- METHOD FOR THE PREPARATION OF OXYCAROTENOIDS
-
A high-yield process for preparing astaxanthin (3,3'-dihydroxy-β, β- carotene-4, 4'- dione) from silylated derivatives of zeaxanthin (3,3'-dihydroxy-β, β- carotene-3, 3'-diol), whether it be of synthetic or natural origin, is described.
- -
-
Page/Page column 8
(2010/07/10)
-
- Method for Improving Flavor of Astaxanthin-Containing Extract
-
A method for improving the flavor of an astaxanthin-containing extract of the present invention includes the steps of: mixing 0.5 to 1000 parts by weight of ethanol and 1 part by weight of the astaxanthin-containing extract so as to obtain an ethanol mixture; collecting a solid precipitated from the ethanol mixture obtained; and drying the solid collected. In particular, the astaxanthin-containing extract, i.e., the starting material, is an extract from a green alga.
- -
-
-
- PROCESS FOR THE PREPARATION OF ASTAXANTHIN
-
The invention therefore relates to a process for the preparation of astaxanthin of the formula I by reacting 2 mol of the triphenylphosphonium salt of the general formula II in which X represents chlorine, bromine or the (HSO4) radical, preferably bromine, in a Wittig reaction with one mol of the C10-dialdehyde of the formula III which is characterized in that a) the starting compounds of the formulae II and III are taken up in a solvent, the mixture is cooled to a temperature of not more than 10°C, preferably -18°C to +5°C, b) about 0.9 to 1.5, preferably 0.9 to 1.2, mol of a base per mole of triphenylphosphonium salt are added to the resulting reaction mixture at a temperature of not more than 10°C, preferably -18°C to +5°C, c) the base is metered and mixed in over a predetermined reaction time T so that at least a ? base equivalent is added to the reaction mixture continuously or quasicontinuously within a timespan T' ?T and the remainder of the base within the remaining reaction time.
- -
-
Page/Page column 5-11
(2008/06/13)
-
- CRYSTAL FORMS OF ASTAXANTHIN
-
This invention describes previously undisclosed mixtures of specific crystal forms of astaxanthin and the individual crystal forms designated crystal Form I and II together with methods for preparing said crystal Forms. Methods for preparing nutritional dosage forms comprising said novel astaxanthin crystal forms for the life science industry are also disclosed.
- -
-
Page/Page column 28
(2008/06/13)
-
- PROCESS FOR THE SYNTHESIS OF INTERMEDIATES FOR THE PREPARATION OF ASTAXANTHIN
-
The present invention relates to a process for the preparation of intermediates useful in the synthesis of Astaxanthin, in particular C15-Wittig salts, but also 4-oxo-β-ionones, 3-hydroxy-4-oxo-β-ionones and the aryl esters thereof. 4-oxo-β-ionone is prepared by starting from a β-ionone by oxidation with bromates in the presence of iodine or iodide. 3-hydroxy-4-oxo-β-ionone is prepared in 4 steps, starting from 4 -oxo- β-ionone by oxidation with peracids; the aryl esters thereof are solids that are easily isolated and purified by crystallisation, and may be converted in 5 steps to C15-Wittig salts and finally, by the Wittig reaction, to Astaxanthin.
- -
-
Page/Page column 33-34
(2010/11/27)
-
- RECOVERY OF COMPOUNDS USING A NATURAL ADSORBENT
-
The invention provides a method for recovery of compounds by adsorption fish scales. The method can be used for natural and synthetic compounds such as various natural pigments including astaxanthin in an esterified or not and synthetic astaxanthin in free form, or other carotenoid compounds. Fish scales with an adsorbed compound may be used as a source of the compound both for human and animal consumption. In particular, fish scales with adsorbed astaxanthin provide a calcium-rich nutritional supplement with beneficial anti-oxidant properties.
- -
-
-
- Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
-
A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a chemical compound including an at least partially water soluble carotenoid analog or derivative. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ether functionality.
- -
-
-
- ASTAXANTHIN MEDIUM-CHAIN FATTY ACID ESTER, PROCESS FOR PRODUCING THE SAME AND COMPOSITION CONTAINING THE ESTER
-
The present invention provides an astaxanthin medium-chain fatty acid ester, which is expected to be applied in the fields of food, cosmetics and pharmaceuticals, and has higher digestibility and tissue penetration than long chain fatty acid ester form astaxanthins. When the synthesis of an astaxanthin medium-chain fatty acid ester is attempted using the catalytic action of lipase by conventional methods, ester cannot be formed. However, according to the present invention, a composition comprising an astaxanthin medium-chain fatty acid monoester and/or diester is produced by adding a certain amount of water into a reaction system and reacting an astaxanthin or a long chain fatty acid ester thereof with a medium-chain fatty acid, a triglyceride thereof or a suitable ester. Moreover, these monoesters and/or diesters are isolated, as necessary. The present invention further provides food or cosmetics comprising the composition of the present invention.
