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1. 发明申请

US20120116116A1 METHOD FOR MANUFACTURING SPILANTHOL AND INTERMEDIATE MANUFACTURING PRODUCT THEREFOR 有权
标题翻译：制造纤维素及其制造产品的方法
公开(公告)号：US20120116116A1
公开(公告)日：2012-05-10
申请号：US13383547
申请日：2010-07-14
申请人： Shigeru Tanaka , Kenya Ishida , Kenji Yagi , Hideo Ujihara
发明人： Shigeru Tanaka , Kenya Ishida , Kenji Yagi , Hideo Ujihara
IPC分类号： C07C231/12 , C07C235/28
CPC分类号： A61K31/16 , A23L2/56 , A23L27/202 , A61K8/42 , A61Q13/00 , C07C231/12 , C07C233/09 , C07C235/28 , C11B9/0007
摘要： Provided is an amide ester that is useful as an intermediate manufacturing product for an aroma compound such as spilanthol or the like. Also provided is a spilanthol manufacturing method using said amide ester. High-purity spilanthol can be manufactured by reacting an amide ester represented by general formula (1) with a basic compound. (In the formula, R1 represents a phenyl group that may be substituted with a C1-6 alkyl group and either a C1-4 alkyl group, a C1-4 alkoxy group, or a halogen atom; R2 represents a C1-8 hydrocarbon group; and the wavy lines represent cis configurations, trans configurations, or a mixture of the two configurations.)
摘要翻译：提供一种酰胺酯，其可用作芳香化合物如稀释剂等的中间制造产品。还提供了使用所述酰胺酯的稀释剂制造方法。可以通过使通式（1）表示的酰胺与碱性化合物反应来制备高纯度的稀释剂。（式中，R 1表示可被C 1-6烷基，C 1-4烷基，C 1-4烷氧基或卤素原子取代的苯基; R 2表示碳数1〜8的烃基 ;波浪线表示顺式构型，反式构型或两种构型的混合物）

2. 发明申请

US20110105773A1 PRODUCTION METHOD OF (2E,6Z,8E)-N-ISOBUTYL-2,6,8-DECATRIENAMIDE (SPILANTHOL), AND FOOD OR DRINK, FRAGRANCE OR COSMETIC, OR PHARMACEUTICAL COMPRISING THE SAME 有权
标题翻译：（2E，6Z，8E）-N-ISOBUTYL-2,6,8-癸胺（SPILANTHOL）的生产方法，以及食品或饮料，香料或化妆品，或包含它们的药物
公开(公告)号：US20110105773A1
公开(公告)日：2011-05-05
申请号：US12673633
申请日：2009-01-16
申请人： Shigeru Tanaka , Kenji Yagi , Hideo Ujihara , Kenya Ishida
发明人： Shigeru Tanaka , Kenji Yagi , Hideo Ujihara , Kenya Ishida
IPC分类号： C07C235/28 , C07C231/02 , C07C231/12 , C07C57/66 , C07C43/303
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： A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.
摘要翻译：作为本发明的目的的一个问题是在不使用昂贵的试剂的情况下大规模地提供大量的生产方法。本发明提供N-异丁基-2,6,8-癸三酰胺的制备方法，其中在所有方法中不需要柱色谱纯化步骤。

3. 发明授权

US08217192B2 Production method of (2E,6Z,8E)-N-isobutyl-2,6,8-decatrienamide (spilanthol), and food or drink, fragrance or cosmetic, or pharmaceutical comprising the same 有权
标题翻译：（2E，6Z，8E）-N-异丁基-2,6,8-十一三烯酰胺（敏兰）和食品或饮料，香料或化妆品或包含其的药物的制备方法
公开(公告)号：US08217192B2
公开(公告)日：2012-07-10
申请号：US12673633
申请日：2009-01-16
申请人： Shigeru Tanaka , Kenji Yagi , Hideo Ujihara , Kenya Ishida
发明人： Shigeru Tanaka , Kenji Yagi , Hideo Ujihara , Kenya Ishida
IPC分类号： C07C231/00
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： A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.
摘要翻译：作为本发明的目的的一个问题是在不使用昂贵的试剂的情况下大规模地提供大量的生产方法。本发明提供N-异丁基-2,6,8-癸三酰胺的制备方法，其中在所有方法中不需要柱色谱纯化步骤。

