification and Quantitation of C=C Location Isomers of Unsaturated Fatty Acids by Epoxidation Reaction and Tandem Mass Spectrometry

Unsaturated fatty acids (FAs) serve as nutrients, energy sources, and signaling molecules for organisms, which are the major components for a large variety of lipids. However, structural characterization and quantitation of unsaturated FAs by mass spectrometry remain an analytical challenge. Here, we report the coupling of epoxidation reaction of the C=C in unsaturated FAs and tandem mass spectrometry (MS) for rapid and accurate identification and quantitation of C=C isomers of FAs in a shotgun lipidomics approach. Epoxidation of the C=C leads to the production of an epoxide which, upon collision induced dissociation (CID), produces abundant diagnostic ions indicative of the C=C location. The total intensity of the same set of diagnostic ions for one specific FA C=C isomer was also used for its relative and absolute quantitation. The simple experimental setup, rapid reaction kinetics (90% for monounsaturated FAs), and easy-to-interpret tandem MS spectra enable a promising methodology particularly for the analysis of unsaturated FAs in complex biological samples such as human plasma and animal tissues.

Selective Epoxidation of Fatty Acids and Fatty Acid Methyl Esters by Fungal Peroxygenases

Recently discovered fungal unspecific peroxygenases from Marasmius rotula and Chaetomium globosum catalyze the epoxidation of unsaturated fatty acids (FA) and FA methyl esters (FAME), unlike the well-known peroxygenases from Agrocybe aegerita and Coprinopsis cinerea. Reactions of a series of unsaturated FA and FAME with cis-configuration revealed high (up to 100 %) substrate conversion and selectivity towards epoxidation, although some significant differences were observed between enzymes and substrates with the best results being obtained with the C. globosum enzyme. This and the M. rotula peroxygenase appear as promising biocatalysts for the environmentally-friendly production of reactive FA epoxides given their self-sufficient monooxygenase activity and the high conversion rate and epoxidation selectivity.

Epoxidation, hydroxylation and aromatization is catalyzed by a peroxygenase from Solanum lycopersicum

Plant peroxygenase (PXG) oxidizes unsaturated fatty acids by transferring an oxygen atom of a hydroperoxide to the double bond, thereby providing epoxides. In this work we investigated the potential of a PXG from tomato (Solanum lycopersicum, SlPXG) to catalyze the oxidation of a variety of natural products. A SlPXG gene was cloned from tomato, heterologously expressed in yeast and the membrane bound recombinant SlPXG protein was used as enzyme source. Unsaturated fatty acids, fatty acid derivatives, and terpenes were epoxidized by SlPXG in the presence of various hydroperoxides exclusively at their cis-double bonds. Terpenes with p-menthene skeleton were transformed in different ways depending on their molecular structures. R-(+)- and S-(-)-limonene were converted to R-(+)-limonene-trans-1,2-epoxide (97%) and cis-S-(-)-limonene-1,2- epoxide (88%), respectively whereas α-terpinenewas hydroxylated to cis-1,4-dihydroxy-p-menth-2-ene and γ-terpinene was aromatized to p-cymene. In the last reaction the hydroperoxide served as hydrogen acceptor rather than an oxygen donor. PXG appears to be a versatile biocatalyst able to perform different kinds of oxidation reactions. As no cofactors like NAD(P)H are required and H2O2is an environmentally friendly oxidant, PXG enables new applications for the synthesis of fine chemicals from renewable resources.

Monooxygenase system of bacillus megaterium ALA2: Studies on linoleic acid epoxidation products

Bacillus megaterium ALA2 produces many oxygenated FA from linoleic acid: 12, 13-dihydroxy- 9(Z)-octadecenoic acid; 12,13,17-trihydroxy-9(Z)-octadecenoic acid; 12,13,16-trihydroxy-9(Z)-octadecenoic acid; 12-hydroxy-13,16-epoxy-9(Z)- octadecenoic acid; and 12,17;13,17-diepoxy-16-hydroxy-9(Z)-octadecenoic acid. Recently, we studied the monooxygenase system of B. megaterium ALA2 by comparing its palmitic acid oxidation products with those of the well-studied catalytically self-sufficient P450 monooxygenase of B. megaterium ATCC 14581 (NRRL B-3712) and of B. subtilis strain 168 (NRRL B-4219). We found that their oxidation products are identical, indicating that their monooxygenase systems (hydroxylation) are similar. Now, we report that strain ALA2 epoxidizes linoleic acid to 12,13-epoxy-9(Z)-octadecenoic acid and 9,10-epoxy-12(Z)-octadecenoic acid, the initial products in the linoleic acid oxidation. The epoxidation enzyme did not oxidize specific double bond of the linoleic acid. The epoxidation activity of strain ALA2 was compared with the above-mentioned two Bacillus strains. These two Bacillus strain also produced 12,13-epoxy-9(Z)- octadecenoic acid and 9,10-epoxy-12(2)-octadecenoic acid, indicating that their epoxidation enzyme systems might be similar. The ratios of epoxy FA production by, these three strains (ALA2, NRRL B-3712, and NRRL B-4219) were, respectively, 5.56:0.66:0.18 for 12,13-epoxy-9(Z)-octadecenoic acid and 2.43:0.41:0.57 for 9,10-epoxy-12(Z)-octadecenoic acid per 50 mL medium per 48 h. Copyright

