Erucic acid

Base Information

• Chemical Name: Erucic acid
• CAS No.: 112-86-7
• Molecular Formula: C22H42O2
• Molecular Weight: 338.574
• Hs Code.: 29161900
• Mol file: 112-86-7.mol

Synonyms:13-Docosenoicacid, (13Z)-;13-Docosenoicacid, (Z)- (8CI);(13Z)-Docosenoic acid;(Z)-13-Docosenoic acid;13(Z)-Docosenoic acid;13-cis-Docosenoic acid;Hystrene 2290;Nouracid RE 07;cis-13-Docosenoic acid;cis-13-Erucic acid;D13-cis-Docosenoicacid;

Chemical Property of Erucic acid

Chemical Property:

• Appearance/Colour: White Waxy Solid
• Melting Point: 28-32 °C(lit.)
• Refractive Index: 1.456 - 1.457
• Boiling Point: 386.1 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 349.9 °C
• PSA: 37.30000
• Density: 0.891 g/cm³
• LogP: 7.66890
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Erucic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Description: Erucic acid also known as cis-13-Docosenoic acid is a monounsaturated omega-9 fatty acid. It occurs at high concentrations mainly in the seeds of species of the Brassicaceae (e.g. rape seed or mustard seed, and seeds from vegetable crops such as kales, cabbages and turnips). High-erucic acid oils are used either directly as lubricants (e.g. in the manufacture of rubber additives) or in formulations. They are used as spinning lubricants in the textile, steel, and shipping industries; as cutting, metal-forming, rolling, fabricating, and drilling oils; and as marine lubes. Erucic acid can also be oxidatively cleaved to brassylic acid for use in the production of polyesters. The oxidative cleavage of erucic acid can be performed via ozonolysis or by reaction with hydrogen peroxide in the presence of an inorganic oxide catalyst. Erucic acid can be used to prepare useful nitrogen derivatives: behenyl amine is used in a corrosion inhibitor; disubstituted amides are effective plasticizers and erucamide is an excellent slip and antiblocking agent for plastic films. Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the formula CH3(CH2)7CH=CH(CH2)11COOH. It is prevalent in wallflower seed, makes up 4.1% of rapeseed oil, and makes up 42% of mustard oil. Erucic acid is also known as cis-13- docosenoic acid and the trans isomer is known as brassidic acid.
• Uses: 13(Z)-Docosenoic acid is a 22-carbon monounsaturated fatty acid. It is found predominantly in canola oil. 13(Z)-Docosenoic acid is metabolized to oleic acid in vivo. Diets rich in 13(Z)-docosenoic acid were shown to cause heart lipidosis in experimental animals. The C-1 amide of docosenoic acid has been identified as one of the anandamide-related neurotransmitters associated with sleep. Erucic acid has many of the same uses as mineral oils, but it is more readily biodegradable than some. It has limited ability to polymerize and dry for use in oil paints. Like other fatty acids, it can be converted into surfactants or lubricants, and can be used as a precursor to bio-diesel fuel. Derivatives of erucic acid have many further uses, such as behenyl alcohol ( CH3(CH2)21OH ) , a pour point depressant (enabling liquids to flow at a lower temperature), and silver behenate, for use in photography. It is also used as an ingredient in appetite suppressants. Erucic acid is a long-chain alcohol that acts as an inhibitor of fatty acid oxidation in the heart. Erucic acid originates in rapeseed plants, and is the major fatty acid constituent of rapeseed plant oil extracts and canola oil.

Technology Process of Erucic acid

There total 30 articles about Erucic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

methyl cis-13-docosenoate (1120-34-9) → cis-13-docosenoic acid (112-86-7)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.8b00734

Reference yield:

→ cis-13-docosenoic acid (112-86-7) + Brassidic acid (506-33-2)

Guidance literature:

With aluminum isopropoxide; Einw_. von Bromwasserstoff auf das entstandene Saeuregemisch und Behandlung mit Zink;

DOI:10.1038/163095a0

Reference yield:

docos-13-enoic acid-anhydride (871893-44-6) → cis-13-docosenoic acid (112-86-7) + ethyl (13Z)-13-docosenoate (37910-77-3)

Guidance literature:

erucic acid anhydride;

upstream raw materials:

pyridine

ethanol

docos-13-enoic acid-anhydride

cis-Octadecenoic acid

Downstream raw materials:

methyl cis-13-docosenoate

docos-13c-enoic acid propyl ester

Brassidic acid

docos-13-enoic acid ethyl ester

Refernces

• 1、 Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.. "Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids". . p. 4115 - 4131. Retrieved 2018/10/02.
• 2、 -. "Suppository base". . . Retrieved 2008/06/13.