- 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; 0029; 0031
(2018/03/25)
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- FORMULATIONS OF LIPOPHILIC BIOACTIVE MOLECULES
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This invention provides aqueous and non-aqueous clear formulations including at least one lipophilic bioactive molecules and an amphiphilic solubilizing agent. Exemplary aqueous formulations include a water-soluble reducing agent, which diminishes or prevents chemical degradation of the lipophilic bioactive molecule. The invention also provides methods of using the formulations of the invention. For example, the invention provides beverages including the formulations of the invention. The invention further provides methods of making the formulations and beverages.
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Paragraph 0365; 0366; 0367
(2014/02/16)
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- COMPOSITION CONTAINING REDUCED COENZYME Q10, AND MANUFACTURING AND STABILISING METHODS THEREFOR
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The present invention relates to a method of producing reduced coenzyme Q10, including reducing oxidized coenzyme Q10 using a reducing agent in terpenes that can highly dissolve oxidized coenzyme Q10 and reduced coenzyme Q10 in the co-existence of at least one kind of additive selected from the group consisting of alcohols, water, a surfactant and diacylglycerol. In addition, the present invention relates to a composition comprising terpenes, a reducing agent, reduced coenzyme Q10 and at least one kind selected from the group consisting of alcohols, water, a surfactant and diacylglycerol, and a method of stabilizing reduced coenzyme Q10 comprising preparing the composition.
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Paragraph 0156
(2013/06/26)
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- Dietary chlorophyll metabolites catalyze the photoreduction of plasma ubiquinone
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Ubiquinol is a plasma antioxidant. The mechanisms responsible for maintenance of plasma ubiquinol are poorly understood. Here, we show that metabolites of chlorophyll can be found in blood plasma of animals that are given a chlorophyll-rich diet. We also show that these metabolites catalyze the reduction of plasma ubiquinone to ubiquinol in the presence of ambient light, in vitro. We propose that dietary chlorophyll or its metabolites, together with light exposure, regulate plasma redox status through maintaining the ubiquinol pool. Blood vessels growing toward the light: can light protect blood plasma from oxidative damage?
- Qu, Jinfeng,Ma, Li,Zhang, Junhua,Jockusch, Steffen,Washington, Ilyas
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p. 310 - 313
(2013/07/19)
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- Kinetic study of the α-tocopherol-regeneration reaction of ubiquinol-10 in methanol and acetonitrile solutions: Notable effect of the alkali and alkaline earth metal salts on the reaction rates
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A kinetic study of regeneration reaction of α-tocopherol (α-TocH) by ubiquinol-10 has been performed in the presence of four kinds of alkali and alkaline earth metal salts (LiClO4, NaClO4, NaI, and Mg(ClO4)2) in methanol and acetonitrile solutions, using double-mixing stopped-flow spectrophotometry. The second-order rate constants (kr's) for the reaction of α-tocopheroxyl (α-Toc?) radical with ubiquinol-10 increased and decreased notably with increasing concentrations of metal salts in methanol and acetonitrile, respectively. The kr values increased in the order of no metal salt 4 ～ NaI 4 4)2 at the same concentration of metal salts in methanol. On the other hand, in acetonitrile, the kr values decreased in the order of no metal salt > NaClO4 ～ NaI > LiClO4 > Mg(ClO4)2 at the same concentration of metal salts. The metal salts having a smaller ionic radius of cation and a larger charge of cation gave a larger kr value in methanol, and a smaller k r value in acetonitrile. The effect of anion was almost negligible in both the solvents. Notable effects of metal cations on the UV-vis absorption spectrum of α-Toc? radical were observed in aprotic acetonitrile solution, suggesting complex formation between α-Toc? and metal cations. On the other hand, effects of metal cations were negligible in protic methanol, suggesting that the complex formation between α-Toc? and metal cations is hindered by the hydrogen bond between α-Toc? and methanol molecules. The difference between the reaction mechanisms in methanol and acetonitrile solutions was discussed on the basis of the results obtained. High concentrations of alkali and alkaline earth metal salts coexist with α-TocH and ubiquinol-10 in plasma, blood, and many tissues, suggesting the contribution of the metal salts to the above regeneration reaction in biological systems.
- Mukai, Kazuo,Oi, Masanori,Ouchi, Aya,Nagaoka, Shin-Ichi
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body text
p. 2615 - 2621
(2012/05/20)
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- METHOD FOR PRODUCTION OF REDUCED COENZYME Q10 USING WATER-CONTAINING ORGANIC SOLVENT
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The present invention aims to provide reduced coenzyme Q10, which is useful as food, food with nutrient function claims, food for specified health use, nutritional supplement, nutritional product, animal drug, drink, feed, cosmetic, pharmaceutical product, therapeutic drug, prophylactic drug and the like, and a production method of reduced coenzyme Q10. The present invention provides a production method of reduced coenzyme Q10, which includes reducing oxidized coenzyme Q10 with ascorbic acid or its analogue(s) as a reducing agent in a water-containing organic solvent at not more than pH 5. Using the method, the reaction time can be drastically shortened even without adding a basic substance and the like, and unpreferable side reactions can be minimized. Therefore, reduced coenzyme Q10 with high quality can be produced.
