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ERUCIC ACID

ERUCIC ACID = cis-eruic acid = (13Z)-Docosenoic acid


CAS-No. : 112-86-7
EC-No. : 204-011-3
MDL number: MFCD00063188
Molecular Formula : C22H42O2

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. 
Erucic acid has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH. 
Erucic acid is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapeseed oil[1] and 42% in mustard oil. 


Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.
The name erucic means "of or pertaining to Eruca", which is a genus of flowering plants in the family Brassicaceae. 
Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the genus Brassica. 


For industrial purposes and production of erucic acid, rapeseed is used; for food purposes a 'low-erucic acid rapeseed' (LEAR) has been developed (canola), which contains fats derived from oleic acid instead of erucic acid.
Erucic acid is a monounsaturated omega-9 fatty acid, which is present in the oil-rich seeds of the Brassicaceae family of plants, particularly rapeseed and mustard.
Edible fats and oils are made up of different fatty acids, ranging from saturated fatty acids to monounsaturated and polyunsaturated ones. 


Erucic acid is one of the monounsaturated fatty acids, having a chain length of 22 carbon atoms with one double bond at the omega 9 position.
Erucic acid naturally occurs in oil-rich seeds of species of the mustard family (Brassicaceae). 
Erucic acid is found primarily in rapeseed oil and mustard oil. 
Erucic acid can constitute about 30 – 60% of the total fatty acids of natural rapeseed and mustard seed. 


Erucic acid has also been reported in some marine animal oils.
Erucic acid, a monounsaturated fatty acid (MUFA), is isolated from the seed of Raphanus sativus L. 
Erucic acid occurs in vegetable oils and fats. 
Erucic acid is a natural component of plant seeds of the Brassicaceae family (crucifers such as rape and mustard). 


Chemically, Erucic acid is a long-chain, simple, unsaturated omega-9 fatty acid. 
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
Erucic acid (22 carbon atoms), from Latin word eruca, meaning arucola or garden rocket (Eruca sativa, a flowering plant of the family of Brassicaceae, synonym Cruciferae) is a unsaturated fatty acid (one cis (Z) double bond, from the methyl end is in omega-9 (ω-9) or n-9, so in shorthand 22:1n-9) member of the sub-group called very long chain fatty acids (VLCFA), from 20 carbon atoms onwards.


Erucic acid is an elongation product of oleic acid and in animals, dietary one can be retroconverted to oleic acid.
In purified form, Erucic acid is a white waxy solid insoluble in water, with melting point at 33.8 °C (92.84 °F; 306.95 K) and boiling point at 381.5 °C (718.7 °F; 654.65 K) at 760 mm Hg.
Erucic acid occurs as glycerol ester particularly in the seed fats of several Brassicaceae like rapeseed (Brassica napus), mustard (Brassica junca and Brassica nigra), up 40 to 50% of the corresponding seed oils (e.g. rapeseed oil), and wallflower, kale, Brussels sprout and broccoli, other members of Brassicaceae.


Erucic acid is a crystalline fatty acid C22H42O2 found in the form of glycerides especially in rapeseed oil.
Erucic Acid acid is a 22-carbon monounsaturated fatty acid. 
Erucic Acid is found predominantly in canola oil. 
Erucic Acid is metabolized to oleic acid in vivo.


Erucic acid is a 22-carbon, monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. 
Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. 
Erucic acid is also known as cis-13-docosenoic acid. 
Erucic acids trans isomer is known as brassidic acid. 
Erucic acid occurs in nature only along with bitter-tasting compounds. 


Erucic acid has many of the same uses as mineral oils but with the advantage that Erucic acid is more readily bio-degradable. 
Erucic acid is a monounsaturated omega-9 fatty acid found in large quantities in the seeds of Brassicaceae, eg old canola varieties. 
The new sorts, which are cultivated for the production of rapeseed oil as a foodstuff, have had their Erucic acid content reduced by breeding. 
Erucic acid is also found in mustard oil. 


Erucic acid can also be found in fish oils. 
High erucic acid rapeseed (HEAR) is a specialty rapeseed selected for its high erucic content.  
Erucic acid has over 50% erucic acid and is grown as a key ingredient for plastics, personal care products and pharmaceuticals.  
The seed, the crop and the oil are visually similar to canola, therefore every step of the supply chain demands robust and effective identity preservation processes. 


Erucic acid originates in rapeseed plants, and is the major fatty acid constituent of rapeseed plant oil extracts and canola oil.
Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. 
Erucic acid has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH. 
Erucic acid is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapeseed oil and 42% in mustard oil. 


Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid. 
Erucic acid is produced by elongation of oleic acid via oleoyl-coenzyme 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.
Erucic acid also known as cis-13-Docosenoic acid is a monounsaturated omega-9 fatty acid. 
Erucic acid 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).

Uses and Applications of Erucic acid:
-Erucic acid has many of the same uses as mineral oils, but Erucic acid is more readily biodegradable than some. 
Erucic acid has limited ability to polymerize and dry for use in oil paints. 
Like other fatty acids, Erucic acid can be converted into surfactants or lubricants, and can be used as a precursor to biodiesel 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.


-Erucic acid can readily cross the blood-brain barrier (BBB), Erucic acid has been reported to normalize the accumulation of very long-chain fatty acids in the brain. 
Erucic acid can improve cognitive impairment and be effective against dementia .
-Erucic acid has the ability to polymerize and dry means Erucic acid can be used as a binder for oil paints. 
-Erucic acids high tolerance to temperature makes Erucic acid suitable for transmission oil. 
-Erucic acid has many of the same uses as mineral oils but with the advantage that Erucic acid is more readily bio-degradable. 


