公开(公告)号：US20120330048A1

公开(公告)日：2012-12-27

申请号：US13583635

申请日：2011-03-09

申请人： Xuejun Lao ,  Runpu Shen ,  Weidong Ye ,  Xiaohua Song ,  Luo Liu ,  Chunlei Wu ,  Yibin Wu ,  Liujiang Hu

发明人： Xuejun Lao ,  Runpu Shen ,  Weidong Ye ,  Xiaohua Song ,  Luo Liu ,  Chunlei Wu ,  Yibin Wu ,  Liujiang Hu

IPC分类号： C07F9/40

CPC分类号： C07F9/4015

摘要： The invention relates to a novel important lycopene intermediate 3,7, 11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3, 5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.

摘要翻译： 本发明涉及一种新型重要的番茄红素中间体3,7,11-三甲基-1,3,6,10-四烯十二烷基二乙基膦酸酯。 目前的番茄红素中间体2,4,6,10-四 - 双十五碳酸膦难以合成。 本发明提供了一种新的中间体，其具有以下合成步骤：由假雄酮制备2,6,10-三甲基-3,5,9-十一烷三烯-1-醛; 由2,6,10-三甲基-3,9,9-十一烷三烯-1-醛制备2,6,10-三甲基-2,5,9-十一烷三烯-1-醛; 并使2,6,10-三甲基-2,5,9-十一烷三烯-1-醛和四亚乙基二膦酸四乙酯进行缩合反应，得到目标产物。 本发明只能通过四个反应从原料假雄酮生成新的中间体，因此反应易于控制，实现了巨大的工业价值。

公开(公告)号：US20120296126A1

公开(公告)日：2012-11-22

申请号：US13521044

申请日：2010-03-18

申请人： Xinde Xu ,  Bin Shao ,  Hongjuan Chao ,  Xuejun Lao ,  Xiaoxia Sun

发明人： Xinde Xu ,  Bin Shao ,  Hongjuan Chao ,  Xuejun Lao ,  Xiaoxia Sun

IPC分类号： C07C29/56

CPC分类号： C07C403/24 ,  C07C2601/16 ,  C09B61/00

摘要： The invention makes public a preparing method for xanthophyll crystals with higher content of zeaxanthin from plant oleoresin. The current methods generally are to get quite pure crystal forms of xanthophyll or zeaxanthin, and they refer to several separation steps. The invention mixes the xanthophyll diester-containing plant oleoresins and food grade alcohol solvents to form even solution, and then soap-dissolve the solution under an alkaline environment; then replenish organic solvents and emulsifiers into the reaction solution and drop some alkali solution into the solution to make partial xanthophyll crystals be transformed to be zeaxanthin through epimerization reaction; after the reaction is finished, add the mixed solvents of alcohol solvent and water to separate out the crystals; use the method of centrifugation or filtration to get the crystals; wash the crystals several times with the mixed solution of deionized water and alcohols to remove the impurities among the crystals; recrystallize the gained crystals with absolute ethyl alcohol, and then dry the crystals to get the products. The invention can gain mixture crystals that contain xanthophyll and zeaxanthin at one time in quite high collection rate, and it is convenient for the followed product application.

摘要翻译： 本发明公开了植物油树脂中玉米黄质含量较高的叶黄素晶体的制备方法。 目前的方法通常是获得相当纯的叶黄素或玉米黄质的晶体形式，它们是指几个分离步骤。 本发明混合含有叶黄素二酯的植物油树脂和食品级醇溶剂，形成均匀的溶液，然后在碱性环境下将溶液皂溶; 然后将有机溶剂和乳化剂补充到反应溶液中，并将一些碱溶液滴入溶液中，使部分叶黄素晶体通过差向异构化反应转化为玉米黄质; 反应完成后，加入醇溶剂和水的混合溶剂分离出晶体; 使用离心或过滤方法得到晶体; 用去离子水和醇的混合溶液洗涤晶体数次以除去晶体中的杂质; 用绝对乙醇重结晶获得的晶体，然后干燥晶体得到产物。 本发明可以以非常高的收集率一次获得含有叶黄素和玉米黄质的混合物晶体，对于随后的产品应用是方便的。

