ChemicalBook CAS DataBase List Nervonic acid

Nervonic acid synthesis

11synthesis methods

Product Name:Nervonic acid
CAS Number:506-37-6
Molecular formula:C24H46O2
Molecular Weight:366.62

Nervonic acid was shown to be identical with selachaleic acid isolated from whale oils. It is obvious that nervonic acid is probably the cis form of erucylacetic acid. Erucylacetic acid has been prepared from erucyl alcohol through the bromide and malonic ester synthesis and has been shown to be identical with nervonic acid obtained from hydrolysis of the cerebroside isolated from human brains.
Nervonic acid is also produced from oleic acid, that undergoes three consecutive chain elongation steps, catalyzed by elongases.Two carbon units are added in each step, with production of gadoleic acid, erucic acid, and finally, nervonic acid.

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Yield:506-37-6 70%

Reaction Conditions:

with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;[bis(acetoxy)iodo]benzene in water;acetonitrile at 20; for 7 h;

Steps:

1 Synthesis of nervonic acid:

Dissolve 1-hydroxy-cis-15-tetracosene(0.5mol) and iodobenzene acetate [PhI(OAc)2 1.1mol] in a system of acetonitrile:water=1:1. The system was stirred uniformly for 3 minutes, and a catalytic amount of TEMPO (0.1 mol) was added to the reaction system. React at room temperature for 7h. After the reaction is complete, add water, ethyl acetate to extract, dry and distill under reduced pressure. The obtained crude product was dissolved in acetone and recrystallized at -20°C. The yield is 70%.

References:

CN111423320,2020,A Location in patent:Paragraph 0062-0066