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公开(公告)号：US20130245286A1
公开(公告)日：2013-09-19
申请号：US13887566
申请日：2013-05-06
发明人： Kenji Yagi , Yasuhiro Komatsuki , Hideo Ujihara , Kenya Ishida
IPC分类号： C07D307/77
CPC分类号： C07D307/83 , C07D307/77
摘要： The present invention relates to a method comprising (A) reacting a β-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an α-methyl-γ-keto acid; and (C) reducing the resulting α-methyl-γ-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof. Alternatively, the present invention relates to a method comprising step (A) as recited above; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, followed by decarboxylation reaction to obtain an α-methyl-γ-keto acid ester; and (E) reducing the resulting α-methyl-γ-keto acid ester in the presence of a ruthenium complex having a specific structure and in the presence of a hydrogen donor to obtain wine lactone or a stereoisomer thereof or a mixture thereof.
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公开(公告)号：US09464257B2
公开(公告)日：2016-10-11
申请号：US14431614
申请日：2013-09-30
发明人： Hiroyuki Matsuda , Tomohiko Hakamata , Hideo Ujihara , Hiroki Ito
摘要： A fragrance composition contains (3S)-(6E)-2,3-dihydrofarnesal. A chemical purity of the (3S)-(6E)-2,3-dihydrofarnesal is 90 mass % or more and an optical purity of the (3S)-(6E)-2,3-dihydrofarnesal is 50% e.e. or more. A fragrance or cosmetic contains the fragrance composition. An odor is improved by using the fragrance composition containing (3S)-(6E)-2,3-dihydrofarnesal having a chemical purity of 90 mass % or more and an optical purity of 50% e.e. or more.
摘要翻译： 香料组合物含有（3S） - （6E）-2,3-二氢法呢那。 （3S） - （6E）-2,3-二氢法氢烯的化学纯度为90质量％以上，（3S） - （6E）-2,3-二氢法呢的光学纯度为50％e.e。 或者更多。 香料或化妆品含有香料组合物。 通过使用含有化学纯度为90质量％以上且光学纯度为50％e.e的（3S） - （6E）-2,3-二氢法呢安的香料组合物，气味得到改善。 或者更多。
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公开(公告)号：US20150275131A1
公开(公告)日：2015-10-01
申请号：US14431614
申请日：2013-09-30
发明人： Hiroyuki Matsuda , Tomohiko Hakamata , Hideo Ujihara , Hiroki Ito
摘要： A fragrance composition contains (3S)-(6E)-2,3-dihydrofarnesal. A chemical purity of the (3S)-(6E)-2,3-dihydrofarnesal is 90 mass % or more and an optical purity of the (3S)-(6E)-2,3-dihydrofarnesal is 50% e.e. or more. A fragrance or cosmetic contains the fragrance composition. An odor is improved by using the fragrance composition containing (3S)-(6E)-2,3-dihydrofarnesal having a chemical purity of 90 mass % or more and an optical purity of 50% e.e. or more.
