(13Z)-DOCOSENOIC ACID
(13Z)-Docosenoic acid has industrial applications in the production of lubricants, plastics, coatings, and cosmetics, thanks to its high oxidative stability and low-temperature fluidity.
Due to increasing environmental concerns and the push for sustainable alternatives to petroleum-derived compounds, (13Z)-Docosenoic acid has garnered interest as a renewable raw material for green chemistry innovations.
Studies have indicated that excessive intake of (13Z)-Docosenoic acid can lead to myocardial lipidosis, a condition characterized by lipid accumulation in heart tissues, which may impair cardiac function and lead to cardiotoxicity.
CAS Number: 112-86-7
EC Number: 204-011-3
Chemical Formula: C22H42O2
Molecular Weight: 338,57 g/mol
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, ERUCIC ACID, (Z)-Docos-13-enoic acid, 112-86-7, cis-13-Docosenoic acid, 13-Docosenoic acid, (Z)-, 13-cis-Docosenoic acid, Hystrene 2290, 13Z-docosenoic acid, 13-Docosenoic acid, (13Z)-, Prifrac 2990, cis-erucic acid, Z-13-Docosenoic acid, 13-Docosenoic acid, (Z)-13-Docosenoic acid, delta13-cis-Docosenoic acid, delta13:14-Docosenoic acid, (13Z)-13-Docosenoic acid, Erucasaeure, CHEBI:28792, cis-eruic acid, HSDB 5015, (13Z)-Docosenoic acid, NSC 6814, EINECS 204-011-3, C22:1n-9, (13Z)-docos-13-enoic acid, .delta.13-cis-Docosenoic acid, Erucic acid, 85%, UNII-075441GMF2, docos-13c-enoic acid, AI3-18180, 22:1omega9, NSC-6814, 13(Z)-Docosenoic Acid, MFCD00063188, NOURACID RE 07, 075441GMF2, JARIC 22:1, cis-Delta(13)-docosenoic acid, DTXSID8026931, FA 22:1, (Z)-13-docosenoate, 22:1(N-9), 1072-39-5, docosensaure, erucasaure, NSC6814, 13-docosenoate, 13-Docosensaure, C22-fatty acid, cis-13-Docosenoate, Edenor C 22 Eruca, Docosensaure, 13-cic, Edenor U 122, Prifac 2990, Cis 13-docosaenoic Acid, Erucic acid, >=99%, delta 13-cis-Docosenoate, delta.13-cis-Docosenoate, Cis-docos-13-enoic Acid, ERUCIC ACID [MI], (Z)-Docos-13-enoicacid, (13Z)-13-Docosenoate, ERUCIC ACID [HSDB], SCHEMBL5987, 13-Docosenoic acid, (Z), C22:1,n-9 cis, delta 13-cis-Docosenoic acid, delta.13-cis-Docosenoic acid, Docosenoic acid, 13-(Z)-, Fatty Acid 22:1 n-9 cis, Fatty Acid cis 22:1 n-9, DTXCID706931, CHEMBL1173380, Erucic acid, analytical standard, HY-N7109A, (13Z)-13-Docosenoic acid #, 13-DOCOSENsaure (ALTSTOFF), HMS3649F15, ALBB-036629, HY-N7109, 13-DOCOSENSAEURE (ALTSTOFF), Tox21_200242, BDBM50463967, LMFA01030089, AKOS015961814, DELTA 13:14-DOCOSENOIC ACID, Erucic acid, >=99% (capillary GC), Erucic acid, technical, ~90% (GC), 13-docosenoic acid (ACD/Name 4.0), CCG-267904, DELTA(13)-CIS-DOCOSENOIC ACID, NCGC00166073-01, NCGC00166073-02, NCGC00166073-04, NCGC00257796-01, CAS-112-86-7, DA-73188, FA(22:1(13Z)), 22:1 n-9, CS-0014094, CS-0203830, D0965, NS00005003, S5383, C08316, F17010, Q413531, SR-01000946653, ERUCIC ACID (CONSTITUENT OF BORAGE SEED OIL), SR-01000946653-1, 084C86E4-C0FF-45E5-9F1D-09913C9193BE
(13Z)-Docosenoic acid is a monounsaturated omega-9 fatty acid with the chemical formula C22H42O2, classified as a long-chain fatty acid due to its 22-carbon structure.
