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10417-94-4

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10417-94-4 Usage

Description

EPA is an ω-3 fatty acid abundantly available in marine organisms. It is oxygenated by COX-1 and COX-2 at rates of about 5% and 30%, respectively, compared to arachidonic acid. EPA has been shown to offer protection against coronary heart disease, thrombosis, ischemic brain injury, scaly dermatitis, and some inflammatory diseases.

Chemical Properties

Colorless Oil

Uses

Different sources of media describe the Uses of 10417-94-4 differently. You can refer to the following data:
1. Important polyunsaturated fatty acid of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. It differs from arachidonic acid (the eicosatetraenoic acid that is a precursor for the prostaglandin and thromboxane-2 families) by the extra double bond between the third and fourth carbons from the “methyl end” of the molecule. Antilipemic.
2. cis-5,8,11,14,17-Eicosapentaenoic acid has been used an analytical standard for the synthesis followed by investigation of pharmacological properties of aconitine-derived lipo-alkaloids.
3. cis-5,8,11,14,17-Eicosapentaenoic acid has been used:to test pharmacologic effect on steatosis in hepatocytesas an analytical standard in Raman spectra measurements to characterize human breast cancer samplesin lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies

Definition

ChEBI: An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.

Brand name

Decabid (Lilly).

General Description

Eicosapentaenoic acid (cis-5,8,11,14,17), also known as EPA, is a long-chain omega-3 fatty acid. Studies suggests that EPA as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders. This certified solution standard is suitable for use as starting material in the preparation of linearity standards, calibrators, or controls in mass spectrometry-based EPA testing applications such as assessment of cardiovascular?disease risk and fatty acid deficiency, and detection and quantification of EPA in nutraceuticals and dietary supplements.

Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

References

1) Lee et al. (1985), Effect of dietary enrichment with eicosapentaenoic and docosahexaenoic acids on in vitro neutrophil and monocyte leukotriene generation and neutrophil function; N. Engl. J. Med., 312 1217 2) Nicholson et al. (2013), The role of marine n-3 fatty acids in improving cardiovascular health: a review; Food Funct., 4 357

Check Digit Verification of cas no

The CAS Registry Mumber 10417-94-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,4,1 and 7 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 10417-94:
(7*1)+(6*0)+(5*4)+(4*1)+(3*7)+(2*9)+(1*4)=74
74 % 10 = 4
So 10417-94-4 is a valid CAS Registry Number.
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-

10417-94-4 Well-known Company Product Price

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  • Sigma

  • (E2011)  cis-5,8,11,14,17-Eicosapentaenoicacid  ≥99%

  • 10417-94-4

  • E2011-10MG

  • 2,290.86CNY

  • Detail
  • Sigma

  • (E2011)  cis-5,8,11,14,17-Eicosapentaenoicacid  ≥99%

  • 10417-94-4

  • E2011-25MG

  • 4,754.88CNY

  • Detail
  • Sigma

  • (E2011)  cis-5,8,11,14,17-Eicosapentaenoicacid  ≥99%

  • 10417-94-4

  • E2011-50MG

  • 6,587.10CNY

  • Detail
  • Sigma

  • (E2011)  cis-5,8,11,14,17-Eicosapentaenoicacid  ≥99%

  • 10417-94-4

  • E2011-100MG

  • 13,139.10CNY

  • Detail
  • Sigma-Aldrich

  • (44864)  cis-5,8,11,14,17-Eicosapentaenoicacid  analytical standard

  • 10417-94-4

  • 44864-100MG

  • 1,296.36CNY

  • Detail
  • Sigma-Aldrich

  • (44864)  cis-5,8,11,14,17-Eicosapentaenoicacid  analytical standard

  • 10417-94-4

  • 44864-500MG

  • 6,282.90CNY

  • Detail

10417-94-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name all-cis-5,8,11,14,17-icosapentaenoic acid

1.2 Other means of identification

Product number -
Other names 5,8,11,14

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10417-94-4 SDS

10417-94-4Synthetic route

eicosapentaenoic acid ethyl ester
86227-47-6

eicosapentaenoic acid ethyl ester

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

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

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

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

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

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

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water93%
With lithium hydroxide In tetrahydrofuran for 15h; Ambient temperature;92%
5,8,11,14,17-eicosapentaynoic acid
5871-07-8

5,8,11,14,17-eicosapentaynoic acid

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

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

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst85.5%
eicosapentaenoic acid ethyl ester
86227-47-6

eicosapentaenoic acid ethyl ester

ethanolamine
141-43-5

ethanolamine

A

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

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

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 80%
eicosapentaenoic acid ethyl ester
86227-47-6

eicosapentaenoic acid ethyl ester

serinol
534-03-2

serinol

A

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

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

B

C23H37NO3

C23H37NO3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 80%
2-Amino-1-propanol
6168-72-5

2-Amino-1-propanol

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

C23H37NO2

C23H37NO2

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction;A n/a
B 78%
3-Dimethylamino-1-propanol
3179-63-3

