Product Name

  • Name

    Arachidonic acid

  • EINECS 208-033-4
  • CAS No. 506-32-1
  • Article Data36
  • CAS DataBase
  • Density 0.929 g/cm3
  • Solubility ethanol: ≥10 mg/mL
  • Melting Point -49 °C(lit.)
  • Formula C20H32O2
  • Boiling Point 407.45 °C at 760 mmHg
  • Molecular Weight 304.473
  • Flash Point 336.308 °C
  • Transport Information
  • Appearance colorless to light yellow oil
  • Safety 24/25
  • Risk Codes 19
  • Molecular Structure Molecular Structure of 506-32-1 (Arachidonic acid)
  • Hazard Symbols
  • Synonyms 5,8,11,14-Eicosatetraenoicacid, (all-Z)- (8CI);(all-Z)-5,8,11,14-Eicosatetraenoic acid;5,8,11,14-all-cis-Eicosatetraenoic acid;5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid;5Z,8Z,11Z,14Z-Eicosatetraenoicacid;A 0871;Arachidonic acid;Immunocytophyte;all-cis-5,8,11,14-Eicosatetraenoic acid;cis-D5,8,11,14-Eicosatetraenoic acid;
  • PSA 37.30000
  • LogP 6.21670

Synthetic route

ethyl arachidonate
95285-77-1, 1808-26-0

ethyl arachidonate

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 30℃; under 7500600 Torr; for 96h;78%
With potassium hydroxide
eicosa-5,8,11,14-tetraynoic acid
1191-85-1

eicosa-5,8,11,14-tetraynoic acid

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate; hydrogen; ethylenediamine; nickel diacetate In ethanol at 20℃;34%
With hydrogen; Lindlar's catalyst In methanol
With quinoline; water; hydrogen; Lindlar's catalyst 1.) AcOEt; Yield given. Multistep reaction;
arachidonic acid methyl ester
38575-18-7

arachidonic acid methyl ester

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With potassium hydroxide; ethanol
1-chloro-nonadeca-4c,7c,10c,13c-tetraene
612852-05-8

1-chloro-nonadeca-4c,7c,10c,13c-tetraene

carbon dioxide
124-38-9

carbon dioxide

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
(i) EtMgBr, Et2O, (ii) /BRN= 1900390/, Et2O; Multistep reaction;
carbon dioxide
124-38-9

carbon dioxide

C19H31ClMg

C19H31ClMg

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
In tetrahydrofuran
2-trans-Alken-5,8,11,14-eicosatetrainsaeure
40924-42-3

2-trans-Alken-5,8,11,14-eicosatetrainsaeure

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With pyridine; hydrogen; Lindlar's catalyst In ethyl acetate
(3Z,6Z)-1-oxo-dodecadienal
13553-09-8

(3Z,6Z)-1-oxo-dodecadienal

(4-carboxybutyl)triphenylphosphonium bromide
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With sodium hexamethyldisilazane 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h; Multistep reaction;
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid methyl ester
86179-96-6

(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid methyl ester

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With lithium aluminium tetrahydride 1.) tosylation;; Multistep reaction;
arachidonic acid TMS ester
113516-18-0

arachidonic acid TMS ester

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With sodium thiosulfate In water Yield given;
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid isobutyl ester
119520-63-7

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid isobutyl ester

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 12h; Ambient temperature; Yield given;
cetyl arachidonate

cetyl arachidonate

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With potassium hydroxide for 4h; Heating;40 mg
arachidonic acid octabromide

arachidonic acid octabromide

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With ethanol beim Erhitzen mit verkupfertem Zink-Staub;
eicosa-5,8,11,14-tetraynoic acid

eicosa-5,8,11,14-tetraynoic acid

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
With quinoline; Petroleum ether Hydrogenation.an Lindlar-Katalysator;
With methanol Hydrogenation.an Lindlar-Katalysator;
1-Heptyne
628-71-7

1-Heptyne

HgO

HgO

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: K2CO3, NaI, CuI / dimethylformamide / 4 h / 20 °C
2: K2CO3 / methanol / 4 h / 20 °C
3: 81.9 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
4: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
5: p-toluenesulfonic acid / methanol / 1 h / 20 °C
6: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
7: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
8: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
9: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
...Expand
5-hexynonitrile
14918-21-9

