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1. 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。

2. 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。

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

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。

5. 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。

6. 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）

7. 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）

8. 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。

9. 发明授权

US08377458B2 Cooling sensation agent composition, sensory stimulation agent composition and use of the same 失效
标题翻译：冷却感觉剂组合物，感觉刺激剂组合物及其用途
公开(公告)号：US08377458B2
公开(公告)日：2013-02-19
申请号：US12898939
申请日：2010-10-06
申请人： Yasuhiro Komatsuki , Tomoko Yamamoto , Takashi Aida , Kenya Ishida
发明人： Yasuhiro Komatsuki , Tomoko Yamamoto , Takashi Aida , Kenya Ishida
IPC分类号： A61Q5/02 , A61Q15/00 , A61Q13/10
CPC分类号： C07C69/34 , A61K8/37 , A61K31/225 , A61K2800/244 , A61Q11/00 , A61Q13/00 , A61Q15/00 , A61Q19/00 , C07C69/40 , C07C69/42 , C07C2601/14
摘要： Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH2 or CH═CH, n represents an integer of 0 to 4 when A is CH2, or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.
摘要翻译：公开了一种冷却感觉剂组合物或感觉刺激剂组合物，其含有由式（1）表示的二羧酸二酯化合物中的至少一种，其中A表示CH 2或CH = CH，n表示0至4的整数，当A为 CH 2或1，当A为CH = CH时，B为具有10至18个碳原子的醇残基，并含有可具有取代基的对位薄荷烷骨架，C为具有6至18个碳原子的醇残基，可以具有取代基以及香料或香料组合物，饮料，食品，香料或化妆品，化妆品，日用具产品或杂货，纤维，纤维制品，衣服，衣服或药物，其中所述冷却感觉剂组合物或所述感觉刺激剂组合物复合。

10. 发明申请

US20140219931A1 P-MENTHANE-3,8-DIOL ISOMER MIXTURE, COOLING SENSATION COMPOSITION COMPRISING THE SAME, AND PRODUCT COMPRISING THE COOLING SENSATION COMPOSITION 审中-公开
标题翻译： P-MENTHANE-3,8-DIOL异构体混合物，包含其的冷却感测组合物和包含冷却感测组合物的产品
公开(公告)号：US20140219931A1
公开(公告)日：2014-08-07
申请号：US14239831
申请日：2012-08-31
申请人： Yasuhiro Komatsuki , Shigeru Tanaka , Kenya Ishida
发明人： Yasuhiro Komatsuki , Shigeru Tanaka , Kenya Ishida
IPC分类号： A61K31/047 , A61Q11/00 , A23G4/06 , A61Q5/02 , A23L1/226 , A61K8/34 , A61K31/085
CPC分类号： A61K31/047 , A23G1/32 , A23G4/06 , A23L2/52 , A23L27/203 , A61K8/34 , A61K8/345 , A61K31/085 , A61K2800/244 , A61Q5/02 , A61Q11/00 , A61Q13/00 , C11B9/0034
摘要： The present invention relates to a p-menthane-3,8-diol isomer mixture 50% by mass or more of which is constituted of (1S)-isomers and a cooling sensation composition containing this mixture. The present invention also relates to a flavor and/or fragrance composition, food, beverage, cosmetic, daily use product, oral cavity composition, or pharmaceutical containing the p-menthane-3,8-diol isomer mixture in an amount of 0.0001 to 90% by mass.
摘要翻译：本发明涉及由（1S） - 异构体构成的50质量％以上的对薄荷烷-3,8-二醇异构体混合物和含有该混合物的冷却感组合物。本发明还涉及一种风味剂和/或香料组合物，食品，饮料，化妆品，日用品，口腔组合物或含有对数薄荷烷-3,8-二醇异构体混合物的药物，其量为0.0001至90 质量％。

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