3-Dimethylamino-1-propanol

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

C25H41NO2

C25H41NO2

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 18h; Green chemistry; Enzymatic reaction;A n/a
B 28%
eicosapentaenoic acid ethyl ester
86227-47-6

eicosapentaenoic acid ethyl ester

serinol
534-03-2

serinol

A

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

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

B

C23H37NO3
1048012-11-8

C23H37NO3

Conditions
ConditionsYield
With Novozym 435 lipase on resin In acetone at 35℃; for 18h; Green chemistry; Enzymatic reaction;A n/a
B 25%
(2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-O-(6Z,9Z,12Z,15Z-octadecatetranoyl)-3-β-D-galactopyranosyl-sn-glycerol
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

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

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

B

(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
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
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
With hydrogenchloride In diethylene glycol dimethyl ether at 120℃; for 1h; Yield given;
2-(1'-oxo-dodeca-5',8',11',14',17'(all Z)-pentaenyl)-1,3,5-trihydroxybenzene
79553-90-5

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

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

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

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

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine; silica gel 1.) aqueous EtOH, reflux, 2.) heat.; Yield given. Multistep reaction. Yields of byproduct given;
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester

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

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

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

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 2h; Ambient temperature;
(3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenal
137682-11-2

(3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenal

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

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

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

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

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

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

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

(3Z,6Z,9Z,12Z, 15Z)-octadeca-3,6,9,12,15-pentaen-1-ol

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

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

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

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

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

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

Conditions
ConditionsYield
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
1-bromo-pent-2-yne
16400-32-1

1-bromo-pent-2-yne

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

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

Conditions
ConditionsYield
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
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

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

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

Conditions
ConditionsYield
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

17,18-Epoxyeicosatetraenoic acid
1283063-45-5

17,18-Epoxyeicosatetraenoic acid

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

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

magnesium bis-lysinate monohydrate

magnesium bis-lysinate monohydrate

magnesium bis-lysinate bis-EPA dihydrate

magnesium bis-lysinate bis-EPA dihydrate

Conditions
ConditionsYield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;100%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

magnesium bis-lysinate monohydrate

magnesium bis-lysinate monohydrate

magnesium bis-lysinate mono-EPA

magnesium bis-lysinate mono-EPA

Conditions
ConditionsYield
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere;100%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

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

L-leucyl-L-leucine

dimethylbiguanide
657-24-9

dimethylbiguanide

C12H24N2O3*C4H11N5*C20H30O2

C12H24N2O3*C4H11N5*C20H30O2

Conditions
ConditionsYield
In methanol at 20℃; for 5h;100%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

pyridoxamine
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

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

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;100%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

(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

(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
ConditionsYield
In tetrahydrofuran for 2h;100%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

L-Aspartic acid
56-84-8

L-Aspartic acid

dimethylbiguanide
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

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
ConditionsYield
In methanol at 60℃; for 1.5h;99%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

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

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

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification;99%
methanol
67-56-1

methanol

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

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

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

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

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

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

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

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

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

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

calcium bis(lysinate) monohydrate

calcium bis(lysinate) monohydrate

calcium bis-lysinate mono-EPA

calcium bis-lysinate mono-EPA

Conditions
ConditionsYield
In methanol for 0.25h;97%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

C10H19IO2

C10H19IO2

C30H48O4

C30H48O4

Conditions
ConditionsYield
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%
3-METHOXYBENZYLAMINE
5071-96-5

3-METHOXYBENZYLAMINE

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

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

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

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

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

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

pilocarpine hydrochloride
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

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

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

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

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

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

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

Conditions
ConditionsYield
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%
pyrrolidine
123-75-1

pyrrolidine

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

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

Conditions
ConditionsYield
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%
piperidine
110-89-4

piperidine

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

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

Conditions
ConditionsYield
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%
morpholine
110-91-8

morpholine

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

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

Conditions
ConditionsYield
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%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

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

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

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

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

benzylamine
100-46-9

benzylamine

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

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

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

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

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

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

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

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

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

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

(S)-1-phenyl-ethylamine

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

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

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

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

ethanolamine
141-43-5

ethanolamine

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

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

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

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

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

N-ε-tert-butoxycarbonyl-L-lysine methyl ester hydrochloride

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

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

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

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

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

(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate

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

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

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; for 2h;95%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

1,3-distearoylglycerol
504-40-5

1,3-distearoylglycerol

1,3-stearoyl-2-eicosapentaenoyl-glycerol

1,3-stearoyl-2-eicosapentaenoyl-glycerol

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;94%
With dmap; dicyclohexyl-carbodiimide
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

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

1,2-distearoyl-sn-glycerol
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

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

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

10417-94-4Related news

DHA and EPA (cas 10417-94-4) nanoemulsions prEPA (cas 10417-94-4)red by the low-energy emulsification method: Process factors influencing droplet size and physicochemical stability08/01/2019

To extend the application of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) in liquid food, and to improve the physicochemical stability, we prepared stable DHA and EPA nanoemulsions, which can be used for large scale production. The Emulsion Phase Inversion (EPI) method was used to ...detailed

