42273-19-8

Upstream product

• 144-68-3 zeaxanthin 
• 127-40-2 lutein 
• 507-09-5 tiolacetic acid 
• 645-96-5 Benzeneselenol 

Relevant academic research and scientific papers

Synthetic Sulfur Carotenoids II: Optically Active Carotenoid Thiols

(3R,3'R)-Zeaxanthin was reacted with thioacetic acid or with thiocyano acid in a Mitsunobu reaction to provide the corresponding thioacetates and thiocyanates with inverted configuration.Reduction or hydrolysis of these intermediates provided (3R,3'S)-3'-

Synthetic Selenium Carotenoids

Lutein was reacted with benzeneselenol and ZnCl2 to provide (3R,3',RS,6'R)-phenylseleno-β,ε-caroten-3-ol. (3R,3'R)-Zeaxanthin provided, in a Mitsunobu reaction with benzeneselenol, (3S)-2',3'-didehydro-β,β-caroten-3-yl phenyl selenide, (3R,3'S)-3-phenylseleno-β,β-caroten-3-ol and (3S,3'S)-β,β-carotene-3,3'-diyl diphenyl diselenide.Spectroscopic properties are discussed and potential applications of these new selenium carotenoids considered.

Synthetic Nitrogen Carotenoids: Optically Active Carotenoid Amines

(3R,3'R)-Zeaxanthin was reacted with hydrazoic acid in a Mitsonobu reaction to yield azides with inverted configuration.Reduction of these azides with hydrogen telluride provided (3S)-2',3'-didehydro-β,β-caroten-3-amine, (3R,3'S)-3'-amino-β,β-caroten-3-ol

Animal carotenoids. 31. Structure elucidation of a sponge metabolite via mesylate elimination.

The structure of a sponge metabolite from Microciona prolifera, previously considered to be (6S)-2,3-didehydro- or 3,4-didehydro-gamma, chi-carotene, has been further studied. Attempted total synthesis of the 3,4-didehydro derivative provided the hitherto unknown gamma, chi-carotene, the synthesis of which is described. Hydrolysis of lutein methanesulfonate diester (dimesylate) gave elimination products possessing the 3,4-didehydro gamma end-group. 1H NMR data for this gamma end-group were identical with those for the sponge carotenoid. The mesylate elimination reaction described may mimic the metabolic formation of the 3,4-didehydro-gamma-carotenoid end-group. In connection with other investigations on functionalized carotenoids we further report the preparation of zeaxanthin and lutein mesylates and their base-catalyzed elimination reactions. SN2 type substitution reactions of zeaxanthin dimesylate with appropriate nucleophiles did not produce beta, beta-carotene, zeaxanthin diacetate or thiozeaxanthin.

Partial Syntheses of Diastereomeric Carotenols

The application of the Mitsunobu reaction was successfully tested on (3R,3'R)-zeaxanthin, giving the (3S,3'S)-enantiomer and meso form.Applied to natural (3R,3'R,6'R)-lutein, this inversion reaction allowed the preparation of the three other 6'R diastereomers. (3S,3'S,6'R)-lutein with 3',6'-cis-configuration of the ε-ring has not been synthesized before.The observed Cotton effects of the eight lutein diastereomers are rationalized by application of the additivity hypothesis.New trivial names are suggested for the eight lutein isomers on the basis of structural relationships.

Carotenoid Sulfates. 5. Preparation and Solvolytic Reactions of Unstable Carotenoid Sulfates

tert-Carotenoid C-5 sulfates obtained from azafrin and its methyl ester, sec allylic sulfates of lutein, lactucaxanthin, isozeaxanthin and β,β-carotene-3,4,3',4'-tetrol and the prim allylic sulfate of β-apo-2'-carotenol were too unstable in solution for practical application.Product analyses from the methanolysis of such unstable carotenoid sulfates support solvolysis via tert or resonance stabilized carbocations.Sulfates as leaving groups, e.g. in the azafrin series, may be synthetically useful.