(13Z)-Docosenoic acid is primarily found in the seeds of plants from the Brassicaceae family, such as rapeseed (Brassica napus), mustard (Brassica juncea), and wallflower (Erysimum species).
(13Z)-Docosenoic acid has industrial applications in the production of lubricants, plastics, coatings, and cosmetics, thanks to its high oxidative stability and low-temperature fluidity.
However, (13Z)-Docosenoic acid's dietary consumption has been a subject of concern, as excessive intake may cause lipid accumulation in the heart and impair myocardial function, leading to potential cardiotoxicity.
This concern led to the development of low-(13Z)-Docosenoic acid rapeseed oil (commonly known as canola oil), which contains significantly reduced levels of the fatty acid to ensure food safety.
In the food industry, (13Z)-Docosenoic acid is sometimes used as a defoaming agent in food processing, though its direct consumption is regulated in many countries.
In contrast, (13Z)-Docosenoic acid's non-food applications continue to expand, particularly in the production of bio-based polymers and biodegradable lubricants, where its unique chemical properties provide an eco-friendly alternative to petroleum-based products.
(13Z)-Docosenoic acid's presence in nature and industry highlights the balance between its functional benefits and potential health risks, making it a subject of continued research and regulatory attention.
(13Z)-Docosenoic acid is a monounsaturated omega-9 fatty acid with the molecular formula C₂₂H₄₂O₂, characterized by its long 22-carbon chain and a single cis-double bond at the omega-9 position.
(13Z)-Docosenoic acid is predominantly found in the seeds of plants belonging to the Brassicaceae family, particularly in high concentrations within rapeseed (Brassica napus), mustard (Brassica juncea), and wallflower (Erysimum species).
Historically, (13Z)-Docosenoic acid has been widely utilized in industrial applications due to its advantageous chemical properties, including high oxidative stability, low-temperature fluidity, and resistance to polymerization.
These qualities make (13Z)-Docosenoic acid an essential component in the production of lubricants, plastics, coatings, and specialty chemicals.
(13Z)-Docosenoic acid is also a key ingredient in the manufacture of erucamide, a slip agent used in plastic film production to reduce surface friction and improve processing efficiency.
Additionally, (13Z)-Docosenoic acid is employed in the cosmetics industry for its emollient properties, as it helps improve the texture and spreadability of skincare products.
Despite its numerous industrial applications, the dietary consumption of (13Z)-Docosenoic acid has been a subject of considerable scrutiny and regulation due to its potential health risks.
Studies have indicated that excessive intake of (13Z)-Docosenoic acid can lead to myocardial lipidosis, a condition characterized by lipid accumulation in heart tissues, which may impair cardiac function and lead to cardiotoxicity.
These concerns led to regulatory restrictions on (13Z)-Docosenoic acid levels in edible oils, especially rapeseed oil, which was once a major dietary source.
In response, plant breeding programs successfully developed low-(13Z)-Docosenoic acid rapeseed (LEAR) varieties, commonly referred to as canola oil, which contain minimal amounts of this fatty acid and are deemed safe for human consumption.
Today, canola oil has largely replaced traditional high-erucic rapeseed oil in food products, while high-erucic varieties remain valuable for non-food industrial applications.
In the food industry, (13Z)-Docosenoic acid is sometimes used as a defoaming agent in food processing, particularly in yeast fermentation processes and certain dairy products.
However, (13Z)-Docosenoic acid's direct use in food products is strictly regulated in many countries, with maximum allowable limits set to ensure consumer safety.
