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Methyl Stearate → Dihomo-Gamma-Linolenic Acid

HRID 394431
Notes
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Reaction equation

HRID 394431 reaction equation
[C:1]([O:20]C)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:22](OC)(=O)[CH2:23]CCCCCC/C=C\CCCCCCCC>>[CH3:22][CH2:23][CH2:18][CH2:17][CH2:16]/[CH:15]=[CH:14]\[CH2:13]/[CH:12]=[CH:11]\[CH2:10]/[CH:9]=[CH:8]\[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 8201Methyl StearateHCID 5364509Methyl Oleate

Product 1

HCID 5280581Dihomo-Gamma-Linolenic Acid

Procedure

Methyl ester of DGLA is recovered preferably by extracting the above-mentioned treated solution with an organic solvent such as hexane, an ether such as ethyl ether, or an ester such as ethyl acetate. Next, the resulting extract is dried on, for example, anhydrous sodium sulfate, and the solvent is distilled off preferably under reduced pressure to obtain a mixture comprising fatty acid esters. This mixture contains, in addition to the desired fatty acid HGLA methyl ester, other fatty acid methyl esters, such as methyl parmitate, methyl stearate, methyl oleate and the like. To isolate methyl ester of DGLA from the mixture of these fatty acid methyl esters, column chromatography, low temperature crystallization, the urea-inclusion method, the liquid/liquid countercurrent chromatography method, and the like can be used alone or in combination.

Workup

  1. custom
Methyl ester of DGLA is recovered preferably
  • extractionby extracting the above-mentioned treated solution with an organic solvent such as hexane
  • extractionNext, the resulting extract
  • dry with materialis dried on, for example, anhydrous sodium sulfate
  • distillationthe solvent is distilled off preferably under reduced pressure
  • customto obtain a mixture
  • Sources & evidence

    ORD record
    ord-188ba38aee054365849e8b30ebbfb5f1
    Source dataset
    uspto-grants-2003_08
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US06602690B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes