- Controlling regiochemistry in negishi carboaluminations. Fine tuning the ligand on zirconium
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The species on the zirconocene catalyst is changed from two Cp's to the Brintzinger ligand and catalytic amounts of MAO are used to usually effect a >99% regiocontrol of Negishi carboaluminations of 1-alkynes in toluene. Copyright
- Lipshutz, Bruce H.,Butler, Tom,Lower, Asher
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Read Online
- A Novel Solvent Effect in the Practical Synthesis of Ubiquinone-10
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The mixed solvent of nitromethane and hexane exhibited high stereoselectivity with good yields in the synthesis of ubiquinone-10 by the coupling of 2,3-dimethoxy-5-methylhydroquinone and isodecaprenol in the presence of a catalytic amount of BF3*OEt2.
- Eto, Hirozumi,Eguchi, Chikahiko
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Read Online
- Method for synthesizing coenzyme Q10 from 5-demethoxy coenzyme Q10
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The invention relates to a method for synthesizing a coenzyme Q10 from a 5-demethoxy coenzyme Q10. The method comprises the following steps of: taking the 5-demethoxy coenzyme Q10 as a raw material, and carrying out a 1,4-addition reaction, a methoxylation reaction and an oxidation reaction to finally prepare the coenzyme Q10. According to the method, the 5-demethoxy coenzyme Q10 is used as a rawmaterial, the process route is short, the yield is high, the product purity is high, the content detected by adopting HPLC (High Performance Liquid Chromatography) of a pharmacopoeia analysis method is 98% or more, and the problem of a byproduct 5-demethoxy coenzyme Q10 generated in a production fermentation process of the coenzyme Q10 is solved, thereby changing wastes into valuables.
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Paragraph 0006; 0020; 0022; 0024; 0026; 0027; 0031
(2018/03/25)
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- Synthesis of coenzyme Q10
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A practical synthesis of coenzyme Q10 has been developed. The route features an improved Friedel-Crafts allylation of tetramethoxytoluene with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride at 40 °C. Replacement of the methyl ether protecting groups of the para-hydroquinone by methoxymethyl groups at Q1 stage proceeded efficiently, and allowed the facile final oxidation to coenzyme Q10 to occur under mild acidic conditions. The overall yield of coenzyme Q 10 from commercially available tetramethoxytoluene reached 53 % in this improved procedure. An improved synthesis gave CoQ10 in 53 % overall yield from tetramethoxytoluene through Friedel-Crafts allylation with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride and a modified oxidation procedure. Copyright
- Oh, Eun-Taek,Taek Oh, Jung,Koo, Sangho,Jin Kim, Hee,Su, Liang,Yun, Inkyun,Nam, Kyunggu,Min, Jae-Hong,Woo Kim, Joon
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p. 4954 - 4962,9
(2020/08/24)
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- POORLY SOLUBLE SUBSTANCE-SURFACTANT COMPLEX PRODUCT, AND PROCESS FOR PRODUCTION THEREOF
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This invention is intended to improve the solubility and permeability of low-solubility drugs, including drugs hardly soluble in water, classified as Class 2 or 4 in accordance with BCS by modifying such drugs into S/W, S/O, or S/O/W preparations. The S/W, S/O, or S/O/W preparations of low-solubility drugs of this invention are prepared by a method for preparing a composite of a low- solubility drug and surfactant by introducing air or nonflammable gas into the gas phase in the upper portion of a liquid level of the dispersion, dissolution, and emulsification tanks, respectively, at a pressure of 1 to 10 atm.
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- Novel Intermediates, Process for Their Preparation and Process for the Preparation of Coq10 Employing the Said Novel Intermediates
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The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme Q10 or CoQ10 has the chemical name 2-[(all-trans)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone and has the formula I. The invention also provides new intermediates useful for the preparation of CoQ10 and processes for their preparation.
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Page/Page column 18
(2008/12/08)
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- PROCESS FOR THE PREPARATION OF UBIHYDROQUINONES AND UBIQUINONES
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A process for the preparation of ubihydroquinones and ubiquinones by condensation of a prenol or isoprenol with a hydroquinone or derivative thereof in the presence of 0.005 - 1.0 mol% of a catalyst which is a Broensted-acid, a Lewis-acid from the group consisting of a derivative of Bi or In or an element of group 3 of the periodic table of the elements, a heteropolyacid, an NH- or a CH-acidic compound, and optionally oxidizing the ubihydroquinone obtained.
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Page/Page column 9; 12-13
(2008/06/13)
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- NOVEL INTERMEDIATES, PROCESS FOR THEIR PREPARATION AND PROCESS FOR THE PREPARATION OF COQ10 EMPLOYING THE SAID NOVEL INTERMEDIATES
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The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme QlO or CoQlO has the chemical name 2- [(all -trans)- 3, 7,l l,15,19,23,27,31,35,39-decamethyl-2, 6, 10, 14, 18, 22, 26, 30, 34, 38 - tetracontadecaenyl]-5-6-dimethoxy -3- methyl -1,4-benzoquinone and has the formula 1. The invention also provides new intermediates useful for the preparation of CoQlO and processes for their preparation.
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Page/Page column 8; 16-17
(2008/06/13)
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- Friedel-Crafts allylation of 2-(benzyloxy)-3,4,5-trimethoxytoluene catalysed by a metal trifluoromethanesulfonic salt: Synthesis of coenzyme Q10
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In the presence of a catalytic amount of scandium triflate, 2-benzyloxy-3,4,5-trimethoxytoluene reacted with allylic derivatives 4, giving the key intermediate 3 (R = benzyl) which was used for preparing coenzyme Q10, in moderate to high yields.
- Zheng, Yun-Feng,Lin, Jing-Du,Li, Cheng-Ping,Li, Jing-Hua
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p. 686 - 688
(2008/09/21)
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- Enhancing regiocontrol in carboaluminations of terminal alkynes. Application to the one-pot synthesis of coenzyme Q10
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Two new "generations" of methodological advances are reported for the Negishi carboalumination of terminal alkynes. Use of simple, inexpensive additives that alter the Al-Zr complex formed between Me3Al and Cp2ZrCl2 give rise to an especially effective reagent mix that results in virtually complete control of regiochemistry upon carboalumination of 1-alkynes. One timely application to coenzyme Q10 is highlighted. Regioisomers from subsequent coupling, which would otherwise be very difficult to separate, are avoided.
- Lipshutz, Bruce H.,Butler, Tom,Lower, Asher,Servesko, Jeff
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p. 3737 - 3740
(2008/02/12)
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- Synthetic studies on coenzyme Q10: Part 31) - An improved C5 + C45 approach to the stereoselective synthesis of coenzyme Q10 via metal-halogen exchange strategy
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An efficient and stereoselective approach to the synthesis of coenzyme Q10 is described (Scheme). The MeOCH2-protected p-hydroquinone 4 containing the C5 (E)-allyl (tert-butyl) dimethylsilyl ether moiety was obtained via a halogen-lithium exchange of the MeOCH2-proctected 2-bromo-5,6-dimethoxy-3-methylhydroquinone 2 and subsequent addition to (E)-(tBuMe2Si)-OCH 2C(Me)= CHCH2Br (3). The reductive desulfonylation of compound 8, obtained from 4 via 5-7, was successfully carried out by employing Li/EtNH2.
- Yu, Xiong-Jie,Dai, Hui-Fang,Chen, Fen-Er
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p. 967 - 971
(2008/02/04)
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- IMPROVED PROCESS FOR THE SYNTHESIS OF COQ10
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The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme Q10 or CoQ10 has the chemical name 2- [(all -trans)- 3, 7,l l,15,19,23,27,31,35,39-decamethyl-2, 6, 10, 14, 18, 22, 26, 30, 34, 38 - tetracontadecaenyl]-5,6-dimethoxy -3- methyl -1,4-benzoquinone and has the formula 1.
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- PURIFICATION METHOD OF REDUCED COENZYME Q10
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The present invention provides reduced coenzyme Q10 with a low reduced coenzyme Q10 analog content, which is useful as a food, nutritional product, nutritional supplement, animal drug, drink, feed, cosmetic, pharmaceutical product, therapeutic drug, prophylactic drug and the like, and a production method of the reduced coenzyme Q10. The present invention also provides a method of producing a reduced coenzyme Q10 crystal or reduced coenzyme Q10-containing composition, which includes subjecting reduced coenzyme Q10 to chromatography under oxidation preventive conditions, or purifying oxidized coenzyme Q10 by chromatography and converting the oxidized coenzyme Q10 to reduced coenzyme Q10. According to this method, high quality reduced coenzyme Q10 containing not more than 1 wt %, relative to reduced coenzyme Q10, of at least one reduced coenzyme Q10 analog selected from the group consisting of cis-reduced coenzyme Q10, reduced coenzyme Q11 and ubichromenol, can be obtained.
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(2008/06/13)
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- Synthetic studies on coenzyme Q10: Part 2 - A efficient and improved synthesis of coenzyme Q10 via the C5 + C 45 approach
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An improved route to coenzyme Q10 (1) starting from commercially available coenzyme Q1 is described. The key steps in this synthesis are the SeO2-mediated oxidation of the protected isoprenylhydroquinone 3 into the (E)-allyl alcohol 5 without the formation of undesired stereoisomer and the one-pot reductive elimination of the phenylsulfonyl and dibenzyl groups in 7 by using naphthalenyllithium.
- Dai, Hui-Fang,Chen, Fen-Er,Yu, Xiong-Jie
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p. 1317 - 1321
(2007/10/03)
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- A process for the preparation of coenzyme Q10
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A process for the preparation of the compound of formula II by removal of the phenylsulfone group from the compound of formula I characterized in that the phenylsulfone group is removed in the presence of PdCl2-1,2-diphenylphosphinoethane and LiHBEt3.
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(2008/06/13)
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- COMPOSITION CONTAINING REDUCED COENZYME Q
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It is an object of the present invention to provide a reduced coenzyme Q, as a composition capable of being stably stored and, at the same time, soluble in water, which has not been used for industrial application because of its auto oxidation and lipophilic property. A reduced coenzyme Q-containing composition capable of being stored in a refrigerator or at room temperature for a prolonged period of time and of being soluble in water can be prepared by contacting or mixing the reduced coenzyme Q and a cyclodextrin to obtain a clathrated compound or by mixing an antioxidant, the reduced coenzyme Q and the cyclodextrin under an appropriate condition.
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Page/Page column 7; 8; 12
(2008/06/13)
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- METHOD OF PURIFYING UBIQUINONE-10
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It is intended to provide a method of purifying ubiquinone-10 characterized by separating and removing a structural analog of ubiquinone-10 contained in a raw material liquid containing ubiquinone-10 by using an acrylic porous cross-linked polymer, more preferably a method of purifying ubiquinone-10 characterized by separating and removing a structural analog of ubiquinone-10 contained in a raw material liquid by feeding the raw material liquid containing ubiquinone-10 to a simulated moving-bed type chromatography apparatus capable of circulating a solution in one direction in a bed packed with an acrylic porous cross-linked polymer and flowing an eluate in the packed bed in one direction.
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Page/Page column 12-13; 1/1
(2008/06/13)
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- METHOD FOR PRODUCING PURE OR ENRICHED Q 10 COENZYME
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The invention relates to a method for producing a pure or enriched Q10 coenzyme of formula (I) by separating a mixture containing the Q10 coenzyme and a compound of formula (II).
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Page/Page column 12-17
(2008/06/13)
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- Practical, cost-effective synthesis of ubiquinones
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The present invention provides a convergent method for the synthesis of ubiquinones and ubiquinone analogues. Also provided are precursors of ubiquinones and their analogues that are useful in the methods of the invention. The invention further provides an improved method for the carboalumination of alkyne substrates.
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Page/Page column 18-19
(2008/06/13)
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- Synthetic studies on coenzyme Q10: Part 1 - An efficient and highly stereocontrolled synthesis of coenzyme Q10 via a C 5+C45 strategy
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A practical, highly stereoselective ten-step synthesis of coenzyme Q 10 (1) has been accomplished (overall yield ca. 28%), starting from commercially available 2,3-dimethoxy-5-methylbenzoquinone (Scheme). The introduction of the first side-chain isoprenyl group with (E)-configuration (compound 6) was realized by means of a coupling reaction of the aromatic system 3 with oxirane, followed by Swern oxidation and Wittig olefination. The tosyl (Ts) group in the sulfone 9 was selectively removed with sodium naphthalenide in THF to afford 1.
- Yu, Xiong-Jie,Chen, Fen-Er,Dai, Hui-Fang,Chen, Xu-Xiang,Kuang, Yun-Yan,Xie, Bin
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p. 2575 - 2581
(2007/10/03)
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- METHOD OF STABILIZING REDUCED COENZYME Q10 AND METHOD OF ACIDIC CRYSTALLIZATION
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The present invention relates to a method of efficiently producing reduced coenzyme Q10 having excellent qualities which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. It is possible to handle reduced coenzyme Q10 in state of being protected from oxidation by molecular oxygen by bringing the reduced coenzyme Q10 in contact with a solvent containing a strong acid. Furthermore, when reduced coenzyme Q10 is crystallized in the presence of a strong acid, crystallization can be carried out while the formation of oxidized coenzyme Q10 as a by product is minimized, and, then high-quality crystals thereof can be produced.
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- METHOD OF PRODUCING REDUCED COENZYME Q10
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The present invention relates to a method of conveniently and efficiently producing high-quality reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. A method of producing a reduced coenzyme Q10 ???which comprises reducing an oxidized coenzyme Q10 in an aqueous medium with the use of hyposulfurous acid or a salt thereof, ???said reduction being carried out in the coexistence of a salt and/or under deoxygenated atmosphere, and at pH of 7 or below. Thus, the formation of the oxidized coenzyme Q10 as a by-product due to oxidation can be minimized, thereby giving reduced coenzyme Q10 having excellent qualities in a high yield.
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- METHOD OF PRODUCING REDUCED COENZYME Q10 USING SOLVENT WITH HIGH OXIDATION-PROTECTIVE EFFECT
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The present invention relates to a method of conveniently and efficiently producing reduced coenzyme Q10 having excellent qualities which is useful in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, drinks, feeds, animal drugs, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. In a method of synthesizing reduced coenzyme Q10 by reducing oxidized coenzyme Q10, followed by crystallization, at least one species selected from among hydrocarbons, fatty acid esters, ethers and nitriles is used as a solvent. Thus, the reduced coenzyme Q10 can be protected from oxidation, and as a result, the formation of the oxidized coenzyme Q10 as a by-product can be minimized, thereby giving reduced coenzyme Q10 having excellent qualities.
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- METHOD OF PURIFYING REDUCED COENZYME Q
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The object of the present invention is to provide a method of purifying reduced coenzyme Q10 to produce a high-quality product which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc., by a efficient manner suitable for an industrial scale production. The present invention relates to a method of purifying reduced coenzyme Q10 which comprises washing crystals and/or oil of reduced coenzyme Q10 with a water-soluble organic solvent or a mixed solvent composed of a water-soluble organic solvent and water to thereby remove water-soluble impurities, especially a reducing agent or impurities derived from a reducing agent, from the crystals and/or oil of reduced coenzyme Q10. The present invention makes it possible to conveniently and efficiently purify reduced coenzyme Q1o in a manner excellent in operationality, and to obtain a high-quality reduced coenzyme Q10.
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- METHOD OF PRODUCING REDUCED COENZYME Q10 CRYSTALS WITH EXCELLENT HANDLING PROPERTIES
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The present invention provides a method of producing reduced coenzyme Q10 crystals suitable for commercial scale production thereof. According to a method of the present invention of producing a reduced coenzyme Q10 crystal which comprises a crystallization of reduced coenzyme Q10 in a solution of alcohols and/or ketones, reduced coenzyme Q10 crystal excellent in slurry properties and crystalline properties maybe obtained. Moreover, an isolation process including a crystal separation or the whole process including the isolation process may be minimized and simplified. Thus, highly pure reduced coenzyme Q10 may be obtained in a high yield.
