- Method for synthesizing aromatic folic acid from methyl heptenone
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The invention provides a method for synthesizing aromatic folic acid from methyl heptenone. The method comprises the following steps: under the actions of a Lewis acid catalyst and a cocatalyst, condensing methyl heptenone and ketene to obtain a beta-propiolactone intermediate, hydrolyzing beta-propiolactone, acidifying and dehydrating to obtain aromatic folic acid. The synthetic route is novel, alarge amount of methyl heptenone and ketene which are easy to obtain and low in price serve as starting materials, the aromatic folic acid is synthesized through two-step reaction, the synthetic route is short, the yield is high, and the cost advantage is good. Secondly, in hydrolysis and dehydration reactions, strong acid resin is used as a catalyst, mixed liquor of ethanol water and the like isused as a solvent, and a tubular reactor is adopted so that continuous hydrolysis and dehydration of beta-propiolactone are realized, the reaction yield is high, and the use amount of the catalyst issmall.
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Paragraph 0053-0064
(2021/03/13)
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- Method for synthesizing beta-damascenone
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The invention discloses a method for synthesizing beta-damascenone. The method mainly comprises the following steps: oxidizing citral through sodium chlorite; carrying out catalytic cyclization through concentrated phosphoric acid to obtain alpha-cyclogeranic acid; eliminating the alkalinity of the alpha-cyclogeranic acid under the action of thionyl chloride to obtain cyclogeranenone; carrying outaddition on the cyclogeranenone and allylmagnesium chloride and carrying out acidic isomerization to obtain alpha-damascenone; carrying out epoxidation on the alpha-damascenon through peroxyacetic acid, and carrying out alkaline ring opening through potassium carbonate; catalytically heating and dehydrating through para-toluenesulfonic acid to obtain the beta-damascenone. The method disclosed bythe invention has the advantages that raw materials are cheap and easy to obtain, reaction conditions are moderate and the operation is simple and convenient; another useful spice alpha-damascenone can be synchronously synthesized and the method is a method which is suitable for industrial production of the beta-damascenone.
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Paragraph 0048; 0049; 0050
(2019/01/14)
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- PLANT OR MICROORGANISM-DERIVED CAROTENOID-OXYGEN COPOLYMER COMPOSITIONS, METHODS OF IDENTIFYING, QUANTIFYING AND PRODUCING SAME AND USES THEREOF
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The present invention relates to carotenoid-oxygen copolymers, compositions, methods of identifying and quantifying carotenoid-oxygen copolymers in food and related sources, and methods of producing compositions comprising same. In one aspect the method of identifying and quantifying carotenoid-oxygen copolymers comprises an analysis of a low molecular weight marker compound in said sources. In another aspect the present invention provides a method of preparing compositions comprising said carotenoid-oxygen copolymers and/or enhancing levels of said copolymers in food sources in a sufficient and practically useful concentration to have beneficial effects in animals and humans, including beneficial immunological and health effects.
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Paragraph 00107
(2017/09/21)
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- Enantioselective rearrangement coupled with water addition: Direct synthesis of enantiomerically pure saturated carboxylic acids from α,β-unsaturated aldehydes
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A novel type of organic synthesis enabling a direct one-pot transformation of α,β-unsaturated aldehydes into saturated carboxylic acids is described. As sole reagent water is required, which is integrated completely in the product. This tandem process proceeds under perfect atom economy, and consists of two coupled redox biotransformations without the need of external co-substrates for cofactor regeneration. The initial reduction of the C=C double bond of an α,β-unsaturated aldehyde is catalyzed by an NADPH-dependent ene reductase, leading to the formation of the saturated aldehyde and NADP+. The aldehyde intermediate is then oxidized to the corresponding carboxylic acid, thus regenerating NADPH for the next catalytic cycle. When using prochiral α,β-unsaturated aldehydes as substrates the corresponding carboxylic acids are formed enantioselectively with up to >99 % ee as demonstrated, e.g., for the transformation of citral to (S)-citronellic acid. Making a splash with citral: The direct one-pot transformation of α,β-unsaturated aldehydes to saturated carboxylic acids using only water proceeds with perfect atom economy. This tandem process involves two redox biotransformations without need of additional external co-substrates for cofactor regeneration. With, for example, citral as prochiral α,β-unsaturated aldehyde, transformation to (S)-citronellic acid proceeds with >99 % conversion and >99 % ee.
