82178-68-5

Upstream product

• 82178-66-3 6,6-dimethoxy-4-hydroxy-4-methyl-1-hexyne 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 3338-53-2 6,6-dimethoxy-4-methyl-hex-3-en-1-yne 
• 79-77-6 (E)-β-ionone 

Downstream Products

• 74352-10-6 (all-E)-(10-²H)retinal 
• 74410-17-6 10-deuterio-13-cis-retinal 
• 77871-13-7 11-monodeuterio-all-trans-retinal 
• 77943-15-8 13-cis-11-monodeuterioretinal 
• 82178-69-6 10,11-dideuterio-all-trans-retinal 

Relevant academic research and scientific papers

Preparation of deuterium-labelled retinals having high deuterium content on specific positions. 10-Mono-, 11-mono, 10,11-di- and 14,20,20,20-tetradeuterioretinal

10-Mono-, 11-mono- and 10,11-dideuterioretinal (in the all-trans, 9-cis, 11-cis and 13-cis forms) of > 98 percent purity and the required (> 96 percent) deuterium incorporation were prepared via LiAlH4 or LiAlD4 reduction of the retinylidene derivative 8.Compound 8 was prepared by coupling β-ionone with 6,6-dimethoxy-4-methyl-3-hexen-1-yne (6), which had been obtained in high yield from 2-propynyl bromide and commercial 4,4-dimethoxy-2-butanone (4).Exchange of 4 with D2O and base gave 4,4-dimethoxy-1,1,1,3,3-pentadeuterio-2-butanone (4a), which in turn, using the same synthetic method, finally provided 14,20,20,20-tetradeuterioretinal.