92760-19-5

Basic information

• Product Name: (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene
• Synonyms: (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene
• CAS NO: 92760-19-5
• Molecular Weight: 550.868
• Mol File: 92760-19-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene(92760-19-5)
• EPA Substance Registry System: (3R,6'R)-3-hydroxy-2',3'-didehydro-β,ε-carotene(92760-19-5)

Safety Data

• Hazardous Substances Data: 92760-19-5(Hazardous Substances Data)

Upstream product

• 144-68-3 zeaxanthin 
• 127-40-2 lutein 
• 851854-29-0 (3R,3'R,6'R)-lutein 3'-propyl ether 
• 547-17-1 (3R,3'R,6'R)-lutein dipalmitate 

Downstream Products

• 144-68-3 zeaxanthin 
• 472-70-8 (3R)-cryptoxanthin 
• 24480-38-4 zeinoxanthin 
• 60497-64-5 (9Z)-zeaxanthin 
• 60497-65-6 (3R,3'R)-13-cis-β,β-carotene-3,3'-diol 

Relevant articles and documents

Process For The Preparation of Beta and Alpha Cryptoxanthin

The present invention relates to a process for converting lutein and/or lutein esters to (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-β-Cryptoxanthin and (3R,6′R)-α-cryptoxanthin are two rare food carotenoids that are not commercially available and the former exhibits vitamin A activity. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to (3R)-β-cryptoxanthin (major product) and (3R,6′R)-α-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII (Pt, Pd, Rh supported on alumina or carbon) in a variety of organic solvents under atmospheric pressure of hydrogen and at temperatures ranging from ?15° C. to 40° C. Among these catalysts, Pt supported on alumina at 40° C. in ethyl acetate provides the best yield of (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin. Several homogeneous catalysts can also promote the regioselective hydrogenation of anhydroluteins to a mixture of (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin in low to moderate yields. The catalysts may be transition metal complexes such as palladium acetylacetonate, Rh(Ph3P)3Cl (Wilkinson's catalyst), [(C6H11)3P[C8H12][C5H5N] Ir+PF6? (Crabtree catalyst), or [C8H12][(MePh2P)2]Ir+PF6?. Among these, Wilkinson catalyst converts anhydroluteins to (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin in nearly quantitative yield. A novel feature of this invention is the regioselective hydrogenation of anhydroluteins while the highly conjugated polyene chain of these carotenoids remains intact.

Method for production of rare carotenoids from commercially available lutein

Disclosed are processes for conversion of (3R,3′R,6′R)-lutein to (3R,6′R)-α-cryptoxanthin, (3R)-β-cryptoxanthin, anhydroluteins I, II, and III (dehydration products of lutein), and a method for separating and purifying the individual carotenoids including the unreacted (3R,3′R)-zeaxanthin. The invention also includes two methods that transform (3R,3′R,6′R)-lutein into (3R,6′R)-α-cryptoxanthin in excellent yields.