Product Name

  • Name

    cis-4,7,10,13,16,19-Docosahexaenoic acid

  • EINECS 612-950-9
  • CAS No. 6217-54-5
  • Article Data20
  • CAS DataBase
  • Density 0.943 g/cm3
  • Solubility
  • Melting Point -44 °C
  • Formula C22H32O2
  • Boiling Point 446.7 °C at 760 mmHg
  • Molecular Weight 328.495
  • Flash Point 343.4 °C
  • Transport Information
  • Appearance achromaticity clarity liquid
  • Safety 23-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 6217-54-5 (cis-4,7,10,13,16,19-Docosahexaenoic acid)
  • Hazard Symbols
  • Synonyms 4,7,10,13,16,19-Docosahexaenoicacid, (all-Z)- (8CI);Docosahexaenoic acid (6CI);(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoicacid;(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid;(all-Z)-4,7,10,13,16,19-Docosahexaenoic acid;4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-Docosahexaenoic acid;DHA;Doconexent;Marinol D 50TG;Martek DHA HM;Martek DHAPowder KS 35;Martek DHA Powder KSF 58;Ropufa 60;all-Z-Docosahexaenoic acid;all-cis-4,7,10,13,16,19-Docosahexaenoic acid;
  • PSA 37.30000
  • LogP 6.54890

Synthetic route

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; edetate disodium In ethanol; water at 60 - 65℃; for 2h;98%
With sodium hydroxide; edetate disodium In ethanol at 65℃;98%
Stage #1: all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate With water; sodium hydroxide In methanol at 20℃; for 1.5h;
Stage #2: With hydrogenchloride In methanol; water Cooling with ice;		91%
docosahexaenoic acid ethyl ester

docosahexaenoic acid ethyl ester

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In ethanol; water at 60℃; for 1h; Inert atmosphere;94%
all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester
2566-90-7

all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water92%
Stage #1: all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 0 - 20℃; for 12h;
Stage #2: With citric acid In water at 0℃; pH=~ 4;
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

serinol
534-03-2

serinol

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

(4Z,7Z,10Z,13Z,16Z,19Z)-N-(1,3-dihydroxypropan-2-yl)docosa-4,7,10,13,16,19-hexaenamide

(4Z,7Z,10Z,13Z,16Z,19Z)-N-(1,3-dihydroxypropan-2-yl)docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 4h; Green chemistry; Enzymatic reaction;A n/a
B 87%
...Expand
3-Amino-1,2-propanediol
616-30-8, 13552-31-3

3-Amino-1,2-propanediol

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2,3-dihydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide
1048012-06-1

(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2,3-dihydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 80%
...Expand
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

ethanolamine
141-43-5

ethanolamine

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

N-docosahexaenoylethanolamine
162758-94-3

N-docosahexaenoylethanolamine

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 75%
...Expand
(R)-2-aminopropan-1-ol
35320-23-1

(R)-2-aminopropan-1-ol

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

(4Z,7Z,10Z,13Z,16Z,19Z)-N-((R)-1-hydroxypropan-2-yl)docosa-4,7,10,13,16,19-hexaenamide
1282618-08-9

(4Z,7Z,10Z,13Z,16Z,19Z)-N-((R)-1-hydroxypropan-2-yl)docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 70%
...Expand
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

(R)-3-amino-1,2-propanediol
66211-46-9

(R)-3-amino-1,2-propanediol

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

C25H39NO3

C25H39NO3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 70%
...Expand
(S)-3-Amino-1,2-propanediol
61278-21-5

(S)-3-Amino-1,2-propanediol

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

C25H39NO3

C25H39NO3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 65%
...Expand
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

ethylenediamine
107-15-3

ethylenediamine

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

(4Z,7Z,10Z,13Z, 16Z,19Z)docosa-4,7,10,13,16,19-hexaenoic acid [2-((4Z,7Z,10Z,13Z, 16Z,19Z)docosa-4,7,10,13,16,19-hexaenoylamino)ethyl]amide
1333067-15-4

