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High quality Erucic Acid supplier in China
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(Z)-Docos-13-enoic acid
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112-86-7 Erucic Acid
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112-86-7 Usage

Purification Methods

Crystallise erucic acid from MeOH. [Beilstein 2 IV 1676.]

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.

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.

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.

Chemical Properties

White crystalline

Description

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the formula CH3(CH2)7CH=CH(CH2)11COOH. It is prevalent in wallflower seed, makes up 4.1% of rapeseed oil, and makes up 42% of mustard oil. Erucic acid is also known as cis-13- docosenoic acid and the trans isomer is known as brassidic acid.

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 [2] H. J. Nieschlag, I. A. Wolff (1971) Industrial uses of high erucic oils, JAOCS, 48, 723-727

Definition

ChEBI: 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.

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.
InChI: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-

112-86-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (L08685)  Erucic acid, tech. 90%    112-86-7 50g 290.0CNY Detail
Alfa Aesar (L08685)  Erucic acid, tech. 90%    112-86-7 250g 1091.0CNY Detail

112-86-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name erucic acid

1.2 Other means of identification

Product number -
Other names Prifac 2990

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fillers,Intermediates,Lubricants and lubricant additives,Surface active agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:112-86-7 SDS

112-86-7Synthetic route

methyl cis-13-docosenoate
1120-34-9

methyl cis-13-docosenoate

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃;86%
pyridine
110-86-1

pyridine

ethanol
64-17-5

ethanol

docos-13-enoic acid-anhydride
871893-44-6

docos-13-enoic acid-anhydride

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

ethyl (13Z)-13-docosenoate
37910-77-3

ethyl (13Z)-13-docosenoate

Conditions
ConditionsYield
erucic acid anhydride;
eicos-11c-enyl-malonic acid

eicos-11c-enyl-malonic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
at 175℃;
ethanol
64-17-5

ethanol

docos-13-enoic acid-anhydride
871893-44-6

docos-13-enoic acid-anhydride

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

ethyl (13Z)-13-docosenoate
37910-77-3

ethyl (13Z)-13-docosenoate

Conditions
ConditionsYield
erucic acid anhydride;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

adipic acid monomethyl ester
627-91-8

adipic acid monomethyl ester

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With methanol; sodium methylate Electrolysis.Hydrolyse des gebildeten Erucasaeure-methylesters durch Erwaermen mit wss.-methanol.Natronlauge;
behenolic acid
506-35-4

behenolic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With nickel Hydrogenation;
With quinoline; ethyl acetate Hydrogenation.Lindlar-Katalysator;
13-hydroxy-docosanoic acid
13980-16-0

13-hydroxy-docosanoic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
at 220℃; under 7 Torr;
docos-13-enoic acid-anhydride
871893-44-6

docos-13-enoic acid-anhydride

water
7732-18-5

water

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
erucic acid anhydride;
tetrachloromethane
56-23-5

tetrachloromethane

13,14-diiodo-docosanoic acid

13,14-diiodo-docosanoic acid

iodine
7553-56-2

iodine

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Kinetics;
bromoerucic acid

bromoerucic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With ethanol; sodium
chloroerucic acid

chloroerucic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With ethanol; sodium
behenolic acid
506-35-4

behenolic acid

acetic acid
64-19-7

acetic acid

hydrogen

hydrogen

nickel

nickel

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Hydrogenation;
rape-oil

rape-oil

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide ueber mehrere Stufen;
With lead(II) oxide bei Extraktion mit Aether bleibt erucasaures Blei ungeloest, das mit Salzsaeure zerlegt wird;
With hydrogenchloride Destillieren die untere, die Methylester enthaltende Schicht bei 25 mm, Verseifen die ueber 240grad siedende Hauptfraktion und Umkrystallisieren die abgeschiedene Erucasaeure bei 0-5grad aus einem Gemisch von Alkohol und Aceton;
ethanol
64-17-5

ethanol

13,14-dichloro-docosanoic acid
851626-69-2

13,14-dichloro-docosanoic acid

sodium amalgam

sodium amalgam

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
erucic acid dichloride;
13,14-dibromo-docosanoic acid
95806-39-6

13,14-dibromo-docosanoic acid

sodium amalgam

sodium amalgam

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
erucic acid dibromide;
ethanol
64-17-5

ethanol

14-chloro-docos-13-enoic acid

14-chloro-docos-13-enoic acid

sodium

sodium

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
ν-chloro-erucic acid;
ethanol
64-17-5

ethanol

13-bromo-docos-13-enoic acid

13-bromo-docos-13-enoic acid

sodium

sodium

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
μ-bromo-erucic acid;
14-methoxy-13-oxo-behenic acid

