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A simple synthesis of [1,3‐ 13 C 2 ]4‐(2,6,6‐trimethylcyclohexen‐1‐yl)buten‐2‐one (ß‐ionone)
Author(s) -
Curley Robert W.,
Blust Michael A.,
Humphries Keith A.
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580291210
Subject(s) - chemistry , ionone , aldol condensation , yield (engineering) , acetone , sodium hydroxide , aldol reaction , enone , aqueous solution , retinoid , condensation , friedel–crafts reaction , organic chemistry , stereochemistry , retinoic acid , catalysis , materials science , thermodynamics , physics , metallurgy , biochemistry , gene
A convenient, one‐step synthesis of doubly 13 C‐labelled ß‐ionone was accomplished by aqueous sodium hydroxide catalyzed aldol condensation of 1,3‐ 13 C 2 ‐acetone with the recently commercially available ß‐cyclocitral. This retinol‐like compound obtained in ca. 60% yield, should prove useful in NMR studies of retinoid binding to its transport proteins.