(4Z,7Z,10Z,13Z, 16Z,19Z)docosa-4,7,10,13,16,19-hexaenoic acid [2-((4Z,7Z,10Z,13Z, 16Z,19Z)docosa-4,7,10,13,16,19-hexaenoylamino)ethyl]amide

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 60%
...Expand
serin
302-84-1

serin

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

C25H37NO4

C25H37NO4

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 55%
...Expand
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

1,3-Diamino-2-hydroxypropane
616-29-5

1,3-Diamino-2-hydroxypropane

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

C25H40N2O2

C25H40N2O2

C

C47H70N2O3

C47H70N2O3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 48%
C 38%
...Expand
C25H40O2Si

C25H40O2Si

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
With sodium thiosulfate In water Yield given;
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: pyridine, Ph3PBr2 / acetonitrile / 0 °C
2: acetonitrile / 24 h / Heating
3: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C
4: 100 percent / H+ / tetrahydrofuran
5: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C
6: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h
7: 95 percent / acetonitrile / Heating
8: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
9: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
1-bromo-3-hexene
84254-20-6

1-bromo-3-hexene

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: acetonitrile / 24 h / Heating
2: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C
3: 100 percent / H+ / tetrahydrofuran
4: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C
5: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h
6: 95 percent / acetonitrile / Heating
7: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
8: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(3Z,6Z,9Z)-dodecatrien-1-ol
81345-02-0

(3Z,6Z,9Z)-dodecatrien-1-ol

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h
2: 95 percent / acetonitrile / Heating
3: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
4: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(3Z)-3-hexenyltriphenylphosphonium bromide
21676-05-1

(3Z)-3-hexenyltriphenylphosphonium bromide

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C
2: 100 percent / H+ / tetrahydrofuran
3: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C
4: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h
5: 95 percent / acetonitrile / Heating
6: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
7: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z)-6,6-diisopropoxyhex-3-en-1-al
162758-88-5

(Z)-6,6-diisopropoxyhex-3-en-1-al

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 51 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C
2: H+ / tetrahydrofuran
3: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
4: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z,Z,Z)-1-bromododeca-3,6,9-triene
169900-26-9

(Z,Z,Z)-1-bromododeca-3,6,9-triene

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / acetonitrile / Heating
2: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
3: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z,Z,Z)-dodeca-3,6,9-trien-1-al
169900-23-6

(Z,Z,Z)-dodeca-3,6,9-trien-1-al

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C
2: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h
3: 95 percent / acetonitrile / Heating
4: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
5: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z,Z)-10-oxodeca-4,7-dienoic acid methyl ester
169900-28-1

(Z,Z)-10-oxodeca-4,7-dienoic acid methyl ester

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
2: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z,Z,Z)-1,1-diisopropoxydodeca-3,6,9-triene
169900-22-5

(Z,Z,Z)-1,1-diisopropoxydodeca-3,6,9-triene

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / H+ / tetrahydrofuran
2: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C
3: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h
4: 95 percent / acetonitrile / Heating
5: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
6: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z,Z)-10,10-diisopropoxydeca-4,7-dienoic acid methyl ester
169900-25-8

(Z,Z)-10,10-diisopropoxydeca-4,7-dienoic acid methyl ester

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H+ / tetrahydrofuran
2: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
3: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
(Z,Z,Z)-dodeca-3,6,9-trienyltriphenylphosphonium bromide

(Z,Z,Z)-dodeca-3,6,9-trienyltriphenylphosphonium bromide

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C
2: 92 percent / LiOH / tetrahydrofuran; H2O
View Scheme
5-((3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl)dihydro-2(3H)-furanone
78144-19-1

5-((3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl)dihydro-2(3H)-furanone

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium iodide / acetonitrile / 1 h / 23 °C
2: sodium thiosulfate / H2O
View Scheme
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

eicosapentaenoic acid ethyl ester
86227-47-6

eicosapentaenoic acid ethyl ester

A

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

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

B

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Stage #1: all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate; eicosapentaenoic acid ethyl ester With water; sodium hydroxide In methanol at 20℃; for 1.5h;
Stage #2: With hydrogenchloride In water Cooling with ice;
...Expand
D-glucose
50-99-7

