8,11-Eicosadienoic acid → Oleic Acid

HRID 1492878Notes

Reaction equation

HRID 1492878 reaction equation
[C:1]([OH:22])(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]CC.[C:23]([O:44]C)(=[O:43])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH2:32][CH:33]=[CH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]CC>>[C:1]([OH:22])(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:23]([OH:44])(=[O:43])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 2

HCID 1510658,11-Eicosadienoic acidHCID 549038methyl 8,11-eicosadienoate

Product 2

HCID 445639Oleic AcidHCID 5280450Linoleic Acid

Procedure

The lipid thus obtained contains 8,11-eicosadienoic acid as a component of the lipid such as fat. Although 8,11-eicosadienoic can be directly isolated, preferably it is isolated as an ester with a lower alcohol, for example, as methyl 8,11-eicosadienoate. The esterification accelerates the separation of the target fatty acid from other lipid components, and from other fatty acids produced during the culturing, such as parmitic acid, oleic acid and linoleic acid (these fatty acids are also esterified simultaneously with the esterification of 8,11-eicosadienoic acid). For example, to obtain methyl ester of 8,11-eicosadienoic acid, the above-mentioned extract is treated with anhydrous methanol/HCl 5 to 10%, or BF3 /methanol 10 to 50% at room temperature for 1 to 24 hours.

Workup

  1. customThe lipid thus obtained
  2. customAlthough 8,11-eicosadienoic can be directly isolated
  3. customthe separation of the target fatty acid from other lipid components

Sources & evidence

ORD record
ord-8a2ae40337fb4ce69ac2e6294fa3ec6b
Source dataset
uspto-grants-1994_12
Patent number
US05376541

Reaction notes

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