- A novel and practical synthetic route for the total synthesis of lycopene
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A novel route for the total synthesis of lycopene 1 is described. The synthesis is based on: (i) a condensation between 4,4-dimethoxy-3-methylbutanal 4 and methylenebisphosphonic acid tetraethyl ester 5, leading to the C6-phosphonate 6, followed by (ii) a modified Wittig-Horner reaction between 6 and 6-methyl-5-hepten-2-one 7 producing dimethoxy-3,5,9-triene 8, and (iii) another modified Wittig-Horner reaction between C15-phosphonate 2 and C10-triene dialdehyde 3 producing all-E-lycopene. The synthetic steps are easily operated and practical for the large-scale production.
- Shen, Runpu,Jiang, Xiaoyue,Ye, Weidong,Song, Xiaohua,Liu, Luo,Lao, Xuejun,Wu, Chunlei
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Read Online
- Kinetic studies of lycopene isomerization in a tributyrin model system at gastric pH
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A semi-preparative HPLC method was developed in order to isolate and purify the 13-cis-lycopene isomer in tomato-based materials. The result was compared with the naturally predominant all-trans-lycopene isomer, in terms of stability to gastric pH at physiological temperature in a tributyrin model system. Kinetic experiments confirmed that lycopene isomerization is a reversible reaction, and under these conditions the all-trans isomer is more stable than the 13-cis isomer. In addition, it was found that at gastric pH 13-cis-lycopene would predominantly isomerize to the all-trans form rather than undergo oxidation/breakdown. A simulation based on the rate constants calculated in the kinetic study indicated that at gastric pH the lycopene isomeric distribution aimed toward an equilibrium characterized by approx 16% 13-cis-, 16% 9-cis-, and 68% all-trans-lycopene. This study suggests that pH-driven isomerization in the stomach is at least partially responsible for the relatively high cis-lycopene proportion found in vivo.
- Moraru, Catalin,Lee, Tung-Ching
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Read Online
- Method for preparing lycopene
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The invention discloses a method for preparing lycopene. According to the method, a target product, i.e., the lycopene can be obtained through subjecting 3,7-dimethyl-1,6-octadiene-diethyl phosphate and 2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadeca-carbon heptaene dialdehyde, which serve as raw materials, to two step reactions, i.e., a rearrangement dissociation reaction and a condensation reaction only. According to the method, the trans-form content is high, isomerization is not required to be carried out, the route is simple, the operation is simple, the source of the raw materials is convenient, the cost is low, and the recovery rate is high, so that the method is applicable to large-batch industrial production.
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Paragraph 0047-0051; 0053-0056; 0058-0061
(2017/12/30)
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- Method for preparing lycopene
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The invention provides a method for preparing lycopene. The method comprises the following steps: under alkaline condition, pseudoionone and methyl chloroacetate are subjected to a reaction to obtain epoxide, then the epoxide is subjected to hydrolysis and decarboxylation under acidic condition to obtain 2,6,10-trimethyl-3,5,9-undecatriene-1-aldehyde; 2,6,10-trimethyl-3,5,9-undecatriene-1-aldehyde and tetraethyl methylenediphosphonate are subjected to a condensation reaction to obtain 3,7,11-trimethyl-1,4,6,10-tetraene dodecyl dialkyl phosphate; 3,7,11-trimethyl-1,4,6,10-tetraene dodecyl dialkyl phosphate is subjected to transposition, and then is subjected to a Wittig-Horner condensation reaction with 2,7-dimethyl-2,4,6-dimethyl-1,8-dialdehyde to obtain lycopene. The preparation method has the advantages of easy acquisition of the raw materials, short synthesis route, and low cost, and is suitable for industrial production.
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Paragraph 0042-0045
(2017/05/03)
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- METHODS FOR PREPARATION OF LYCOPENES FROM C15-WITTIG SALTS AND METHODS FOR PURIFICATION OF HIGH ALL-E CONTAINING AND HIGH 6Z CONTAINING C15-WITTIG SALTS
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The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig slats mixtures. (with high all-E-contents and high 6Z-contents, respectively). C15-Wittig slats mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C15-Wittig salts are, used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high All-E contents.