In contrast, (13Z)-Docosenoic acid's role in non-food applications continues to expand, particularly in the production of bio-based polymers, biodegradable lubricants, and eco-friendly surfactants.
Due to increasing environmental concerns and the push for sustainable alternatives to petroleum-derived compounds, (13Z)-Docosenoic acid has garnered interest as a renewable raw material for green chemistry innovations.
(13Z)-Docosenoic acid is used in the production of bioplastics, as well as in the synthesis of specialty waxes and surfactants that serve as environmentally friendly alternatives in detergents and personal care products.
Ongoing research continues to explore (13Z)-Docosenoic acid's potential uses in pharmaceuticals, biofuels, and advanced materials, further emphasizing its importance in both traditional and emerging industries.
As sustainability and environmental consciousness grow, the role of (13Z)-Docosenoic acid in bio-based solutions is likely to expand, positioning it as a key ingredient in future innovations.
(13Z)-Docosenoic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9.
(13Z)-Docosenoic acid has the chemical formula: CH3(CH2)7CH=CH(CH2)11CO2H.
(13Z)-Docosenoic acid is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high (13Z)-Docosenoic acid rapeseed oil and 42% in mustard oil.
(13Z)-Docosenoic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.
(13Z)-Docosenoic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9.
(13Z)-Docosenoic acid has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH.
(13Z)-Docosenoic acid is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high (13Z)-Docosenoic acid rapeseed oil[1] and 42% in mustard oil.
(13Z)-Docosenoic 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.
(13Z)-Docosenoic 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 (13Z)-Docosenoic acid, rapeseed is used; for food purposes a 'low-(13Z)-Docosenoic acid rapeseed' (LEAR) has been developed (canola), which contains fats derived from oleic acid instead of (13Z)-Docosenoic acid.
(13Z)-Docosenoic 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.
(13Z)-Docosenoic 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.
(13Z)-Docosenoic acid naturally occurs in oil-rich seeds of species of the mustard family (Brassicaceae).
(13Z)-Docosenoic acid is found primarily in rapeseed oil and mustard oil.
(13Z)-Docosenoic acid can constitute about 30 – 60% of the total fatty acids of natural rapeseed and mustard seed.
(13Z)-Docosenoic acid has also been reported in some marine animal oils.
(13Z)-Docosenoic acid, a monounsaturated fatty acid (MUFA), is isolated from the seed of Raphanus sativus L.
(13Z)-Docosenoic acid occurs in vegetable oils and fats.
(13Z)-Docosenoic acid is a natural component of plant seeds of the Brassicaceae family (crucifers such as rape and mustard).
Chemically, (13Z)-Docosenoic acid is a long-chain, simple, unsaturated omega-9 fatty acid.
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(13Z)-Docosenoic 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.
(13Z)-Docosenoic acid is an elongation product of oleic acid and in animals, dietary one can be retroconverted to oleic acid.
In purified form, (13Z)-Docosenoic 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.
(13Z)-Docosenoic 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.
(13Z)-Docosenoic acid is a crystalline fatty acid C22H42O2 found in the form of glycerides especially in rapeseed oil.
(13Z)-Docosenoic acid acid is a 22-carbon monounsaturated fatty acid.
(13Z)-Docosenoic acid is found predominantly in canola oil.
(13Z)-Docosenoic acid is metabolized to oleic acid in vivo.
(13Z)-Docosenoic 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 (13Z)-Docosenoic acid.
(13Z)-Docosenoic acid is also known as cis-13-docosenoic acid.
(13Z)-Docosenoic acids trans isomer is known as brassidic acid.
(13Z)-Docosenoic acid occurs in nature only along with bitter-tasting compounds.
(13Z)-Docosenoic acid has many of the same uses as mineral oils but with the advantage that (13Z)-Docosenoic acid is more readily bio-degradable.
(13Z)-Docosenoic 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 (13Z)-Docosenoic acid content reduced by breeding.
(13Z)-Docosenoic acid is also found in mustard oil.
(13Z)-Docosenoic acid can also be found in fish oils.
