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13 C nuclear magnetic resonance of mono‐and dihydroxy saturated and unsaturated fatty methyl esters
Author(s) -
Rakoff Henry,
Weisleder David,
Emken Edward A.
Publication year - 1979
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02533573
Subject(s) - double bond , chemical shift , chemistry , carbon fibers , diastereomer , vicinal , cis–trans isomerism , resonance (particle physics) , carbon 13 , organic chemistry , stereochemistry , medicinal chemistry , materials science , composite number , composite material , physics , particle physics , quantum mechanics
13 C nuclear magnetic resonance spectra were obtained for methyl esters of erythro ‐ and threo ‐9,10‐dihydroxystearates, for 12‐hydroxy‐ cis ‐ and trans ‐9‐octadecenoates, and for threo ‐12,13‐dihydroxy‐ cis ‐and trans ‐9‐octadecenoates. Erythro and threo compounds may be distinguished easily by the difference in the chemical shifts of the carbons alpha to the hydroxy‐bearing carbons. Monohydroxy compounds are easily distinguished from vicinal dihydroxy compounds by differences in chemical shifts of both the hydroxy‐bearing carbons and of the carbons alpha to them. The presence of a hydroxy‐bearing carbon beta to a double bond results in the two carbons of the double bond of a hydroxy‐bearing carbon beta to a double bond results in the two carbons of the double bond having different chemical shifts, with the numerical values being different for the cis and trans isomers. The chemical shift of a carbon alpha to both a doubly bonded carbon and a hydroxy‐bearing carbon is influenced both by the geometry of the double bond and the number of hydroxy‐bearing carbons.