Epoxidation of polyunsaturated fatty acid double bonds by dioxirane reagent: Regioselectivity and lipid supramolecular organization

The use of dimethyldioxirane (DMD) as the epoxidizing agent for polyunsaturated fatty acids was investigated. With fatty acid methyl esters, this is a convenient method for avoiding acidic conditions, using different solvents, and simplifying the isolation procedures, with less contamination due to by-products. The reagent was also tested with free fatty acids in water. In this case, the supramolecular organization of fatty acids influenced the reaction outcome, and the epoxidation showed interesting regioselective features. The C=C bonds closest to the aqueous-micelle interface is the most favored for the interaction with dimethyldioxirane. The preferential epoxidation of linoleic acid (=(9Z,12Z)-octadeca-9,12-dienoic acid) to the 9,10-monoepoxy derivative was achieved, with a high yield and 65% regioselectivity. In case of arachidonic acid (=(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acid) micelles, the regioselective outcome with formation of the four possible monoepoxy isomers was studied under different conditions. It resulted to be a convenient synthesis of 'cis-5,6-epoxyeicosatrienoic acid' (=3-[(2Z,5Z,8Z)-tetradeca-2,5,8- trienyl]oxiran-2-butanoic acid), whereas in reverse micelles, epoxidation mostly gave 'cis-14,15-epoxyeicosatrienoic acid (= (5Z,8Z,11Z)-13-(3-pentyloxiran-2- yl)trideca-5,8,11-trienoic acid).

Analysis of fatty acid epoxidation by high performance liquid chromatography coupled with evaporative light scattering detection and mass spectrometry

Conventionally, epoxidation of unsaturated fatty acids has been studied either with titrimetric methods or in a lengthy procedure involving derivatization followed by gas chromatography (GC). We have developed a more rapid and descriptive analysis procedure for the substances using high performance liquid chromatography (HPLC) with evaporative light scattering detection (ELSD). Chemo-enzymatic epoxidation of unsaturated fatty acids (oleic, linoleic and linolenic acid, respectively) has been performed using hydrogen peroxide and immobilized lipase from Candida antarctica (Novozym 435). The fatty acids and their epoxidation products were separated by HPLC on a C-18 reversed-phase column using methanol-water containing 0.05% acetic acid as mobile phase. The method facilitated the simultaneous determination of fatty acids and epoxides differing from each other in the number of epoxide rings, the degree of unsaturation and the position of the epoxide rings and double bonds. An important aspect of the method development was the use of electrospray ionization and tandem mass spectrometry to confirm the structure of the epoxide products. It is suggested that the HPLC method, providing more information about the kind and concentration of fatty acids and their epoxides, represents a powerful complement to the existing methods for monitoring epoxidation processes on fatty acids.

Preparation of the enantiomers of hydroxy-C18 fatty acids and their anti-rice blast fungus activities

In order to examine the correlation between the anti-rice blast fungus activity and the chirality of allylic alcohols 1-3, which were characterized from the infected rice plants as an enantiomeric mixture with 10% e.e., a procedure for the chemical prepa

Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants

Expecting that the different characteristics of rice plants against rice blast fungus, that is, susceptibility of the weaker cultivar, Sasanishiki and resistance of the stronger cultivars, Fukuyuki and Fukunishiki, may be due to the absence or presence of anti-fungus compounds in the rice plants, the anti-rice blast fungus substances in these three kinds of rice plants were explored.We found five epoxides and five allyl alcohols as anti-rice blast fungus compounds.The epoxides were 12,13-epoxy- and 9,10-epoxylinoleic acids, and 15,16-epoxy-, 12,13-epoxy-, and 9,10-epoxylinolenic acids.The allyl alcohols are 13-hydroxy and 9-hydroxy linoleic acids, and 16-hydroxy, 13-hydroxy, and 9-hydroxy linolenic acids.In inoculated Sasanishiki, the activity is due to the formation of the allyl alcohols.

An Isotopic Study (2H and 18O) of the Enzymatic Conversion of Linoleic Acid into Colneleic Acid with Carbon Chain Fracture: the Origin of Shorter Chain Aldehydes

Contrary to earlier reports, the divinyl 9-ether oxygen of colneleic acid is shown by experiment with 18O2 to originate from oxygen, not water.Using -9(S)-hydroperoxyoctadeca-10(E),12(Z)-dienoic acid, made enzymatically from synthetic linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneic acid formed by potato enzyme, is consistent with the intervention of an epoxy carbonium ion intermediate.Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.

UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE

In addition to the previously described epoxy fatty acids, five hydroxy fatty acids were characterized as self defensive substances produced in the rice plant against rice blast disease.