- -
-
-
- Fatty acid selectivity of microbial lipase and lipolytic enzymes from salmonid fish intestines toward astaxanthin diesters
-
The objective of the work described in this paper was to study a possible FA selectivity of digestive lipolytic enzymes isolated from salmon and trout intestines toward astaxanthin diesters of various FA composition and compare it with the FA selectivity of microbial lipase. Astaxanthin diesters of varying FA composition were prepared in excellent yields (>90%) by chemical esterification using a carbodiimide coupling agent. The astaxanthin diesters were screened in a hydrolysis reaction by various commercially available lipases. The highest conversion rates were observed with the Candida rugosa lipase, which discriminated against n-3 PUFA. The rate of hydrolysis was determined by HPLC. Digestive lipolytic enzymes isolated from salmon and rainbow trout intestines displayed reversed FA selectivity. Thus, astaxanthin diesters highly enriched with n-3 PUFA including EPA and DHA were observed to be hydrolyzed at a considerably higher rate than the more saturated esters. Similar trends in FA selectivity were observed in the hydrolysis of fish oil TAG by the digestive lipolytic enzyme mixtures.
- Halldorsson, Arnar,Haraldsson, Gudmundur G.
-
p. 347 - 353
(2007/10/03)
-
- Preparation of astaxanthin
-
The present invention provides a method for preparing astaxanthin from zeaxanthin. Specifically, the present invention provides a method for said conversion using a halogenating agent with the salt of chloric or bromic acid in an inert solvent.
- -
-
-
- Preparation of 4,4′-diketo-β-carotene derivatives
-
A method of preparing β-carotene derivatives such as canthaxanthin and astaxanthin is described. The method employs an in situ system to generate hypobromous acid as the oxidizing agent using a salt of sulfite, hydrogen sulfite or bisulfite in combination with a bromate salt. Astaxanthin and canthaxanthin are obtained in good yield with a significantly reduced reaction time.
- -
-
Page column 4
(2008/06/13)
-
- Process for making 4,4′-diketo-carotenoids
-
A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Br?nsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.
- -
-
-
- Synthesis and characterization of all-E-(4,4'-13C2)-astaxanthin strategies for labelling the C15-end groups of carotenoids
-
The all-E isomer of (4,4'-13C2)astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% 13C enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C15 + C10 + C15 strategy was used. The central C10-synthon, 2,7-dimethylocta-2,4,6-triene- 1,8-dial (3), was coupled with 13C-enriched C15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C15-phosphonium salt.
- Jansen, Frans Jos H. M.,Lugtenburg, Johan
-
p. 829 - 836
(2007/10/03)
-
- Relative one-electron reduction potentials of carotenoid radical cations and the interactions of carotenoids with the vitamin E radical cation
-
Pulse radiolysis studies have been used to determine the electron- transfer rate constants between various pairs of carotenoids, one of which is present as the radical cation. These dietary carotenoids include those of importance to vision, namely zeaxanthin and lutein. These results have suggested the order of relative ease of electron transfer between six carotenoids. Additional experiments, involving electron transfer between astaxanthin (ASTA), β-apo-8'-carotenal (APO), and vitamin E (TOH), lead to the following order in terms of relative ease of electron transfer for the seven carotenoid radical cations studied: astaxanthin > β-apo-8'-carotenal > canthaxanthin > lutein > zeaxanthin > β-carotene > lycopene, such that lycopene is the strongest reducing agent (the most easily oxidized) and astaxanthin is the weakest, and the radical cations of the visual carotenoids, lutein (LUT) and zeaxanthin (ZEA), are reduced by lycopene (LYC) but not by β-carotene (β-CAR). Work on 7,7'-dihydro-β-carotene (77DH) and vitamin E allows us to better understand the interaction of the vitamin E radicals with carotenoids.
- Edge, Ruth,Land, Edward J.,McGarvey, David,Mulroy, Louise,Truscott, T. George
-
p. 4087 - 4090
(2007/10/03)
-
- Preparation of astaxanthin
-
Improved process for the preparation of astaxanthin by Wittig reaction of 2 mol of 3-methyl-5-(2,6,6-trimethyl-3-oxo-4-hydroxy-1-cyclohexenyl)-2,4-pentadienyltriarylphosphonium salts with one mol of 2,7-dimethyl-2,4,6-octatrienedial avoiding the use of halohydrocarbons as solvents.
