54739-30-9

Basic information

• Product Name: 9(Z),11(E)-OCTADECADIENOIC ACID
• Synonyms: 9(Z),11(E)-OCTADECADIENOIC ACID;13-KETO-OCTADECA-9Z,11E-DIENOIC ACID;13-KODE;13-OXO-9(Z),11(E)-OCTADECADIENOIC ACID;13-OXOODE;(e,z)-13-oxo-9,11-octadecadienoicacid;13-oxo-,(e,z)-11-octadecadienoicacid;9,11-Octadecadienoic acid, 13-oxo-, (E,Z)-
• CAS NO: 54739-30-9
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 280.45
• Mol File: 54739-30-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 425.5 °C at 760 mmHg
• Flash Point: 225.2 °C
• Appearance: /
• Density: 0.966 g/cm³
• Vapor Pressure: 1.98E-08mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: 9(Z),11(E)-OCTADECADIENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9(Z),11(E)-OCTADECADIENOIC ACID(54739-30-9)
• EPA Substance Registry System: 9(Z),11(E)-OCTADECADIENOIC ACID(54739-30-9)

Safety Data

• Hazardous Substances Data: 54739-30-9(Hazardous Substances Data)

Usage

Description

9(Z),11(E)-OCTADECADIENOIC ACID, also known as linoleic acid, is a polyunsaturated omega-6 fatty acid with a double bond at the 9th and 11th carbon atoms. It is an essential fatty acid that plays a crucial role in various biological processes and is commonly found in plant-based oils, such as sunflower and safflower oil.

Uses

Used in Pharmaceutical Applications:
9(Z),11(E)-OCTADECADIENOIC ACID is used as a precursor for the production of biologically active compounds, such as 13-oxoODE, which has been found to stimulate cell proliferation and act as an activator of PPAR α (peroxisome proliferator-activated receptor α). This makes it a valuable compound in the development of pharmaceuticals targeting various health conditions.
Used in Nutritional Applications:
As an essential fatty acid, 9(Z),11(E)-OCTADECADIOENOIC ACID is used as a vital component in the human diet to support overall health and well-being. It is particularly important for maintaining healthy skin, hair, and nails, as well as for its role in the production of prostaglandins, which are involved in various physiological processes.
Used in the Food Industry:
9(Z),11(E)-OCTADECADIENOIC ACID is used as an ingredient in the food industry, particularly in the production of vegetable oils and margarines. Its presence in these products contributes to the overall health benefits of consuming a balanced diet rich in essential fatty acids.
Used in Cosmetic Applications:
Due to its beneficial properties for skin health, 9(Z),11(E)-OCTADECADIENOIC ACID is used as an ingredient in various cosmetic products, such as moisturizers, creams, and lotions. Its inclusion in these products helps to promote healthy skin and maintain its natural barrier function.

InChI:InChI=1/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+

Upstream product

• 60-33-3 linoleic acid 
• 10219-69-9 (R,S)-coriolic acid 
• 29623-28-7 (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid 
• 18320-18-8 13(S)-HpODE 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 60900-56-3 methyl 9Z,11E-13-hydroperoxyoctadecadienoate 
• 33964-75-9 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid 
• 79790-32-2 13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester 

Downstream Products

• 79790-32-2 13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester 
• 6410-93-1 methyl coriolate 
• 2540-76-3 Methyl-13-hydroxystearat 
• 10219-69-9 (R,S)-coriolic acid 
• 2389-06-2 13-oxooctadecanoic acid 
• 2825-91-4 (R)-δ-decalactone 

Relevant articles and documents

The acid-promoted reaction of ethyl linoleate with nitrite. New insights from 15N-labelling and peculiar reactivity of a model skipped diene

The acid-promoted reaction of ethyl linoleate with nitrite ions was re-examined by an integrated approach based on the use of 15NO2- combined with extensive GC-MS (EI, NICI, PICI) and 2D 1H,15N and 1H,13C NMR analysis. The less polar products proved to be regioisomeric E-nitroalkenes, novel Z-nitroalkenes, and 3-nitro-1,5-hexadienes derivatives. A medium polarity fraction consisted mainly of stereo- and regioisomeric 1,2-nitronitrates along with 1,5-dinitro-1,3-pentadiene compounds. Novel 5-nitro-2,4-pentadienone products could be identified in the most polar fraction, which featured 1,2-nitroalcohols as the most abundant components. Under similar conditions 1,4-hexadiene gave mainly a nitrofuroxan derivative.