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Paragraph 0027
(2016/02/10)
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- C5 BENZOTHIAZOLYL SULFONE COMPOUND, METHOD OF PREPARING THE SAME, METHOD OF PREPARING POLYENE DIALDEHYDE COMPOUND USING THE SAME, AND METHOD OF SYNTHESIZING LYCOPENE USING THE SAME
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Disclosed are a novel C5 benzothiazolyl sulfone compound having an acetal protecting group, a method of preparing the same, and a method of efficiently preparing an apo-carotene dialdehyde compound having a polyene dialdehyde structure using the same. Also, a method of efficiently preparing lycopene by olefination (Julia-Kocienski) between the apo-carotene dialdehyde compound (C20 crocetin dialdehyde) and C10 benzothiazolyl geranyl sulfone is provided.
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Paragraph 0062; 0063; 0064
(2016/03/04)
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- Methods for preparation of lycopenes from C-15 Wittig salts and methods for purification of high all-E containing and high 6Z containing C15-Wittig salts
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The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig salts mixtures (with high all-E-contents and high 6Z-contents, respectively). C15-Wittig salts mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C 15-Wittig salts are used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high all-E contents.
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- Stable and bioavailable compositions of isomers of carotenoids for skin and hair
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Compositions that provide health benefits and methods regarding same are presented. In an embodiment, the present invention provides a primary composition comprising at least one carotenoid-containing material, enriched in Z isomers of the carotenoid compound. For example, the carotenoid-containing material contains by weight a greater percentage of an isomer selected from the group consisting of 5-Z, 9-Z and combinations thereof than of 13-Z isomer.
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Page/Page column 8; 9
(2015/09/28)
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- Whey protein vehicle for active agent delivery
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The present invention relates to whey protein micelles, a process for the preparation of aggregates of the sane and particularly to their use as a delivery vehicle for active agents in the field of nutrition or cosmetics.
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- INTERMEDIATE OF LYCOPENE AND PREPARATION METHOD OF INTERMEDIATE
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The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.
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Paragraph 0098; 0099; 0100; 0101; 0102; 0103; 0104
(2014/02/15)
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- A conjunctive diiodoheptaene for the synthesis of C2-symmetric carotenoids
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(2E,4E,6E,8E,10E,12E,14E)-2,15-Diiodo-6,11-dimethylhexadeca-2,4,6,8,10,12, 14-heptaene, prepared by homometathesis, has been used in palladium-catalyzed Suzuki and Stille cross-coupling reactions with the appropriate partners to construct the C2-symmetric carotenoids β,β-carotene, lycopene, synechoxanthin and 4,4′-diapo-ψ,ψ-carotene-4,4′- dial. The Royal Society of Chemistry 2013.
- Fontán, Noelia,Vaz, Belén,álvarez, Rosana,De Lera, ángel R.
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p. 2694 - 2696
(2013/04/10)
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- 1-Methoxyl-2, 6, 10-Trimethyl-1, 3, 5, 9-Undec-Tetraene, and Preparation Method and Uses thereof
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The invention discloses an intermediate 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2,6,10-trimethyl-2,5,9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.
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- 1-METHOXYL-2,6,10-TRIMETHYL-1,3,5,9-UNDEC-TETRAENE AND PREPARATION METHOD AND USES THEREOF
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The invention discloses an intermediate 1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2, 6, 10-trimethyl-2, 5, 9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2, 6, 10-trimethyl-1, 3, 5, 9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.
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Paragraph 0056; 0057
(2013/03/26)
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- INTERMEDIATE OF LYCOPENE AND PREPARATION METHOD OF INTERMEDIATE
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The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl- 1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.
