Hexane → Geranyl-geranyl eicosapentaenoate

HRID 2105708Notes

Reaction equation

HRID 2105708 reaction equation
[CH2:1]([CH2:11][C:12](=[CH:14][CH2:15][CH2:16]/[C:17](=[CH:19]/[CH2:20][OH:21])/[CH3:18])[CH3:13])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[CH3:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][C:41](O)=[O:42].CCCCCC>C(CC(C)(C)C)(C)C>[C:41]([O:21][CH2:20]/[CH:19]=[C:17](/[CH2:16][CH2:15]/[CH:14]=[C:12](\[CH3:13])/[CH2:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4])\[CH3:18])(=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=[CH:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

5

Reactant 3

HCID 8058HexaneHCID 446284IcosapentHCID 865915033,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol

Product 1

HCID 131727593Geranyl-geranyl eicosapentaenoate

Reagents, catalysts & solvents 1

HCID 109072,2,4-TrimethylpentaneSolvent

Conditions

Temperature
60 °C

Procedure

There were dissolved, in 1 g of isooctane, 100 mg of geranyl geraniol and 600 mg of ethyl ester of eicosapentaenoic acid, followed by the addition of lipase in an amount of 1% relative to the total amount of the resulting solution and then stirring the mixture at 60° C. for 24 hours. After confirming whether the reaction system reached its equilibrium state or not by the GC technique, the reaction solution was diluted by the addition of hexane to the solution in an amount of 10 times the volume thereof, followed by the removal of the lipase from the reaction solution through filtration and then the removal of the hexane through distillation to thus give a crude reaction product. The crude product was purified by silica gel column chromatography to give 102 mg of geranyl-geranyl eicosapentaenoate.

Workup

  1. customfollowed by the removal of the lipase from the reaction solution through filtration
  2. customthe removal of the hexane
  3. distillationthrough distillation
  4. customto thus give a crude
  5. customreaction product
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-595d69e89e2c4d35b6fde86611dc9155
Source dataset
uspto-grants-2009_08
Patent number
US07579374B2

Reaction notes

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