99302-43-9

Upstream product

• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 99302-33-7 C₁₈⁽¹³⁾CH₂₇NO₂ 
• 99302-36-0 C₁₆⁽¹³⁾CH₂₃N 
• 62924-18-9 β-ionylidene-acetonitrile 
• 72214-33-6 3-(2,6,6-Trimethylcyclohex-1-enyl)prop-2-enenitrile 
• 472-80-0 beta-Ionol 
• 53018-97-6 3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal 
• 917-64-6 methyl magnesium iodide 
• 99302-39-3 C₁₆⁽¹³⁾CH₂₄O 
• 141207-96-7 ethyl 5-methyl-7-(2,6,6-trimethyl-1-cyclohexenyl)heptatrienoate 
• 917-54-4 methyllithium 
• 141208-00-6 N-methoxy-N,5-dimethyl-7-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6-heptanetrienamide 

Downstream Products

• 103741-05-5 all-E-(13,14-⁽¹³⁾C₂)retinal 
• 87922-16-5 C₁₉⁽¹³⁾CH₂₈O 
• 99302-45-1 C₁₉⁽¹³⁾CH₂₇N 
• 141208-03-9 C₁₈⁽¹³⁾C₂H₂₇N 

Relevant academic research and scientific papers

Synthesis of (12,13-(13)C2)retinal and (13,14-(13)C2)retinal: a strategy to prepare multiple-(13)C-labeled conjugated systems

(12,13-(13)C2)Retinal, (13,14-(13)C2)retinal, (19-(13)C)retinal and (20-(13)C)retinal (1) were prepared in a simple fashion in high yield via a consecutive strategy.The key step is the reaction of a N-methoxy-N-methylamide with an alkyllithium or a Grignard reagent.The preparation of the required N-methoxy-N-methylamide is discussed.In this scheme, only three commercially available (13)C-labeled starting materials (ethyl bromoacetate, acetonitrile and methyl iodide) are sufficient to construct retinals with any possible combination of (13)C labeling in the conjugated tail end.This strategy is applicable to the preparation of many other conjugated systems, such as retinoids, carotenoids and polyenes.

Synthesis of 8-, 9-, 12-, and 13-mono-13C-retinal

The 8-, 9-, 12-, and 13-mono-13C-retinals were synthesized with >98percent chemical purity and 93percent 13C incorporation from 13C-labelled acetonitrile.Their 13C-13C and 13C-1H nmr coupling constants were determined.