130321-04-9

Upstream product

• 3351-86-8 fucoxanthin 
• 26289-05-4 (3R)-4-[(2R,4S)-4-acetoxy-2-hydroxy-2,6,6-trimethylcyclohexylidene] but-3-en-2-one 
• 22451-58-7 (1'R,2'R,4'R)-4-(4'-acetoxy-2'-hydroxy-2',6',6'-trimethylcyclohexyliden)but-3-en-2-on 
• 130224-16-7 (1'R,2'R)-4-(2'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohexyliden)but-3-en-2-on 

Downstream Products

• 22451-58-7 (1'S,2'R,4'R)-4-(4'-acetoxy-2'-hydroxy-2',6',6'-trimethylcyclohexyliden)but-3-en-2-on 

Relevant academic research and scientific papers

Degradation of fucoxanthin to elucidate the relationship between the fucoxanthin molecular structure and its antiproliferative effect on caco-2 cells

Fucoxanthin has an antiproliferative effect on cancer cells, but its detailed structure–activity correlation has not yet been elucidated. To elucidate this correlation, fucoxanthin was degraded by ozonolysis. The degraded compounds of fucoxanthin obtained by ozonolysis were purified by HPLC and analyzed by NMR. The polyene chain of fucoxanthin was cleaved by ozonolysis, and the fucoxanthin was divided into two types of cyclohexyl derivatives, one with a β,γ-epoxy ketone group and the other with an allenic bond. In order to elucidate the structure–activity correlation, Caco-2 cells (human colorectal carcinoma) were treated with fucoxanthin degradation compounds. It was found that the entire structure of fucoxanthin is not essential for its antiproliferative effect and that even a partial structure exerts this effect.

Carotenoids and Related Polyenes. Part 2. Photoisomerization of an Allenic Carotenoid, Peridinin, and Allenic Model Compounds

Iodine-catalysed photoisomerization of peridinin 1a gave the novel (6S)-allenic isomer 1b whose structure was confirmed by chemical synthesis.In addition, the photochemical behaviour of several model compounds having a part structure of allenic carotenoid

72. Synthesis of Optically Pure Grasshopper Ketone and its Diastereoisomers and Related Compounds

Starting from our previously described synthon 1, the synthesis of four enantiomerically pure grasshopper ketons (diastereoisomeric 4-(2',4'-dihydroxy-2',6',6'-trimethylcyclohexylidene)but-3-en-2-ons) and of their oxo derivatives was performed.Spectral an

CHIRALITY OF PERIDININ AND DINOXANTHIN

Details are reported for the configurational assignment of peridinin as 3S, 5R, 6R, 3'S, 5'R, 6'S including ozonolytic degradation of its p-bromobenzoate to derivatives of known chirality obtained from fucoxanthin and violaxanthin.Details regarding derivatization and CD correlations in favour of the same chirality for dinoxanthin = neoxanthin 3-acetate are given.Key Word Index - Dinoflagellate carotenoids; chirality; peridinin; dinoxanthin.