80952-82-5

Upstream product

• 118205-56-4 (2E,4E)-5-[(1'S,2'R,4'S)-4'-hydroxy-1',2'-epoxy-2',6',6'-trimethylcyclohexa-1'-yl]-3-methylpenta-2,4-diene-1-ol 
• 28874-44-4 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal 
• 20584-58-1 (3S,5R,6S,3'S,5'R,6'S)-violaxanthin diacetate 
• 62777-81-5 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al 

Relevant academic research and scientific papers

THE CONSTITUTION AND ABSOLUTE STEREOCHEMISTRY OF PERSICAXANTHIN

Key Word Index - Prunus persica; Rosaceae; C25-epoxy-apo-carotenoids; apo-carotenols; persicaxanthin; persicachrome.Persicaxanthin, obtained from the fruits of peach, has been isolated in crystalline form.By spectroscopic (MS, 1H NMR and CD) methods, its constitution and absolute stereochemistry have been determined as (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-carotene-3,12'-diol.The structural conclusions have received full support by comparison with semi-synthetic persicaxanthin obtained from natural violaxanthin.

210. Synthesis of Enantiomerically Pure Apoviolaxanthinoic Acids, Apoviolaxanthinols, and Apoviolaxanthinals (Including Persicaxanthin, Sinensiaxanthin, and β-Citraurin Epoxide

Starting from (1'S,2'R,4'S,2E,4E)-5-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal (3), a recently described synthon , a full range of C20-, C25-, C27-, and C30-polyenic acids, alcohols, and aldehydes and their (8R)- and (8S)-diastereomeric furanoid rearrangement products was prepared.The synthetic C25-alcohols proved to be identical with persicaxanthin (= 12'-apoviolaxanthin-12'-ol) and persicachromes (= 12'-apoauroxanthin-12'-ols) and the C27-alcohols analogously with sinensiaxanthin and sinensiachromes.A correlation between the sign of the Cotton effects in the CD spectra of 5,6- and 5,8-epoxides and their configuration at C(6) and C(8), respectively, was established.