78660-21-6

Upstream product

• 41641-11-6 2,6,6-trimethyl-1-hydroxy-1-[3-hydroxy-but-1-ynyl]-cyclohex-2-ene 
• 108-24-7 acetic anhydride 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 

Downstream Products

• 82760-69-8 2,6,6-trimethyl-1-(3-acetoxy-but-1-ynyl)cyclohexa-1,3-diene 
• 23726-93-4 Damascenon 
• 79925-81-8 9-hydroxymegastigma-3,5-dien-7-yne 

Relevant academic research and scientific papers

Identification of a precursor to naturally occurring β-damascenone

9-Hydroxymegastigma-3,5-dien-7-yne 8a was synthesised and shown to be identical to an intermediate found in the acid-catalysed conversion of 3,5,9-trihydroxymegastigma-6,7-diene 4 to β-damascenone 1, 3-hydroxydamascone 5 and megastigma-5-en-7-yne-3,9-diol 6. When subjected to acid hydrolysis, 8a produced β-damascenone 1, in high yield. Importantly, the hydrolysate was completely free of 3-hydroxydamascone 5.

Process for the preparation of damascenone

A novel method of preparing 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene comprises treating an ester of the formula STR1 with a proton acid under essentially anhydrous conditions.