49816-95-7Relevant academic research and scientific papers
Synthesis method of spice megastigmatrienone intermediate 3-oxo-alpha-ionol
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Paragraph 0031-0032; 0034-0036; 0038; 0040; 0042-0044; 0046, (2020/07/03)
The invention discloses a synthesis method of a spice megastigmatrienone intermediate 3-oxo-alpha-ionol, and relates to the technical field of spice synthesis, wherein the synthesis method comprises the following steps: (1) synthesis of 3-oxo-alpha-ionone
Method for efficiently preparing oxo-ionone
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Paragraph 0017; 0019-0027, (2019/10/01)
The invention discloses a method for efficiently preparing oxo-ionone. The method uses manganese dioxide as a catalyst, and oxo-ionone is obtained by catalytic oxidation at an allylic position of ionone. Oxo-ionone can be synthesized in high yield by the method, the operation is simple, the cost is low, and the method is green and environment-friendly.
Oxidation of alkenes with non-heme iron complexes: Suitability as an organic synthetic method
Clemente-Tejeda, David,Bermejo, Francisco A.
, p. 9381 - 9386 (2015/03/05)
In the course of a preliminary study to determine the preparative value and the synthetic applications of the non-heme iron(II) complexes Fe(bpmen)(OTf)2 and Fe(tpa)(OTf)2, in particular the oxidation of alkenes by using hydrogen peroxide as the terminal oxidant, we have found significant differences in catalyst behavior. After several attempts it was clear that the preparative relevance of the oxidation processes was linked to the concentration of the catalyst and optimal results were obtained when the concentration value was 5 mol %. At that concentration, the Fe(bpmen)(OTf)2 catalyst mostly gave rise to mixtures of the epoxide and the trans-dihydroxylation products formed by water-assisted hydrolytic cleavage of the epoxides. Furthermore, the use of the tripodal ligand tpa led to cis dihydroxylation products. When deactivated olefins were used as substrates for the oxidation reaction, the cis-diols were obtained exclusively, although with modest conversions, regardless of the catalyst used.
Regio- and stereoselective hydroxylation of optically active α-ionone enantiomers by engineered cytochrome P450 BM3 mutants
Venkataraman, Harini,Beer, Stephanie B. A. De,Geerke, Daan P.,Vermeulen, Nico P. E.,Commandeur, Jan N. M.
, p. 2172 - 2184,13 (2012/12/12)
The selective hydroxylation of an unactivated C-H bond is a crucial step in the synthesis of fine chemicals such as hydroxylated terpenoids. In the present study, the ability of 40 cytochrome P450 BM3 mutants to perform the regio- and stereoselective hydroxylation of α-ionone has been investigated. Based on their activity and selectivity to produce 3-hydroxy-α-ionone from racemic α-ionone, 6 BM3 mutants were selected. Out of these, 3 mutants (M01 A82W, M11 A82W and M11 V87I) showed high selectivity for trans-3-hydroxy-α- ionone formation while 3 other mutants (M11 L437N, M11 L437S and M11 L437T) formed almost equal amounts of both cis-3-hydroxy- and trans-3-hydroxy-α- ionone. Incubation with individual enantiomers showed that M11 L437N, M11 L437S and M11 L437T exhibited opposite stereoselectivity producing (3S,6S)-hydroxy-α-ionone with the (6S)-enantiomer and (3S,6R)-hydroxy- α-ionone with the (6R)-enantiomer. Thus for the first time, BM3 mutants that can selectively produce diastereomers of 3-hydroxy-α-ionone (>90% de), with high turnover numbers and minimal secondary metabolism, have been identified. Docking studies have been performed to rationalize the basis of the experimentally observed selectivity. In conclusion, engineered P450 BM3s are promising biocatalysts for regio- and stereoselective production of hydroxylated α-ionones for industrial applications. Copyright
Regio- and stereoselective hydroxylation of optically active α-ionone enantiomers by engineered cytochrome P450 BM3 mutants
Venkataraman, Harini,Beer, Stephanie B. A. De,Geerke, Daan P.,Vermeulen, Nico P. E.,Commandeur, Jan N. M.
, p. 2172 - 2184 (2013/01/14)
The selective hydroxylation of an unactivated C-H bond is a crucial step in the synthesis of fine chemicals such as hydroxylated terpenoids. In the present study, the ability of 40 cytochrome P450 BM3 mutants to perform the regio- and stereoselective hydroxylation of α-ionone has been investigated. Based on their activity and selectivity to produce 3-hydroxy-α-ionone from racemic α-ionone, 6 BM3 mutants were selected. Out of these, 3 mutants (M01 A82W, M11 A82W and M11 V87I) showed high selectivity for trans-3-hydroxy-α- ionone formation while 3 other mutants (M11 L437N, M11 L437S and M11 L437T) formed almost equal amounts of both cis-3-hydroxy- and trans-3-hydroxy-α- ionone. Incubation with individual enantiomers showed that M11 L437N, M11 L437S and M11 L437T exhibited opposite stereoselectivity producing (3S,6S)-hydroxy-α-ionone with the (6S)-enantiomer and (3S,6R)-hydroxy- α-ionone with the (6R)-enantiomer. Thus for the first time, BM3 mutants that can selectively produce diastereomers of 3-hydroxy-α-ionone (>90% de), with high turnover numbers and minimal secondary metabolism, have been identified. Docking studies have been performed to rationalize the basis of the experimentally observed selectivity. In conclusion, engineered P450 BM3s are promising biocatalysts for regio- and stereoselective production of hydroxylated α-ionones for industrial applications. Copyright
TWO DIASTEREOMERIC 3-OXO-α-IONOL β-D-GLUCOSIDES FROM RASPBERRY FRUIT
Pabst, Anni,Barron, Denis,Semon, Etienne,Schreier, Peter
, p. 1649 - 1652 (2007/10/02)
From a methanolic extract of raspberry fruit two 3'-O-β-D-glucopyranosides of diastereomeric 4-(3'-hydroxy-1'-butenyl)-3,3,5-trimethyl-2-cyclohexen-1-one (3-oxo-α-ionol) were isolated by adsorption chromatography on XAD-2 followed by LC on Sephadex LH-20,
