methyl 6,9-octadecadienoate → Palmitic Acid

HRID 1109707Notes

Reaction equation

HRID 1109707 reaction equation
[C:1]([O:22]C)(=[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]CCCC.[C:24]([O:43]C)(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][CH2:31][CH:32]=[CH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].CC[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]/[CH:53]=[CH:54]\[CH2:55]/[CH:56]=[CH:57]\[CH2:58]/[CH:59]=[CH:60]\[CH2:61][CH2:62][CH2:63][C:64]([OH:66])=[O:65]>>[C:1]([OH:22])(=[O:21])[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][CH3:16].[C:24]([OH:43])(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[C:64]([OH:66])(=[O:65])[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]/[CH:56]=[CH:55]\[CH2:54]/[CH:53]=[CH:52]\[CH2:51][CH2:50][CH2:49][CH2:48][CH3:47]

Participants

6

Reactant 3

HCID 549027methyl 6,9-octadecadienoateHCID 549038methyl 8,11-eicosadienoateHCID 5312531Mead acid

Product 3

HCID 985Palmitic AcidHCID 445639Oleic AcidHCID 5280450Linoleic Acid

Procedure

The lipid thus obtained contains omega 9 type polyunsaturated fatty acid as a component of the lipid, such as fat. Although omega 9 type polyunsaturated fatty acid can be directly isolated, preferably it is isolated as an ester with a lower alcohol, for example, as methyl 8,11-eicosadienate, methyl 6,9-octadecadienoate, methyl ester of mead acid and the like. 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 palmitic acid, oleic acid and linoleic acid (these fatty acids are also esterified simultaneously with the esterification of omega 9 type polyunsaturated fatty acid). For example, to obtain methyl ester of omega 9 type polyunsaturated fatty 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 separation of the target fatty acid from other lipid components

Sources & evidence

ORD record
ord-052dbc9e8d104b7bb23cbd5afaf2b8ff
Source dataset
uspto-grants-1994_06
Patent number
US05322780

Reaction notes

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