Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; | 86% |
pyridine
ethanol
docos-13-enoic acid-anhydride
A
cis-13-docosenoic acid
B
ethyl (13Z)-13-docosenoate
Conditions | Yield |
---|---|
erucic acid anhydride; |
cis-13-docosenoic acid
Conditions | Yield |
---|---|
at 175℃; |
ethanol
docos-13-enoic acid-anhydride
A
cis-13-docosenoic acid
B
ethyl (13Z)-13-docosenoate
Conditions | Yield |
---|---|
erucic acid anhydride; |
cis-Octadecenoic acid
adipic acid monomethyl ester
cis-13-docosenoic acid
Conditions | Yield |
---|---|
With methanol; sodium methylate Electrolysis.Hydrolyse des gebildeten Erucasaeure-methylesters durch Erwaermen mit wss.-methanol.Natronlauge; |
Conditions | Yield |
---|---|
With nickel Hydrogenation; | |
With quinoline; ethyl acetate Hydrogenation.Lindlar-Katalysator; |
13-hydroxy-docosanoic acid
cis-13-docosenoic acid
Conditions | Yield |
---|---|
at 220℃; under 7 Torr; |
Conditions | Yield |
---|---|
erucic acid anhydride; |
Conditions | Yield |
---|---|
Kinetics; |
cis-13-docosenoic acid
Conditions | Yield |
---|---|
With ethanol; sodium |
cis-13-docosenoic acid
Conditions | Yield |
---|---|
With ethanol; sodium |
Conditions | Yield |
---|---|
Hydrogenation; |
cis-13-docosenoic acid
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
erucic acid dichloride; |
13,14-dibromo-docosanoic acid
cis-13-docosenoic acid
Conditions | Yield |
---|---|
erucic acid dibromide; |
Conditions | Yield |
---|---|
ν-chloro-erucic acid; |
Conditions | Yield |
---|---|
μ-bromo-erucic acid; |
Conditions | Yield |
---|---|
With aluminum isopropoxide Einw. von Bromwasserstoff auf das entstandene Saeuregemisch und Behandlung mit Zink; |
docos-13-enoic acid-anhydride
A
cis-13-docosenoic acid
B
ethyl (13Z)-13-docosenoate
Conditions | Yield |
---|---|
erucic acid anhydride; |
Conditions | Yield |
---|---|
erucic acid dichloride; |
13-iodo-docosanoic acid
A
cis-13-docosenoic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
tetradec-5-ynoic acid
cis-13-docosenoic acid
Conditions | Yield |
---|---|
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
cis-13-docosenoic acid
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
cis-13-docosenoic acid
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
cis-13-docosenoic acid
Conditions | Yield |
---|---|
With Candida antarctica Lipase A; sodium chloride In aq. phosphate buffer; isopropyl alcohol pH=7.5; Catalytic behavior; Enzymatic reaction; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
cis-13-docosenoic acid
N-{2-[(2,6-dimethylphenyl)-amino]-2-oxoethyl}-N,N-diethyl-benzenemethanaminium eruciate
Conditions | Yield |
---|---|
In methanol at 30 - 60℃; for 1 - 2h; | 100% |
cis-13-docosenoic acid
2-(pyridin-4-yl)-thiazolidine-4-carboxylic acid
Conditions | Yield |
---|---|
In pyridine (6 ml)-methylene chloride | 99% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 1h; | 96% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With choline chloride; zinc(II) chloride at 110℃; for 12h; | 95% |
Conditions | Yield |
---|---|
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 peroxide | 91% |
With potassium hydroxide; potassium permanganate; water at 0℃; |
cis-13-docosenoic acid
4-bromopiperidine hydrobromide
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With choline chloride; zinc(II) chloride at 110℃; for 12h; | 93% |
Conditions | Yield |
---|---|
With sodium methylate In methanol for 0.533333h; electrolysis, 1A (1F/mol), Pt-plate anode, titanium cathode; | 92% |
cis-13-docosenoic acid
1-amino-3-(dimethylamino)propane
N-erucamidopropyl-N,N-dimethylamine
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; Cooling with ice; | 91.8% |
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
With chloroformic acid ethyl ester; triethylamine In acetonitrile for 0.5h; Ambient temperature; | 90% |
cis-13-docosenoic acid
Conditions | Yield |
---|---|
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
cis-13-docosenoic acid
4-methoxycarbonyl-1-isocyanobenzene
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Passerini Condensation; | 90% |
cis-13-docosenoic acid
N1,N8-bis(tert-butoxycarbonyl)spermidine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h; Inert atmosphere; | 89.4% |
Conditions | Yield |
---|---|
With oxygen; ozone In water; acetone at 0℃; Flow reactor; | A 74% B 88% |
cis-13-docosenoic acid
(Z)-N-hydroxydocos-13-enamide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
tolyldocosanoic acid
Conditions | Yield |
---|---|
With sulfuric acid In toluene | 82% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
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
1-O-cholesteryl-β-D-galactopyranoside
cholesteryl 6-O-erucoyl-β-D-galactopyranoside
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With piperazine; 9-(2-chlorophenyl)acridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 25 - 27℃; for 14h; Irradiation; | 80% |
vinyl acetate
cis-13-docosenoic acid
(Z)-Docos-13-enoic acid vinyl ester
Conditions | Yield |
---|---|
With palladium diacetate; potassium hydroxide for 24h; Ambient temperature; | 79% |
cis-13-docosenoic acid
hexadecanoic acid 2-decanoyloxy-1-hydroxymethyl-ethyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Esterification; | 77% |
Molecule structure of Erucic acid (CAS NO.112-86-7):
IUPAC Name: (Z)-Docos-13-enoic acid
Molecular Weight: 338.56768 g/mol
Molecular Formula: C22H42O2
Melting Point: 28-32 °C(lit.)
Density: 0.891 g/cm3
Boiling Point: 386.1 °C at 760 mmHg
Flash Point: 349.9 °C
Index of Refraction: 1.467
Molar Refractivity: 105.59 cm3
Molar Volume: 379.9 cm3
Polarizability: 41.86×10-24 cm3
Surface Tension: 33.8 dyne/cm
Enthalpy of Vaporization: 69.72 kJ/mol
Vapour Pressure: 4.91E-07 mmHg at 25 °C
Storage Temp.: 2-8 °C
XLogP3: 8.7
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 19
Exact Mass: 338.318481
MonoIsotopic Mass: 338.318481
Topological Polar Surface Area: 37.3
Heavy Atom Count: 24
Complexity: 284
Canonical SMILES: CCCCCCCCC=CCCCCCCCCCCCC(=O)O
Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCCCCC(=O)O
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-
InChIKey: DPUOLQHDNGRHBS-KTKRTIGZSA-N
EINECS: 204-011-3
Product Categories: Intermediates; Biochemistry; Higher Fatty Acids & Higher Alcohols; Unsaturated Higher Fatty Acids
Erucic Acid(112-86-7) can be used as an ingredient in appetite depressants. It is also can be used for the preparation of lubricants, surfactants and plastics additives.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 1
RTECS: JR1280000
F: 10-23
Hazardous Substances Data: 112-86-7(Hazardous Substances Data)
Erucic acid (CAS NO.112-86-7) is also named as 13-cis-Docosenoic acid ; AI3-18180 ; HSDB 5015 ; Hystrene 2290 ; NSC 6814 ; Z-13-Docosenoic acid ; cis-13-Docosenoic acid ; delta13-cis-Docosenoic acid ; delta13:14-Docosenoic acid .
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