5-hexynonitrile

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 75.5 percent / gaseous HCl / methanol; H2O / 6 h / 60 °C
2: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
3: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
4: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
methyl hex-5-ynoate
77758-51-1

methyl hex-5-ynoate

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
2: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
3: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
undeca-2,5-diyn-1-ol
35378-79-1

undeca-2,5-diyn-1-ol

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 81.9 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
2: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
3: p-toluenesulfonic acid / methanol / 1 h / 20 °C
4: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
5: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
6: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
7: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
1-bromo-2,5-undecadiyne
34498-24-3

1-bromo-2,5-undecadiyne

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
2: p-toluenesulfonic acid / methanol / 1 h / 20 °C
3: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
4: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
5: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
6: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
1-bromo-2,5,8-tetradecatriyne
34498-26-5

1-bromo-2,5,8-tetradecatriyne

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
2: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
3: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
1-hydroxy-2,5,8-tetradecatriyne
35378-84-8

1-hydroxy-2,5,8-tetradecatriyne

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
2: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
3: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
4: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
Eicosa-5,8,11,14-tetrain-1-saeuremethylester
102471-97-6

Eicosa-5,8,11,14-tetrain-1-saeuremethylester

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
2: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
2-Tetradeca-2,5,8-triynyloxy-tetrahydro-furan

2-Tetradeca-2,5,8-triynyloxy-tetrahydro-furan

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: p-toluenesulfonic acid / methanol / 1 h / 20 °C
2: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
3: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
4: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
5: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
Benzoic acid undeca-2,5-diynyl ester

Benzoic acid undeca-2,5-diynyl ester

A

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

B

KMnO4

KMnO4

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: K2CO3 / methanol / 4 h / 20 °C
2: 81.9 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
3: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
4: p-toluenesulfonic acid / methanol / 1 h / 20 °C
5: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C
6: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C
7: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C
8: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt
View Scheme
(Z)-3-nonenal
31823-43-5

(Z)-3-nonenal

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaN(SiMe3)2 / 1.) THF, toluene, RT, 1 h, 2.) from -100 to 0 deg C, 4 h
2: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating
3: 1.) NaN(SiMe3)2 / 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h
View Scheme
(Z)-3-nonenal diisopropyl acetal
120018-49-7

(Z)-3-nonenal diisopropyl acetal

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating
2: 1.) NaN(SiMe3)2 / 1.) THF, toluene, RT, 1 h, 2.) from -100 to 0 deg C, 4 h
3: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating
4: 1.) NaN(SiMe3)2 / 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h
View Scheme
(Z,Z)-3,6-dodecadienal diisopropyl acetal
117203-38-0

(Z,Z)-3,6-dodecadienal diisopropyl acetal

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating
2: 1.) NaN(SiMe3)2 / 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h
View Scheme
hexanal
66-25-1

hexanal

magnesium aluminium-isopropylate

magnesium aluminium-isopropylate

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) NaN(SiMe3)2 / 1.) THF, toluene, RT, 1 h, 2.) from -100 to 0 deg C, 4 h
2: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating
3: 1.) NaN(SiMe3)2 / 1.) THF, toluene, RT, 1 h, 2.) from -100 to 0 deg C, 4 h
4: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating
5: 1.) NaN(SiMe3)2 / 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h
View Scheme
N-(p-nitrophenyl)-arachidonamide
119520-58-0

N-(p-nitrophenyl)-arachidonamide

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) phosgene, 2.) pyridine / 1.) CH2Cl2, 0 deg C, 2.) CH2Cl2, rt, 30 min, 3.) CH2Cl2, 3 h
2: 3 N aq. NaOH / ethanol / 12 h / Ambient temperature
View Scheme
6-chloro-1-hexanol
2009-83-8

6-chloro-1-hexanol

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium iodide / acetone / 8 h / Heating
2: potassium carbonate / acetonitrile / 10 h / Heating
3: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min
4: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min
5: 2.) lithium aluminum hydride / 1.) tosylation;
View Scheme
diazomethane
186581-53-3, 908094-01-9

diazomethane

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

methyl arachidonate
2566-89-4

methyl arachidonate

Conditions
ConditionsYield
In methanol at 0℃; for 0.333333h;100%
In diethyl ether
In diethyl ether at 0℃; Yield given;
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

arachidonyl alcohol
13487-46-2

arachidonyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether 1.) 30 min, 10 deg C, 2.) 30 min, reflux;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;99%
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: With water; sodium hydroxide In tetrahydrofuran for 1h;		99%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