High (13Z)-Docosenoic acid rapeseed (HEAR) is a specialty rapeseed selected for its high erucic content.
(13Z)-Docosenoic acid has over 50% (13Z)-Docosenoic 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.
(13Z)-Docosenoic acid originates in rapeseed plants, and is the major fatty acid constituent of rapeseed plant oil extracts and canola oil.
(13Z)-Docosenoic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9.
(13Z)-Docosenoic acid has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH.
(13Z)-Docosenoic acid is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high (13Z)-Docosenoic acid rapeseed oil and 42% in mustard oil.
(13Z)-Docosenoic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.
(13Z)-Docosenoic acid is produced by elongation of oleic acid via oleoyl-coenzyme A and malonyl-CoA.
(13Z)-Docosenoic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain acyl CoA dehydrogenase enzyme.
(13Z)-Docosenoic acid also known as cis-13-Docosenoic acid is a monounsaturated omega-9 fatty acid.
(13Z)-Docosenoic 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 (13Z)-Docosenoic Acid:
(13Z)-Docosenoic acid has many of the same uses as mineral oils, but it is more readily biodegradable than some.
(13Z)-Docosenoic acid has limited ability to polymerize and dry for use in oil paints.
Like other fatty acids, (13Z)-Docosenoic acid can be converted into surfactants or lubricants, and can be used as a precursor to biodiesel fuel.
Derivatives of (13Z)-Docosenoic 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.
(13Z)-Docosenoic acid can readily cross the blood-brain barrier (BBB), (13Z)-Docosenoic acid has been reported to normalize the accumulation of very long-chain fatty acids in the brain.
(13Z)-Docosenoic acid can improve cognitive impairment and be effective against dementia.
(13Z)-Docosenoic acid has the ability to polymerize and dry means (13Z)-Docosenoic acid can be used as a binder for oil paints.
(13Z)-Docosenoic acids high tolerance to temperature makes (13Z)-Docosenoic acid suitable for transmission oil.
(13Z)-Docosenoic acid has many of the same uses as mineral oils but with the advantage that (13Z)-Docosenoic acid is more readily bio-degradable.
(13Z)-Docosenoic acids high tolerance to temperature makes (13Z)-Docosenoic acid suitable for transmission oil.
(13Z)-Docosenoic acids ability to polymerize and dry means (13Z)-Docosenoic acid can be -and is - used as a binder for oil paints.
(13Z)-Docosenoic acid will readily form many organic compounds.
Adding this ability to (13Z)-Docosenoic acids polymerizing characteristics makes (13Z)-Docosenoic acid very suitable for use as organic matrices that need to be polymeric.
This makes (13Z)-Docosenoic acid especially useful in the manufacture of emulsions to coat photographic films and papers.
A complex cocktail of many different (13Z)-Docosenoic acid compounds are commonly used in just one roll of color film.
(13Z)-Docosenoic acid is widely used to produce emollients, especially for skin and healthcare products.
Like other fatty acids, (13Z)-Docosenoic acid gets converted into surfactants.
(13Z)-Docosenoic acid is especially valued in tribology as a superior lubricant.
When used in the manufacture of plastic films in the form of erucamide, (13Z)-Docosenoic 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, (13Z)-Docosenoic acid can be a valuable component of bio-diesel.
When converted into behenyl alcohol (CH3(CH2)21OH), (13Z)-Docosenoic 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
(13Z)-Docosenoic acid has limited ability to polymerize and dry for use in oil paints.
Like other fatty acids, (13Z)-Docosenoic acid can be converted into surfactants or lubricants, and can be used as a precursor to biodiesel fuel.
Derivatives of (13Z)-Docosenoic 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-(13Z)-Docosenoic 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.
(13Z)-Docosenoic acid can also be oxidatively cleaved to brassylic acid for use in the production of polyesters.
The oxidative cleavage of (13Z)-Docosenoic acid can be performed via ozonolysis or by reaction with hydrogen peroxide in the presence of an inorganic oxide catalyst.