D-glucose

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
Stage #1: D-glucose; Labyrinthulae strain mh313 microorganism In water at 28℃; for 96h; pH=6.0; Enzymatic reaction;
Stage #2: With hydrogenchloride; methanol Product distribution / selectivity;
carbon dioxide
124-38-9

carbon dioxide

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
With Nannochloropsis Gaditana Microbiological reaction; Photolysis; Large scale;
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
81926-94-5

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

glycerol
56-81-5

glycerol

A

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

B

(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2,3-dihydroxy-propyl ester

(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2,3-dihydroxy-propyl ester

C

1,3-didocosahexaenoylglycerol

1,3-didocosahexaenoylglycerol

Conditions
ConditionsYield
With Novozyme 435 immobilized on polystyrene at 35℃; for 24h; Solvent; Green chemistry; Enzymatic reaction;
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester
2566-90-7

all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester

Conditions
ConditionsYield
In diethyl ether100%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl chloride
98776-99-9

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h;100%
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Cooling with ice;100%
With oxalyl dichloride In chloroform for 2h;
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(±)-19,20-epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid
895127-62-5

(±)-19,20-epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid

Conditions
ConditionsYield
With human recombinant cytochrome P450 1A1 Enzymatic reaction; stereoselective reaction;100%
With MS-PPOH
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

magnesium bis(lysinate) trihydrate

magnesium bis(lysinate) trihydrate

magnesium Bis-Lysinate Mono-EPA Mono-DHA dihydrate

magnesium Bis-Lysinate Mono-EPA Mono-DHA dihydrate

Conditions
ConditionsYield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;100%
...Expand
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

tert-butyl 4-(4Z,7Z,10Z,13Z,16Z, 19Z)-docosa-4,7,10,13,16,19-hexaenoylpiperazine-1-carboxylate
1204318-13-7

tert-butyl 4-(4Z,7Z,10Z,13Z,16Z, 19Z)-docosa-4,7,10,13,16,19-hexaenoylpiperazine-1-carboxylate

Conditions
ConditionsYield
With triethylamine; HATU In acetonitrile at 20℃; for 16h;99%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

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

1,2-di-O-palmitoyl-sn-glycerol

1-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl)-2,3-dihexadecanoyl-sn-glycerol

1-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl)-2,3-dihexadecanoyl-sn-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification;99%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(2R)-1,2-bis-O-stearylglycerol
1429-59-0

(2R)-1,2-bis-O-stearylglycerol

1-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl)-2,3-dioctadecanoyl-sn-glycerol

1-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl)-2,3-dioctadecanoyl-sn-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification;99%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

taxol
33069-62-4

taxol

[3H]-Docosahexaenoic acid-Paclitaxel

[3H]-Docosahexaenoic acid-Paclitaxel

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1 - 2h;98%
With dmap; dacarbazine In dichloromethane at 20℃;
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

calcium bis(lysinate) monohydrate

calcium bis(lysinate) monohydrate

calcium bis-lysinate bis-DHA

calcium bis-lysinate bis-DHA

Conditions
ConditionsYield
In methanol at 50℃; Inert atmosphere;98%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

5-((3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl)dihydro-2(3H)-furanone
78144-19-1

5-((3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl)dihydro-2(3H)-furanone

Conditions
ConditionsYield
With hydrogen iodide; iodine; potassium hydrogencarbonate In ethanol at 0 - 4℃; for 18h; Inert atmosphere; Darkness;97%
With 2,6-dimethylpyridine; iodine In dichloromethane at 0℃; for 15h; Inert atmosphere; Cooling with ice;96%
With iodine; potassium hydrogencarbonate; potassium iodide In tetrahydrofuran; water for 48h; Ambient temperature;95%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

methyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)acetate

methyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)acetate

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid; glycine ethyl ester hydrochloride With dmap; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;		97%
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In dichloromethane at 20℃; for 18h;55%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h;55%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h;55%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