4. 发明授权

US09029593B2 Method for manufacturing spilanthol and intermediate manufacturing product therefor 有权
标题翻译：制备微量金属的方法及其中间制造产品
公开(公告)号：US09029593B2
公开(公告)日：2015-05-12
申请号：US13383547
申请日：2010-07-14
申请人： Shigeru Tanaka , Kenya Ishida , Kenji Yagi , Hideo Ujihara
发明人： Shigeru Tanaka , Kenya Ishida , Kenji Yagi , Hideo Ujihara
IPC分类号： C07C231/12 , C07C235/28 , A61K31/16 , A61K8/42 , A61Q13/00 , C07C233/09 , A23L2/56 , A23L1/226 , C11B9/00
CPC分类号： A61K31/16 , A23L2/56 , A23L27/202 , A61K8/42 , A61Q13/00 , C07C231/12 , C07C233/09 , C07C235/28 , C11B9/0007
摘要： Provided is an amide ester that is useful as an intermediate manufacturing product for an aroma compound such as spilanthol or the like. Also provided is a spilanthol manufacturing method using said amide ester. High-purity spilanthol can be manufactured by reacting an amide ester represented by general formula (1) with a basic compound. (In the formula, R1 represents a C1-6 alkyl group or a phenyl group that may be substituted with a C1-4 alkyl group, a C1-4 alkoxy group, or a halogen atom; R2 represents a C1-8 hydrocarbon group; and the wavy lines represent cis configurations, trans configurations, or a mixture of the two configurations.)
摘要翻译：提供一种酰胺酯，其可用作芳香化合物如稀释剂等的中间制造产品。还提供了使用所述酰胺酯的稀释剂制造方法。可以通过使通式（1）表示的酰胺与碱性化合物反应来制备高纯度的稀释剂。（式中，R 1表示可被C 1-4烷基，C 1-4烷氧基或卤素原子取代的C 1-6烷基或苯基; R 2表示碳原子数1〜8的烃基; 并且波浪线表示顺式构型，反式构型或两种构型的混合物）

5. 发明授权

US08741958B2 Synthetic spilanthol and use thereof 有权
标题翻译：合成稀释剂及其用途
公开(公告)号：US08741958B2
公开(公告)日：2014-06-03
申请号：US12505283
申请日：2009-07-17
申请人： Louis Lombardo , Michael E. Lankin , Kenya Ishida , Shigeru Tanaka , Hideo Ujihara , Kenji Yagi , Jennifer B. Mei , Carter B. Green , Amrit S. Mankoo
发明人： Louis Lombardo , Michael E. Lankin , Kenya Ishida , Shigeru Tanaka , Hideo Ujihara , Kenji Yagi , Jennifer B. Mei , Carter B. Green , Amrit S. Mankoo
IPC分类号： A23L1/221
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。

6. 发明申请

US20100184863A1 SYNTHETIC SPILANTHOL AND USE THEREOF 有权
标题翻译：合成螺旋体及其用途
公开(公告)号：US20100184863A1
公开(公告)日：2010-07-22
申请号：US12505283
申请日：2009-07-17
申请人： Louis Lombardo , Michael E. Lankin , Kenya Ishida , Shigeru Tanaka , Hideo Ujihara , Kenji Yagi , Jennifer B. Mei , Carter B. Green , Amrit S. Mankoo
发明人： Louis Lombardo , Michael E. Lankin , Kenya Ishida , Shigeru Tanaka , Hideo Ujihara , Kenji Yagi , Jennifer B. Mei , Carter B. Green , Amrit S. Mankoo
IPC分类号： A61K31/16 , C07C233/09 , A61P43/00
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。

7. 发明授权

US08481759B2 Process for producing wine lactone 失效
标题翻译：生产葡萄酒内酯的方法
公开(公告)号：US08481759B2
公开(公告)日：2013-07-09
申请号：US13483373
申请日：2012-05-30
申请人： Kenji Yagi , Yasuhiro Komatsuki , Hideo Ujihara , Kenya Ishida
发明人： Kenji Yagi , Yasuhiro Komatsuki , Hideo Ujihara , Kenya Ishida
IPC分类号： C07D305/12
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。