cis-14,15-epoxyeicosatrienoic acid
197508-62-6

cis-14,15-epoxyeicosatrienoic acid

Conditions
ConditionsYield
With human recombinant cytochrome P450 2E1 Enzymatic reaction; stereoselective reaction;100%
With dihydrogen peroxide; sodium sulfate In diethyl ether
Multi-step reaction with 2 steps
1.1: CH2Cl2 / 0.33 h
2.1: H2O2; sodium imidazolate / CH2Cl2; diethyl ether / 0.05 h / 20 °C
2.2: KHSO4 / CH2Cl2; diethyl ether / 0.05 h / 20 °C
View Scheme
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

3-O-stearoyl-1-O-(tert-butyl-dimethyl-silanyl)-sn-glycerol
1360614-23-8

3-O-stearoyl-1-O-(tert-butyl-dimethyl-silanyl)-sn-glycerol

2-O-arachidonoyl-3-O-(tert-butyldimethylsilyl)-1-O-stearoyl-sn-glycerol
1363901-86-3

2-O-arachidonoyl-3-O-(tert-butyldimethylsilyl)-1-O-stearoyl-sn-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Darkness;99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide Inert atmosphere; Darkness;99%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

3-(5-methyl-4-(trifluoromethyl)thiazol-2-yl)bicyclo[1.1.1]pentan-1-amine hydrochloride

3-(5-methyl-4-(trifluoromethyl)thiazol-2-yl)bicyclo[1.1.1]pentan-1-amine hydrochloride

(5Z,8Z,11Z,14Z)-N-(3-(5-methyl-4-(trifluoromethyl)thiazol-2-yl)bicyclo[1.1.1]pentan-1-yl)icosa-5,8,11,14-tetraenamide

(5Z,8Z,11Z,14Z)-N-(3-(5-methyl-4-(trifluoromethyl)thiazol-2-yl)bicyclo[1.1.1]pentan-1-yl)icosa-5,8,11,14-tetraenamide

Conditions
ConditionsYield
With pyridine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;99%
1,3-dibutanoyloxy-2-propanol
17364-00-0

1,3-dibutanoyloxy-2-propanol

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate
1274596-36-9

2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 0℃; for 4h;98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;88%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;72%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

6-((3Z,6Z,9Z)-1-iodopentadeca-3,6,9-trien-1-yl)tetrahydro-2Hpyran-2-one
742103-77-1

6-((3Z,6Z,9Z)-1-iodopentadeca-3,6,9-trien-1-yl)tetrahydro-2Hpyran-2-one

Conditions
ConditionsYield
With 2,6-dimethylpyridine; iodine In dichloromethane at 0℃; for 15h; Inert atmosphere; Cooling with ice;96%
With 2,4,6-trimethyl-pyridine; iodine In dichloromethane at 0℃; for 14h;83%
With potassium hydrogencarbonate In ethanol; hexane; water at 24℃; for 16h;62%
With potassium triiodide; potassium hydrogencarbonate In tetrahydrofuran; water at 0℃;
With iodine; sodium hydrogencarbonate In ethanol5 g
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

ethanolamine
141-43-5

ethanolamine

anandamide
94421-68-8

anandamide

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: ethanolamine In dichloromethane for 12h;		96%
Stage #1: all cis 5,8,11,14-eicosatetraenoic 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 Candida antarctica lipase B In hexane at 50℃; for 6h; Inert atmosphere; Enzymatic reaction;72.7%
(E)-N-methoxy-N-methyloctadec-9-enamide
288862-96-4

(E)-N-methoxy-N-methyloctadec-9-enamide

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

N-Methoxy-N-methyl-arachidonamide
229021-66-3

N-Methoxy-N-methyl-arachidonamide

Conditions
ConditionsYield
96%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine
134179-38-7

2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine

N-{{[(azidoethoxy)ethoxy]ethoxy}ethyl}arachidonoylamide
1391826-57-5

N-{{[(azidoethoxy)ethoxy]ethoxy}ethyl}arachidonoylamide

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h; Inert atmosphere;
Stage #3: 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;		96%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

