5,8,11,14,17-Eicosapentaenoicacid, (5Z,8Z,11Z,14Z,17Z)- supplier

Name
Icosapent
EINECS
CAS No. 10417-94-4
Article Data26
CAS DataBase
Density 0.941 g/cm³
Solubility
Melting Point -54--53 °C(lit.)
Formula C₂₀H₃₀O₂
Boiling Point 439.3 °C at 760 mmHg
Molecular Weight 302.457
Flash Point 336 °C
Transport Information UN 3265 8/PG 3
Appearance Smell slightly yellow transparent
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 5,8,11,14,17-Eicosapentaenoic Acid;5,8,11,14,17-Icosapentaenoic Acid;Acid, Eicosapentanoic;Eicosapentaenoic Acid;eicosapentanoic acid;Icosapent;omega 3 Eicosapentaenoic Acid;omega-3-Eicosapentaenoic Acid;Timnodonic Acid
PSA 37.30000
LogP 5.99270

Synthetic route

: 86227-47-6
eicosapentaenoic acid ethyl ester

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; edetate disodium In ethanol; water at 60 - 65℃; for 2h;	98%
With immobilized lipase from Candida Antarctica; water In 1,4-dioxane at 55℃; for 3h; Enzymatic reaction;	98%
With Candida antarctica lipase; water at 40℃; Hydrolysis;	97.6%

: 2734-47-6
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water	93%
With lithium hydroxide In tetrahydrofuran for 15h; Ambient temperature;	92%

: 5871-07-8
5,8,11,14,17-eicosapentaynoic acid

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
With hydrogen; Lindlar's catalyst	85.5%

: 86227-47-6
eicosapentaenoic acid ethyl ester

: 141-43-5
ethanolamine

A: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

B: (5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)eicosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;	A n/a B 80%

...Expand

: 86227-47-6
eicosapentaenoic acid ethyl ester

: 534-03-2
serinol

A: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

B: C23H37NO3

Conditions

Conditions	Yield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;	A n/a B 80%

...Expand

: 6168-72-5
2-Amino-1-propanol

: 86227-47-6
eicosapentaenoic acid ethyl ester

A: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

B: C23H37NO2

Conditions

Conditions	Yield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;	A n/a B 78%

...Expand

: 3179-63-3
3-Dimethylamino-1-propanol

: 86227-47-6
eicosapentaenoic acid ethyl ester

A: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

B: C25H41NO2

Conditions

Conditions	Yield
With Novozym 435 lipase on resin In acetone at 35℃; for 18h; Green chemistry; Enzymatic reaction;	A n/a B 28%

...Expand

: 86227-47-6
eicosapentaenoic acid ethyl ester

: 534-03-2
serinol

A: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

B: 1048012-11-8
C23H37NO3

Conditions

Conditions	Yield
With Novozym 435 lipase on resin In acetone at 35℃; for 18h; Green chemistry; Enzymatic reaction;	A n/a B 25%

...Expand

: 121245-05-4
(2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-O-(6Z,9Z,12Z,15Z-octadecatetranoyl)-3-β-D-galactopyranosyl-sn-glycerol

A: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

B: 144118-12-7
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid (R)-1-hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Conditions

Conditions	Yield
With Lypase type XIII In 1,4-dioxane; water at 37℃; for 4h; Yield given;

: ((3Z,6Z,9Z,12Z,15Z)-2-Octadeca-3,6,9,12,15-pentaenyl)-malonic acid

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
With hydrogenchloride In diethylene glycol dimethyl ether at 120℃; for 1h; Yield given;

: 79553-90-5
2-(1'-oxo-dodeca-5',8',11',14',17'(all Z)-pentaenyl)-1,3,5-trihydroxybenzene

A: 108-73-6
3,5-dihydroxyphenol

B: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

C: (5Z,8Z,11Z,14Z,17Z)-N-hydroxyicosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
With sodium hydroxide; hydroxylamine; silica gel 1.) aqueous EtOH, reflux, 2.) heat.; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 2h; Ambient temperature;

: 137682-11-2
(3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenal

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 84 percent / NaBH4 / methanol / 0.33 h / Ambient temperature 2: 74 percent / PPh3*Br2 / acetonitrile 3: 1.) Na / 1.)diglyme 2.) diglyme 140 deg C, 2h 4: 40percent aq NaOH / H2O; ethanol / 4 h / Ambient temperature 5: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C View Scheme

