Erucic Acid Chemical Properties

Melting point:

28-32 °C (lit.)

Boiling point:

358 °C/400 mmHg (lit.)

Density 

0,86 g/cm³

refractive index 

nD45 1.4534; nD65 1.44794

Flash point:

265°C/15mm

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

4.78±0.10(Predicted)

form 

Solid

color 

White to Off-White

Merck 

14,3674

BRN 

1728049

LogP

9.459 (est)

CAS DataBase Reference

112-86-7(CAS DataBase Reference)

NIST Chemistry Reference

Erucic acid(112-86-7)

EPA Substance Registry System

13-Docosenoic acid, (13Z)- (112-86-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

RTECS 

JR1280000

F 

10-23

TSCA 

Yes

HS Code 

29161900

Hazardous Substances Data

112-86-7(Hazardous Substances Data)

MSDS

• Language:English Provider:cis-13-Docosenoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Erucic Acid Usage And Synthesis

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.

Chemical Properties

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the formula CH3(CH2)7CH=CH(CH2)11COOH. Colorless needle crystal. Melting point 33.5°C, boiling point 381.5°C (decomposition), 358°C (53.3kPa), 265°C (2.0kPa), relative density 0.86 (55°C), refractive index 1.4534 (45°C). Erucic acid is highly soluble in ether and soluble in ethanol and methanol, but it is insoluble in water. It is commonly found in wallflower seeds, accounting for 4.1% of rapeseed oil, and makes up 42% of mustard oil.

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.

Uses

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.

Definition

ChEBI: Erucic acid is a docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers. It is a long-chain alcohol that acts as an inhibitor of fatty acid oxidation in the heart.

Biotechnological Applications

Erucic acid is produced by elongation of oleic acid via oleoylcoenzyme A and malonyl- CoA. Erucic acid is broken down into shorter- chain fatty acids in the human liver by the long - chain Acyl CoA dehydrogenase enzyme.

Purification Methods

Crystallise erucic acid from MeOH. [Beilstein 2 IV 1676.]

References

[1] J.M. Vargas-Lopez, D. Wiesenborna, K. Tostenson , L. Cihacek (1999) Processing of Crambe for Oil and Isolation of Erucic Acid, JAOCS, 76, 801-809 DOI:10.1007/S11746-999-0069-4
[2] H. J. Nieschlag, I. A. Wolff (1971) Industrial uses of high erucic oils, JAOCS, 48, 723-727 DOI:10.1007/BF02638529
[3] Erucic Acid (22:1n-9) in Fish Feed, Farmed, and Wild Fish and Seafood Products DOI:10.3390/nu10101443
[4] Erucic acid--an inhibitor of fatty acid oxidation in the heart. DOI:10.1016/0005-2760(72)90130-0
[5] Purification-of-Laboratory-Chemicals
[6] Christophersen, B. & Bremer, J.: BBA-Lipid. Lipid Met., 280, 506 (1972); Ecke, W., et al.: Theor. Appl. Gen., 91, 972 (1995); Metz, J., et al.: Plant Phys., 122, 635 (2000)

Erucic Acid(112-86-7)Related Product Information

• Oleic acid
• CANOLA OIL
• trans-erucic acid
• (Z)-docos-13-enyl (Z)-docos-13-enoate
• 1-Propanaminium, N-(2-hydroxyethyl)-N,N-dimethyl-3-[[(13Z)-1-oxo-13-docosenyl]amino]-, chloride (9CI)
• ALPHA-BOSWELLIC ACID
• ERUCIC ACID ETHYL ESTER,CIS-13-DOCOSENOIC ACID ETHYL ESTER
• ERUCIC ACID METHYL ESTER,ERUCIC ACID METHYL ESTER 90+%,CIS-13-DOCOSENOIC ACID METHYL ESTER,Erucic acid methyl
• Erucic Acid
• CHOLESTERYL ERUCATE
• 11-KETO-BETA-BOSWELLIC ACID
• 3-ACETYL-11-KETO-BETA-BOSWELLIC ACID
• BETA-BOSWELLIC ACID
• TRIERUCIN
• Erucic acid 2,3-dihydroxypropyl ester
• Erucamide
• medicagenic acid
• MEDICAGENIC ACID 3,28-DI-O-GLUCOSIDE