1,3-dioxoisoindolin-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

1,3-dioxoisoindolin-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 14h;96%
With dmap; diisopropyl-carbodiimide In dichloromethane
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

glycine
56-40-6

glycine

N-arachidonoylglycine
179113-91-8

N-arachidonoylglycine

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: glycine In dichloromethane for 12h;		96%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

vanillylamine hydrochloride
7149-10-2

vanillylamine hydrochloride

arvanil
128007-31-8

arvanil

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In tetrahydrofuran for 1.5h;95%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0℃; for 0.25h;79%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

oxiranyl-methanol
556-52-5

oxiranyl-methanol

oxiran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
439146-24-4

oxiran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;95%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;42%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

15-azido-14,14-bis(azidomethyl)-3,6,9,12-tetraoxapentadecan-1-amine

15-azido-14,14-bis(azidomethyl)-3,6,9,12-tetraoxapentadecan-1-amine

N-(15-azido-14,14-bis(azidomethyl)-3,6,9,12-tetraoxapentadecan)arachidonoylamide

N-(15-azido-14,14-bis(azidomethyl)-3,6,9,12-tetraoxapentadecan)arachidonoylamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 35℃; for 16h; Inert atmosphere;95%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

1,3-Bis-triisopropylsilanyloxy-propan-2-ol
98264-26-7

1,3-Bis-triisopropylsilanyloxy-propan-2-ol

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid 2-triisopropylsilanyloxy-1-triisopropylsilanyloxymethyl-ethyl ester
223259-26-5

(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid 2-triisopropylsilanyloxy-1-triisopropylsilanyloxymethyl-ethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; Ambient temperature;94%
C37H60O4Si
1037195-40-6

C37H60O4Si

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

C57H90O5Si
1037195-83-7

C57H90O5Si

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane94%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

3-O-[2',3',4',6'-tetracetyl-β-galactose]-1-[6''-pyreneacetamidohexanoyl]glycerol

3-O-[2',3',4',6'-tetracetyl-β-galactose]-1-[6''-pyreneacetamidohexanoyl]glycerol

C61H77NO15

C61H77NO15

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;93%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

cholesterol
57-88-5

cholesterol

cholesteryl 5,8,11,14-eicosatetraenoate
604-34-2

cholesteryl 5,8,11,14-eicosatetraenoate

Conditions
ConditionsYield
With pseudomonas lipase In water at 40℃; for 24h; Esterification; Enzymatic reaction;92.1%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid
70981-96-3

(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid

Conditions
ConditionsYield
With ammonium sulfate soybean lipoxygenase;92%
With soybean lipoxygenase; oxygen at 23℃; Km and Vmax value at pH=9.2;
With ammonium hydroxide (enzymatic oxidation);
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

1-(1’-β-D-[2’,3’,4’,6’-tetracetyl]galactosyl)glycerol
28069-18-3

1-(1’-β-D-[2’,3’,4’,6’-tetracetyl]galactosyl)glycerol

C37H56O13
1613026-83-7

C37H56O13

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;92%
6-nitroveratryl alcohol
1016-58-6

6-nitroveratryl alcohol

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

4,5-dimethoxy-2-nitrobenzyl arachidonate
1446428-04-1

4,5-dimethoxy-2-nitrobenzyl arachidonate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere;91%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

benzylamine
100-46-9

benzylamine

N-benzylicosa-5Z,8Z,11Z,14Z-tetraenamide

N-benzylicosa-5Z,8Z,11Z,14Z-tetraenamide

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic 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;		91%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

isobutyl chloroformate
543-27-1

isobutyl chloroformate

arachidonoyl isobutyl carbonate

arachidonoyl isobutyl carbonate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0℃; for 0.333333h; Inert atmosphere;90%
With triethylamine In acetonitrile at 0 - 4℃; for 0.333333h;
With 4-methyl-morpholine In acetonitrile at 0℃; for 0.666667h;
With 4-methyl-morpholine; triethylamine In tetrahydrofuran at -15℃; for 0.25h;
With triethylamine In acetone at 20℃; for 0.5h; Inert atmosphere;
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

2-chloroethanamine hydrochloride
870-24-6

2-chloroethanamine hydrochloride

arachidonoyl-2-chloroethylamide

arachidonoyl-2-chloroethylamide

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 1h;
Stage #2: 2-chloroethanamine hydrochloride With pyridine In dichloromethane at 0 - 20℃; for 0.5h;		90%
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: 2-chloroethanamine hydrochloride With triethylamine In tetrahydrofuran at 0℃; for 3.5h;		80%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

combrestatin A4
117048-62-1, 117048-59-6

combrestatin A4

C38H50O6

C38H50O6

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;90%
3-METHOXYBENZYLAMINE
5071-96-5

