Linoleic acid, methyl ester (8CI)/9,12-Octadecadienoic acid (Z,Z)-, methyl ester/Methyl (9Z,12Z)-9,12-octadecadienoate/Methyl linoleate/9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester/Linoleic acid methyl ester/Methyl (9Z,12Z)-octadeca-9,12-dienoate/Methyl octadecadienoate/9,12-Octadecadienoic acid, methyl ester, (9Z,12Z)-/Methyl lineoleate/Methyl (Z,Z)-9,12-octadecadienoate/9,12-Octadecadienoic acid, methyl ester, (Z,Z)-/Methyl 9-cis,12-cis-octadecadienoate/Methyl cis,cis-9,12-octadecadienoate/Methyl cis,cis-octadeca-9,12-dienoate
Chloroform; Ethyl Acetate
373.3±21.0 °C at 760 mmHg
HS Code Reference
Personal Projective Equipment
For Reference Standard and R&D, Not for Human Use Directly.
provides coniferyl ferulate(CAS#:112-63-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
A new peroxide compound (ML-X) was isolated from an autoxidation product of methyl linoleate and was determined as methyl 9-hydroperoxy-12, 13-epoxy-10-octadecenoate. This compound inhibited state 3 respiration of rat heart- and liver mitochondria when glutamate and malate were used as substrates, but not when the substrate was succinate. State 4 respiration of mitochondria was not affected when glutamate-malate was used as the substrate, but it was stimulated when the substrate was succinate. ML-X inhibited oxidative phosphorylation of the mitochondria and abolished the membrane potential formed by respiration or by added ATP. NADH oxidase activity of submitochondrial particles was inhibited by ML-X but succinate oxidase activity was not inhibited. NADH-acceptor reductase activities of submitochondrial particles were inhibited by ML-X to the same extents as by rotenone. These findings show that ML-X has dual effects on mitochondrial respiration as (1) an inhibitor of NADH dehydrogenase complex and (2) an uncoupler. Neither methyl linoleate monohydroperoxide nor methyl epoxy stearate has such effects. ML-X is a new type of inhibitor-uncoupler of mitochondrial respiration in which hydroperoxy- and epoxy groups co-operate.
Methyl Hydroperoxy-Epoxy-Octadecenoate as an Autoxidation Product of Methyl Linoleate: A New Inhibitor-Uncoupler of Mitochondrial Respiration
T Imagawa, S Kasai, K Matsui, T Nakamura
alpha-Tocopherol and methyl (9Z,11E)-(S)-13-hydroperoxy-9,11-octadecadienoate (13-MeLOOH) were allowed to stand at 100 degrees C in bulk phase. The products were isolated and identified as methyl 13-hydroxyoctadecadienoate (1), stereoisomers of methyl 9,11,13-octadecatrienoate (2), methyl 13-oxo-9,11-octadecadienoate (3), epoxy dimers of methyl linoleate with an ether bond (4), a mixture of methyl (E)-12,13-epoxy-9-(alpha-tocopheroxy)-10-octadecenoates and methyl (E)-12,13-epoxy-11-(alpha-tocopheroxy)-9-octadecenoates (5), a mixture of methyl 9-(alpha-tocopheroxy)-10,12-octadecadienoates and methyl 13-(alpha-tocopheroxy)-9,11-octadecadienoates (6), alpha-tocopherol spirodiene dimer (7), and alpha-tocopherol trimer (8). alpha-Tocopherol and 13-MeLOOH were dissolved in methyl myristate, and the thermal decomposition rate and the distributions of reaction products formed from alpha-tocopherol and 13-MeLOOH were analyzed. alpha-Tocopherol disappeared during the first 20 min, and the main products of alpha-tocopherol were 5 and 6 with the accumulation of 1-4 which were the products of 13-MeLOOH. The results indicate that the alkyl and alkoxyl radicals from the thermal decomposition of 13-MeLOOH could be trapped by alpha-tocopherol to produce 5 and 6. The reaction products of alpha-tocopherol during the thermal oxidation of methyl linoleate were compounds 6 and 7. Since the radical flux during the autoxidation might be low, the excess alpha-tocopheroxyl radical reacted with each other to form 7.
Reaction of Alpha-Tocopherol in Heated Bulk Phase in the Presence of Methyl Linoleate (13S)-hydroperoxide or Methyl Linoleate
R Yamauchi 1 , K Goto, K Kato
The mixture of conjugated diene hyperperoxide isomers obtained from autoxidation of methyl linoleate was separated by high performance liquid chromatography (HPLC). Four major isomers were obtained from adsorption chromatography and identified as the 9 and 13 positional isomers having the trans-trans and cis-trans configurations. The latter geometrical isomers have the trans double bond adjacent to the hydroperoxide group. The hydroxy compounds (methyl hydroxylinoleates) obtained from the hydroperoxides by NaBH4 reduction were similarly separated but with improved resolution. This is the first instance of the complete separation of these compounds and provides a rapid method for their analysis. Unlike adsorption chromatography, reversed-phase chromatography separates the mixtures only according to the geometrical isomerism of the double bonds and not according to the position of the hydroxy or hydroperoxide function.
Autoxidation of Methyl Linoleate. Separation and Analysis of Isomeric Mixtures of Methyl Linoleate Hydroperoxides and Methyl Hydroxylinoleates
H W Chan, G Levett