105452-20-8

Basic information

• Product Name: (3S,3'R,6'S)-β,ε-Carotene-3,3'-diol
• Synonyms: (3S,3'R,6'S)-β,ε-Carotene-3,3'-diol;Lutein G
• CAS NO: 105452-20-8
• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.87144
• Mol File: 105452-20-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 702.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.004±0.06 g/cm3(Predicted)
• PKA: 14.61±0.70(Predicted)
• CAS DataBase Reference: (3S,3'R,6'S)-β,ε-Carotene-3,3'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3'R,6'S)-β,ε-Carotene-3,3'-diol(105452-20-8)
• EPA Substance Registry System: (3S,3'R,6'S)-β,ε-Carotene-3,3'-diol(105452-20-8)

Safety Data

• Hazardous Substances Data: 105452-20-8(Hazardous Substances Data)

Upstream product

• 23984-55-6 (3R,6'R)-3-hydroxy-β,ε-caroten-3'-one 
• 127-40-2 lutein 

Downstream Products

• 23984-55-6 (3R,6'R)-3-hydroxy-β,ε-caroten-3'-one 

Relevant articles and documents

Combination of carotenoids and epi-lutein

The invention describes the preparation and use of carotenoid and epi-lutein compositions to treat various ocular diseases.

Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers

(3R,3′R,6′R)-Lutein and (3R,3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US. These carotenoids accumulate in the human plasma, major organs, and ocular tissues. In the past decade, numerous epidemiological and experimental studies have shown that lutein and zeaxanthin play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and Western World. The invention provides a process for the synthesis of (3R,3′R,6′R)-lutein and its stereoisomers from commercially available (rac)-α-ionone by a C15+C10+C15 coupling strategy. In addition, the present invention also provides access to the precursors of optically active carotenoids with 3-hydroxy-ε-end group that are otherwise difficult to synthesize. The process developed for the synthesis of lutein and its stereoisomers is straightforward and has potential for commercialization.

Separation and identification of carotenoids and their oxidation products in the extracts of human plasma

Eighteen carotenoids as well as vitamin A and two forms of vitamin E (γ- and α-tocopherol) have been separated from extracts of human plasma by high-performance liquid chromatography (HPLC) on reversed-phase and silica-based nitrile-bonded columns. In the order of chromatographic elution on a C18 reversed-phase column, the carotenoids were identified as (3R,3′R,6′R)-β,ε-carotene-3,3′-dlol [(3R,3′R,6′R)-lutein], (3R,3′R)-β,β-carotene-3,3′-dlol [(3R,3′R)-zeaxanthin], 5,6-dihydroxy-5,6-dihydro-ψ,ψ-carotene,3-hydroxy-2′,3′- didehy-dro-β,ε-carotene,β,ε-caroten-3-ol,3-hydroxy-β- carotene,ψ,ψ-carotene, 7,8-dihydro-ψ,ψ-carotene, β,ψ-carotene, 7,8,7′,8′-tetrahydro-′,′-carotene, β,ε-carotene, β,β-carotene, 7,8,11,12,7′,8′-hexahydro-ψ,ψ-carotene, and 7,8,11,12,7′,8′,-11′,12′-octahydro-ψ,ψ-carotene. The polar carotenoids, which eluted in the vicinity of lutein and were unresolved on the C18 column, have been separated on a nitrile-bonded column employing isocratic HPLC conditions. In the order of elution, the carotenoids were ε,ε-carotene-3,3′-dione, 3′-hydroxy-ε,ε-caroten-3-one, 5,6-dihydroxy-5,6-dihydro-ψ,ψ-carotene, 3-hydroxy-β,ε-caroten-3′-one, (all-E,3r,3′R,6′R)-lutein, (all-E,3R,3′R)-zeaxanthin, and (all-E,3R,3′S,6′R)-β,ε-carotene-3,3′-diol (3′-epilutein) followed by several geometrical isomers of lutein and zeaxanthin.