摘要翻译： 香料组合物含有（3S） - （6E）-2,3-二氢法呢那。 （3S） - （6E）-2,3-二氢法氢烯的化学纯度为90质量％以上，（3S） - （6E）-2,3-二氢法呢的光学纯度为50％e.e。 或者更多。 香料或化妆品含有香料组合物。 通过使用含有化学纯度为90质量％以上且光学纯度为50％e.e的（3S） - （6E）-2,3-二氢法呢安的香料组合物，气味得到改善。 或者更多。
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公开(公告)号：US09486395B2
公开(公告)日：2016-11-08
申请号：US14257755
申请日：2014-04-21
发明人： Louis Lombardo , Michael E. Lankin , Kenya Ishida , Shigeru Tanaka , Hideo Ujihara , Kenji Yagi , Jennifer B. Tartaglia , Carter B. Green , Amrit S. Mankoo
IPC分类号： A61K31/16 , A61K8/42 , A23L1/226 , A61Q5/00 , A61Q11/00 , A61Q15/00 , C07C43/303 , C07C45/41 , C07C57/66 , C07C231/12 , C07C233/09 , C07C235/28 , C07C309/66 , C12P13/02 , A23G1/32 , A23G3/36 , A23G4/06
CPC分类号： A61K8/42 , A23G1/32 , A23G3/36 , A23G4/06 , A23L27/202 , A61Q5/00 , A61Q11/00 , A61Q15/00 , C07C43/303 , C07C45/41 , C07C57/66 , C07C231/12 , C07C233/09 , C07C235/28 , C07C309/66 , C12P13/02 , C07C47/21
摘要： The present application provides a synthetic spilanthol flavor composition that includes (2E,6Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide. The synthetic spilanthol composition can also contain, and at least one of (2E,6E,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide and (2E,6Z,8Z)—N-(2-methylpropyl)-2,6,8-decatrienamide, the (N-(2-methylpropyl)-2,6,8-decatrienamide being present in amounts effective to impart a salivating or tingle effect while reducing the perception of off notes, as compared to the off-notes perceived upon consumption of natural spilanthol (e.g. spilanthol obtained from jambu oleoresin). Methods of increasing salivation and/or providing a tingling sensation upon consuming an orally consumable product that include adding to the product a synthetic spilanthol flavor composition are also provided. Synthetic spilanthol flavor compositions can be added to orally consumed products, such as, but not limited to, foods, beverages, pharmaceuticals, nutraceuticals, or therapeutic compositions, oral personal care products, gums (e.g. chewing gum or bubble gum), candy or lozenges.
摘要翻译： 本申请提供了包括（2E，6Z，8E）-N-（2-甲基丙基）-2,6,8-十一三烯酰胺的合成稀释剂风味组合物。 （2E，6E，8E）-N-（2-甲基丙基）-2,6,8-十一三烯酰胺和（2E，6Z，8Z）-N-（2- 甲基丙基）-2,6,8-十一三烯酰胺，（N-（2-甲基丙基）-2,6,8-癸三酰胺以有效赋予唾液或叮咬效果同时减少脱落感觉的量存在，相比之下 在消费口服消耗品时，增加唾液分泌和/或提供刺痛感的方法包括向产品中加入合成的稀释剂风味组合物的方法也是 合成的稀释剂风味组合物可以添加到口服食品中，例如但不限于食品，饮料，药物，营养保健品或治疗组合物，口腔个人护理产品，牙龈（例如口香糖或泡泡糖），糖果 或锭剂。
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公开(公告)号：US20150218072A1
公开(公告)日：2015-08-06
申请号：US14425115
申请日：2013-09-06
发明人： Hideo Ujihara , Mitsuhiko Fujiwhara
IPC分类号： C07C45/00 , C07C211/21
CPC分类号： C07C211/21 , C07B53/00 , C07B2200/07 , C07C45/00 , C07C47/21 , C07C51/42 , C07C47/02
摘要： A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis:
摘要翻译： 公开了制备式（1）的光学活性2,3-二氢法呢的方法。 该方法包括在胺的锂盐存在下使式（2）的芳烃化合物胺化得到通式（3）的（2E） - 法呢基烯丙胺; （2E） - 法呢基烯丙胺进行不对称异构化，得到通式（4）的光学活性法呢基烯胺; 并对光学活性法呢基烯胺进行溶剂解：
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公开(公告)号：US20140227200A1
公开(公告)日：2014-08-14
申请号：US14257755
申请日：2014-04-21
发明人： Louis Lombardo , Michael E. Lankin , Kenya Ishida , Shigeru Tanaka , Hideo Ujihara , Kenji Yagi , Jennifer B. Tartaglia , Carter B. Green , Amrit S. Mankoo
CPC分类号： A61K8/42 , A23G1/32 , A23G3/36 , A23G4/06 , A23L27/202 , A61Q5/00 , A61Q11/00 , A61Q15/00 , C07C43/303 , C07C45/41 , C07C57/66 , C07C231/12 , C07C233/09 , C07C235/28 , C07C309/66 , C12P13/02 , C07C47/21
摘要： The present application provides a synthetic spilanthol flavor composition that includes (2E,6Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide. The synthetic spilanthol composition can also contain, and at least one of (2E,6E,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide and (2E,6Z,8Z)—N-(2-methylpropyl)-2,6,8-decatrienamide, the (N-(2-methylpropyl)-2,6,8-decatrienamide being present in amounts effective to impart a salivating or tingle effect while reducing the perception of off notes, as compared to the off-notes perceived upon consumption of natural spilanthol (e.g. spilanthol obtained from jambu oleoresin). Methods of increasing salivation and/or providing a tingling sensation upon consuming an orally consumable product that include adding to the product a synthetic spilanthol flavor composition are also provided. Synthetic spilanthol flavor compositions can be added to orally consumed products, such as, but not limited to, foods, beverages, pharmaceuticals, nutraceuticals, or therapeutic compositions, oral personal care products, gums (e.g. chewing gum or bubble gum), candy or lozenges.