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- PROCESS FOR ISOMERISATION OF LYCOPENE IN THE PRESENCE OF THIOUREA
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The present invention relates to isomerization of Z-lycopene in mixtures of isomers to mixtures enriched with all E-lycopene.
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Page/Page column 3
(2012/08/08)
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- Lycopene Intermediate 1, 3, 6, 10-Tetra-Double Bond Pentadec-Carbon Phosphonate as well as Preparation Method and Use Thereof
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The invention relates to a novel important lycopene intermediate 3,7, 11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3, 5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.
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- 1,4,6,10-Tetra-Double Bond Pentadec-Carbon Phosphonate, Preparation Method Thereof, And Preparation Method Of Lycopene Using The Same
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1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4), and preparation method thereof are provided. The preparation method comprises: reacting a pseudo ionone of formula (2) with sulfonium salt to prepare a epoxide of formula (9), and then reacting the epoxide of formula (9) with magnesium bromide to prepare a C-14 aldehyde of formula (3); condensing the C-14 aldehyde of formula (3) with tetra-alkyl methylene diphosphonate to obtain 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4). Furthermore, the preparation method of lycopene via 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4) is also provided. The present method has the advantages of short route, easily obtained raw materials, and low cost.
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- PREPARATION METHOD OF CAROTENOID OIL SUSPENSIONS WITH LOW VISCOSITY AND HIGH FLUIDITY AND ITS USE
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The present invention relates to a method of preparing for an oil suspension of carotenoid with low viscosity and high fluidity and use thereof. The method comprises the following steps: mixing carotenoid crystals with tetrahydrofuran, heating the mixture to reflux temperature 50～70°C under stirring to dissolve the crystal, filtering and condensing to obtain the concentrate; mixing the concentrate with ketone solvent, heating the mixture to reflux temperature 60～800□ to dissolve the concentrate, filtering, condensing, adding absolute alcohol, crystallizing under stirring at room temperature, filtering and drying in vacuum to obtain carotenoid crystals; mixing carotenoids crystals after granded with plant oil or grinding carotenoid crystals with plant oils and then adding plant oil, to obtain the oil suspension of carotenoid with low viscosity and high fluidity. While the content of carotenoid is 10.0～45.0wt.% in the oil suspension of carotenoid obtained from the present invention, the oil suspension of carotenoid has high fluidity at temperature 5～25°C, and in the meanwhile do not need any extra heating steps during applications.
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- Use of tall oil pitch extract and compositions which contain it
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Use of the unsaponificable fraction of tall oil pitch in the preparation of a food, cosmetic and/or pharmaceutical composition for the treatment, care and/or prevention of a disease, disorder and/or condition associated with the 5-α-reductase activity.
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- Synthesis of C40-symmetrical fully conjugated carotenoids by olefin metathesis
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In an effort to push olefin metathesis to the limits of conjugation in reactants and products, the C40-symmetrical carotenoids β,β-carotene (1), lycopene (2), (3R,3′R)-zeaxanthin (3), and rac-isozeaxanthin (4), which are conjugated undecaenes, have been synthesized from C21-terminal hexaenes by treatment with Grubbs' second-generation Ru catalyst in dichloromethane at 50 °C.
- Fontan, Noelia,Dominguez, Marta,Ulvarez, Rosana,De Lera, Ungel R.