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Page/Page column 8
(2010/09/18)
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- COMPOSITIONS CONTAINING COENZYME Q-10 AND DIHYDROLIPOIC ACID
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The invention describes compositions, including soft gelatin capsules, that include dihydrolipoic acid and the reduced form of coenzyme Qn wherein the dihydrolipoic acid acts as a reducing agent for the coenzyme Qn and also, optionally, as a solvent.
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Page/Page column title page; 7; 8; Sheet 1; 2
(2008/12/06)
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- Composition containing reduced coenzyme Q10 and production method thereof
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The present invention provides a particulate composition wherein an oil component containing reduced coenzyme Q10 is polydispersed forming a domain in a matrix containing a water-soluble excipient, which simultaneously shows high oxidative stability and high oral absorbability, a production method thereof, and a stabilizing method thereof. It also provides a food, food with nutrient function claims, food for specified health uses, dietary supplement, nutritional product, animal drug, drink, feed, pet food, cosmetic, pharmaceutical product, therapeutic drug, prophylactic drug and the like, which contain the composition.
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Page/Page column 14
(2008/06/13)
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- SKIN AGENT FOR EXTERNAL USE AND COSMETIC AGENT INCLUDING UBIQUINONE DERIVATIVE OR SALT THEREOF AND METHOD USING THE SAME
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A skin agent for external use and a cosmetic agent are provided, by transdermal administration of which expected actions and effects of ubiquinone derivatives, salts thereof, ubiquinones and ubiquinols are effectively obtained. The skin agent for external use includes a ubiquinone derivative or a salt thereof as an active ingredient. The ubiquinone derivative is represented by the formula (1): wherein R1 and R2 are each a hydrogen atom or a phosphoric group, at least one of R1 and R2 is a phosphoric group, and n is an integer in the range of 1 to 9.
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Page/Page column 45
(2008/12/05)
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- COMPOSITION FOR LIFE EXTENSION AND METHOD OF EXTENDING THE LIFE
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The present invention relates to a composition for life extension, comprising reduced coenzyme Q10 as an active ingredient, as well as relates to a method of extending a life span using the composition comprising reduced coenzyme Q10 as an active ingredient. In the present invention, it has been found that long-term ingestion of feed that contains reduced coenzyme Q10 enables the life span of senescence-accelerated model mice to be extended. No sign indicating toxicity is observed in the senescence-accelerated model mice that have been fed with reduced coenzyme Q10 over a long period. Based on these findings, it was found that the composition containing reduce coenzyme Q10 as an active ingredient has potential to be a composition for life extension with high safety, capable of being taken for a long period. The present invention provides a composition, which can extend the life span of humans or animals, enables them to spend active and healthy senectitudes and shows high safety during the ingestion over a long period.
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Page/Page column 7
(2008/12/05)
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- Method for cancer treatment, carcinogenesis suppression or mitigation of adverse reactions of anticancer agents
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Provided is a method for suppressing carcinogenesis, treating cancer, or mitigating adverse reactions of anticancer agents, with low prevalence of adverse reactions by administering an effective amount of a reduced coenzyme Q as an active ingredient. In the method, the reduced coenzyme Q can be administered in the form of pharmaceuticals, cosmeceutical, cosmetics, foods such as functional foods (supplements, health aid foods, nutritional supplementary foods, nutrient-fortified foods, nutrient-adjusted foods, health beverages, foods for specified health uses, foods with nutrient function claims), animal drugs, animal feeds, or animal foods.
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Page/Page column 7
(2008/12/06)
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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 17
(2008/12/08)
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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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- MITOCHONDRIA ACTIVATORS
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The present invention provides a mitochondrial activator containing pyrroloquinoline quinone, preferably pyrroloquinoline quinone and coenzyme Q (particularly reduced coenzyme Q) as active ingredients. In addition, the present invention provides a mitochondrial activator containing citric acid, preferably citric acid and coenzyme Q (particularly reduced coenzyme Q), as active ingredients. Since pyrroloquinoline quinone or citric acid exhibits a synergistic mitochondria activating effect with coenzyme Q (particularly reduced coenzyme Q), a high effect can be obtained even at a low dose. According to the present invention, therefore, a safer and practical mitochondrial activator is provided. The present invention further provides an agent for the prophylaxis or treatment of a disease caused by mitochondrial dysfunction.
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Page/Page column 11
(2008/06/13)
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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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Page/Page column 8
(2008/06/13)
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- Method for preserving reduced coenzyme Q10
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The present invention has its object to provide a method for stably preserving a capsule containing reduced coenzyme Q10, which is useful as foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. The present invention relates to a method for preserving reduced coenzyme Q10 which comprises producing or obtaining a capsule containing reduced coenzyme Q10, and controlling environment surrounding the capsule to a relative humidity of not less than 0% but not more than 60%. According to this method, reduced coenzyme Q10 can be preserved stably, without requiring huge cost and labor, or special equipment.
