122346-90-1

Basic information

• Product Name: 15,15'-Didehydroviolaxanthin
• Synonyms: 15,15'-Didehydroviolaxanthin
• CAS NO: 122346-90-1
• Molecular Weight: 598.866
• Mol File: 122346-90-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 15,15'-Didehydroviolaxanthin(CAS DataBase Reference)
• NIST Chemistry Reference: 15,15'-Didehydroviolaxanthin(122346-90-1)
• EPA Substance Registry System: 15,15'-Didehydroviolaxanthin(122346-90-1)

Safety Data

• Hazardous Substances Data: 122346-90-1(Hazardous Substances Data)

Upstream product

• 122203-82-1 <2R-<1R*(E),2α,4β>>-5-(2,4-Dihydroxy-2,6,6-trimethylcyclohexylidene)-3-methylpenta-2,4-dienal 
• 142204-42-0 Diethyl-12'-apo-15,15'-didehydroviolaxanthin-12'-phosphonat 
• 122203-82-1 (1'R,2'R,4'S,2Z)-5-(2',4'-dihydroxy-2',6',6'-trimethylcyclohexyliden)-3-methylpenta-2,4-dienal 

Downstream Products

• 126-29-4 Violaxanthin 
• 126-29-4 (15Z)-Violaxanthin 

Relevant articles and documents

Synthesis of (6R,all-E)-Neoxanthin and Related Allenic Carotenoids

We present the first synthesis of enantiomerically pure neoxanthin (1) by a Wittig-Horner condensation between the ylide from the novel diethyl 12'-apo-15,15'-didehydroviolaxanthin-12'-phosphonate (35) and the allenic C15-aldehyde 31 (Scheme 4) via the crystalline 15,15'-didehydroneoxanthin (36; 70percent yield).After partial hydrogenation of the triple bond of 36 and isomerisation of the (15Z)-intermediate 37, neoxanthin (1) was obtained in good yield.Similar syntheses gave (15Z,9'Z)-neoxanthin (45; Scheme 5) and (9Z)-15,15'-didehydroneoxanthin (47; Scheme 6).Comparison of the physical data of synthetic 1 with those of a freshly isolated sample of neoxanthin from the flowers of Trollius europaeus confirmed their identity.The unusually low melting point of 1 is caused by a very easy thermal isomerisation into a mixture of the neochromes 4 and 5 (Scheme 1).Such a thermal rearrangement is not observed with 15,15'-didehydroneoxanthin (36).To explain this, we assume a zwitterionic excited state of the allenic group that induces the rearrangement of the violaxanthin end group into the furanoid epoxide (Scheme 7).