(13Z)-Docosenoic 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.
Uses:
(13Z)-Docosenoic acid has a wide range of applications across various industries, including industrial manufacturing, food processing, cosmetics, pharmaceuticals, and agriculture.
In industrial applications, (13Z)-Docosenoic acid is used in the production of biodegradable lubricants and greases due to its high oxidative stability and low-temperature fluidity.
(13Z)-Docosenoic acid also serves as a precursor to erucamide, a slip agent that reduces surface friction in plastic films, improving the processing of polyethylene and polypropylene.
Additionally, (13Z)-Docosenoic acid-derived compounds are used in coatings, paints, varnishes, and rubber additives that enhance flexibility and durability.
In the food industry, (13Z)-Docosenoic acid functions as a defoaming agent in food processing, particularly in yeast fermentation and dairy production, though its direct consumption is regulated due to potential health concerns.
The development of low-(13Z)-Docosenoic acid rapeseed (LEAR) varieties, commonly known as canola oil, has helped minimize its presence in edible oils while preserving its industrial value.
In cosmetics and personal care products, (13Z)-Docosenoic acid is used as an emollient in skincare and hair care formulations, as well as in biodegradable soaps and surfactants.
Pharmaceuticals also utilize (13Z)-Docosenoic acid derivatives for their emollient properties and as part of controlled-release drug delivery systems.
Additionally, in agriculture, (13Z)-Docosenoic acid is used in bio-based insecticides and fungicides.
As environmental concerns drive the demand for sustainable and biodegradable materials, (13Z)-Docosenoic acid continues to be a valuable resource for industrial and commercial applications.
(13Z)-Docosenoic acid is a precursor to brassylic acid, a C13-dicarboxylic acid that is used to make specialty polyamides and polyesters.
The conversion entails ozonolysis, which selectively cleaves the C=C bond in (13Z)-Docosenoic acid:
CH3(CH2)7CH\dCH(CH2)11CO2H + O3 + 0.5 O2 -> CH3(CH2)7CO2H + HO2C(CH2)11CO2H
Amides of (13Z)-Docosenoic acid are used as lubricants and surfactants.
Hydrogenation of (13Z)-Docosenoic acid gives behenyl alcohol, CH3(CH2)21OH, a pour point depressant (enabling liquids to flow at a lower temperature), and silver behenate, for use in photography.
(13Z)-Docosenoic acid has a wide range of applications in various industries, including industrial manufacturing, food processing, cosmetics, pharmaceuticals, and agriculture.
Below are (13Z)-Docosenoic acid's key uses:
Industrial Applications:
Lubricants and Greases:
Due to its high oxidative stability and low-temperature fluidity, (13Z)-Docosenoic acid is used in the production of biodegradable lubricants and greases, which are eco-friendly alternatives to petroleum-based products.
Plastics and Polymers:
(13Z)-Docosenoic acid is a precursor to erucamide, a slip agent that reduces surface friction in plastic films and improves the processing of polyethylene and polypropylene.
Coatings and Paints:
(13Z)-Docosenoic acid-derived compounds are used in the production of specialty coatings, varnishes, and drying oils for industrial applications.
Rubber Processing:
(13Z)-Docosenoic acid is used in the manufacture of rubber additives that enhance flexibility and durability in rubber products.
Food Industry:
Defoaming Agent:
Small amounts are used in food processing, particularly in yeast fermentation and dairy production, to prevent excessive foaming.
Low-(13Z)-Docosenoic acid Rapeseed (Canola Oil):
Traditional rapeseed oil contained high levels of (13Z)-Docosenoic acid, but modern varieties (canola oil) have reduced levels to ensure food safety.
Cosmetics and Personal Care:
Skincare Products:
(13Z)-Docosenoic acid is used as an emollient in creams, lotions, and hair care products to provide moisture and improve texture.
Soaps and Surfactants:
(13Z)-Docosenoic acid helps produce biodegradable detergents, soaps, and surfactants with mild cleansing properties.