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p. 6704 - 6712
(2012/01/03)
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- Plant carotene cis-trans isomerase CRTISO: A new member of the FAD red-dependent flavoproteins catalyzing non-redox reactions
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The carotene cis-trans isomerase CRTISO is a constituent of the carotene desaturation pathway as evolved in cyanobacteria and prevailing in plants, in which a tetra-cis-lycopene species, termed prolycopene, is formed. CRTISO, an evolutionary descendant of the bacterial carotene desaturase CRTI, catalyzes the cis-to-trans isomerization reactions leading to all-trans-lycopene, the substrate for the subsequent lycopene cyclization to form all-trans-α/ β-carotene. CRTISO and CRTI share a dinucleotide binding motif at the N terminus. Here we report that this site is occupied by FAD in CRTISO. The reduced form of this cofactor catalyzes a reaction not involving net redox changes. Results obtained with C(1)- and C(5)-deaza-FAD suggest mechanistic similarities with type II isopentenyl diphosphate: dimethylallyl diphosphate isomerase (IDI-2). CRTISO, together with lycopene cyclase CRTY and IDI-2, thus represents the third enzyme in isoprenoid metabolism belonging to the class of non-redox enzymes depending on reduced flavin for activity. The regional specificity and the kinetics of the isomerization reaction were investigated in vitro using purified enzyme and biphasic liposome-based systems carrying specific cis-configured lycopene species as substrates.Thereaction proceeded from cis to trans, recognizing half-sides of the symmetrical prolycopene and was accompanied by one trans-to-cis isomerization step specific for the C(5)-C(6) double bond. Rice lycopene β-cyclase (OsLCY-b), when additionally introduced into the biphasic in vitro system used, was found to be stereospecific for all-trans-lycopene and allowed the CRTISO reaction to proceed toward completion by modifying the thermodynamics of the overall reaction.
- Yu, Qiuju,Ghisla, Sandro,Hirschberg, Joseph,Mann, Varda,Beyer, Peter
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experimental part
p. 8666 - 8676
(2012/03/08)
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- Lifeforce liquid supplement
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Two very important factors in human life—which play vital roles in promoting well being—includes returning the body to homeostasis and giving boost to body called lifeforce to get overall health free from diseases, i.e., its optimal balanced functioning ability. When the body is at homeostasis, there is no place for disease. It is only when the body is out of balance (something is deficient, in excess or stagnating) that pain, illness or disease can occur. The application described is based on returning the body to homeostasis (removing the problem and balancing the body) by providing lifeforce and not on dealing with the symptom (e.g., pain, vitamin deficiency). Imbalance results in various diseases and adverse health conditions (starting from aging to diabetes and cancers). This wonderful composition will interact with the body in a way that allows it to boost lifeforce and reach homeostasis no matter which direction it was. In this combination, in the form of liquid, all the 14 ingredients (Lepidium meyenii (Maca), Croton planstigma (Dragon's blood) tree sap, Uncaria tomentosa (Cat's Claw), Morinda citrifolia (Noni fruit) 4:1 PE, Lutein, Lycopene 5%, Flaxseed Oil (Omega-3-Fatty Acids), Vinpocetine, Phosphatidyl Serine 50%, Korean Ginseng 80%, Bacopa monnieri (Bacopin), CDP Choline (Cognizing), Guaranine (Guarana Seed PE 12%), Yerba Mate Ext. 8%) work as mixture for returning the body to homeostasis and give it lifeforce.
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- Artificially coloring the skin with a carotene compound, a xanthophyll compound and a lipophilic green dye composition
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A method for artificially coloring the skin entails topical application thereon of a composition containing, formulated into a physiologically acceptable medium: a) at least one compound of the carotene type,b) at least one compound of the xanthophyll type,c) at least one lipophilic green dye; the composition advantageously includes a mixture of dyes including:a) at least one compound of the carotene type,b) at least astaxanthin,c) at least one lipophilic green dye.
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- Dialdehyde compound, preparation method thereof, and synthetic method of carotenoids using the same
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The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and β-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and β-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.
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Page/Page column 11
(2009/12/28)
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- NUTRITIONAL FORMULATION
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The present invention relates to nutritional supplements that provide an adult with essential vitamins and minerals that may be lacking in the adult's diet and prevent chronic diseases, such as osteoporosis. A number of combinations of nutrients in set ratios are provided to increase the body's ability to absorb and use the nutrients. These combinations are important in helping the body reach the proper balance required for maximized function. Because adults over the age of 50 years have different nutritional needs, nutritional supplements specifically designed for them are also provided.
