A simple synthesis of [1,3-13C2]4-(2,6,6-trimethylcyclohexen-1-yl)buten-2-one (ß-ionone)
✍ Scribed by Robert W. Curley Jr.; Michael A. Blust; Keith A. Humphries
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- French
- Weight
- 210 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
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.
📜 SIMILAR VOLUMES
## Abstract (E)‐ and (Z)‐3‐(2‐butenyl)‐2,4,4‐trimethyl‐2‐cyclohexen‐1‐one **1** and **2** have been isolated from an absolue of Osmanthus Fragrance Lour. and a fusel oil concentrate. Structural proof for these compounds has been obtained via their synthesis from β‐ionone. The key step in this synth
The d e u t e r a t e d d i e n e was p r e p a r e d as r e p o r t e d by us [3]. from 1,2-dibromoethane-1 ,2-13C2 v i a t h e c y a n i d e , s u c c i n l c a c i d , bromosuccinic a c i d , fumaric a c i d and maleic a n h y d r i d e C4,51. The 13C-labelled maleic anhydride was p r e p a r e d