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6217-54-5

Basic Information
CAS No.: 6217-54-5
Name: 4,7,10,13,16,19-Docosahexaenoicacid, (4Z,7Z,10Z,13Z,16Z,19Z)-
Article Data: 20
Cas Database
Molecular Structure:
Molecular Structure of 6217-54-5 (4,7,10,13,16,19-Docosahexaenoicacid, (4Z,7Z,10Z,13Z,16Z,19Z)-)
Formula: C22H32O2
Molecular Weight: 328.495
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;
EINECS: 612-950-9
Density: 0.943 g/cm3
Melting Point: -44 °C
Boiling Point: 446.7 °C at 760 mmHg
Flash Point: 343.4 °C
Solubility: N/A
Appearance: achromaticity clarity liquid
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 23-24/25
Transport Information: N/A
PSA: 37.30000
LogP: 6.54890
Synthetic route
81926-94-5

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

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

6217-54-5

docosahexaenoic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In ethanol; water at 60℃; for 1h; Inert atmosphere;94%
2566-90-7

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

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;
81926-94-5

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

534-03-2

serinol

A

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

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

3-Amino-1,2-propanediol

81926-94-5

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

A

6217-54-5

docosahexaenoic acid

B

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%
81926-94-5

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

141-43-5

ethanolamine

A

6217-54-5

docosahexaenoic acid

B

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%
35320-23-1

(R)-2-aminopropan-1-ol

81926-94-5

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

A

6217-54-5

docosahexaenoic acid

B

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%
81926-94-5

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

66211-46-9

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

A

6217-54-5

docosahexaenoic acid

B

C25H39NO3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 70%
61278-21-5

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

81926-94-5

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

A

6217-54-5

docosahexaenoic acid

B

C25H39NO3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 65%
81926-94-5

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

107-15-3

ethylenediamine

A

6217-54-5

docosahexaenoic acid

B

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%
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  • 4,7,10,13,16,19-Docosahexaenoicacid, (4Z,7Z,10Z,13Z,16Z,19Z)-

  • Casno:

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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