10417-94-4Relevant articles and documents

Apoptosis-inducing galactolipids from a cultured marine diatom, Phaeodactylum tricornutum

Andrianasolo, Eric H.,Haramaty, Liti,Vardi, Assaf,White, Eileen,Lutz, Richard,Falkowski, Paul

, p. 1197 - 1201 (2008)

Two monogalactosyl diacylglycerols, 1 and 2, were isolated from the marine diatom Phaeodactylum tricornutum, using the patented ApopScreen cell-based screen for apoptosis-inducing, potential anticancer compounds. The molecular structures of the galactolipids were determined using a combination of NMR, mass spectrometry, and chemical degradation. The bioactivities were confirmed using a specific apoptosis induction assay based on genetically engineered mammalian cell lines with differential, defined capacities for apoptosis. The galactolipids induce apoptosis in micromolar concentrations. This is the first report of apoptosis induction by galactolipids.

A simple preparation of 17(R)-hydroxyeicosatetraenoic and eicosapentaenoic acids from the eicosanoylphloroglucinols, components of the brown alga, Zonaria diesingiana

Munakata, Tatsuo,Ooi, Takashi,Kusumi, Takenori

, p. 249 - 250 (1997)

The alkaline treatment of 17(R)-hydroxyeicosatetraenoylphloroglucinol and eicosapentaenoylphloroglucinol, which are the major components of the methanol extract of the brown alga, Zonaria diesingiana (Dictyota) afforded 17(R)-hydroxyeicosatetraenoic and eicosapentaenoic acids, respectively, in good yields. The conformation of methyl ester of the 17(R)-hydroxy acid in a solution was studied by using 2NMA, a chiral anisotropic reagent.

Chemoenzymatic synthesis of symmetrically structured triacylglycerols possessing short-chain fatty acids

Magnusson, Carlos D.,Haraldsson, Gudmundur G.

, p. 2728 - 2731 (2010)

Synthesis of symmetrically structured triacylglycerols possessing bioactive n-3 polyunsaturated fatty acids (eicosapentaenoic acid or docosahexaenoic acid) at the 2-position and a short-chain fatty acid (C2, C4, C6) located at the end-positions by a highly efficient two-step chemoenzymatic process is described. Full regiocontrol devoid of any acyl-migration side reactions was obtained in both a lipase promoted step to introduce the short-chain fatty acids exclusively into the primary alcohol positions of glycerol using activated vinyl esters at low temperature and a subsequent coupling reaction involving free EPA and DHA using EDAC as a coupling agent.

An allelopathic polyunsaturated fatty acid from red algae

Suzuki, Minoru,Wakana, Isamu,Denboh, Takashi,Tatewaki, Masakazu

, p. 63 - 65 (1996)

An allelopathic substance, which displays growth-inhibitory activity and spore-settlement suppressive activity, was isolated from some red algae and identified as (5Z,8Z, 11Z, 14Z, 17Z)-eicosapentaenoic acid on the basis of spectroscopic and chemical evidence.

Lyophilized extracts from vegetable flours as valuable alternatives to purified oxygenases for the synthesis of oxylipins

Sanfilippo, Claudia,Paterna, Angela,Biondi, Daniela M.,Patti, Angela

, (2019/10/05)

In this work, the whole aqueous extracts of soybean flour and oat flour have been used as valuable alternatives to purified oxygenase enzymes for the preparation of oxylipins derived from (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid (EPA). The lipoxygenase activity in the aqueous extracts of soybean (Glycine max. L.) flour was monitored with linoleic acid as substrate and compared with the commercially available purified enzyme (LOX-1). Oat flour extracts (Avena sativa L.) were evaluated for their peroxygenase activity by comparing different enzyme preparations in the epoxidation of methyl oleate. It was found that lyophilization of the aqueous extracts from these vegetable flours offers advantages in terms of enzyme stability, reproducibility and applicability to preparative organic synthesis. The lyophilized enzyme preparations were tested for the oxyfunctionalization of EPA and the formed products were isolated in satisfactory yields. In the presence of lyophilized extract from soybean, EPA gave 15S-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoic acid in enantiopure form as exclusive product. Peroxygenase from oat flour was less selective and catalyzed the formation of different epoxides of EPA. However, the biocatalyzed epoxidation of EPA under controlled conditions allowed to obtain optically active (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid (65% ee) as the main monoepoxide, among the five possible ones.

ENTERAL FEEDING DEVICE

-

, (2018/10/21)

The present invention relates to a fluid dispensing container in the field of enteral nutritional feeding, and in. particular to a dispenser for dispensing of a supplemental enteral fluid to a subject. Particularly, the invention provides a small-volume dispenser p refilled with an enteral fluid, which can be coupled with a feeding or medical tube port. Preferably, the enteral fluid is a composition of omega-3 fatty acids. The invention further provides a method for administering an enteral fluid to a subject using such dispenser. Yet further, the invention provides a method for supplementing an enteral nutritional product with an enteral fluid using such dispenser.

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