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    METHOD FOR MANUFACTURING SPILANTHOL AND INTERMEDIATE MANUFACTURING PRODUCT THEREFOR
    1.
    发明申请
    METHOD FOR MANUFACTURING SPILANTHOL AND INTERMEDIATE MANUFACTURING PRODUCT THEREFOR 有权
    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）

    Synthetic spilanthol and use thereof
    5.
    发明授权
    Synthetic spilanthol and use thereof 有权
    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。

    SYNTHETIC SPILANTHOL AND USE THEREOF
    6.
    发明申请
    SYNTHETIC SPILANTHOL AND USE THEREOF 有权
    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。

    Process for producing wine lactone
    7.
    发明授权
    Process for producing wine lactone 失效
    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。

    PROCESS FOR PRODUCING WINE LACTONE
    8.
    发明申请
    PROCESS FOR PRODUCING WINE LACTONE 失效
    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。

    Production process of cyclohexenyl ketones
    9.
    发明授权
    Production process of cyclohexenyl ketones 失效
    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。