-Erucic acids high tolerance to temperature makes Erucic acid suitable for transmission oil. 
Erucic acids ability to polymerize and dry means Erucic acid can be -and is - used as a binder for oil paints. 
-Erucic acid will readily form many organic compounds. 
Adding this ability to Erucic acids polymerizing characteristics makes Erucic acid very suitable for use as organic matrices that need to be polymeric. 
This makes Erucic acid especially useful in the manufacture of emulsions to coat photographic films and papers. 


-A complex cocktail of many different erucic acid compounds are commonly used in just one roll of color film.
-Erucic acid is widely used to produce emollients, especially for skin and healthcare products.
-Like other fatty acids, Erucic acid gets converted into surfactants. 
Erucic acid is especially valued in tribology as a superior lubricant. 
When used in the manufacture of plastic films in the form of erucamide, Erucic acid migrates to the surfaces and so resists the sticking of each film to its neighbor. 


-Being a hydrocarbon of high calorific value, with a very low flash point, high cetane rating, and good lubrication qualities, erucic acid can be a valuable component of bio-diesel. 
-When converted into behenyl alcohol (CH3(CH2)21OH), erucic acid has many further uses such as a pour point depressant, enabling liquids to flow at a lower temperature and silver behenate for use in photography
-Erucic acid has limited ability to polymerize and dry for use in oil paints. 
Like other fatty acids, Erucic acid can be converted into surfactants or lubricants, and can be used as a precursor to biodiesel 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.
-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.


Synonyms : 
Prifac 2990
cis-13-Docosenoic acid
(13Z)-13-docosenoic acid        
(Z)-13-docosenoic acid    
(Z)-docos-13-enoic acid    
13-cis-docosenoic acid
(Z)-docos-13-enoic acid
delta13-cis-docosenoic acid
delta13:14-docosenoic acid


Sources of Erucic acid:
Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the brassica family. 
Erucic acid is highest in some of the rapeseed varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli. 
For industrial purposes, a High-Erucic Acid Rapeseed (HEAR) has been developed. 
These cultivars can yield 40% to 60% of the total oil recovered as erucic acid.


Physical and chemical properties of Erucic acid:
Appearance: White to Off-White Low-Melting Solid
Molecular weight : 338,57 g/mol
Color: white
Functional group: carboxylic acid
Odor: No data available
Odor Threshold: No data available
pH: No data available
Melting point/freezing point: Melting point/range: 28 - 32 °C - lit.
Initial boiling point and boiling range: 358 °C at 533 hPa - lit.
Flash point: 113 °C - closed cup
Evaporation rate: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available
Vapor pressure: No data available
Vapor density: No data available
Relative density: No data available
Water solubility: No data available
Partition coefficient: n-octanol/water: No data available
Autoignition temperature: No data available
Decomposition temperature: No data available
Viscosity: 
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Explosive properties: No data available
Oxidizing properties: No data available
Refractive Index: n20D 1.45
pK Values: pKa: 4.78
Solubility: Chloroform (Slightly), Methanol (Slightly)


Substituents of Erucic acid:
-Very long-chain fatty acid
-Unsaturated fatty acid
-Straight chain fatty acid
-Monocarboxylic acid or derivatives
-Carboxylic acid
-Carboxylic acid derivative
-Organic oxygen compound
-Organic oxide
-Hydrocarbon derivative
-Organooxygen compound
-Carbonyl group
-Aliphatic acyclic compound

First aid measures of Erucic acid:
-Description of first-aid measures:

General advice:
Show this material safety data sheet to the doctor in attendance.

If inhaled:
After inhalation: fresh air.

In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with water/ shower.

In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.

If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.

Exposure controls/personal protection of Erucic acid:
-Control parameters:
Ingredients with workplace control parameters.

-Exposure controls:
Personal protective equipment:

Eye/face protection:
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Safety glasses.

Skin protection:
This recommendation applies only to the product stated in the safety data sheet, supplied by us and for the designated use. 
When dissolving in or mixing with other substances and under conditions deviating from those stated in EN374 please contact the supplier of CE-approved gloves.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,45 mm
Break through time: 480 min
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 30 min

Body Protection:
Protective clothing.

Respiratory protection: 
Required when dusts are generated.
Our recommendations on filtering respiratory protection are based on the following standards: DIN EN 143, DIN 14387 and other accompanying standards relating to the used respiratory protection system.
Recommended Filter type: Filter type P2
The entrepeneur has to ensure that maintenance, cleaning and testing of respiratory protective devices are carried out according to the instructions of the producer.
These measures have to be properly documented.

Control of environmental exposure:
Do not let product enter drains.

Firefighting measures of Erucic acid:
-Extinguishing media:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.


-Special hazards arising from the substance or mixture:
Nature of decomposition products not known.
Combustible.
Vapors are heavier than air and may spread along floors.
Forms explosive mixtures with air on intense heating.
Development of hazardous combustion gases or vapours possible in the event of fire.


-Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus. 
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.


Accidental release measures of Erucic acid:
-Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel: 
Avoid inhalation of dusts. 
Avoid substance contact.
Ensure adequate ventilation. 
Evacuate the danger area, observe emergency procedures, consult an expert.

-Environmental precautions:
Do not let product enter drains.

-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area. 
Avoid generation of dusts.

Handling and storage of :
-Precautions for safe handling:
-Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed. 
Dry.
Store under inert gas. 
Air sensitive.


 

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