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- Stable and bioavailable compositions of isomers of carotenoids for skin and hair
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The present invention relates to a method of manufacturing a stable composition enriched in cis-lycopene (z-isomers) by prolonged heating in solvents of tomatoes, parts of tomatoes, derivative thereof or tomato extracts in solvents.
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- All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use
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Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.
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Page/Page column 2; 21-22; Sheet 3/24
(2008/12/08)
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- Expeditious and practical synthesis of lycopene
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Our lycopene synthesis highlights the expeditious assembly of the carbon skeleton by the use of a readily available ten-carbon unit, geraniol, rather than the original natural five-carbon building block, isopentenyl pyrophosphate. Furthermore, four oxidation steps by the enzyme desaturases to produce the conjugated carbon-carbon double bonds of lycopene are merged into one-pot double elimination reactions in our synthesis. These accomplished the highly efficient synthesis of all-(E)-lycopene from geraniol through a seven-step sequence in 51% overall yield.
- Choi, Eunho,Jung, Eun Yeo,Koo, Sangho
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supporting information; experimental part
p. 365 - 369
(2009/04/08)
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- DIALDEHYDE COMPOUND, PREPARATION METHOD THEREOF, AND SYNTHETIC METHOD OF CAROTENOIDS USING THE SAME
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The novel C dialdehyde compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the expeditious and practical synthetic processes for lycopene and β-carotene by the use of the above novel compound are disclosed. The syntheses of lycopene and β-carotene are characterized by the processes of the coupling reaction between two equivalents of geranyl sulfone or cyclic geranyl sulfone and the above C dialdehyde, the functional group transformation reactions of the diol in the resulting C 40 coupling products to X's (either halogens or ethers), and the double elimination reactions of the functional groups of the benzenesulfonyl and X to produce the fully conjugated polyene chain of the carotenoids.
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Page/Page column 18
(2010/11/29)
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- New syntheses of retinal and its acyclic analog γ-retinal by an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. A formal route to lycopene and β-carotene
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Since the C15 β-end-group aldehyde 10 ((β-ionylidene) acetaldehyde), an excellent intermediate in the syntheses of retinoids, can be synthesized in many ways from β-ionone, and since the corresponding acyclic C15 ψ-end-group aldehyde 5 can easily be synthesized from citral (1) (Scheme 3), we applied the C15 + C5 route to the syntheses of γ-retinal ((all-E)-8) (Scheme 3) and retinal ((all-E)-13) (Scheme 4), and therefore, by coupling (2 x C20 → C 40), to the preparation of lycopene (14) and β-carotene (15) (Scheme 5). Our new syntheses of retinal ((all-E)-13) and γ-retinal ((all-E)-8 use an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation.
- Valla, Alain,Valla, Benoist,Le Guillou, Regis,Cartier, Dominique,Dufosse, Laurent,Labia, Roger
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p. 512 - 520
(2008/02/07)
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- Sulfone coupling and double-elimination strategy for carotenoid synthesis
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A highly efficient synthetic method of carotenoid compounds has been developed on the basis of the sulfone coupling and double-elimination strategy. This method highlighted the sulfone-mediated coupling with the novel C 10 dialdehyde, 2,7-dimethyl-4-octenedial, which was easily prepared and efficiently utilized in the synthesis of the conjugated polyene chains.
- Guha, Samar Kumar,Koo, Sangho
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p. 9662 - 9665
(2007/10/03)
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- Allylic sulfones containing triene moieties as key synthons for carotenoid synthesis
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An efficient synthetic method for the allylic sulfone 2 containing a conjugated triene moiety has been proposed involving i) coupling of allylic sulfones 4 with the C5 bromoallylic sulfide 5, ii) base-promoted dehydrosulfonation in the presence of allylic sulfide, and iii) selective oxidation of the resulting trienyl sulfide to the corresponding sulfone. Total synthesis of lycopene starting from the C15 allylic sulfone 2b has been described, where the new C10 bis(chloroallylic) sulfone 11 proved to be a useful substitute for the C10 bis(chloroallylic) sulfide 3, which did not require the problematic chemoselective sulfur oxidation in a conjugated polyene.