14-methoxy-13-oxo-behenic acid

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

Brassidic acid
506-33-2

Brassidic acid

Conditions
ConditionsYield
With aluminum isopropoxide Einw. von Bromwasserstoff auf das entstandene Saeuregemisch und Behandlung mit Zink;
docos-13-enoic acid-anhydride
871893-44-6

docos-13-enoic acid-anhydride

petroleum ether

petroleum ether

alcoholic KOH-solution

alcoholic KOH-solution

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

ethyl (13Z)-13-docosenoate
37910-77-3

ethyl (13Z)-13-docosenoate

Conditions
ConditionsYield
erucic acid anhydride;
ethanol
64-17-5

ethanol

13,14-dichloro-docosanoic acid
851626-69-2

13,14-dichloro-docosanoic acid

sodium

sodium

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

chlorobrassidic acid

chlorobrassidic acid

Conditions
ConditionsYield
erucic acid dichloride;
13-iodo-docosanoic acid
801980-02-9

13-iodo-docosanoic acid

alcoholic KOH-solution

alcoholic KOH-solution

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

isoerucic acid

isoerucic acid

iodobehenic acid

iodobehenic acid

A

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

B

isoerucic acid

isoerucic acid

Conditions
ConditionsYield
With potassium hydroxide
tetradec-5-ynoic acid
55182-81-5

tetradec-5-ynoic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit wss.-aethanol.Kalilauge
2: methanol; sodium / Electrolysis.anschliessenden Behandlung mit wss.-aethanol.Kalilauge
3: quinoline; ethyl acetate / Hydrogenation.Lindlar-Katalysator
View Scheme
pentadec-6-ynoic acid
92791-10-1

pentadec-6-ynoic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit wss.-aethanol.Kalilauge
2: methanol; sodium / Electrolysis.anschliessenden Behandlung mit wss.-aethanol.Kalilauge
3: quinoline; ethyl acetate / Hydrogenation.Lindlar-Katalysator
View Scheme
Stearolic acid
506-24-1

Stearolic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; sodium / Electrolysis.anschliessenden Behandlung mit wss.-aethanol.Kalilauge
2: quinoline; ethyl acetate / Hydrogenation.Lindlar-Katalysator
View Scheme
dodec-6-ynedioic acid monomethyl ester
408536-68-5

dodec-6-ynedioic acid monomethyl ester

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit warmer wss.-aethanol.Kalilauge
2: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit wss.-aethanol.Kalilauge
3: methanol; sodium / Electrolysis.anschliessenden Behandlung mit wss.-aethanol.Kalilauge
4: quinoline; ethyl acetate / Hydrogenation.Lindlar-Katalysator
View Scheme
hexanoic acid
142-62-1

hexanoic acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit warmer wss.-aethanol.Kalilauge
2: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit wss.-aethanol.Kalilauge
3: methanol; sodium / Electrolysis.anschliessenden Behandlung mit wss.-aethanol.Kalilauge
4: quinoline; ethyl acetate / Hydrogenation.Lindlar-Katalysator
View Scheme
valeric acid
109-52-4

valeric acid

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit warmer wss.-aethanol.Kalilauge
2: methanol; sodium / Electrolysis.Behandlung des Reaktionsprodukts mit wss.-aethanol.Kalilauge
3: methanol; sodium / Electrolysis.anschliessenden Behandlung mit wss.-aethanol.Kalilauge
4: quinoline; ethyl acetate / Hydrogenation.Lindlar-Katalysator
View Scheme
p-nitrophenyl erucate

p-nitrophenyl erucate

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Conditions
ConditionsYield
With Candida antarctica Lipase A; sodium chloride In aq. phosphate buffer; isopropyl alcohol pH=7.5; Catalytic behavior; Enzymatic reaction;
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

erucyl alcohol
629-98-1

erucyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 3.5h; Heating;100%
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 2.25h; Inert atmosphere; Green chemistry;96.2%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether
Multi-step reaction with 2 steps
1: sulfuric acid / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
View Scheme
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

A

1,26-hexacos-13-enedioic acid
53481-03-1

1,26-hexacos-13-enedioic acid

B

9-octadecene
5557-31-3

9-octadecene

Conditions
ConditionsYield
With [1,3-bis(2,4,5-Me3Ph)-2-imidazolidinylidene]Ru=CHPh(PCy3)Cl2 at 45℃; for 24h;A 100%
B n/a
Stage #1: cis-13-docosenoic acid; dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III) at 45℃; for 72h; Neat (no solvent);
Stage #2: With ethyl vinyl ether Product distribution / selectivity;
A 70%
B n/a
denatonium hydroxide

denatonium hydroxide

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

N-{2-[(2,6-dimethylphenyl)-amino]-2-oxoethyl}-N,N-diethyl-benzenemethanaminium eruciate
890843-19-3

