- Synthesis of retinyl palmitate catalyzed by Candida sp.99-125 lipase immobilized on fiber-like SBA-15 mesoporous material
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Candida sp.99-125 lipase was suitable for transesterification of fats and oils to produce fatty acid methyl ester. The adsorption of Candida sp.99-125 lipase onto the fiber-like SBA-15 mesoporous material has been studied. The unaltered structural order of the fiber-like SBA-15 before and after the adsorption has been confirmed by FT-IR, SEM and N2 adsorption. The amount of adsorbed Candida sp.99-125 lipase depends both on the solution pH and reaction time. Good adsorption capacity of Candida sp.99-125 lipase on fiber-like SBA-15 may be due to solution pH from 5.0 to 9.0 especially at 7.0 (93.99 mg enzyme per gram silica is obtained and the activity recovery is 281.05%). A high lipase loading (135.9 mg enzyme per gram silica) was obtained, but it did not produce a proportionate level of catalytic activity. The immobilized Candida sp.99-125 lipase showed increased adaptability in the hydrolysis of p-nitrophenyl acetate compared to free Candida sp.99-125 lipase at pH 5.0-9.0. Meanwhile, the immobilized Candida sp.99-125 lipase showed higher thermal stability than that of free Candida sp.99-125 lipase. And the synthesis of retinyl palmitate in organic solvent with the immobilized Candida sp.99-125 lipase was investigated. The influence factors, such as: the solvent used, the molar ratio and concentrations of substrates, the reaction time and the amount of lipase were studied and optimized. In the conditions of transesterificating 0.164 g retinyl acetate and 0.32 g palmitic acid, 10 mL of solvent hexane, 1:4 of mass ratio of lipase to retinyl acetate, and 6 hours of reaction time, 74.6% of retinyl acetate was converted into retinyl plamitate. Copyright
- Zhu, Kai,Wang, Jianqiang,Wang, Yan-Hua,Liu, Hui,Han, Ping-Fang,Wei, Ping
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- Synthesis method of 4-palmitoyloxy-2-methyl-2-butenal and synthesis method of vitamin A palmitate
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The invention discloses a synthesis method of a vitamin A palmitate intermediate 4-palmitoyloxy-2-methyl-2-butenal, application of the vitamin A palmitate intermediate 4-palmitoyloxy-2-methyl-2-butenal in vitamin A palmitate synthesis, and a method for synthesizing vitamin A palmitate by using the intermediate. According to the method, in the process of introducing aldehyde group, solvent-free reaction conditions are adopted, so that the use of organic solvents is avoided while the reaction yield is increased, the production cost is reduced, the operation is simple and convenient, and the method is suitable for industrial large-scale production.
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- Method for preparing vitamin A and vitamin A ester
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The invention provides a novel method for preparing vitamin A and vitamin A ester by taking farnesol as a raw material. The method comprises the following steps: carrying out oxidation reaction on farnesol and oxygen under the action of a catalyst and a cocatalyst to generate farnesal; carrying out dehydrogenation reaction on farnesal to generate dehydrofarnesal; carrying out cyclization reactionon the dehydrofarnesal under the catalysis of acid to generate a cyclized intermediate; carrying out a reaction on the cyclized intermediate with chloroisopentenol to generate vitamin A; carrying outan esterification reaction on vitamin A to generate vitamin A ester. The method avoids the defects of an existing process, and the process line is economical and effective.