Catalytic production of oxo-fatty acids by lipoxygenases is mediated by the radical-radical dismutation between fatty acid alkoxyl radicals and fatty acid peroxyl radicals in fatty acid assembly

Oxo-octadecadienoic acids (OxoODEs) act as peroxisome proliferator-activated receptor (PPAR) agonists biologically, and are known to be produced in the lipoxygenase/linoleate system. OxoODEs seem to originate from the linoleate alkoxyl radicals that are generated from (E/Z)-hydroperoxy octadecadienoic acids ((E/Z)HpODEs) by a pseudoperoxidase reaction that is catalyzed by ferrous lipoxygenase. However, the mechanism underlying the conversion of alkoxyl radical into OxoODE remains obscure. In the present study, we confirmed that OxoODEs are produced in the lipoxygenase/linoleate system in an oxygen-dependent manner. Interestingly, we revealed a correlation between the (E/Z)-OxoODEs content and the (E/E)-HpODEs content in the system. (E/E)-HpODEs could have been derived from (E/E)-linoleate peroxyl radicals, which are generated by the reaction between a free linoleate allyl radical and an oxygen molecule. Notably, the ferrous lipoxygenase-linoleate allyl radical (LOx(Fe2+)-L·) complex, which is an intermediate in the lipoxygenase/linoleate system, tends to dissociate into LOx(Fe2+) and a linoleate allyl radical. Subsequently, LOx(Fe2+) converts (E/Z)-HpODEs to an (E/Z)-linoleate alkoxyl radical through one-electron reduction. Taken together, we propose that (E/Z)-OxoODEs and (E/E)-HpODEs are produced through radical-radical dismutation between (E/Z)-linoleate alkoxyl radical and (E/E)-linoleate peroxyl radical. Furthermore, the production of (E/Z)OxoODEs and (E/E)-HpODEs was remarkably inhibited by a hydrophobic radical scavenger, 2,2,6,6-tetra-methylpiperidine 1-oxyl (TEMPO). On the contrary, water-miscible radical scavengers, 4-hydroxyl-2,2,6,6-tetramethylpiperidine 1-oxyl (OH-TEMPO) and 3-carbamoyl-2,2,5,5-tetramethyl-3-pyrroline-N-oxyl (CmΔP) only modestly or sparingly inhibited the production of (E/Z)-OxoODEs and (E/E)-HpODEs. These facts indicate that the radical-radical dismutation between linoleate alkoxyl radical and linoleate peroxyl radical proceeds in the interior of micelles.

Macamides compound and synthetic method and application thereof

The invention relates to the field of drugs, in particular to a macamides compound and a synthetic method and application thereof. The synthetic method of macamides comprises the steps that linoleic acid and an oxidizing agent are subjected to catalytic oxidation through pyridine derivatives to obtain a macaenes mixture; the macaenes mixture and benzylamine or benzylamine derivatives are subjected to amidation and then separated through preparative chromatography, wherein the oxidizing agent is one of 2,2,6,6-tempol-nitrogen-oxide, pyridinium tribromide, 2-Iodoxybenzoic acid; the benzylamine derivatives are 3-trimethoprim or 3,4-dimethoxybenzamine. Linoleic acid is adopted as a starting reactant to be synthesized, and compared with the prior art that mecamide is extracted from plant maca, the needed raw material is low in cost and easy to obtain; in addition, in the synthesis preparation process, operation is easy, few by-products are produced, the needed reagents and solvents are small in toxicity and easy to obtain, and the novel path is provided for preparing a large number of macamides monomeric compounds.