: 181213-48-9
all-(Z)-1-bromo-3,6,9,12,15-octadecapentaene

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Na / 1.)diglyme 2.) diglyme 140 deg C, 2h 2: 40percent aq NaOH / H2O; ethanol / 4 h / Ambient temperature 3: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C View Scheme

: 181213-44-5
(3Z,6Z,9Z,12Z, 15Z)-octadeca-3,6,9,12,15-pentaen-1-ol

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / PPh3*Br2 / acetonitrile 2: 1.) Na / 1.)diglyme 2.) diglyme 140 deg C, 2h 3: 40percent aq NaOH / H2O; ethanol / 4 h / Ambient temperature 4: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C View Scheme

: 181213-54-7
((3Z,6Z,9Z,12Z,15Z)-2-Octadeca-3,6,9,12,15-pentaenyl)-malonic acid diethyl ester

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 40percent aq NaOH / H2O; ethanol / 4 h / Ambient temperature 2: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C View Scheme

: 16400-32-1
1-bromo-pent-2-yne

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 2: TsOH / methanol / 2 h / 20 °C 3: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C 4: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 5: TsOH / methanol / 2 h / 20 °C 6: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 7: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 8: 5percent aq. NaOH / methanol / 4 h / 20 °C 9: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme
Multi-step reaction with 9 steps 1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 2: TsOH / methanol / 2 h / 20 °C 3: 64.2 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 4: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 5: TsOH / methanol / 2 h / 20 °C 6: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 7: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 8: 5percent aq. NaOH / methanol / 4 h / 20 °C 9: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme

Yield

Multi-step reaction with 9 steps
1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
2: TsOH / methanol / 2 h / 20 °C
3: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C
4: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
5: TsOH / methanol / 2 h / 20 °C
6: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C
7: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
8: 5percent aq. NaOH / methanol / 4 h / 20 °C
9: 85.5 percent / H2 / Pd/CaCO3/Pb
View Scheme

Multi-step reaction with 9 steps
1: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
2: TsOH / methanol / 2 h / 20 °C
3: 64.2 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C
4: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
5: TsOH / methanol / 2 h / 20 °C
6: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C
7: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
8: 5percent aq. NaOH / methanol / 4 h / 20 °C
9: 85.5 percent / H2 / Pd/CaCO3/Pb
View Scheme

: 6261-22-9
pent-2-yn-1-ol

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 78 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C 2: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 3: TsOH / methanol / 2 h / 20 °C 4: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C 5: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 6: TsOH / methanol / 2 h / 20 °C 7: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 8: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 9: 5percent aq. NaOH / methanol / 4 h / 20 °C 10: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme
Multi-step reaction with 10 steps 1: 78 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C 2: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 3: TsOH / methanol / 2 h / 20 °C 4: 64.2 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 5: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 6: TsOH / methanol / 2 h / 20 °C 7: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C 8: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C 9: 5percent aq. NaOH / methanol / 4 h / 20 °C 10: 85.5 percent / H2 / Pd/CaCO3/Pb View Scheme

Yield

Multi-step reaction with 10 steps
1: 78 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C
2: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
3: TsOH / methanol / 2 h / 20 °C
4: 85 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C
5: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
6: TsOH / methanol / 2 h / 20 °C
7: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C
8: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
9: 5percent aq. NaOH / methanol / 4 h / 20 °C
10: 85.5 percent / H2 / Pd/CaCO3/Pb
View Scheme

Multi-step reaction with 10 steps
1: 78 percent / CBr4, PPh3 / CH2Cl2 / 0.67 h / 0 °C
2: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
3: TsOH / methanol / 2 h / 20 °C
4: 64.2 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C
5: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
6: TsOH / methanol / 2 h / 20 °C
7: 67 percent / KOH, K2CO3 / H2O; acetone / 1.5 h / 20 °C
8: K2CO3, NaI, CuI / dimethylformamide / 6 h / 20 °C
9: 5percent aq. NaOH / methanol / 4 h / 20 °C
10: 85.5 percent / H2 / Pd/CaCO3/Pb
View Scheme

all cis-5,8,11,14,17-eicosapentaenoic acid: all cis-5,8,11,14,17-eicosapentaenoic acid

: 1283063-45-5
17,18-Epoxyeicosatetraenoic acid

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 6217-54-5
docosahexaenoic acid

: magnesium bis(lysinate) trihydrate

: magnesium Bis-Lysinate Mono-EPA Mono-DHA dihydrate

Conditions

Conditions	Yield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;	100%

...Expand

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: magnesium bis-lysinate monohydrate