8. 发明申请

US20130030193A1 PROCESS FOR PRODUCING WINE LACTONE 失效
标题翻译：生产葡萄酒的方法
公开(公告)号：US20130030193A1
公开(公告)日：2013-01-31
申请号：US13483373
申请日：2012-05-30
申请人： Kenji Yagi , Yasuhiro Komatsuki , Hideo Ujihara , Kenya Ishida
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：本发明涉及一种方法，其包括（A）在碱性条件下使β-卤代酯与2-卤代酯反应，得到2-乙酰-3-甲基 - 琥珀酸酯; （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存在下，在氢供体存在下还原所得的α-甲基-γ-酮酸酯，得到葡萄糖内酯或其立体异构体或其混合物。

9. 发明授权

US06822121B2 Production process of cyclohexenyl ketones 失效
标题翻译：环己烯酮的生产工艺
公开(公告)号：US06822121B2
公开(公告)日：2004-11-23
申请号：US09875158
申请日：2001-06-07
申请人： Shinya Watanabe , Hideo Ujihara , Takeshi Yamamoto , Toshimitsu Hagiwara
发明人： Shinya Watanabe , Hideo Ujihara , Takeshi Yamamoto , Toshimitsu Hagiwara
IPC分类号： C07C4567
CPC分类号： C07C403/16 , C07C45/67 , C07C45/69 , C07C2601/16 , C07C49/543
摘要： An economical process for producing (2- and/or 1-)cyclohexenyl methyl ketones which are intermediates for the synthesis of &agr;- or &bgr;-damascone. In the presence of a catalyst, a 3-cyclohexenyl methyl ketone represented by the following formula (1a): wherein, R1, R2 and R3 each independently represents a hydrogen atom or a methyl group and at least two of R1, R2 and R3 are methyl groups, is isomerized.
摘要翻译：用于生产（2-和/或1-）环己烯基甲基酮的经济方法，其是用于合成α-大脑皮质或大黄酮的中间体。在催化剂存在下，由下式（1a）表示的3-环己烯基甲基酮：其中，R 1，R 2和R 3各自独立地表示氢原子或甲基，R 1，R 2和R 3中的至少两个为甲基，异构化。

10. 发明授权

US06770618B2 (1S,6R)-2,2,6-Trimethylcyclohexyl methyl ketone and/or (1R,6S)-2,2,6-trimethylcyclohexyl methyl ketone, process for producing the same, and perfume composition containing the same 失效
标题翻译：（1S，6R）-2,2,6-三甲基环己基甲基酮和/或（1R，6S）-2,2,6-三甲基环己基甲基酮，其制备方法和含有它们的香料组合物
公开(公告)号：US06770618B2
公开(公告)日：2004-08-03
申请号：US09876883
申请日：2001-06-07
申请人： Hideo Ujihara , Shinya Watanabe , Takeshi Yamamoto , Toshimitsu Hagiwara
发明人： Hideo Ujihara , Shinya Watanabe , Takeshi Yamamoto , Toshimitsu Hagiwara
IPC分类号： A61K746
CPC分类号： C07C403/16 , C07B2200/07 , C07B2200/09 , C07C29/40 , C07C45/002 , C07C45/292 , C07C45/54 , C07C49/303 , C07C69/007 , C07C2601/14 , C11B9/0034 , C07C49/203 , C07C33/02 , C07C31/1355
摘要： Trans-2,2,6-trimethylcyclohexyl methyl ketone, including (1S,6R)-2,2,6-trimethylcyclohexyl methyl ketone represented by the formula (1a): and (1R,6S)-2,2,6-trimethylcyclohexyl methyl ketone represented by the formula (1b): are useful components in a perfume composition. A process for producing the same is also described. A unique eucalyptus, mint-like and white floral perfume material is provided using the ketone compounds disclosed in the present invention. The process of the present invention produces the optically active ketone compounds having optical purity up to at least 98.0 % e.e.
摘要翻译：包括由式（1a）表示的（1S，6R）-2,2,6-三甲基环己基甲基酮和（1R，6S）-2,2,6-三甲基环己基甲基酮的反式-2,2,6-三甲基环己基甲基酮由式（1b）表示的甲基酮：是香料组合物中有用的组分。还描述了其制造方法。使用本发明公开的酮化合物提供了独特的桉树，薄荷状和白色香料。本发明的方法生产光学纯度高达至少98.0％e.e的光学活性酮化合物。

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