STUDIES ON ACETONE-GLYCERALDEHYDE, AND OPTICALLY ACTIVE GLYCERIDES
1941; Elsevier BV; Volume: 140; Issue: 2 Linguagem: Inglês
10.1016/s0021-9258(18)51328-4
ISSN1083-351X
AutoresErich Baer, Hermann O. L. Fischer,
Tópico(s)Mass Spectrometry Techniques and Applications
ResumoThe occurrence of monoethers of glycerol with higher aliphatic alcohols, such as octadecyl, cetyl, and oleyl alcohols, in the liver oils of various marine animals, especially those of the elasmobranch group, was first demonstrated by Tsujimoto and Toyama (2) and later by Nakamiya (3).Andre and Bloch (4) showed that in the original fish oils these ethers are present in the form of fatty acid esters.From 1928 to 1933 a thorough investigation into the structure of batyl alcohol and chimyl alcohol was carried out by Heilbron and Owens (5), Davies, Heilbron, and Owens (6), and Davies, Heilbron, and Jones (7).Their syntheses (6) of racemic octadecyl glycerol and cetyl glycerol were accomplished by condensation of octadecyl chloride or hexadecyl chloride with sodium allylate, and subsequent oxidation of the octadecyl ally1 ethers with perhydrol.These syntheses and the lead tetraacetate titration of the naturally occurring ethers (8) proved that batyl alcohol, chimyl alcohol, and selachyl alcohol, which last can be catalytically reduced to batyl alcohol, must be the cr-glycerol ethers of octadecyl alcohol, hexadecyl alcohol, and oleyl alcohol, respectively.Although no direct comparison with the naturally occurring chimyl alcohol was possible for lack of material, there was little doubt that chimyl alcohol is ar-cetylglycerol ether.
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