- Ji, Minkoo,Choi, Hojin,Jeong, Young Cheol,Jin, Jingquan,Baik, Woonphil,Lee, Sijoon,Kim, Jeong Soo,Park, Minsoo,Koo, Sangho
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p. 2620 - 2628
(2007/10/03)
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- Process for preparing carotenoid polyene chain compounds and intermediates for preparing the same
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The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.
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- A highly efficient chain-extension process in the systematic syntheses of carotenoid natural products
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Successive elongation by a C5 unit is possible when an allylic sulfone is couple with 4-bromo-3-methyl-2-butenyl phenyl sulfide (1). The thiosulfone compound formed was then oxidized to the corresponding disulfone, which, upon coupling with another equivalent of 1 and oxidation, produced the trisulfone 2, again elongated by a C5 unit (see scheme). This process, which can be repeated again, is the basis for a highly efficiently synthesis of carotenoids.
- Ji, Minkoo,Choi, Hojin,Park, Minsoo,Kee, Minyong,Jeong, Young Cheol,Koo, Sangho
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p. 3627 - 3629
(2007/10/03)
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- Process for producing lycopene and intermediate thereof
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There are disclosed a sulfonaldehyde derivative of formula (2): a phosphonium salt of formula (3): processes for producing the same and a sulfone derivative of formula (4): a process for producing the same and a process for producing lycopene therefrom.
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- C-15 phosphonate reagent compositions for the manufacture of compounds such as lycopene and methods of synthesizing the same
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The present invention describes novel phosphonate reagent compositions of the formula: STR1 wherein R and R'=C1 -C4 alkyl groups, or R, R'=(CH2)n (n=2 or 3) or [CH2 C(CH3)2 CH2 ]. The invention also describes allylic C-15 phosphonate compounds of the formula: STR2 wherein R and R'=C1 -C4 alkyl groups. The invention also describes methods of preparing phosphonate reagent compositions (4), allylic phosphonate compounds (5), and lycopene.
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- Method for the manufacture of carotinoids and the novel intermediates
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Phosphonium salts of the formula STR1 wherein A signifies aryl and Y- signifies C1 -C6 -alkanoate or hydroxytrifluoroborate, as well as their manufacture from 3,7,11-trimethyldodeca-1,4,6,10-tetraen-3-ol with a triarylphosphine and with a C1 -C6 -alkanoic acid or a boron trifluoride etherate and, if desired after conversion into the phosphonium salt of a strong acid, further reaction to give lycopene.
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- Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes
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Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS-spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5'Z)-, (7Z,7'Z)-, (7Z,9Z)-, (9Z,9'Z)-, and (7Z,9Z,7'Z,9'Z)-lycopene.Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9'Z)-, (9Z,13'Z)-, (5Z,9Z,5'Z)-, and (5Z,13Z,5'Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep.HPLC and were identified by 1H-NMR spectroscopy.
- Hengartner, Urs,Bernhard, Kurt,Meyer, Karl,Englert, Gerhard,Glinz, Ernst
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p. 1848 - 1865
(2007/10/02)
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- Synthesen von Carotinen mit ψ-Endgruppen und (Z)-Konfiguration an terminalen konjugierten Doppelbindungen
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Five carotenes bearing (5Z)-ψ-end groups were synthesized and carefully characterized: (5Z)-lycopene (6), (5Z,5'Z)-lycopene (7), (5'Z)-neurosporene (8), (5'Z)-β,ψ-carotene (12), and (5'Z)-εψ-carotene (14).
- Zumbrunn, Albrecht,Uebelhart, Peter,Eugster, Conrad Hans
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p. 1519 - 1539
(2007/10/02)
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- Manufacture of symmetrical carotenoids
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Symmetrical carotenoids are prepared from the half-molecules by dimerizing the phosphonium salts of the half-molecules with peroxides, peroxo compounds or peroxy compounds in an alkaline medium.
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