N-{2-[(2,6-dimethylphenyl)-amino]-2-oxoethyl}-N,N-diethyl-benzenemethanaminium eruciate

Conditions
ConditionsYield
In methanol at 30 - 60℃; for 1 - 2h;100%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

2-(pyridin-4-yl)-thiazolidine-4-carboxylic acid
51226-84-7

2-(pyridin-4-yl)-thiazolidine-4-carboxylic acid

N-erucoyl-2-(4-pyridinyl)-4-thiazoline carboxylic acid

N-erucoyl-2-(4-pyridinyl)-4-thiazoline carboxylic acid

Conditions
ConditionsYield
In pyridine (6 ml)-methylene chloride99%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Unislip 1753
112-84-5

Unislip 1753

Conditions
ConditionsYield
With ammonia; zircornium(IV) n-propoxide at 165℃; for 6h; Reagent/catalyst;98.8%
Multi-step reaction with 2 steps
1: oxalyl dichloride / dichloromethane / Inert atmosphere
2: ammonium hydroxide
View Scheme
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

Methyl 2,5-dihydroxybenzoate
2150-46-1

Methyl 2,5-dihydroxybenzoate

(Z)-methyl 5-(henicos-12-enoyloxy)-2-hydroxybenzoate

(Z)-methyl 5-(henicos-12-enoyloxy)-2-hydroxybenzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 1h;96%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

diethylamine
109-89-7

diethylamine

N,N-diethylerucic acid amide

N,N-diethylerucic acid amide

Conditions
ConditionsYield
With Zn-MCM-22 catalyst at 80 - 340℃; under 15001.5 Torr; for 6h; Inert atmosphere; Large scale;96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

1-Hexadecanol
36653-82-4

1-Hexadecanol

C38H74O2

C38H74O2

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 12h;95%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

13,14-dihydroxy-behenic acid
616-01-3

13,14-dihydroxy-behenic acid

Conditions
ConditionsYield
Stage #1: cis-13-docosenoic acid With dihydrogen peroxide In formic acid; water at 20℃;
Stage #2: With potassium hydroxide In water for 4h; Reflux;
94%
With formic acid; dihydrogen peroxide91%
With potassium hydroxide; potassium permanganate; water at 0℃;
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

4-bromopiperidine hydrobromide
54288-70-9

4-bromopiperidine hydrobromide

(Z)-1-(4-bromopiperidin-1-yl)docos-13-en-1-one

(Z)-1-(4-bromopiperidin-1-yl)docos-13-en-1-one

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;94%
erucyl alcohol
629-98-1

erucyl alcohol

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

erucyl erucate

erucyl erucate

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 12h;93%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

propionic acid
802294-64-0

propionic acid

9,33-dotetracontadiene

9,33-dotetracontadiene

Conditions
ConditionsYield
With sodium methylate In methanol for 0.533333h; electrolysis, 1A (1F/mol), Pt-plate anode, titanium cathode;92%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

N-erucamidopropyl-N,N-dimethylamine
149968-48-9

N-erucamidopropyl-N,N-dimethylamine

Conditions
ConditionsYield
With sodium fluoride at 155 - 160℃; for 10h; Inert atmosphere;92%
With aluminum oxide; sodium fluoride at 160℃; for 10h; Inert atmosphere;82%
With aluminum oxide; sodium fluoride In neat (no solvent) at 155 - 160℃; for 10h; Inert atmosphere;
oleoyl alcohol
143-28-2

oleoyl alcohol

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

docos-13-enoic acid octadec-9-enyl ester

docos-13-enoic acid octadec-9-enyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; Cooling with ice;91.8%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

n-docosanoic acid
112-85-6

n-docosanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20 - 30℃; under 4500.45 - 6000.6 Torr;90.3%
bei der Reduktion an platinierten Platinkathoden.Electrolysis;
With selenium at 300℃;
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

aniline
62-53-3

aniline

(13Z)-docosenanilide

(13Z)-docosenanilide

Conditions
ConditionsYield
With chloroformic acid ethyl ester; triethylamine In acetonitrile for 0.5h; Ambient temperature;90%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

(Z)-Henicosa-1,12-diene

(Z)-Henicosa-1,12-diene

Conditions
ConditionsYield
With acridine; dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III) In dichloromethane; acetonitrile at 25 - 27℃; for 36h; Irradiation;90%
Stage #1: cis-13-docosenoic acid With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium iodide at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: With acetic anhydride at 160℃; for 5h; Inert atmosphere; Schlenk technique; regioselective reaction;
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; N,N-diphenylaminobenzene; acetic anhydride; potassium iodide at 160℃; for 12h; Inert atmosphere; Green chemistry; chemoselective reaction;
(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde
4933-77-1