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- METHOD OF PRODUCING REDUCED COENZYME Q10 AS OILY PRODUCT
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The present invention provides a method for obtaining reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. suited for a commercial scale production in high quality and efficiently. The high-quality oily reduced coenzyme Q10 which has low viscosity and thereby easily handled may be produced by separating an aqueous phase from the reaction mixture obtainable by oily reacting oxidized coenzyme Q10 with a reducing agent in water, or by distilling off an coexisting organic solvent at or above the melting temperature of reduced coenzyme Q10 in concentrating the organic phase containing reduced coenzyme Q10. Moreover, a solution or slurry of reduced coenzyme Q10 may be obtained by adding a desired solvent to the obtained oily product, or a solid of reduced coenzyme Q10 may be produced by contacting the oily product with a seed crystal.
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- The Friedel-Crafts allylation of a prenyl group stabilized by a sulfone moiety: Expeditious syntheses of ubiquinones and menaquinones
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An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel-Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene (7b). Expeditious total syntheses of coenzyme Q-10 and vitamin K2(20) have been demonstrated from these valuable key compounds 4a and 4b.
- Min, Jae-Hong,Lee, Jun-Sup,Yang, Jae-Deuk,Koo, Sangho
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p. 7925 - 7927
(2007/10/03)
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- A short, highly efficient synthesis of coenzyme Q10
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The most efficient synthesis reported to date of ubiquinone (CoQ10) is described. A sequence consisting of six operations is involved which leads to crystalline material in an overall yield of >64%. Copyright
- Lipshutz, Bruce H.,Mollard, Paul,Pfeiffer, Steven S.,Chrisman, Will
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p. 14282 - 14283
(2007/10/03)
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- A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q10
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Chemical equation presented A truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q10, (E,Z,E)-geranylgeranoil, and other natural or unnatural compounds have been synthesized efficiently.
- Negishi, Ei-Ichi,Liou, Show-Yee,Xu, Caiding,Huo, Shouquan
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p. 261 - 264
(2007/10/03)
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- Synthesis and spectroscopic characterization of [5-13C]- and [6-13C]ubiquinone-10 for studies of bacterial photosynthetic reaction centers
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This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-13C]- and [3-13C]ubiquinone-0 and of [5-13C]- and [6-13C]ubiquinone-10. A scheme based on the synthetic approach to [5-13C]ubiquinone-10 has been worked out for the synthesis of ubiquinones 13C-labeled at any individual position and at every combination of positions in the quinone ring. The [5-13C]- and [6-13C]ubiquinone-10 isotopomers were incorporated into the QA-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of QA with a dynamic perturbation involving the 4-carbonyl functionality.
- Boers, Rutger B.,Gast, Peter,Hoff, Arnold J.,De Groot, Huub J. M.,Lugtenburg, Johan
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p. 189 - 202
(2007/10/03)
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- Synthesis and spectroscopic characterisation of 13C-labelled ubiquinone-0 and ubiquinone-10
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(1-13C)-, (2-13C)-, (3-13C)-, (3-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-10 and the corresponding (1-13C)-, (6-13C)-, (5-13C)-, (5-13CH3)-, (4-13C)-, and (13CH3O)2-ubiquinone-0 have been synthesised from simple labelled starting materials via a single reaction scheme.The ubiquinones have been characterised using mass spectrometry, 1H NMR and 13C NMR.The spectroscopic results indicate that, within experimental error, the syntheses have been accomplished without scrambling or dilution of label.All labelled ubiquinones have been synthesised on a decigram scale.
- Liemt, W. B. S. van,Steggerda, W. F.,Esmeijer, R.,Lugtenburg, J.
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p. 153 - 162
(2007/10/02)
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- Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10
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Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.