公开(公告)号：US09622497B2

公开(公告)日：2017-04-18

申请号：US13997273

申请日：2011-01-30

申请人： Xinde Xu ,  Bin Shao ,  Xuejun Lao

发明人： Xinde Xu ,  Bin Shao ,  Xuejun Lao

IPC分类号： A23D9/007 ,  A61K9/10 ,  A61K31/015 ,  A61K47/44 ,  A23K20/179 ,  A23K20/158

CPC分类号： A23D9/007 ,  A23K20/158 ,  A23K20/179 ,  A61K9/10 ,  A61K31/015 ,  A61K47/44

摘要： A carotenoid oil suspension and preparation method thereof are provided. The method includes the following steps: a) mixing carotenoid with organic solvent, heating the mixture to dissolve the carotenoid sufficiently to obtain carotenoid solution; b) introducing the carotenoid solution obtained in step a) into a vegetable oil solution stirred in high speed by spraying, meanwhile recovering the organic solvent generated during spraying under vacuum condition, then, simultaneously completing recycling and spraying, thereafter, obtaining carotenoid oil suspension; wherein, the carotenoid oil suspension comprises a carotenoid crystal with an average particle size of less than 5 μm. The method is applicable in industrial scale with continuous operation and increased efficiency without additional carotenoid crystal grinding processes, and decreases the degradation of carotenoid during the preparation process of carotenoid oil suspension.

公开(公告)号：US08765988B2

公开(公告)日：2014-07-01

申请号：US13583635

申请日：2011-03-09

申请人： Xuejun Lao ,  Runpu Shen ,  Weidong Ye ,  Xiaohua Song ,  Luo Liu ,  Chunlei Wu ,  Yibin Wu ,  Liujiang Hu

发明人： Xuejun Lao ,  Runpu Shen ,  Weidong Ye ,  Xiaohua Song ,  Luo Liu ,  Chunlei Wu ,  Yibin Wu ,  Liujiang Hu

IPC分类号： C07F9/40

CPC分类号： C07F9/4015

摘要： The invention relates to a novel important lycopene intermediate 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.

摘要翻译： 本发明涉及新型重要的番茄红素中间体3,7,11-三甲基-1,3,6,10-四烯十二烷基二乙基膦酸酯。 目前的番茄红素中间体2,4,6,10-四 - 双十五碳酸膦难以合成。 本发明提供了一种新的中间体，其具有以下合成步骤：由假雄酮制备2,6,10-三甲基-3,5,9-十一烷三烯-1-醛; 由2,6,10-三甲基-3,5,9-十一烷三烯-1-醛制备2,6,10-三甲基-2,5,9-十一烷三烯-1-醛; 并使2,6,10-三甲基-2,5,9-十一烷三烯-1-醛和四亚乙基二膦酸四乙酯进行缩合反应，得到目标产物。 本发明只能通过四个反应从原料假雄酮生成新的中间体，因此反应易于控制，实现了巨大的工业价值。

公开(公告)号：US07351854B2

公开(公告)日：2008-04-01

申请号：US11749793

申请日：2007-05-17

申请人： Runpu Shen ,  Guoqi Yu ,  Weidong Ye ,  Kui Wang ,  Xuejun Lao

发明人： Runpu Shen ,  Guoqi Yu ,  Weidong Ye ,  Kui Wang ,  Xuejun Lao

IPC分类号： C07C67/02

CPC分类号： C07C67/08 ,  C07C29/66 ,  C07C67/14 ,  C07C67/293 ,  C07C33/423 ,  C07C69/007 ,  C07C69/63

摘要： 1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.

摘要翻译： 1-异-2-甲基-4-酰氧基-2-丁烯衍生物可以从异戊二烯开始以良好的产率和高纯度合成，并且在由N-氯异氰尿酸衍生物和水制成的体系中使用氯代醇形成反应，随后酯化 和粗产物混合物的重排。

公开(公告)号：US20070270607A1

公开(公告)日：2007-11-22

申请号：US11749793

申请日：2007-05-17

申请人： Runpu SHEN ,  Guoqi YU ,  Weidong YE ,  Kui WANG ,  Xuejun LAO

发明人： Runpu SHEN ,  Guoqi YU ,  Weidong YE ,  Kui WANG ,  Xuejun LAO

IPC分类号： C07C67/02

CPC分类号： C07C67/08 ,  C07C29/66 ,  C07C67/14 ,  C07C67/293 ,  C07C33/423 ,  C07C69/007 ,  C07C69/63

摘要： 1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.