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

4-methoxycarbonyl-1-isocyanobenzene
198476-21-0

4-methoxycarbonyl-1-isocyanobenzene

C43H67NO10

C43H67NO10

Conditions
ConditionsYield
In dichloromethane at 20℃; Passerini Condensation;90%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

N1,N8-bis(tert-butoxycarbonyl)spermidine
83392-10-3

N1,N8-bis(tert-butoxycarbonyl)spermidine

N1, N8-bis-tert-butoxycarbonyl-N4-(erucoyl)spermidine

N1, N8-bis-tert-butoxycarbonyl-N4-(erucoyl)spermidine

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h; Inert atmosphere;89.4%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

A

nonanoic acid
112-05-0

nonanoic acid

B

brassylic acid
505-52-2

brassylic acid

Conditions
ConditionsYield
With oxygen; ozone In water; acetone at 0℃; Flow reactor;A 74%
B 88%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

(Z)-N-hydroxydocos-13-enamide
119042-56-7

(Z)-N-hydroxydocos-13-enamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; potassium hydroxide In methanol for 24h; Reflux;85%
Stage #1: cis-13-docosenoic acid With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; acetonitrile at 20℃; for 0.5h;
Stage #2: With hydroxylamine hydroxide In ethyl acetate; acetonitrile at 20℃;
72%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

erucic acid diethanolamide

erucic acid diethanolamide

Conditions
ConditionsYield
Stage #1: cis-13-docosenoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;
Stage #2: 2,2'-iminobis[ethanol] In dichloromethane at 20℃; for 18h;
83%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

tolyldocosanoic acid
857197-45-6

tolyldocosanoic acid

Conditions
ConditionsYield
With sulfuric acid In toluene82%
pyrrolidine
123-75-1

pyrrolidine

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

(Z)-1-(pyrrolidin-1-yl)docos-13-en-1-one

(Z)-1-(pyrrolidin-1-yl)docos-13-en-1-one

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;82%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

13-hydroxytridecanoic acid
7735-38-8

13-hydroxytridecanoic acid

Conditions
ConditionsYield
Stage #1: cis-13-docosenoic acid With 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate In 1,3-dioxane; water at 20℃; for 16h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 3.25h; Inert atmosphere;
81%
With sodium hydroxide; sodium tetrahydroborate; ozone 1.) ethanol, cyclohexane, 0 deg C, 2.) water, ethanol, cyclohexane, room temp., 10 h; Yield given. Multistep reaction;
Stage #1: cis-13-docosenoic acid With ozone In ethanol; cyclohexane at 0 - 5℃; Ozonolysis;
Stage #2: With potassium borohydride Reduction;
Stage #1: cis-13-docosenoic acid With ozone In ethanol; cyclohexane at 0 - 5℃; for 4h;
Stage #2: With potassium borohydride In methanol at 0℃; for 8h; Further stages.;
Multi-step reaction with 2 steps
1: O3 / ethanol; cyclohexane / 0 - 5 °C
2: KBH4
View Scheme
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

1-O-cholesteryl-β-D-galactopyranoside
51704-23-5

1-O-cholesteryl-β-D-galactopyranoside

cholesteryl 6-O-erucoyl-β-D-galactopyranoside
1383956-38-4

cholesteryl 6-O-erucoyl-β-D-galactopyranoside

Conditions
ConditionsYield
Stage #1: cis-13-docosenoic acid With pyridine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 1-O-cholesteryl-β-D-galactopyranoside at 20℃; for 36h; Inert atmosphere; regioselective reaction;
81%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine at 0 - 20℃; for 48h;52%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

acrolein
107-02-8

acrolein

C24H46O

C24H46O

Conditions
ConditionsYield
With piperazine; 9-(2-chlorophenyl)acridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 25 - 27℃; for 14h; Irradiation;80%
vinyl acetate
108-05-4

vinyl acetate

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

(Z)-Docos-13-enoic acid vinyl ester
104719-35-9

(Z)-Docos-13-enoic acid vinyl ester

Conditions
ConditionsYield
With palladium diacetate; potassium hydroxide for 24h; Ambient temperature;79%
cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

hexadecanoic acid 2-decanoyloxy-1-hydroxymethyl-ethyl ester
199274-79-8

hexadecanoic acid 2-decanoyloxy-1-hydroxymethyl-ethyl ester

(Z)-Docos-13-enoic acid 3-decanoyloxy-2-hexadecanoyloxy-propyl ester

(Z)-Docos-13-enoic acid 3-decanoyloxy-2-hexadecanoyloxy-propyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Esterification;77%

112-86-7Upstream product

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