- An Efficient Alternative to the Total Synthesis of Isophytol
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An improved and alternative method for the total synthesis of isophytol from citral via using pseudoionone intermediate was developed and described in this manuscript. This alternative commercially viable approach involves six steps and it represents an alternative method commercially viable over existing published synthetic methods in the literature. This goal was achieved by developing and optimizing an efficient and high yield procedure for the synthesis of a key intermediate i.e. 6,10,14-trimethylpentadectrimethylpentadec-5-en-2-one, by reacting 2-methoxypro-pene with a tertiary alcohol (3,7,11-trimethyldodec-1-ene-3-ol). Isophytol was provided in 58-60% overall yield from citral with >99% purity, evaluated by TLC, GC, and NMR.
- Yerramreddy, Thirupathi R.,Yiannikouris, Alexandros
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p. 996 - 999
(2022/02/17)
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- (6R,10R)-6,10,14-TRIMETYLPENTADECAN-2-ONE PREPARED FROM 3,7-DIMETYLOCT-2-ENAL OR 3,7-DIMETYLOCTA-2,6-DIENAL
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The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimetylpentadecan-2-one in a multistep synthesis from 3,7-dimetyloct-2-enal or 3,7-dimetylocta-2,6-dienal. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.
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Page/Page column 50
(2014/07/08)
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- (6R,10R)-6,10,14-TRIMETYLPENTADECAN-2-ONE PREPARED FROM 6,10-DIMETYLUNDEC-5-EN-2-ONE OR 6,10-DIMETYLUNDECA-5,9-DIEN-2-ONE
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The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimetylpentadecan-2-one in a multistep synthesis from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
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Page/Page column 68
(2014/07/08)
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- (6R,10R)-6,10,14-TRIMETYLPENTADECAN-2-ONE PREPARED FROM (R)-3,7-DIMETYLOCT-6-ENAL
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The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimetylpentadecan-2-one in a multistep synthesis from (R)-3,7-dimethyloct-6-enal. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
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Page/Page column 45
(2014/07/08)
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- (6R,10R)-6,10,14-TRIMETYLPENTADECAN-2-ONE PREPARED FROM 6,10-DIMETYLUNDECA-3,5,9-TRIEN-2-ONE
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The present invention relates to a process of manufacturing (6R,10R) -6,10,14-trimethylpentadecan-2-one in a multistep synthesis from 6,10- dimethylundeca-3,5,9-trien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
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Page/Page column 39
(2014/07/08)
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- Preparation of C10-C30-alkenes by partial hydrogenation of alkynes over fixed-bed supported palladium catalysts
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Alkenes are prepared by partial hydrogenation of alkynes in the liquid phase at from 20 to 250° C. and hydrogen partial pressures of from 0.3 to 200 bar over fixed-bed supported palladium catalysts which are obtainable by heating the support material in the air, cooling, applying a palladium compound and, if required, additionally other metal ions for doping purposes, molding and processing to give monolithic catalyst elements, by a process in whichA) alkynes of 10 to 30 carbon atoms are used as starting compounds,B) the palladium compound and, if required, the other metal ions are applied to the support material by impregnation of the heated and cooled support material with a solution containing palladium salts and, if required, other metal ions and subsequent drying, andC) from 10 to 2000 ppm of carbon monoxide (CO) are added to the hydrogenation gas or a corresponding amount of CO is allowed to form in the liquid phase by slight decomposition of a compound which is added to the reaction mixture and eliminates CO under the reaction conditions.The process is particularly advantageous if the partial hydrogenation is carried out in a tube reactor by the trickle-bed or liquid phase procedure with product recycling at cross-sectional loadings of from 20 to 500 m3/m2*h. The process is particularly suitable for the preparation of 3,7,11,15-tetramethyl-1-hexadecen-3-ol (isophytol), 3,7,11-trimethyl-l-dodecen-3-ol (tetrahydronerolidol), 3,7,11-trimethyl-1,4-dodecadien-3-ol, 3,7,11-trimethyl-1,6-dodecadien-3-ol (dihydronerolidol), 3,7-dimethyloct-1,6-dien-3-ol or 3,7-dimethyloct-1-en-3-ol from the corresponding alkynes.
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- Process for the preparation of tocopherol derivatives and catalyst
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A process is provided for the preparation of an α-tocopherol derivatives which are useful as antisterile vitamins, hypolipidemics, blood flow increasing agents, anti-cytosenility agents, antioxidants and the like. Catalysts are also provided. The α-tocopherol derivatives are represented by the following formula (VII): STR1 wherein n stands for 0 or an integer of from 1 to 5. The derivatives can be industrially prepared by employing as catalyst a metal ion-exchanged montmorillonite, metal ion-exchanged bentonite or metal ion-exchanged saponite which is substituted with one metal ion selected from the group consisting of scandium, yttrium, lanthanide element, aluminium, iron, tin, copper, titanium, zinc, nickel, gallium or zirconium.
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- Synthesis of vitamin E analogues: Possible active forms of vitamin E
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We synthesized several vitamin E analogues containing oxygenated functional groups in place of the 8-methyl group which is common to all the natural vitamin E congeners, based on the hypothesis that the methyl group might be metabolically oxidized to produce active forms which might have specific functions other than the antioxidant function. All the vitamin E analogues examined had antioxidant activity. 8-[6-Hydroxy-2,5,7-trimethyl-2(4,8,12-trimethyltridecanyl)chroman]meth anol (1d) and 2,5,7-trimethyl-2-(4,8,12-trimethyltridecanyl)chroman-6-ol (4d) showed similar activity to α-tocopherol. 6-Hydroxy-2,5,7-trimethyl-2(4,8,12-trimethyltridecanyl)chroman-8-carba ldehyde (2d) and 6-hydroxy-2,5,7-trimethyl-2-(4,8,12-trimethyltridecanyl)chroman-8-carb oxylic acid (3d) showed weaker activity than α-tocopherol, but their duration of action, especially that of 3d was considerably longer.
- Fujishima, Toshie,Kagechika, Hiroyuki,Shudo, Koichi
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