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Jochen Mattay - One of the best experts on this subject based on the ideXlab platform.
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diastereomeric 5 6 dimethyl 4h 1 3 dioxin 4 ones from 1r 4s Menthone synthesis and nmr analysis
European Journal of Organic Chemistry, 1991Co-Authors: Ursula Jansen, Jan Runsink, Jochen MattayAbstract:The two diastereomers of spirocyclic 5,6-dimethyl-4H-1,3-dioxin-4-one (5,6) have been synthesized by acetalization of tert-butyl 2-methyl-3-oxobutanoate (2) with (-)-Menthone (4). Their structures have been determined by NMR analysis.
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Diastereomeric 5,6-dimethyl-4H-1,3-dioxin-4-ones from (−)-(1R,4S)Menthone: synthesis and NMR analysis
European Journal of Organic Chemistry, 1991Co-Authors: Ursula Jansen, Jan Runsink, Jochen MattayAbstract:The two diastereomers of spirocyclic 5,6-dimethyl-4H-1,3-dioxin-4-one (5,6) have been synthesized by acetalization of tert-butyl 2-methyl-3-oxobutanoate (2) with (-)-Menthone (4). Their structures have been determined by NMR analysis.
Ursula Jansen - One of the best experts on this subject based on the ideXlab platform.
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diastereomeric 5 6 dimethyl 4h 1 3 dioxin 4 ones from 1r 4s Menthone synthesis and nmr analysis
European Journal of Organic Chemistry, 1991Co-Authors: Ursula Jansen, Jan Runsink, Jochen MattayAbstract:The two diastereomers of spirocyclic 5,6-dimethyl-4H-1,3-dioxin-4-one (5,6) have been synthesized by acetalization of tert-butyl 2-methyl-3-oxobutanoate (2) with (-)-Menthone (4). Their structures have been determined by NMR analysis.
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Diastereomeric 5,6-dimethyl-4H-1,3-dioxin-4-ones from (−)-(1R,4S)Menthone: synthesis and NMR analysis
European Journal of Organic Chemistry, 1991Co-Authors: Ursula Jansen, Jan Runsink, Jochen MattayAbstract:The two diastereomers of spirocyclic 5,6-dimethyl-4H-1,3-dioxin-4-one (5,6) have been synthesized by acetalization of tert-butyl 2-methyl-3-oxobutanoate (2) with (-)-Menthone (4). Their structures have been determined by NMR analysis.
Jan Runsink - One of the best experts on this subject based on the ideXlab platform.
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diastereomeric 5 6 dimethyl 4h 1 3 dioxin 4 ones from 1r 4s Menthone synthesis and nmr analysis
European Journal of Organic Chemistry, 1991Co-Authors: Ursula Jansen, Jan Runsink, Jochen MattayAbstract:The two diastereomers of spirocyclic 5,6-dimethyl-4H-1,3-dioxin-4-one (5,6) have been synthesized by acetalization of tert-butyl 2-methyl-3-oxobutanoate (2) with (-)-Menthone (4). Their structures have been determined by NMR analysis.
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Diastereomeric 5,6-dimethyl-4H-1,3-dioxin-4-ones from (−)-(1R,4S)Menthone: synthesis and NMR analysis
European Journal of Organic Chemistry, 1991Co-Authors: Ursula Jansen, Jan Runsink, Jochen MattayAbstract:The two diastereomers of spirocyclic 5,6-dimethyl-4H-1,3-dioxin-4-one (5,6) have been synthesized by acetalization of tert-butyl 2-methyl-3-oxobutanoate (2) with (-)-Menthone (4). Their structures have been determined by NMR analysis.
Mitsuo Miyazawa - One of the best experts on this subject based on the ideXlab platform.
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biotransformation of 1r 4s Menthone and 1s 4r Menthone by the common cutworm spodoptera litura larvae
Journal of Oleo Science, 2017Co-Authors: Shinsuke Marumoto, Yoshiharu Okuno, Yuki Hagiwara, Mitsuo MiyazawaAbstract:Using biotransformation as a biocatalytic process has the advantage of being able to proceed under mild conditions and with high regio- and enantioselectivity. This study investigated the biotransformation of (-)-(1R,4S)-Menthone (1) and (+)-(1S,4R)-Menthone (2) by Spodoptera litura larvae. Compound 1 was converted to (-)-(1R,4S)-7-hydroxyMenthone (1-1), (+)-(1R,3S,4S)-7-hydroxyneomenthol (1-2) and (-)-(1R,4S,8R)-p-menth-3-one-9-oic acid (1-3). The metabolism of substrate 2 generated three enantiomers of the above metabolites, designated as 2-1 to 2-3, respectively. The C-9 position of (-)-Menthone and (+)-Menthone was oxidized to carboxylic acid by S. litura, which is a metabolic pathway not observed in any other example of biocatalysis.
