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Erucic Acid

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
MDL Number:
MFCD00063188
MOL File:
112-86-7.mol
MSDS File:
SDS
Last updated:2023-11-15 17:17:25

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)
EWG's Food Scores 1
FDA UNII 075441GMF2
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)  GHS hazard pictograms
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(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 45629 Erucic acid analytical standard 112-86-7 1g $71.4 2024-03-01 Buy
Sigma-Aldrich 45630 Erucic acid technical, ~90% (GC) 112-86-7 1kg $699 2024-03-01 Buy
Sigma-Aldrich 45629 Erucic acid analytical standard 112-86-7 5G $287 2024-03-01 Buy
TCI Chemical D0965 Erucic Acid >85.0%(GC) 112-86-7 25g $23 2024-03-01 Buy
TCI Chemical D0965 Erucic Acid >85.0%(GC) 112-86-7 100g $60 2024-03-01 Buy
Product number Packaging Price Buy
45629 1g $71.4 Buy
45630 1kg $699 Buy
45629 5G $287 Buy
D0965 25g $23 Buy
D0965 100g $60 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

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)

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View Lastest Price from Erucic Acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Erucic acid pictures 2024-04-15 Erucic acid
112-86-7
US $1.00-1.00 / mg 100mg 85.0% 5ton/month ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD
Erucic acid pictures 2024-01-08 Erucic acid
112-86-7
US $9.00 / KG 1KG 99% 50000tons Wuhan Boyuan Import & Export Co., LTD
Erucic Acid pictures 2023-11-30 Erucic Acid
112-86-7
US $110.00-90.00 / kilograms 1kilograms 99% 5000 tons Henan Tengmao Chemical Technology Co. LTD
  • Erucic acid pictures
  • Erucic acid
    112-86-7
  • US $1.00-1.00 / mg
  • 85.0%
  • ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD
  • Erucic acid pictures
  • Erucic acid
    112-86-7
  • US $9.00 / KG
  • 99%
  • Wuhan Boyuan Import & Export Co., LTD
  • Erucic Acid pictures
  • Erucic Acid
    112-86-7
  • US $110.00-90.00 / kilograms
  • 99%
  • Henan Tengmao Chemical Technology Co. LTD
(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 Ethyl Acetate Impurity 94 112-86-7