Pharmaceuticals:
Drug Formulations:
Some pharmaceutical formulations use (13Z)-Docosenoic acid derivatives for their emollient properties and controlled-release drug delivery systems.
Agriculture:
Insecticides and Pesticides:
(13Z)-Docosenoic acid is used in bio-based insecticides and fungicides due to its natural properties.
Industry Uses:
Intermediates
Intermediate
Fuel
Fillers
Lubricants and lubricant additives
Softener and conditioner
Lubricating agent
Consumer Uses:
Lubricants and lubricant additives
Not Known or Reasonably Ascertainable
Lubricating agent
Softener and conditioner
Sources of (13Z)-Docosenoic Acid:
The seed oil of the rape plant is rich in (13Z)-Docosenoic acid.
The name erucic means "of or pertaining to Eruca", which is a genus of flowering plants in the family Brassicaceae.
The genus includes colewort (E. sativa), which today is better known as arugula (US) or rocket (UK).
(13Z)-Docosenoic 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 (13Z)-Docosenoic acid, rapeseed is used; for food purposes a 'low-(13Z)-Docosenoic acid rapeseed' (LEAR) has been developed (canola), which contains fats derived from oleic acid instead of (13Z)-Docosenoic acid.
Biochemistry of (13Z)-Docosenoic Acid:
(13Z)-Docosenoic acid is produced by elongation of oleic acid via oleoyl-coenzyme A and malonyl-CoA.
(13Z)-Docosenoic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain acyl CoA dehydrogenase enzyme.
Action Mechanism of (13Z)-Docosenoic Acid:
An (13Z)-Docosenoic acid mitochondrial metabolite inhibits mitochondrial oxidn of other fatty acids, esp in heart.
Would explain accum of triglycerides in heart of rats fed rapeseed oil containing (13Z)-Docosenoic acid.
The effects of (13Z)-Docosenoic acid on the oxygen uptake of heart and liver mitochondria of young was studied by providing the carnitine ester of (13Z)-Docosenoic acid (in comparison to palmitylcarnitine).
The presence of erucylcarnitine caused a significant inhibition of the mitochondrial oxidation of palmitylcarnitine.
These findings suggest that a mitochondrial metabolite of (13Z)-Docosenoic acid inhibits the mitochondrial oxidation of other fatty acids, especially in the heart, and that this causes the accumulation of triglycerides in the hearts of rats fed rapeseed oil.
The effects of high (13Z)-Docosenoic acid rapeseed oil (HER) on fatty acid oxidation in rat liver compared with low (13Z)-Docosenoic acid rapeseed oil (LER) were studied.
The results showed that feeding HER to rats led to a decr in the hepatic oxidation capacity of palmitic acid and the liver weight positively correlated with the content of (13Z)-Docosenoic acid in diets and with the length of HER feeding period.
The inhibitory action of HER on the oxidation of long-chain fatty acids probably resulted from the incorporation of (13Z)-Docosenoic acid into mitochondrial membranes, interfering the fatty acyl-CoA transferring system on the membranes, but not from the beta-oxidation enzyme system in mitochondria being directly inhibited.
Human Metabolite Information of (13Z)-Docosenoic Acid:
Tissue Locations:
Adrenal Gland
Placenta
Cellular Locations:
Extracellular
Membrane
General Manufacturing Information of (13Z)-Docosenoic Acid:
(13Z)-Docosenoic acid plays a crucial role in manufacturing due to its unique chemical properties, making it a valuable raw material in various industries.
One of (13Z)-Docosenoic acid's primary applications is in the production of biodegradable lubricants and greases, where its high oxidative stability and resistance to polymerization ensure long-lasting performance.
(13Z)-Docosenoic acid is also widely used in the plastics industry, where it serves as a precursor to erucamide, a slip agent that reduces surface friction in plastic films, improving their processability and preventing adhesion in packaging materials.
