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Erucic Acid

Erucic Acid Structure
CAS No.
112-86-7
Chemical Name:
Erucic Acid
Synonyms
CIS-13-DOCOSENOIC ACID;DOCOSENOIC ACID;13-DOCOSENOIC ACID;Erucic;Pellitorin;13(Z)-DOCOSENOIC ACID;(Z)-13-DOCOSENOIC ACID;Nsc6814;AI3-19560;Erucasαure
CBNumber:
CB1208647
Molecular Formula:
C22H42O2
Molecular Weight:
338.57
MOL File:
112-86-7.mol
MSDS File:
SDS
Modify Date:
2024/11/17 16:00:36

Erucic Acid 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

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  1
RTECS  JR1280000
10-23
TSCA  Yes
HS Code  29161900
NFPA 704
0
0 0

Erucic Acid price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) E3385 Erucic acid ≥99% (capillary GC) 112-86-7 1G ₹15025.1 2022-06-14 Buy
Sigma-Aldrich(India) E3385 Erucic acid ≥99% (capillary GC) 112-86-7 5G ₹38039.05 2022-06-14 Buy
Sigma-Aldrich(India) 45629 Erucic acid analytical standard 112-86-7 1G ₹6614.08 2022-06-14 Buy
Sigma-Aldrich(India) 45630 Erucic acid technical, ~90% (GC) 112-86-7 1KG ₹17157.63 2022-06-14 Buy
Sigma-Aldrich(India) 45629 Erucic acid analytical standard 112-86-7 5G ₹15241.6 2022-06-14 Buy
Product number Packaging Price Buy
E3385 1G ₹15025.1 Buy
E3385 5G ₹38039.05 Buy
45629 1G ₹6614.08 Buy
45630 1KG ₹17157.63 Buy
45629 5G ₹15241.6 Buy

Erucic Acid Chemical Properties,Uses,Production

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

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)

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(Z)-docos-13-enoicacid 13-cis-Docosenoicacid 13-Docosenoic acid, (Z)- 13-Docosenoicacid,(13Z)- Erucasαure Prifrac 2990 Δ13-cis-Docosenoicacid Erucic acid 0 DELTA 13 CIS DOCOSENOIC ACID ERUCIC ACID ERUCIC ACID (C22:1,[CIS]-13) Erucic acid≥ 99% (GC) 13-Docosenoicacid,(Z)- 13-Docosensαure cis-13-docosenecarboxylicacid cis-13-Docosensαure cis-docos-13-enoicacid delta13:14-docosenoicacid erucic acid 90-95% Prifac 2990 Erunic Acid ERUCIC ACID, 99+% ERUCIC ACID, STANDARD FOR GC ERUCIC ACID APPROX. 90% ERUCIC ACID 98% ErucicAcid,~90% docos-13-enoic acid ERUCIC ACID: TECH., 85% Erucic acid cis-13-Docosenoic acid ERUCIC ACID, 85%, 90% (Z-13-DOCOSENOIC ACID) SINAPIC ACID(P) SINAPIC ACID(RG) Erucidic acid cis-13-Docosenoic acid, Prifac 2990 Hystrene 2290 CIS-13-DOCOSENSRE Nsc6814 Erucic acid,cis-13-Docosenoic acid, Prifac 2990 13C DOCOSENOIC ACID (13Z)-13-Docosenoic acid (z)-13-docosenoicaci Erucic Acid(C22:1) Erucie acid Erucic acid (22:1), ultrapure Erucic Acid > cis-13-Docosenoic acid Solution in Isooctane, 1000μg/mL Cosmetic Ingredients CAS: 112-86-7 13-Docosenoic Acid/Erucic Acid with Good Quality TIANFUCHEM--High purity 112-86-7 Erucic Acid AI3-19560 (Z)-13-DOCOSENOIC ACID CIS-13-DOCOSENOIC ACID DOCOSENOIC ACID Erucic 13(Z)-DOCOSENOIC ACID 13-DOCOSENOIC ACID Pellitorin Prifac 2990|||13(Z)-Docosenoic Acid|||cis-13-docosenoic acid Ethyl Acetate Impurity 94