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Biotransformation of (-)-(1R,4S)-Menthone and (+)-(1S,4R)-Menthone by the Common Cutworm Spodoptera litura Larvae.
Journal of Oleo Science, 2017Co-Authors: Shinsuke Marumoto, Yoshiharu Okuno, Yuki Hagiwara, Mitsuo MiyazawaAbstract:Using biotransformation as a biocatalytic process has the advantage of being able to proceed under mild conditions and with high regio- and enantioselectivity. This study investigated the biotransformation of (-)-(1R,4S)-Menthone (1) and (+)-(1S,4R)-Menthone (2) by Spodoptera litura larvae. Compound 1 was converted to (-)-(1R,4S)-7-hydroxyMenthone (1-1), (+)-(1R,3S,4S)-7-hydroxyneomenthol (1-2) and (-)-(1R,4S,8R)-p-menth-3-one-9-oic acid (1-3). The metabolism of substrate 2 generated three enantiomers of the above metabolites, designated as 2-1 to 2-3, respectively. The C-9 position of (-)-Menthone and (+)-Menthone was oxidized to carboxylic acid by S. litura, which is a metabolic pathway not observed in any other example of biocatalysis.
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biotransformation of Menthone by human liver microsomes
Bioscience Biotechnology and Biochemistry, 2006Co-Authors: Mitsuo Miyazawa, Kyousuke NakanishiAbstract:The aim of the current study was to investigate the metabolism of (−)-Menthone by liver microsomes of humans. (−)-Menthone (1) was metabolized to (+)-neomenthol (2) (3-reduction) and 7-hydroxyMenthone (3) by human liver microsomes. The metabolites formed were analyzed on GC and GC–MS. Kinetic analysis showed that K m and V max values for the metabolized (−)-Menthone to respective (+)-neomenthol and 7-hydroxyMenthone by liver microsomes of human sample HG70 were 0.37 mM and 4.91 nmol/min/mg protein and 0.07 mM and 0.71 nmol/min/mg protein.
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Biotransformation of (−)-Menthone by Human Liver Microsomes
Bioscience Biotechnology and Biochemistry, 2006Co-Authors: Mitsuo Miyazawa, Kyousuke NakanishiAbstract:The aim of the current study was to investigate the metabolism of (−)-Menthone by liver microsomes of humans. (−)-Menthone (1) was metabolized to (+)-neomenthol (2) (3-reduction) and 7-hydroxyMenthone (3) by human liver microsomes. The metabolites formed were analyzed on GC and GC–MS. Kinetic analysis showed that K m and V max values for the metabolized (−)-Menthone to respective (+)-neomenthol and 7-hydroxyMenthone by liver microsomes of human sample HG70 were 0.37 mM and 4.91 nmol/min/mg protein and 0.07 mM and 0.71 nmol/min/mg protein.
Irena Katzir - One of the best experts on this subject based on the ideXlab platform.
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chiral gc analysis of Menthone and isoMenthone with high enantiomeric purities in laboratory made and commercial essential oils
Flavour and Fragrance Journal, 1994Co-Authors: Uzi Ravid, Eli Putievsky, Irena KatzirAbstract:Direct separation of the enantiomers of the two diastereomers, Menthone and isoMenthone, was performed using an octakis-(3-O-butyryl-2,6-di-O-pentyl)-α-cyclodextrin phase. Enantiomerically pure (—)-Menthone and (+)-isoMenthone were detected in many oils of Mentha, Micromeria fruticosa (L.) Druce and Calamintha incana (Sm.) Heldr. High enantiomeric purities of (+)-Menthone and (—)-isoMenthone were detected in commercial and freshly distilled geranium oils.
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Chiral gc analysis of Menthone and isoMenthone with high enantiomeric purities in laboratory‐made and commercial essential oils
Flavour and Fragrance Journal, 1994Co-Authors: Uzi Ravid, Eli Putievsky, Irena KatzirAbstract:Direct separation of the enantiomers of the two diastereomers, Menthone and isoMenthone, was performed using an octakis-(3-O-butyryl-2,6-di-O-pentyl)-α-cyclodextrin phase. Enantiomerically pure (—)-Menthone and (+)-isoMenthone were detected in many oils of Mentha, Micromeria fruticosa (L.) Druce and Calamintha incana (Sm.) Heldr. High enantiomeric purities of (+)-Menthone and (—)-isoMenthone were detected in commercial and freshly distilled geranium oils.