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Upstream product

• 110875-15-5 (4E,6E,8E)-3,7-dimethyl-3-hydroxy-9-(2,6,6-trimethyl-1-cyclohexenyl)-4,6,8-nonatrienenitrile 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 20638-88-4 (4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenenitrile 

Relevant academic research and scientific papers

Synthesis of retinals labelled at positions 14 and 15 (with 13C and/or 2H)

Eight retinals labelled at positions 14 and 15 with 13C and/or 2H were obtained with 98 percent chemical purity, 92 percent 13C incorporation, 95 percent 2H incorporation at position 14 and 99 percent 2H incorporation at position 15. (14-13C)retinal, (15-13C)retinal and (14,15-13C)retinal were synthesized from (2-13C)-, (1-13C)- and (1,2-13C)acetonitrile, respectively, while for the synthesis of (14-2H)retinal, 2CH3CN was used.Via a three-step process these retinals were transformed into (14,15-2H)retinal, (14-13C,15-2H)retinal, (15-13C,15-2H)retinal and (14,15-13C2,15-2H)retinal.Their 13C-13C, 13C-2H and 13C-H NMR coupling constants were determined.

A SHORT PATH SYNTHESIS OF RETINALS. SYNTHESIS OF 13C- OR 2H-LABELED RETINALS

Trimethylsilylated acetaldehyde t-butylimine 4 was found to be an effective two carbon-homologenation reagent in the synthesis of retinals and its congeners.A short path synthesis of retinals (1 and 2) by using 4 and its application to the synthesis of 13C-labeled retinal 12 and octadeuterium retinal 27 is described.KEYWORDS - retinal; retinoid; vitamin A aldehyde; visual pigment; α,β-unsaturated aldehyde synthesis; silylated imine