: magnesium bis-lysinate bis-EPA dihydrate

Conditions

Conditions	Yield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;	100%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: magnesium bis-lysinate monohydrate

: magnesium bis-lysinate mono-EPA

Conditions

Conditions	Yield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;	100%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 3303-31-9
L-leucyl-L-leucine

: 657-24-9
dimethylbiguanide

: C12H24N2O3*C4H11N5*C20H30O2

Conditions

Conditions	Yield
In methanol at 20℃; for 5h;	100%

...Expand

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 85-87-0
pyridoxamine

: (3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methanaminium (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	100%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1
Duloxetine

: (S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl) propan-1-aminium (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

Conditions

Conditions	Yield
In tetrahydrofuran for 2h;	100%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 56-84-8
L-Aspartic acid

: 657-24-9
dimethylbiguanide

: bis[{[(dimethylamino)(imino)methyl]amino}(imino)methanaminium]-(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate-(3S)-3-ammonio-3-carboxypropanoate

Conditions

Conditions	Yield
In methanol at 60℃; for 1.5h;	99%

...Expand

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 6076-30-8
1,2-di-O-palmitoyl-sn-glycerol

: 1-((5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl)-2,3-dihexadecanoyl-sn-glycerol

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification;	99%

: 67-56-1
methanol

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 2734-47-6
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With oxalyl dichloride In benzene at 20℃; for 2h; Stage #2: methanol at 0 - 20℃; for 2h;	98%
With acetyl chloride at 20℃; for 1.5h; Inert atmosphere;
With boron trifluoride diethyl etherate In benzene at 100℃; for 1h;

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 234087-56-0
6-[(3Z,6Z,9Z,12Z)-1-iodopentadeca-3,6,9,12-tetraen-1-yl]-tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; iodine In dichloromethane at 0℃; for 15h; Inert atmosphere; Cooling with ice;	97%
With iodine; potassium hydrogencarbonate; potassium iodide In tetrahydrofuran; water for 48h; Ambient temperature;	95%
With 2,4,6-trimethyl-pyridine; iodine In acetonitrile at 20℃;	88%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: calcium bis(lysinate) monohydrate

: calcium bis-lysinate mono-EPA

Conditions

Conditions	Yield
In methanol for 0.25h;	97%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: C10H19IO2

: C30H48O4

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With triethylamine; sodium iodide In ethyl acetate at 20℃; for 0.0333333h; Inert atmosphere; Stage #2: C10H19IO2 In ethyl acetate at 50℃;	97%
With triethylamine; sodium iodide In ethyl acetate for 16h; Inert atmosphere; Reflux;	97%

: 5071-96-5
3-METHOXYBENZYLAMINE

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: N-(3-methoxybenzyl)icosa-5Z,8Z,11Z,14Z,17Z-pentaenamide

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Inert atmosphere; Stage #2: 3-METHOXYBENZYLAMINE In dichloromethane Inert atmosphere;	97%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 54-71-7
pilocarpine hydrochloride

: 5-(((3R,4S)-4-ethyl-5-oxotetrahydrofuran-3-yl)methyl)-1-methyl-1H-imidazol-1-ium (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

Conditions

Conditions	Yield
Stage #1: pilocarpine hydrochloride With sodium hydrogencarbonate In methanol for 0.0833333h; Stage #2: all cis-5,8,11,14,17-eicosapentaenoic acid In methanol at 20℃; for 16h;	96.8%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: (5Z,8Z,11Z,14Z,17Z)-N-hydroxyicosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: With hydroxylamine In dichloromethane for 12h;	96%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane for 12h;	96%

: 123-75-1
pyrrolidine

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: (5Z,8Z,11Z,14Z,17Z)-1-(pyrrolidin-1-yl)icosa-5,8,11,14,17-pentaen-1-one

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: pyrrolidine In dichloromethane for 12h;	96%

: 110-89-4
piperidine

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: (5Z,8Z,11Z,14Z,17Z)-1-(piperidin-1-yl)icosa-5,8,11,14,17-pentaen-1-one

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: piperidine In dichloromethane for 12h;	96%

: 110-91-8
morpholine

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: (5Z,8Z,11Z,14Z,17Z)-1-morpholinoicosa-5,8,11,14,17-pentaen-1-one

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: morpholine In dichloromethane for 12h;	96%