L-valyl-L-lysine
22677-62-9

L-valyl-L-lysine

L-valyl-L-lysine DHA salt

L-valyl-L-lysine DHA salt

Conditions
ConditionsYield
With Tocopherol In ethanol; ethyl acetate at 60℃;97%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

ethanolamine
141-43-5

ethanolamine

N-docosahexaenoylethanolamine
162758-94-3

N-docosahexaenoylethanolamine

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: ethanolamine In dichloromethane for 12h;		96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;92%
With Novozym 435, consisting of immobilized Candida antarctica lipase B In acetonitrile at 40℃; for 15h; Enzymatic reaction;20%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

magnesium bis-lysinate monohydrate

magnesium bis-lysinate monohydrate

magnesium bis-lysinate bis-DHA dihydrate

magnesium bis-lysinate bis-DHA dihydrate

Conditions
ConditionsYield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;96%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-N-hydroxydocosa-4,7,10,13,16,19-hexaenamide
89017-02-7

(4Z,7Z,10Z,13Z,16Z,19Z)-N-hydroxydocosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: With hydroxylamine In dichloromethane for 12h;		96%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamide

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: With ammonia In dichloromethane for 12h;		96%
pyrrolidine
123-75-1

pyrrolidine

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-1-(pyrrolidin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one

(4Z,7Z,10Z,13Z,16Z,19Z)-1-(pyrrolidin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: pyrrolidine In dichloromethane for 12h;		96%
piperidine
110-89-4

piperidine

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-1-(piperidin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one

(4Z,7Z,10Z,13Z,16Z,19Z)-1-(piperidin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: piperidine In dichloromethane for 12h;		96%
morpholine
110-91-8

morpholine

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-1-morpholinodocosa-4,7,10,13,16,19-hexaen-1-one

(4Z,7Z,10Z,13Z,16Z,19Z)-1-morpholinodocosa-4,7,10,13,16,19-hexaen-1-one

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: morpholine In dichloromethane for 12h;		96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(4Z,7Z,10Z,13Z,16Z,19Z)-1-(4-methylpiperazin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one

(4Z,7Z,10Z,13Z,16Z,19Z)-1-(4-methylpiperazin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: 1-methyl-piperazine In dichloromethane for 12h;		96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

benzylamine
100-46-9

benzylamine

(4Z,7Z,10Z,13Z,16Z,19Z)-N-benzyldocosa-4,7,10,13,16,19-hexaenamide

(4Z,7Z,10Z,13Z,16Z,19Z)-N-benzyldocosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: benzylamine In dichloromethane for 12h;		96%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

(4Z,7Z,10Z,13Z,16Z,19Z)-N-(1-phenylethyl)docosa-4,7,10,13,16,19-hexaenamide

(4Z,7Z,10Z,13Z,16Z,19Z)-N-(1-phenylethyl)docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: rac-methylbenzylamine In dichloromethane for 12h;		96%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

(4Z,7Z,10Z,13Z,16Z,19Z)-N-((S)-1-phenylethyl)docosa-4,7,10,13,16,19-hexaenamide

(4Z,7Z,10Z,13Z,16Z,19Z)-N-((S)-1-phenylethyl)docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: (R)-1-phenyl-ethyl-amine In dichloromethane for 12h;		96%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

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

(S)-1-phenyl-ethylamine

(4Z,7Z,10Z,13Z,16Z,19Z)-N-((R)-1-phenylethyl)docosa-4,7,10,13,16,19-hexaenamide

(4Z,7Z,10Z,13Z,16Z,19Z)-N-((R)-1-phenylethyl)docosa-4,7,10,13,16,19-hexaenamide

Conditions
ConditionsYield
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: (S)-1-phenyl-ethylamine In dichloromethane for 12h;		96%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

1,3-dilauroylglycerol
539-93-5

1,3-dilauroylglycerol

1,3-dilauroyl-2-docosahexaenoylglycerol

1,3-dilauroyl-2-docosahexaenoylglycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h;95%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 80h;25%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

glycerol 1,3-dimyristate
7770-09-4

glycerol 1,3-dimyristate

(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2-tetradecanoyloxy-1-tetradecanoyloxymethyl-ethyl ester