- Yanagisawa,Nomura,Noritake,Yamamoto
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p. 1130 - 1136
(2007/10/02)
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- Total Synthesis of Linear Polyprenoids. 3. Syntheses of Ubiquinones via Palladium-Catalyzed Oligomerization of Monoterpene Monomers
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A general methodology for highly regio- and stereoselective Pd(0)-catalyzed, stepwise allylic coupling of bifunctional monomers was developed, representing a practical approach for total synthesis of naturally occuring polyprenoids.As an example, the total synthesis of the cardiovascular agent ubiquinone 10 (coenzyme Q10), as well as shorter ubiquinones, was carried out via selective coupling of monomers easily derived from geraniol that contain either one or two reacting functional end groups.One of these funcionalities is a latent allylic electrophyle activated by the Pd(0) catalyst and the other is a latent nucleophile activated by an appropriate base.After the desired decaprenyl carbon skeleton of Q10 was achieved, the synthesis was completed by removal of the activating groups: Methyl ester was deleted via a highly efficient demethoxycarbonylation procedure involving 4-aminothiophenol and catalytic amounts of cesium carbonate, and the allylic sulfones were deleted by Pd(0)-catalyzed allylic reduction.Finally, oxidation of the aromatic ring to quinone affords ubiquinone 10.
- Eren, Doron,Keinan, Ehud
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p. 4356 - 4362
(2007/10/02)
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- Palladium-Catalyzed Regio- and Stereoselective Reduction of Allylic Compounds with LiHBEt3. Application to the Synthesis of Co-enzyme Q10
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Regio- and stereoselective desulfonylation of allylic sulfones with LiHBEt3 in the presence of a catalytic amount of was succesfully applied to the synthesis of co-enzyme Q10.It was found that this reduction system was applicable to a wide variety of allylic functional groups.
- Mohri, Mitsunobu,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi,Takagaki, Hidetsugu,Yamazaki, Keiji
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p. 1177 - 1180
(2007/10/02)
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- Synthetic Studies on Isoprenoidquinones. II. Syntheses of Ubiquinone-10, Phylloquinone, and Menaquinone-4 by a Chain-Extending Method Utilizing Terminally Functionalized Isoprenoidhydroquinones
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Physiologically active polyisopreoidquinones, ubiquinone-10 (coenzyme Q10), phylloquinone (vitamin K1), and menaquinone-4 (vitamin K2(20)) were synthesized by a chain-extending method utilizing protected hydroquinones with the omega-hydroxyprenyl or omega-hydroxygeranyl side chain.Conditions for reductive desulfurization subsequent to allylic homologation was investigated. Keywords - polyisoprenoidquinone synthesis; ubiquinone-10; phylloquinone; menaquinone-4; chain-extending method; sulfone coupling; reductive desulfurization
- Masaki, Yukio,Hashimoto, Kinji,Kaji, Kenji
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p. 3959 - 3967
(2007/10/02)
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- An Efficient Stereoselective Synthesis of Co-enzyme Q10
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Co-enzyme Q10 was efficiently synthesised by stereo- and regio-selective prenylation of the protected hydroquinone (2) with isoprene epoxide and solanesyl p-tolyl sulphone in a good overall yield.
- Sato, Kikumasa,Miyamoto, Osamu,Inoue, Seiichi,Yamamoto, Tomoya,Hirasawa, Yukihiko
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p. 153 - 154
(2007/10/02)
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- REGIOSELECTIVE POLYPRENYL REARRANGEMENT OF POLYPRENYL 2,3,4,5-TETRASUBSTITUTED PHENYL ETHERS PROMOTED BY BORON TRIFLUORIDE
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4-Acetoxy-6-polyprenyl-2,3,5-trimethylphenols or 2,3-dimethoxy-5-methyl-6-polyprenylhydroquinones were obtained selectively by the BF3*OEt2 catalyzed polyprenyl rearrangement of polyprenyl 4-acetoxy-2,3,5-trimethylphenyl ethers or polyprenyl 2,3-dimethoxy-4-hydroxy-5-methylphenyl ethers.
- Yoshizawa, Toyokichi,Toyofuku, Hatsunori,Tachibana, Koichi,Kuroda, Toshio
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p. 1131 - 1134
(2007/10/02)
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- Ubidecarenone compositions having enhanced absorption properties
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A novel ubidecarenone composition comprising ubidecarenone and higher fatty acid(s) or monoglyceride(s) of higher fatty acid(s), or a mixture thereof, which has improved absorptivity through the lymphatic duct.
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