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Methyl Linoleate

$288

  • Brand : BIOFRON

  • Catalogue Number : BD-D1349

  • Specification : 98%(HPLC)

  • CAS number : 112-63-0

  • Formula : C19H34O2

  • Molecular Weight : 294.47

  • PUBCHEM ID : 5284421

  • Volume : 100MG

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Catalogue Number

BD-D1349

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

294.47

Appearance

Liquid

Botanical Source

Cottonseed Oil

Structure Type

Aliphatic Compounds

Category

Standards;Natural Pytochemical;API

SMILES

CCCCCC=CCC=CCCCCCCCC(=O)OC

Synonyms

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

IUPAC Name

methyl (9Z,12Z)-octadeca-9,12-dienoate

Applications

Density

0.9±0.1 g/cm3

Solubility

Chloroform; Ethyl Acetate

Flash Point

96.9±20.4 °C

Boiling Point

373.3±21.0 °C at 760 mmHg

Melting Point

-35ºC(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2916190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

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

No Technical Documents Available For This Product.

PMID

7174640

Abstract

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.

Title

Methyl Hydroperoxy-Epoxy-Octadecenoate as an Autoxidation Product of Methyl Linoleate: A New Inhibitor-Uncoupler of Mitochondrial Respiration

Author

T Imagawa, S Kasai, K Matsui, T Nakamura

Publish date

1982 Oct;

PMID

9470176

Abstract

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.

Title

Reaction of Alpha-Tocopherol in Heated Bulk Phase in the Presence of Methyl Linoleate (13S)-hydroperoxide or Methyl Linoleate

Author

R Yamauchi 1 , K Goto, K Kato

Publish date

1998 Jan

PMID

834127

Abstract

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.

Title

Autoxidation of Methyl Linoleate. Separation and Analysis of Isomeric Mixtures of Methyl Linoleate Hydroperoxides and Methyl Hydroxylinoleates

Author

H W Chan, G Levett

Publish date

1977 Jan