(4Z,7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoic acid 2-tetradecanoyloxy-1-tetradecanoyloxymethyl-ethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h;95%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride
5680-80-8

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

N-docasahexanoyl-L-serine methyl ester

N-docasahexanoyl-L-serine methyl ester

Conditions
ConditionsYield
With triethylamine; carbonochloridic acid, butyl ester In tetrahydrofuran; methanol; acetonitrile at 20℃; for 2h;95%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

(R)-1-O-octadecyl-3-decanoyl-sn-glycerol
1278408-35-7

(R)-1-O-octadecyl-3-decanoyl-sn-glycerol

(R)-1-O-octadecyl-2-docosahexaenoyl-3-decanoyl-sn-glycerol
1278408-81-3

(R)-1-O-octadecyl-2-docosahexaenoyl-3-decanoyl-sn-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; Inert atmosphere;95%

cis-4,7,10,13,16,19-Docosahexaenoic acid Specification

The CAS registry number of Docosahexaenoic acid is 6217-54-5. The IUPAC name is (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid. In addition, the molecular formula is C22H32O2 and the molecular weight is 328.49. It is also called 4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-docosahexaenoic acid. What's more, it is an omega-3 fatty acid and belongs to the classes of Biochemistry; Higher Fatty Acids & Higher Alcohols; Unsaturated Higher Fatty Acids; Fatty Acid Derivatives & Lipids; Glycerols. It should be stored in sealed container which filled with nitrogen, and put them in a cool and dry place

Physical properties about this chemical are: (1)ACD/LogP: 6.78; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.81; (4)ACD/LogD (pH 7.4): 4.01; (5)ACD/BCF (pH 5.5): 8976.76; (6)ACD/BCF (pH 7.4): 141.05; (7)ACD/KOC (pH 5.5): 12478.48; (8)ACD/KOC (pH 7.4): 196.07; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.52; (14)Molar Refractivity: 105.88 cm3; (15)Molar Volume: 347.9 cm3; (16)Polarizability: 41.97 ×10-24cm3; (17)Surface Tension: 36 dyne/cm; (18)Density: 0.943 g/cm3; (19)Flash Point: 343.4 °C; (20)Enthalpy of Vaporization: 77.28 kJ/mol; (21)Boiling Point: 446.7 °C at 760 mmHg; (22)Vapour Pressure: 3.16E-09 mmHg at 25°C.

Preparation of Docosahexaenoic acid: it is commercially manufactured from microalgae; crypthecodinium cohnii and another of the genus schizochytrium. It is manufactured internally from α-linolenic acid, a shorter omega-3 fatty acid manufactured by plants (and also occurring in animal products as obtained from plants). Moreover, it can be prepared by cis-4,7,10,13,16,19-docosahexaneoic acid ethyl ester. This reaction will need reagents EDTA and Na2EDTA*2H2O, and solvents ethanol and H2O. The reaction time is 2 hours at reaction temperature of 60-65 °C. The yield is about 98%.

Docosahexaenoic acid can be prepared by cis-4,7,10,13,16,19-docosahexaneoic acid ethyl ester

Uses of Docosahexaenoic acid: it can be used as a nutritional fortifiersit. And it can be used to treat hypertension, diabetes, menopausal syndrome, Parkinson's disease, asthma and eczema. Moreover, it is actively promoted by manufacturers as a food additive. In addition, it can react with diazomethane to get docosa-4c,7c,10c,13c,16c,19c-hexaenoic acid methyl ester. This reaction will need solvent diethyl ether. The yield is about 100%.

Docosahexaenoic acid can react with diazomethane to get docosa-4c,7c,10c,13c,16c,19c-hexaenoic acid methyl ester

When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes. And do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CC/C=C/C/C=C/C\C=C/C/C=C/C/C=C/C/C=C/CC
(2)InChI: InChI=1/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3+,7-6+,10-9+,13-12-,16-15+,19-18+
(3)InChIKey: MBMBGCFOFBJSGT-CHRIZAQABI

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