Additionally, (13Z)-Docosenoic acid is utilized in the rubber industry as an additive to enhance flexibility, durability, and resistance to wear.
In coatings and paints, (13Z)-Docosenoic acid's derivatives are incorporated into specialty varnishes, drying oils, and protective finishes for industrial and consumer applications.
The textile industry also benefits from (13Z)-Docosenoic acid, where it is used in the manufacture of textile lubricants that enhance fiber processing.
Furthermore, (13Z)-Docosenoic acid's role in green chemistry is expanding, as it serves as a feedstock for the production of bioplastics, surfactants, and eco-friendly solvents, offering sustainable alternatives to petroleum-based materials.
As industries continue to seek renewable and biodegradable solutions, (13Z)-Docosenoic acid remains an essential component in modern manufacturing processes.
Industry Processing Sectors:
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
All Other Chemical Product and Preparation Manufacturing
Oil and Gas Drilling, Extraction, and Support activities
Petroleum Lubricating Oil and Grease Manufacturing
Other (requires additional information)
All Other Basic Organic Chemical Manufacturing
History of (13Z)-Docosenoic Acid:
The history of (13Z)-Docosenoic acid dates back to ancient times when oil-rich seeds from the Brassicaceae family, such as mustard and rapeseed, were cultivated for their nutritional and medicinal properties.
Early civilizations, particularly in India and China, used mustard seed oil for cooking and traditional medicine, unaware of its high (13Z)-Docosenoic acid content.
By the 19th century, rapeseed oil became an important industrial lubricant, especially in steam engines and machinery, due to (13Z)-Docosenoic acid's ability to withstand high temperatures without breaking down.
During World War II, demand for rapeseed oil increased as (13Z)-Docosenoic acid was used to lubricate naval and military equipment.
In the mid-20th century, concerns about the potential health risks of consuming high-(13Z)-Docosenoic acid oils emerged after studies suggested a link between excessive (13Z)-Docosenoic acid intake and myocardial lipidosis, a condition affecting heart function.
This led to extensive breeding programs in Canada and Europe in the 1960s and 1970s, resulting in the development of low-(13Z)-Docosenoic acid rapeseed (LEAR) varieties, which later became known as canola oil.
Canola oil quickly gained popularity as a healthier alternative to traditional rapeseed oil, leading to regulatory limits on (13Z)-Docosenoic acid content in edible oils in many countries.
Despite its decline in the food industry, (13Z)-Docosenoic acid remained valuable for industrial applications.
(13Z)-Docosenoic acid continued to be used in the production of lubricants, plastics, coatings, and bio-based chemicals.
As environmental awareness grew in the late 20th and early 21st centuries, interest in biodegradable and sustainable materials led to renewed research into (13Z)-Docosenoic acid’s role in bioplastics, bio-lubricants, and eco-friendly surfactants.
Today, (13Z)-Docosenoic acid is recognized as an important natural compound with a long history, balancing its industrial benefits with regulatory measures to ensure food safety.
Handling and Storage of (13Z)-Docosenoic Acid:
(13Z)-Docosenoic acid should be handled in a well-ventilated area, away from heat, sparks, and open flames, as it may degrade under high temperatures.
Protective gloves, safety goggles, and appropriate protective clothing should be worn to prevent skin and eye contact.
Storage should be in tightly sealed containers, kept in a cool, dry place away from strong oxidizing agents and incompatible substances.
Proper labeling and spill containment measures should be in place to minimize risks.
Reactivity and Stability of (13Z)-Docosenoic Acid:
(13Z)-Docosenoic acid is generally stable under normal conditions but may oxidize upon prolonged exposure to air, light, or heat, leading to degradation.
(13Z)-Docosenoic acid is incompatible with strong oxidizing agents, which can cause hazardous reactions.
Thermal decomposition may release irritating fumes, including carbon oxides.
Proper storage conditions and antioxidant additives can help maintain (13Z)-Docosenoic acid's stability over time.
First Aid Measures of (13Z)-Docosenoic Acid:
Inhalation:
Move the affected person to fresh air immediately.