- Winkler, Till,Groeger, Harald,Hummel, Werner
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p. 961 - 964
(2014/05/06)
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- NOVEL REACTION WITH A GOLD CATALYST
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The invention relates to a process for the catalytic conversion of a carbohydrate, an alcohol, an aldehyde or a polyhydroxy compound in the presence of a catalyst containing gold in a solvent.
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Page/Page column 27-28
(2009/01/24)
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- Molecular iodine as efficient co-catalyst for facile oxidation of alcohols with hypervalent(III) iodine
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A simple and mild procedure for the facile oxidation of alcohols to ketones and acids using a catalytic quantity of molecular iodine in combination with (diacetoxyiodo)benzene in acetonitrile is described. Direct oxidative methyl esterification of alcohols is also reported in methanol as solvent. Oxidation of alcohols is induced by iodonium ion generated in situ by the chemical oxidation of molecular iodine with (diacetoxyiodo)benzene. Georg Thieme Verlag Stuttgart.
- Karade,Tiwari,Huple
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p. 2039 - 2042
(2007/10/03)
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- Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1
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Heterologous expression in Escherichia coli, purification, and reconstitution of house fly P450 6A1 and NADPH-cytochrome P450 reductase were used to study the metabolism of terpenoids. In addition to the epoxidation of cyclodiene insecticides demonstrated previously [Andersen et al. (1994) Biochemistry 33, 2171-2177], this cytochrome P450 was shown to epoxidize a variety of terpenoids such as farnesyl, geranyl, and neryl methyl esters, juvenile hormones I and III, and farnesal but not farnesol or farnesoic acid. P450 6A1 reconstituted with NADPH-cytochrome P450 reductase and phosphatidylcholine did not metabolize α-pinene, limonene, or the insect growth regulators hydroprene and methoprene. The four geometric isomers of methyl farnesoate were metabolized predominantly to the 10,11-epoxides, but also to the 6,7-epoxides and to the diepoxides. The 10,11-epoxide of methyl (2E,6E)-farnesoate was produced in a 3:1 ratio of the (10S) and (10R) enantiomers. Monoepoxides of methyl farnesoate were metabolized efficiently to the diepoxides. Methyl farnesoate epoxidation was strongly inhibited by a bulky substituted imidazole. The active site topology of P450 6A1 was studied by the reaction of the enzyme with phenyldiazene to form a phenyl-iron complex. Ferricyanide-induced in situ migration of the phenyl group showed formation of the N-phenylprotoporphyrinporphyrin IX adducts in a 17:25:33:24 ratio of the N(B):N(A):N(C):N(D) isomers. These experiments suggest that metabolism of xenobiotics by this P450, constitutively overexpressed in insecticide-resistant strains of the house fly, is not severely limited by stereochemically constrained access to the active site.
- Andersen, John F.,Walding, Jennifer K.,Evans, Philip H.,Bowers, William S.,Feyereisen, Rene
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p. 156 - 164
(2007/10/03)
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- A Practical O2-Oxidation of Functionalized Alcohols Producing Carboxylic Acids Catalyzed by the Pd-C/Pb(OAc)2 System
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The Pd-C/Pb(OAc)2 system catalyzes selective O2-oxidation of ArCH(R)CH2OH to ArCH(R)COOH (useful intermediates for drug synthesis) in high yields without contamination of ArCOOH.The turnover number (substrate/Pd) is improved to 85 and > 1800 by recycling the catalyst and using a special reactor, respectively.Alkanols are also efficiently oxidized to alkanoic acids by the title catalyst system.
- Akada, Mitsuo,Nakano, Shinji,Sugiyama, Toshiyuki,Ichitoh, Kazumoto,Nakao, Hiroki,et al.
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p. 1511 - 1515
(2007/10/02)
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- OXIDATION OF α,β-UNSATURATED ALDEHYDES
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A variety of methods for the conversion of α,β-unsaturated aldehydes to the corresponding acids have been explored.The best approach uses sodium chlorite and gives the desired transformation even in systems where steric hindrance and/or sensitive functionality are present.
- Bal, Balkrishna S.,Childers, Wayne E.,Pinnick, Harold W.
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p. 2091 - 2096
(2007/10/02)
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