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Paragraph 0067; 0072
(2020/04/17)
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- Preparation method of vitamin A ester intermediate C15 and vitamin A ester
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The invention provides a preparation method of a vitamin A ester intermediate C15 and vitamin A ester. The method comprises the following steps: carrying out a halogenation reaction and a cyclizationreaction on 3, 7-dimethyl-3-hydroxy-1, 6-octadiene as an initial raw material, carrying out a substitution reaction on the obtained product and triphenylphosphine or triester phosphite to prepare a corresponding Wittig reagent, carrying out a Wittig reaction on the Wittig reagent and 2-methyl-4-acetoxy-2-butenal, performing acidifying, hydrolyzing and acidifying the obtained product, and carryingout a substitution reaction on the hydrolyzed and acidified product and triphenylphosphine or triester phosphite to prepare C15. The vitamin A ester can be prepared by carrying out a Wittig reaction on the obtained C15 and 2-methyl-4-R3 substituent carbonyloxy-2-butenal. The method has the advantages of single reaction type, easy operation and realization of reaction conditions, safe and environment-friendly operation, simple post-treatment and low cost; and the reaction activity is strong, the reaction selectivity is high, the atom economy is high, and the target product yield and purity arehigh.
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- Preparation method of vitamin A palmitate
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The invention belongs to the technical field of medicines, in particular to preparation of vitamin A palmitate and a composition thereof. Aiming at solving the technical problem, the invention provides a preparation method of vitamin A palmitate. The preparation method comprises the steps of carrying out alcoholysis on vitamin A acetate with an alcohol solvent to obtain retinol, and then adding methyl palmitate for alcoholysis again to obtain vitamin A palmitate. The preparation method is simple in process, is environmentally friendly, and has high purity and high yield.
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Paragraph 0017-0028
(2018/10/27)
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- Synthesis method of vitamin A higher fatty acid ester
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The invention discloses a synthesis method of vitamin A higher fatty acid ester, which includes the following steps: a) performing an esterification reaction to vitamin A alcohol and higher fatty acid anhydride in an organic solvent under catalysis of an alkaline metal oxide; and b) performing after treatment after the reaction is finished to obtain the vitamin A higher fatty acid ester. The method is less in reaction by-products, is high in product purity and is good in product quality. The product is more than 97.5% in content and is more than 96.5% in yield through high performance liquid chromatography detection. The vitamin A higher fatty acid ester enables storage, transportation and application of vitamin A to be more convenient. An analytic method in pharmacopeia proves that vitamin A palmitate is 1750000-1780000 IU/g in biological titer and is more than 97.5% in content through the high performance liquid chromatography detection, so that the vitamin A palmitate can be marketed as commodity directly, and is widely applied in the fields of medicines, feed additives and food additives.
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Paragraph 0034; 0035; 0036; 0037
(2016/11/09)
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- TRANSESTERIFICATION PROCESS OF RETINOL ESTERS
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The present invention relates to a transesterification process of specific compounds comprising isoprenoid units.
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Page/Page column 9
(2014/03/21)
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- An LC/MS/MS method for stable isotope dilution studies of β-carotene bioavailability, bioconversion, and vitamin A status in humans
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Isotope dilution is currently the most accurate technique in humans to determine vitamin A status and bioavailability/ bioconversion of provitamin A carotenoids such as α -carotene. However, limits of MS detection, coupled with extensive isolation procedures, have hindered investigations of physiologically-relevant doses of stable isotopes in large intervention trials. Here, a sensitive liquid chromatography- tandem mass spectrometry (LC/MS/MS) analytical method was developed to study the plasma response from coadministered oral doses of 2 mg [ 13 C 10 ] α -carotene and 1 mg [ 13 C 10 ]retinyl acetate in human subjects over a 2 week period. A reverse phase C 18 column and binary mobile phase solvent system separated α -carotene, retinol, retinyl acetate, retinyl linoleate, retinyl palmitate/retinyl oleate, and retinyl stearate within a 7 min run time. Selected reaction monitoring of analytes was performed under atmospheric pressure chemical ionization in positive mode at m/z 537 ? 321 and m/z 269 ? 93 for respective [ 12 C] α -carotene and [ 12 C] retinoids; m/z 547 ? 330 and m/z 274 ? 98 for [ 13 C 10 ] α -carotene and [ 13 C 5 ] cleavage products; and m/z 279 ? 100 for metabolites of [ 13 C 10 ]retinyl acetate. A single one-phase solvent extraction, with no saponification or purification steps, left retinyl esters intact for determination of intestinally-derived retinol in chylomicrons versus retinol from the liver bound to retinol binding protein. Coadministration of [ 13 C 10 ] retinyl acetate with [ 13 C 10 ] α -carotene not only acts as a reference dose for inter-individual variations in absorption and chylomicron clearance rates, but also allows for simultaneous determination of an individual's vitamin A status. - Oxley, A., P. Berry, G. A. Taylor, J. Cowell, M. J. Hall, J. Hesketh, G. Lietz, and A. V. Boddy. An LC/MS/MS method for stable isotope dilution studies of α -carotene bioavailability, bioconversion, and vitamin A status in humans. Copyright
- Oxley, Anthony,Berry, Philip,Taylor, Gordon A.,Cowell, Joseph,Hall, Michael J.,Hesketh, John,Lietz, Georg,Boddy, Alan V.