3-METHOXYBENZYLAMINE

all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

O 1986

O 1986

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic 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;		90%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

(R)-4-(phenylmethyl)-2-oxazolidinone
40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7

(R)-4-(phenylmethyl)-2-oxazolidinone

(R)-N-arachidonyl-4-benzyl-2-oxazolidinone
372504-81-9

(R)-N-arachidonyl-4-benzyl-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -78 - 0℃; for 0.666667h;
Stage #2: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 3.5h;		88%
all cis 5,8,11,14-eicosatetraenoic acid
506-32-1

all cis 5,8,11,14-eicosatetraenoic acid

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

(5Z,8Z,11Z,14Z)-N-[2-(3,4-dimethoxyphenyl)ethyl]eicosa-5,8,11,14-tetraenamide
869881-08-3

(5Z,8Z,11Z,14Z)-N-[2-(3,4-dimethoxyphenyl)ethyl]eicosa-5,8,11,14-tetraenamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃; for 12h;88%
Stage #1: all cis 5,8,11,14-eicosatetraenoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 0.166667h;
Stage #2: 2-(3,4-dimethoxyphenyl)-ethylamine With triethylamine at 20℃;		76%

Arachidonic acid Specification

The IUPAC name of Arachidonic acid is (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid. With the CAS registry number 506-32-1, it is also named as 5,8,11,14-Eicosatetraenoic acid. The product's categories are Industrial / Fine Chemicals; Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives; Mixed Fatty Acids; Higher Fatty Acids & Higher Alcohols; Unsaturated Higher Fatty Acids; Biochemistry; Fatty Acid Derivatives & Lipids; Glycerols. Besides, it is colorless to light yellow oil, which should be stored in in a tightly closed container in a cool, dry, well-ventilated area away from incompatible substances below -20 °C. It may form explosive peroxides. When you are using this chemical, please avoid contact with skin and eyes.

The other characteristics of this product can be summarized as: (1)EINECS: 208-033-4; (2)ACD/LogP: 6.99; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): 6.175; (5)ACD/LogD (pH 7.4): 4.378; (6)ACD/BCF (pH 5.5): 18467.777; (7)ACD/BCF (pH 7.4): 294.752; (8)ACD/KOC (pH 5.5): 23056.098; (9)ACD/KOC (pH 7.4): 367.984; (10)#H bond acceptors: 2; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 14; (13)Index of Refraction: 1.501; (14)Molar Refractivity: 96.502 cm3; (15)Molar Volume: 327.755 cm3; (16)Surface Tension: 35.226 dyne/cm; (17)Density: 0.929 g/cm3; (18)Flash Point: 336.308 °C; (19)Melting point: -49.5 °C; (20)Solubility: Ethanol: ≥10 mg/mL; (21)Enthalpy of Vaporization: 72.345 kJ/mol; (22)Boiling Point: 407.45 °C at 760 mmHg; (23)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Arachidonic acid: you can get mycelium by the fermentation and cultivating of white Mortierella alpina. Then please filtrate and squeeze. And you will obtain the product by purification, after use CO2 to extract.

Uses of Arachidonic acid: this chemical is a precursor in the production of eicosanoids. It is also used to produce the prostaglandins, prostacyclin, thromboxanes, and leukotrienes. Moreover, it is used in the biosynthesis of anandamide. The product is necessary for the repair and growth of skeletal muscle tissue. In addition, it can help to maintain hippocampal cell membrane fluidity and protect the brain from oxidative stress by activating perioxisomal proliferator-activated receptor-y. Furthermore, it can be used to produce Eicosa-5c,8c,11c,14c-tetraen-1-ol.



This reaction needs LiAlH4 and Diethyl ether at temperature of 10 °C for 30 min. The yield is 100 %.

People can use the following data to convert to the molecule structure.
(1)SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
(2)InChI: InChI=1/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
(3)InChIKey: YZXBAPSDXZZRGB-DOFZRALJBE
(4)Std. InChI: InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
(5)Std. InChIKey: YZXBAPSDXZZRGB-DOFZRALJSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 39200ug/kg (39.2mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 274, Pg. 4, 1985.

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