摘要翻译： 本申请提供了包括（2E，6Z，8E）-N-（2-甲基丙基）-2,6,8-十一三烯酰胺的合成稀释剂风味组合物。 （2E，6E，8E）-N-（2-甲基丙基）-2,6,8-十一三烯酰胺和（2E，6Z，8Z）-N-（2- 甲基丙基）-2,6,8-十一三烯酰胺，（N-（2-甲基丙基）-2,6,8-癸三酰胺以有效赋予唾液或叮咬效果同时减少脱落感觉的量存在，相比之下 在消费口服易消化产品时，增加唾液分泌和/或提供刺痛感的方法包括向产品中加入合成的稀释剂风味组合物也是 合成的稀释剂风味组合物可以添加到口服食品中，例如但不限于食品，饮料，药物，营养保健品或治疗组合物，口腔个人护理产品，牙龈（例如口香糖或泡泡糖），糖果 或锭剂。
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公开(公告)号：US09284246B2
公开(公告)日：2016-03-15
申请号：US14425115
申请日：2013-09-06
发明人： Hideo Ujihara , Mitsuhiko Fujiwhara
IPC分类号： C07C45/00 , C07C211/21 , C07B53/00 , C07C47/21
CPC分类号： C07C211/21 , C07B53/00 , C07B2200/07 , C07C45/00 , C07C47/21 , C07C51/42 , C07C47/02
摘要： A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis:
摘要翻译： 公开了制备式（1）的光学活性2,3-二氢法呢的方法。 该方法包括在胺的锂盐存在下使式（2）的芳烃化合物胺化得到通式（3）的（2E） - 法呢基烯丙胺; （2E） - 法呢基烯丙胺进行不对称异构化，得到通式（4）的光学活性法呢基烯胺; 并对光学活性法呢基烯胺进行溶剂解：
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公开(公告)号：US20130245287A1
公开(公告)日：2013-09-19
申请号：US13887564
申请日：2013-05-06
发明人： Kenji Yagi , Yasuhiro Komatsuki , Hideo Ujihara , Kenya Ishida
IPC分类号： C07D307/83
CPC分类号： C07D307/83 , C07D307/77
摘要： The present invention relates to a method comprising (A) reacting a β-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an α-methyl-γ-keto acid; and (C) reducing the resulting α-methyl-γ-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof. Alternatively, the present invention relates to a method comprising step (A) as recited above; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, followed by decarboxylation reaction to obtain an α-methyl-γ-keto acid ester; and (E) reducing the resulting α-methyl-γ-keto acid ester in the presence of a ruthenium complex having a specific structure and in the presence of a hydrogen donor to obtain wine lactone or a stereoisomer thereof or a mixture thereof.
摘要翻译： 本发明涉及包含（A）在碱性条件下使β-酮酯与2-卤代酯反应得到2-乙酰-3-甲基 - 琥珀酸酯的方法; （B）在碱性条件下使所得2-乙酰-3-甲基 - 琥珀酸酯与甲基乙烯基酮反应，任选地进行脱羧反应和水解等，得到α-甲基-γ-酮酸; 和（C）将所得的α-甲基-γ-酮酸还原得到葡萄酒内酯或其立体异构体或其混合物。 或者，本发明涉及包含上述步骤（A）的方法; （B）在碱性条件下使所得的2-乙酰-3-甲基 - 琥珀酸酯与甲基乙烯基酮反应，然后进行脱羧反应，得到α-甲基-γ-酮酸酯; 和（E）在具有特定结构的钌络合物和氢供体存在下还原所得的α-甲基-γ-酮酸酯以获得葡萄糖内酯或其立体异构体或其混合物。
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