公开(公告)号：US20110118500A1

公开(公告)日：2011-05-19

申请号：US13012199

申请日：2011-01-24

申请人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

发明人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

IPC分类号： C07C69/78 ,  C07C69/533 ,  C07C69/63 ,  C07C69/24 ,  C07C69/708

CPC分类号： C12P7/26 ,  A23L2/56 ,  A23L27/204 ,  A61K8/37 ,  A61Q11/00 ,  A61Q13/00 ,  C07B53/00 ,  C07B2200/07 ,  C07C403/08 ,  C07C403/12 ,  C07C403/14 ,  C07C2601/16 ,  C12G3/06 ,  C12P41/004

摘要： Provided that a method for inexpensively producing optically active α-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active α-ionone obtained by the aforementioned method. A method for producing optically active α-ionone, comprising allowing α-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained α-ionone enol ester; a method for producing optically active α-ionone comprising subjecting α-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active α-ionol to react with an esterification agent to give an optically active α-ionol ester, hydrolyzing the obtained optically active α-ionol ester after purification as necessary, and then oxidizing the obtained optically active α-ionol; and a perfume composition comprising thus obtained optically active α-ionone.

摘要翻译： 本发明提供了一种低成本地生产光学活性α-紫罗兰酮的方法，其具有高产率和高不对称产率，并且在短时间内具有良好的可加工性，以及包含通过上述方法获得的光学活性α-紫罗兰酮的香料组合物。 一种光学活性α-紫罗兰酮的制造方法，其特征在于，使作为旋光异构体的混合物的α-紫罗烯酮与酯化反应，水解得到的α-紫罗烯酮烯醇酯; 一种光学活性α-紫罗兰酮的制造方法，其特征在于，将α-紫罗烯酮作为光学异构体的混合物进行不对称还原，使得所得光学活性α-离子酚与酯化反应，得到光学活性α-离子醇酯，水解 根据需要纯化后得到的光学活性α-离子醇酯，然后氧化所得光学活性α-离子醇; 和包含这样得到的光学活性α-紫罗兰酮的香料组合物。

公开(公告)号：US07902404B2

公开(公告)日：2011-03-08

申请号：US11991966

申请日：2006-09-13

申请人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

发明人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

IPC分类号： C07C45/42

CPC分类号： C12P7/26 ,  A23L2/56 ,  A23L27/204 ,  A61K8/37 ,  A61Q11/00 ,  A61Q13/00 ,  C07B53/00 ,  C07B2200/07 ,  C07C403/08 ,  C07C403/12 ,  C07C403/14 ,  C07C2601/16 ,  C12G3/06 ,  C12P41/004

摘要： Provided that a method for inexpensively producing optically active α-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active α-ionone obtained by the aforementioned method. A method for producing optically active α-ionone, comprising allowing α-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained α-ionone enol ester; a method for producing optically active α-ionone comprising subjecting α-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active α-ionol to react with an esterification agent to give an optically active α-ionol ester, hydrolyzing the obtained optically active α-ionol ester after purification as necessary, and then oxidizing the obtained optically active α-ionol; and a perfume composition comprising thus obtained optically active α-ionone.

公开(公告)号：US20090216039A1

公开(公告)日：2009-08-27

申请号：US11991966

申请日：2006-09-13

申请人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

发明人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

IPC分类号： C12P7/26 ,  C07C69/75 ,  C07C45/42

CPC分类号： C12P7/26 ,  A23L2/56 ,  A23L27/204 ,  A61K8/37 ,  A61Q11/00 ,  A61Q13/00 ,  C07B53/00 ,  C07B2200/07 ,  C07C403/08 ,  C07C403/12 ,  C07C403/14 ,  C07C2601/16 ,  C12G3/06 ,  C12P41/004

摘要： Provided that a method for inexpensively producing optically active α-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active α-ionone obtained by the aforementioned method. A method for producing optically active α-ionone, comprising allowing α-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained α-ionone enol ester; a method for producing optically active α-ionone comprising subjecting α-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active α-ionol to react with an esterification agent to give an optically active α-ionol ester, hydrolyzing the obtained optically active α-ionol ester after purification as necessary, and then oxidizing the obtained optically active α-ionol; and a perfume composition comprising thus obtained optically active α-ionone.

摘要翻译： 本发明提供了一种低成本地生产光学活性α-紫罗兰酮的方法，其具有高产率和高不对称产率，并且在短时间内具有良好的可加工性，以及包含通过上述方法获得的光学活性α-紫罗兰酮的香料组合物。 一种光学活性α-紫罗兰酮的制造方法，其特征在于，使作为光学异构体的混合物的α-紫罗兰酮与酯化剂反应，水解得到的α-紫罗兰酮烯醇酯; 制备光学活性α-紫罗兰酮的方法，包括将α-紫罗烯酮作为光学异构体的混合物进行不对称还原，使得到的光学活性α-离子酚与酯化反应得到光学活性α-离子醇酯，水解 根据需要纯化后得到的光学活性α-离子醇酯，然后氧化得到的光学活性α-离子醇; 和包含由此获得的光学活性α-紫罗兰酮的香料组合物。

公开(公告)号：US08053592B2

公开(公告)日：2011-11-08

申请号：US13012199

申请日：2011-01-24

申请人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

发明人： Tetsuya Yamamoto ,  Kenji Yagi ,  Kenya Ishida

IPC分类号： C07C69/78 ,  C07C69/533 ,  C07C69/63

CPC分类号： C12P7/26 ,  A23L2/56 ,  A23L27/204 ,  A61K8/37 ,  A61Q11/00 ,  A61Q13/00 ,  C07B53/00 ,  C07B2200/07 ,  C07C403/08 ,  C07C403/12 ,  C07C403/14 ,  C07C2601/16 ,  C12G3/06 ,  C12P41/004

摘要： Provided that a method for inexpensively producing optically active α-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active α-ionone obtained by the aforementioned method. A method for producing optically active α-ionone, comprising allowing α-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained α-ionone enol ester; a method for producing optically active α-ionone comprising subjecting α-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active α-ionol to react with an esterification agent to give an optically active α-ionol ester, hydrolyzing the obtained optically active α-ionol ester after purification as necessary, and then oxidizing the obtained optically active α-ionol; and a perfume composition comprising thus obtained optically active α-ionone.

摘要翻译： 本发明提供了一种低成本地生产光学活性α-紫罗兰酮的方法，其具有高产率和高不对称产率，并且在短时间内具有良好的可加工性，以及包含通过上述方法获得的光学活性α-紫罗兰酮的香料组合物。 一种光学活性α-紫罗兰酮的制造方法，其特征在于，使作为旋光异构体的混合物的α-紫罗烯酮与酯化反应，水解得到的α-紫罗烯酮烯醇酯; 一种光学活性α-紫罗兰酮的制造方法，其特征在于，将α-紫罗烯酮作为光学异构体的混合物进行不对称还原，使得所得光学活性α-离子酚与酯化反应，得到光学活性α-离子醇酯，水解 根据需要纯化后得到的光学活性α-离子醇酯，然后氧化所得光学活性α-离子醇; 和包含这样得到的光学活性α-紫罗兰酮的香料组合物。

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）

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。

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。

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。

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。

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）