If breathing difficulties occur, seek medical attention.
Skin Contact:
Wash affected skin with soap and water.
If irritation persists, seek medical advice.
Eye Contact:
Rinse cautiously with water for several minutes.
Remove contact lenses if present and continue rinsing.
Seek medical help if irritation continues.
Ingestion:
Rinse mouth with water and do not induce vomiting unless instructed by medical personnel.
Seek medical attention if large amounts are swallowed.
Firefighting Measures of (13Z)-Docosenoic Acid:
(13Z)-Docosenoic acid is combustible, though not highly flammable.
In case of fire, use carbon dioxide (CO₂), dry chemical, foam, or water spray to extinguish.
Firefighters should wear self-contained breathing apparatus (SCBA) and protective gear to avoid inhalation of combustion byproducts.
Avoid using direct water streams, as they may spread the burning substance.
Accidental Release Measures of (13Z)-Docosenoic Acid:
In case of spills, eliminate all ignition sources and wear appropriate protective equipment (gloves, goggles, and respiratory protection if necessary).
Small spills should be absorbed with inert material (e.g., sand or vermiculite) and collected in a sealed container for disposal.
Large spills should be contained to prevent environmental contamination.
Avoid release into soil and waterways.
Exposure Controls/Personal Protection of (13Z)-Docosenoic Acid:
Engineering Controls:
Use in a well-ventilated area or with local exhaust ventilation to minimize exposure.
Personal Protective Equipment (PPE):
Respiratory Protection:
Not typically required under normal conditions, but use a respirator if aerosolized or heated.
Hand Protection:
Wear chemical-resistant gloves.
Eye Protection:
Safety goggles or face shields should be used to prevent eye contact.
Skin Protection:
Wear protective clothing to minimize skin exposure.
Hygiene Measures:
Wash hands and exposed skin thoroughly after handling. Do not eat, drink, or smoke while handling (13Z)-Docosenoic acid.
Identifiers of (13Z)-Docosenoic Acid:
CAS Number: 112-86-7
Beilstein Reference: 1728049
ChEBI: CHEBI:28792
ChEMBL: ChEMBL1173380
ChemSpider: 4444561
ECHA InfoCard: 100.003.647
EC Number: 204-011-3
Gmelin Reference: 177365
KEGG: C08316
PubChem CID: 5281116
UNII: 075441GMF2
CompTox Dashboard (EPA): DTXSID8026931
InChI: InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
Key: DPUOLQHDNGRHBS-KTKRTIGZSA-N
InChI=1/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
Key: DPUOLQHDNGRHBS-KTKRTIGZBD
SMILES: O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC
Properties of (13Z)-Docosenoic 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, 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)
Chemical formula: C22H42O2
Molar mass: 338.576 g·mol−1
Appearance: White waxy solid
Density: 0.860 g/cm3
Melting point: 33.8 °C (92.8 °F; 306.9 K)
Boiling point: 381.5 °C (718.7 °F; 654.6 K) (decomposes)
Solubility in water: Insoluble
Solubility in methanol and ethanol: Soluble
Molecular Weight: 338.6 g/mol
XLogP3: 8.7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 19
Exact Mass: 338.318480578 Da
Monoisotopic Mass: 338.318480578 Da
Topological Polar Surface Area: 37.3 Ų
Heavy Atom Count: 24
Complexity: 284
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Substituents of (13Z)-Docosenoic 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
Names of (13Z)-Docosenoic Acid:
IUPAC names:
Fatty acids
rape-oil
(13Z)-Docosenoic acid-low
Preferred IUPAC name:
(13Z)-Docos-13-enoic acid
Regulatory process names:
Fatty acids, rape-oil, (13Z)-Docosenoic acid-low
Fatty acids, rape-oil, (13Z)-Docosenoic acid-low
rapeseed oil fatty acids
Other name:
C22:1 (Lipid numbers)
Other identifier:
93165-31-2