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p. 319 - 328
(2014/02/14)
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- Preparation of retinyl esters
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Long-chain esters of retinol are prepared via a chemoenzymatic process from short-chain retinyl esters and an appropriate long-chain acid or ester in the presence of an enzyme. Use of various additives enhance the yield of the desired ester and facilitated its purification.
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Page/Page column 11
(2009/08/14)
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- USE OF NANODISPERSIONS IN PHARMACEUTICAL END FORMULATIONS
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A description is given of the use of a nanodispersion, which comprises (a) a membrane-forming molecule, (b) a coemulsifier and (c) a lipophilic component, in pharmaceutical end formulations, the nanodispersion being obtainable by (α) mixing the components (a), (b) and (c) until a homogeneous clear liquid is obtained, and (β) adding the liquid obtained in step (α) to the water phase of the pharmaceutical end formulations, steps (α) and (β) being carried out without any additional supply of energy. The nanodispersions used according to this invention are suitable as transport vehicles for pharmaceutical active agents.
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- Process for producing vitamin a ester
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The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.
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- DNA encoding human κ casein and process for obtaining the protein
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The present invention relates to an expression system comprising a DNA sequence encoding a polypeptide which has a biological activity of human κ-casein, the system comprising a 5′-flanking sequence capable of mediating expression of said DNA sequence. In preferred embodiments the 5′-flanking sequence is from a milk protein gene of a mammal such as a casein gene or whey acidic protein (WAP) gene and the DNA sequence contains at least one intron sequence selected from the intron sequences presented in SEQ ID NO:30. The invention also relates to DNA sequences, replicable expression vectors and cells harboring said vectors, recombinant polypeptide e.g. in glycosylated form, and milk, infant formula or nutrient supplement comprising recombinant polypeptide. The invention further relates to a transgenic non-human mammal such as a mouse, rat, rabbit, goat, sheep, pig, lama, camel or bovine species whose germ cells and somatic cells contain a DNA sequence as defined above as a result of chromosomal incorporation into the non-human mammalian genome, or into the genome of an ancestor of said non-human mammal.
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- Retinal, derivatives and their therapeutic use
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Therapeutic as well as preventive measures to improve cosmetic conditions and to alleviate the symptoms of dermatologic disorders with retinal and its derivatives is disclosed. Cosmetic conditions and dermatologic disorders in humans and domestic animals in which retinal and its derivatives may be useful include age spots, wrinkles, warts, eczema, seborrheic keratoses, acne, oily skin, psoriasis, dandruff, xerosis, inflammatory and pruritic skin, disturbed keratinization skin changes associated with aging and possibly viral infections. Retinal and its derivatives include their stereoisomers, for example, all-trans, 13-cis, 11-cis, 9-cis, 7-cis, 11,13-cis and 9,13-cis vitamin A aldehydes, their hydrate, hemiacetal and acetal forms, and their adduct compounds. Compositions containing retinal or its derivative may be administered systemically such as orally, or topically to the affected areas of the skin.
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