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Erucic Acid

Product Name
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
Formula Weight
338.57
MOL File
112-86-7.mol
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Erucic Acid Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
45629
Product name
Erucic acid
Purity
analytical standard
Packaging
1g
Price
$71.4
Updated
2024/03/01
Sigma-Aldrich
Product number
45630
Product name
Erucic acid
Purity
technical, ~90% (GC)
Packaging
1kg
Price
$699
Updated
2024/03/01
Sigma-Aldrich
Product number
45629
Product name
Erucic acid
Purity
analytical standard
Packaging
5G
Price
$287
Updated
2024/03/01
TCI Chemical
Product number
D0965
Product name
Erucic Acid
Purity
>85.0%(GC)
Packaging
25g
Price
$23
Updated
2024/03/01
TCI Chemical
Product number
D0965
Product name
Erucic Acid
Purity
>85.0%(GC)
Packaging
100g
Price
$60
Updated
2024/03/01
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Erucic Acid Chemical Properties,Usage,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)

Erucic Acid Preparation Products And Raw materials

Raw materials

FATTY ACID MIXTURE RAPESEED OIL

Preparation Products

Erucamide RAPESEEDOIL,SUPERGLYCERINATED,FULLYHYDROGENATED CANOLA OIL 1,11-Undecanedicarboxylic acid Rape oil, hydrogenated
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View Lastest Price from Erucic Acid manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
cis-13-Docosenoic acid 112-86-7
Price
US $70.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-05-27
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Erucic Acid 112-86-7
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-27
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Erucic Acid 112-86-7
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-31

112-86-7, Erucic AcidRelated Search:

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

  • 13C DOCOSENOIC ACID
  • (13Z)-13-Docosenoic acid
  • (z)-13-docosenoicaci
  • (Z)-docos-13-enoicacid
  • 13-cis-Docosenoicacid
  • 13-Docosenoic acid, (Z)-
  • 13-Docosenoicacid,(13Z)-
  • Erucasαure
  • Prifrac 2990
  • Δ13-cis-Docosenoicacid
  • (Z)-13-DOCOSENOIC ACID
  • Erucic acid 0
  • DELTA 13 CIS DOCOSENOIC ACID
  • CIS-13-DOCOSENOIC ACID
  • DOCOSENOIC ACID
  • ERUCIC ACID
  • ERUCIC ACID (C22:1,[CIS]-13)
  • Erucic
  • Erucic acid≥ 99% (GC)
  • 13(Z)-DOCOSENOIC ACID
  • 13-DOCOSENOIC ACID
  • 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
  • Erucic Acid(C22:1)
  • Erucie acid
  • Erucic acid (22:1), ultrapure
  • Erucic Acid &gt
  • 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
  • Pellitorin
  • Prifac 2990|||13(Z)-Docosenoic Acid|||cis-13-docosenoic acid
  • Ethyl Acetate Impurity 94