: 109-01-3
1-methyl-piperazine

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: (5Z,8Z,11Z,14Z,17Z)-1-(4-methylpiperazin-1-yl)icosa-5,8,11,14,17-pentaen-1-one

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 1-methyl-piperazine In dichloromethane for 12h;	96%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 100-46-9
benzylamine

: (5Z,8Z,11Z,14Z,17Z)-N-benzylicosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: benzylamine In dichloromethane for 12h;	96%
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.25h; Inert atmosphere; Stage #2: benzylamine In dichloromethane Inert atmosphere;	90%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 618-36-0
rac-methylbenzylamine

: (5Z,8Z,11Z,14Z,17Z)-N-(1-phenylethyl)icosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: rac-methylbenzylamine In dichloromethane for 12h;	96%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 2627-86-3
(S)-1-phenyl-ethylamine

: (5Z,8Z,11Z,14Z,17Z)-N-((S)-1-phenylethyl)icosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: (S)-1-phenyl-ethylamine In dichloromethane for 12h;	96%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 141-43-5
ethanolamine

: (5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)eicosa-5,8,11,14,17-pentaenamide

Conditions

Conditions	Yield
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: ethanolamine In dichloromethane for 12h;	95%
Stage #1: all cis-5,8,11,14,17-eicosapentaenoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ethanolamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;	85%
With Novozym 435, consisting of immobilized Candida antarctica lipase B In hexane at 40℃; for 15h; Enzymatic reaction;	83%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 2389-48-2
N-ε-tert-butoxycarbonyl-L-lysine methyl ester hydrochloride

: 1269181-97-6
(S)-methyl 6-(tert-butoxycarbonyl)-2-((5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenamido)hexanoate

Conditions

Conditions	Yield
With 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h;	95%
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; for 2h;

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 3017-32-1
(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate

: 1269181-97-6
(S)-methyl 6-(tert-butoxycarbonyl)-2-((5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenamido)hexanoate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; for 2h;	95%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 504-40-5
1,3-distearoylglycerol

: 1,3-stearoyl-2-eicosapentaenoyl-glycerol

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	94%
With dmap; dicyclohexyl-carbodiimide

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 1429-59-0, 10567-21-2
1,2-distearoyl-sn-glycerol

: 3-((5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl)-1,2-dioctadecanoyl-sn-glycerol

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification;	94%

5,8,11,14,17-Eicosapentaenoicacid, (5Z,8Z,11Z,14Z,17Z)- Specification

The 5,8,11,14,17-Eicosapentaenoicacid,(5Z,8Z,11Z,14Z,17Z)- with CAS registry number of 10417-94-4 is also called Eicosapentanoic acid. The IUPAC name is (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid. In addition, the molecular formula is C₂₀H₃₀O₂ and the molecular weight is 302.45. It is a kind of colorless oil and belongs to the classes of Mixed Fatty Acids; Biochemistry; Higher Fatty Acids & Higher Alcohols; Unsaturated Higher Fatty Acids; Fatty Acid Derivatives & Lipids; Glycerols.

Physical properties about this chemical are: (1)ACD/LogP: 6.23; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.41; (4)ACD/LogD (pH 7.4): 3.62; (5)ACD/BCF (pH 5.5): 4869.14; (6)ACD/BCF (pH 7.4): 77.71; (7)ACD/KOC (pH 5.5): 8879; (8)ACD/KOC (pH 7.4): 141.71; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 13; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.512; (14)Molar Refractivity: 96.55 cm³; (15)Molar Volume: 321.3 cm³; (16)Polarizability: 38.27 ×10^-24cm³; (17)Surface Tension: 35.7 dyne/cm; (18)Density: 0.941 g/cm³; (19)Flash Point: 336 °C; (20)Enthalpy of Vaporization: 76.33 kJ/mol; (21)Boiling Point: 439.3 °C at 760 mmHg; (22)Vapour Pressure: 6.04E-09 mmHg at 25°C.

Uses of 5,8,11,14,17-Eicosapentaenoicacid, (5Z,8Z,11Z,14Z,17Z)-: it can react with diazomethane to get methyl eicosapentaenoate. This reaction will need solvent diethyl ether. The yield is about 93% at reaction temperature of 0 °C.

When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
(2)InChI: InChI=1/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
(3)InChIKey: JAZBEHYOTPTENJ-JLNKQSITBZ

Product Name

Icosapent

Synthetic route

5,8,11,14,17-Eicosapentaenoicacid, (5Z,8Z,11Z,14Z,17Z)- Specification

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