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Page/Page column 5-6
(2008/06/13)
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- FATTY ACID-BENZENEDIOL DERIVATIVES AND METHODS OF MAKING AND USING THEREOF
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Disclosed are compounds comprising a benzenediol derivative bound to one or more fatty acids. Also disclosed are nutritional supplements, pharmaceutical formulations, delivery devices, and foodstuffs comprising the disclosed compounds. Methods of using the disclosed compounds and compositions to improve health are also disclosed.
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Page/Page column 41
(2008/06/13)
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- FATIGUE REDUCING AGENT
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To maintain physical fitness and health of middle-aged and older persons living in the threshold of the aging society, the present invention provides a fatigue reducing agent which is highly effective for preventing and reducing fatigue, wherein the agent is made of a composition of substances that are very safe so that long-term administration is possible. A composition containing reduced coenzyme Q was found to be effective for preventing and reducing fatigue, including muscle fatigue. Since the fatigue reducing effect of the composition of the present invention is seen not only in young rats but also more pronounced in aged rats, the present invention can provide the fatigue reducing agent which is very useful, especially, for middle-aged and older persons as well as for young people.
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Page/Page column 6
(2008/06/13)
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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
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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 FOR STABILIZING REDUCED COENZYME Q 10 AND COMPOSITION THEREFOR
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The present invention relates to a method for stabilizing reduced coenzyme Q10, which is useful as an ingredient in good foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc., and to a composition therefor. The composition comprises reduced coenzyme Q10, a fat and oil (excluding olive oil) and/or a polyol, and doesn't substantially inhibit the stabilization of reduced coenzyme Q10. Additionally, the composition is a reduced coenzyme Q10-containing composition which comprises reduced coenzyme Q10, a polyglycerol fatty acid ester, and a fat and oil and/or a polyol.
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- METHOD OF STABILIZING REDUCED COENZYME Q sb 10 /sb
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The present invention provides a stabilization method, a preservation method and the like method of reduced coenzyme Q10, which is useful as functional nutritive foods, specific health foods and the like. Furthermore, the present invention provides a method for efficiently obtaining reduced coenzyme Q10 of high quality and by a method suitable for a commercial production. It is possible to handle and stably preserve reduced coenzyme Q10 under a condition that oxidation by a molecular oxygen is inhibited by contacting reduced coenzyme Q10 with an ascorbic acid and citric acid or a related compound thereof, and thus a stabilized composition is obtained. Moreover, reduced coenzyme Q10 is converted into a crystalline state in such a condition that the formation of oxidized coenzyme Q10 as a byproduct is minimized by crystallizing reduced coenzyme Q10 in the presence of ascorbic acid or a related compound thereof, etc., and thus a reduced coenzyme Q10 crystal of high quality is produced. Furthermore, by successively crystallizing the generated reduced coenzyme Q10 in the presence of ascorbic acid or a related compound thereof after reducing oxidized coenzyme Q10 to reduced coenzyme Q10 using ascorbic acid or a related compound thereof, operations are simplified and minimized, and thus reduced coenzyme Q10 of high quality is produced.
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Page/Page column 17
(2008/06/13)
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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 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 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 surprisingly high reactivity of phenoxyl radicals
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Rate constants have been measured in nonaqueous media for hydrogen atom abstraction by the phenoxyl radical from some biologically important phenols and related compounds. Although the thermochemistry for these reactions must be very similar to the thermochemistry for H atom abstraction from the same substrate by a peroxyl radical, the phenoxyl rate constants, k5, are ca. 100-300 times greater than the (already well-known) peroxyl rate constants, k1. For example, with α-tocopherol in benzene/di-tert-butyl peroxide (1:3, v/v) k5293K = 1.1 × 109 M-1 s-1 vs k1303K = 3.2 × 106 M-1 s-1 in a similar nonpolar medium, and with ubiquinol-10 in the same solvent mixture k5293k = 8.4 × 107 M-1 s-1, while the corresponding value for k1 is 3.5 × 105 M-1 s-1. The greater reactivity of the phenoxyl radical has been traced to the fact that the Arrhenius preexponential factors are much larger than for the corresponding peroxyl radical reactions, i.e., A5 ～ 102A1. For example, with α-naphthol log(A5/M-1 s-1) = 8.9 and E5 = 2.2 kcal/mol vs log(A1/M-1 s-1) = 6.4 and E1 = 1.7 kcal/mol. The preexponential factors for H-atom donors more reactive than α-naphthol are even greater; for example, with α-tocopherol in CH3CN/di-tert-butyl peroxide (1:2, v/v) log(A5/M-1 s-1) = 10.0 and E5 = 2.0 kcal/mol, and with ubiquinol-0 in benzene/di-tert-butyl peroxide (1:3, v/v) log(A5/M-1 s-1) = 10.5 and E5 = 3.5 kcal/mol. The role that intermediate hydrogen-bonded complexes between the reacting radical and the phenolic hydrogen donor may play in these reactions is discussed, and it is pointed out that our results are likely to be relevant to in vivo radical chemistry.
- Foti,Ingold,Lusztyk
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p. 9440 - 9447
(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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