- -
-
-
- Preparation of astaxanthin novel intermediates therefor and the preparation thereof
-
Compounds of the formula I STR1 where R1 is H or C1 -C4 -alkyl, R2 is C1 -C4 -alkyl and R3 is an ether, silyl ether or acetal protective group which can be converted into a hydroxyl group by hydrolysis, in particular one of the radicals STR2 and a process for preparing these compounds by reacting an alkenyne of the formula II STR3 in an inert solvent in the presence of lithium amide with a cyclohexenone of the formula III STR4 and the use of the compounds of the formula I for preparing astaxanthin, are described.
- -
-
-
- Interactions between carotenoids and the CCl3O2? radical
-
The reactions of CCl3O2? (a model of alkyl peroxyl radicals which can be selectively generated in nanoseconds) with a range of carotenoids (β-carotene, septapreno-β-carotene, canthaxanthin, astaxanthin, zeaxanthin, and lutein) in the heterogeneous micellar environment, aqueous 2% Triton X-100, have been studied by pulse radiolysis. For all carotenoids investigated two reaction products, absorbing in the near-infrared region, are observed and assigned to the carotenoid radical cation and an addition radical. With the exception of astaxanthin, the carotenoid radical cation formation is biexponential and the slower component matches the first-order decay of the addition radical. In the case of astaxanthin, no radical cation is formed directly by reaction with CCl3O2?, it is formed exclusively from the decay of the addition radical. The results are discussed in terms of the antioxidant properties of carotenoid pigments.
- Hill, Tessa J.,Land, Edward J.,McGarvey, David J.,Schalch, Wolfgang,Tinkler, Jane H.,Truscott, T. George
-
p. 8322 - 8326
(2007/10/03)
-
- Synthesis and characterization of all-E (12,12'-13C2)-, (13,13'-13C2)-, (14,14'-13C2)-, (15,15'-13C2)- and (20,20'-13C2)astaxanthin
-
The all-E isomers of (12,12'-13C2)-, (13,13'-13C2)-, (14,14'-13C2)-, (15,15'-13C2)- and (20,20'-13C2)astaxanthin were prepared by total synthesis starting from commercially available 99percent 13C-enriched acetonitrile, acetic acid and methyl iodide.The astaxanthins were obtained in high purity and with high isotope incorporation (>99percent for every position).For this synthesis, the C15 + C10 + C15 strategy was used.The central C10-synthon, 2,7-dimethylocta-2,4,6-triene-1,8-dial, was symmetrically dilabelled at any position using two new synthetic schemes.The 13C2-enriched C10-dialdehydes were then converted in one step to the 13C2-enriched astaxanthins.
- Jansen, F. J. H. M.,Kwestro, M.,Schmitt, D.,Lugtenburg, J.
-
p. 552 - 562
(2007/10/02)
-
- Preparation of canthaxanthin and astaxanthin
-
A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I STR1 where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II STR2 where R is H (a) or OH (b), with trifluoroacetic acid, reacting the resulting novel trifluoroacetate of the formula III STR3 with triphenylphosphine, and reacting the resulting novel triphenylphosphonium trifluoroacetate of the formula IV STR4 with 2,7-dimethyl-2,4,6-octatriene-1,8-dial under the conditions of a Wittig synthesis. The present invention also relates to the novel trifluoroacetates of the formula III and the corresponding triphenylphosphonium trifluoroacetates of the formula IV.
- -
-
-
- Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. II. Ein neues Konzept fuer die Synthese von (3RS,3'RS)-Astaxanthin
-
Starting from 6-oxo-isophorone (2) a new concept for a seven-step synthesis of (3RS,3'RS)-astaxanthin (1) has been developed.As a key feature of the new approach, the oxidation state of astaxanthin (1) is adjusted already at an early stage of the synthesis.Thus, manipulation on more complex intermediates later in the synthesis is reduced to a minimum.Acetonide 10 or dimer 13 represent the key intermediates of this concept (Scheme 2).The whole sequence has been run on a kg scale with an overall yield of 52percent (s.Scheme 5).
- Widmer, Erich,Zell, Reinhard,Broger, Emil Albin,Crameri, Yvo,Wagner, Hans Peter,et al.
-
p. 2436 - 2446
(2007/10/02)
-