Abstract: The present invention relates to a novel process for crystallizing high purity lutein and zeaxanthin esters from marigold oleoresin. In another aspect, the present invention relates to the removal of soft and hard waxes by adsorption on diatomaceous earth or other filter aid using acetone or other organic solvent. Another aspect of the present invention relates to achieving high-purity lutein and zeaxanthin esters, including purity levels that are about 90 to 95%.

Abstract: The present invention relates to a process for converting commercially available lutein and/or lutein esters from extracts of marigold flower petals to (3R)-?-cryptoxanthin (major) and (3R,6?R)-?-cryptoxanthin (minor) in ratios ranging from 95:5 to 98:2 in a one-pot reaction at room temperature. Because the entire process can be carried out by employing safe and environmentally friendly food-grade reagents, the resulting mixture of these carotenoids is suitable for human consumption as a dietary supplement.

Abstract: The present invention is in the field of organic and natural product chemistry. The present invention relates to an efficient process for purification, simultaneous extraction, and separation of monohydroxycarotenoids from dihydroxycarotenoids in various natural products or in synthetic mixtures. Similarly, the process can also be applied to the simultaneous extraction, saponification, and separation of esterified mono- and dihydroxycarotenoids in natural products and their oleoresins or in their synthetic mixtures. Therefore, esterified and unesterified monohydroxycarotenoids such as (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin can be efficiently separated from their corresponding dihydroxycarotenoids such as (3R,3?R,6?R)-lutein and (3R,3?R)-zeaxanthin that are found in various plants or in synthetic mixtures.

Abstract: The present invention is in the field of organic and natural product chemistry. The present invention relates to an efficient process for purification, simultaneous extraction, and separation of monohydroxycarotenoids from dihydroxycarotenoids in various natural products or in synthetic mixtures. Similarly, the process can also be applied to the simultaneous extraction, saponification, and separation of esterified mono- and dihydroxycarotenoids in natural products and their oleoresins or in their synthetic mixtures. Therefore, esterified and unesterified monohydroxycarotenoids such as (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin can be efficiently separated from their corresponding dihydroxycarotenoids such as (3R,3?R,6?R)-lutein and (3R,3?R)-zeaxanthin that are found in various plants or in synthetic mixtures.

Abstract: The present invention relates to a process for converting commercially available lutein and/or lutein esters from extracts of marigold flower petals to (3R)-?-cryptoxanthin (major) and (3R,6?R)-?-cryptoxanthin (minor) in ratios ranging from 95:5 to 98:2 in a one-pot reaction at room temperature. Because the entire process can be carried out by employing safe and environmentally friendly food-grade reagents, the resulting mixture of these carotenoids is suitable for human consumption as a dietary supplement.

Abstract: Disclosed is a process for the synthesis of (3R)-3-hydroxy-?-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-?-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-?-ionone ketal that was prepared from (rac)-?-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-?-ionone ketal followed by deprotection, lead to 3-hydroxy-?-ionone that was transformed into (rac)-3-hydrox-?-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-?-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-?-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(?-ionylideneethyl)triphenylphosphonium chloride [(3R)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-Wittig salt] according to known procedures.

Abstract: The present invention relates to a process for converting lutein and/or lutein esters to (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-?-Cryptoxanthin and (3R,6?R)-?-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)-?-cryptoxanthin (major product) and (3R,6?R)-?-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.

Abstract: (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 and accumulate in the human plasma, major organs, and ocular tissues. Another stereoisomer of (3R,3?R)-zeaxanthin that is not of dietary origin but is found in the human ocular tissues is (3R,3?S;meso)-zeaxanthin. There is growing evidence that these carotenoids 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 the Western World. In view of the potential therapeutic application of dietary lutein, (3R,3?R)-zeaxanthin, and (3R,3?S;meso)-zeaxanthin, the industrial production of these carotenoids is of considerable importance.

Abstract: (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)-?-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-?-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.

Abstract: The present invention relates to a process for converting lutein and/or lutein esters to (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-?-Cryptoxanthin and (3R,6?R)-?-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)-?-cryptoxanthin (major product) and (3R,6?R)-?-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.

Abstract: (3R)-3-Hydroxy-?-ionone and (3S)-3-hydroxy-?-ionone are two important intermediates in the synthesis of carotenoids with ?-end group such as lutein, zeaxanthin, ?-cryptoxanthin, and their stereoisomers. Among the various stereoisomers of these carotenoids, only (3R,3?R,6?R)-lutein, (3R,3?R)-zeaxanthin, and (3R)-?-cryptoxanthin are present in commonly consumed fruits and vegetables. There are 3 possible stereoisomers for zeaxanthin, these are: dietary (3R,3?R)-zeaxanthin (1), non-dietary (3S,3?S)-zeaxanthin (2), and non-dietary (3R,3?S;meso)-zeaxanthin (3) which is a presumed metabolite of dietary lutein. Dietary lutein as well as 1 and 3 are accumulated in the human macula and have been implicated in the prevention of age-related macular degeneration. (3R)-?-Cryptoxanthin (4) is also present in selected ocular tissues at a very low concentration whereas its enantiomer (3S)-?-cryptoxanthin (5) is absent in foods and human plasma.

Abstract: (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)-?-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-?-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.

Abstract: (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 and accumulate in the human plasma, major organs, and ocular tissues. Another stereoisomer of (3R, 3?R)-zeaxanthin that is not of dietary origin but is found in the human ocular tissues is (3R, 3?S; meso)-zeaxanthin. There is growing evidence that these carotenoids 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 the Western World. In view of the potential therapeutic application of dietary lutein, (3R, 3?R)-zeaxanthin, and (3R, 3?S; meso)-zeaxanthin, the industrial production of these carotenoids is of considerable importance.

Abstract: A process for extracting and isolating carotenoid esters or carotenoids in high purity from plants without the use of harmful organic solvents. Zeaxanthin esters were isolated and purified from the berries of Lycium Chinese Mill (LCM berries). The esters isolated according to the invention contain substantially no isomerized double bonds. The purified carotenoid esters or carotenoids isolated by this process are free from impurities and serve as a safe source of nutritional supplement for human consumption as well as providing a suitable and effective color additive for human foods.

Abstract: Disclosed is a process for purification of a mixture of carotenoids from palm oil concentrate to produce a crystalline mixture of a ?-carotene, ?-carotene, ?-carotene, and ?,?-carotene as well as a product enriched in geometrical isomers of a ?-carotene (9-cis-?-carotene, 13-cis-?-carotene) and ?-carotene as well as ?,?-carotene and ?-carotene.

Abstract: The present invention relates to a method of reacting (3R,3?R,6?R)-lutein with a catalytic amount of an acid to obtain a mixture of anhydroluteins, rich in anhydrolutein III, with substantially no Z-isomers being formed. The mixture is converted to (3R)-?-cryptoxanthin (major product) and (3R,6?R)-?-cryptoxanthin (minor product) by reacting the anhydroluteins with borane-amine complexes (e.g. Me3N.BH3) or other hydride donors and an acid in a chlorinated solvent, preferably dichloromethane, at ambient temperature to produce (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin.

Abstract: The present invention relates to a process for converting lutein and/or lutein esters to (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-?-Cryptoxanthin and (3R,6?R)-?-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)-?-cryptoxanthin (major product) and (3R,6?R)-?-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.

Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.

Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.

Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.