摘要翻译： 1-异-2-甲基-4-酰氧基-2-丁烯衍生物可以从异戊二烯开始以良好的产率和高纯度合成，并且在由N-氯异氰尿酸衍生物和水制成的体系中使用氯代醇形成反应，随后酯化 和粗产物混合物的重排。

公开(公告)号：US08871984B2

公开(公告)日：2014-10-28

申请号：US13521044

申请日：2010-03-18

申请人： Xinde Xu ,  Bin Shao ,  Hongjuan Chao ,  Xuejun Lao ,  Xiaoxia Sun

发明人： Xinde Xu ,  Bin Shao ,  Hongjuan Chao ,  Xuejun Lao ,  Xiaoxia Sun

IPC分类号： C07C27/02 ,  C07C29/09 ,  C07C29/56 ,  C07C403/24 ,  C09B61/00

CPC分类号： C07C403/24 ,  C07C2601/16 ,  C09B61/00

摘要： The invention makes public a method for preparing xanthophyll crystals with higher content of zeaxanthin from plant oleoresin. The current methods generally are to get quite pure crystal forms of xanthophyll or zeaxanthin, and they refer to several separation steps. The invention mixes the xanthophyll diester-containing plant oleoresins and food grade alcohol solvents to form smooth solution, and then soap-dissolve the solution under an alkaline environment; then replenish organic solvents and emulsifiers into the reaction solution and drop some alkali solution into the solution to make partial xanthophyll crystals be transformed to be zeaxanthin through epimerization reaction; after the reaction is finished, add the mixed solvents of alcohol solvent and water to separate out the crystals; use the method of centrifugation or filtration to get the crystals; wash the crystals several times with the mixed solution of deionized water and alcohols to remove the impurities among the crystals; recrystallize the gained crystals with absolute ethyl alcohol, and then dry the crystals to get the products. The invention can gain mixture of crystals that contain xanthophyll and zeaxanthin at one time in quite high collection rate.

摘要翻译： 本发明公开了一种从植物油树脂制备玉米黄质含量较高的叶黄素晶体的方法。 目前的方法通常是获得相当纯的叶黄素或玉米黄质的晶体形式，它们是指几个分离步骤。 本发明混合含有叶黄素二酯的植物油树脂和食品级醇溶剂，形成光滑的溶液，然后在碱性环境下将溶液皂溶; 然后将有机溶剂和乳化剂补充到反应溶液中，并将一些碱溶液滴入溶液中，使部分叶黄素晶体通过差向异构化反应转化为玉米黄质; 反应完成后，加入醇溶剂和水的混合溶剂分离出晶体; 使用离心或过滤方法得到晶体; 用去离子水和醇的混合溶液洗涤晶体数次以除去晶体中的杂质; 用绝对乙醇重结晶获得的晶体，然后干燥晶体得到产物。 本发明可以以相当高的收集率一次获得含有叶黄素和玉米黄质的晶体的混合物。

公开(公告)号：US08697919B2

公开(公告)日：2014-04-15

申请号：US13639852

申请日：2011-04-06

申请人： Xuejun Lao ,  Runpu Shen ,  Weidong Ye ,  Xiaohua Song ,  Luo Liu ,  Chunlei Wu ,  Xiongsheng Sun ,  Siping Hu

发明人： Xuejun Lao ,  Runpu Shen ,  Weidong Ye ,  Xiaohua Song ,  Luo Liu ,  Chunlei Wu ,  Xiongsheng Sun ,  Siping Hu

IPC分类号： C07C45/42 ,  C07C41/30 ,  C07C43/15

CPC分类号： C07C43/16 ,  C07C41/30 ,  C07C45/42 ,  C07C47/21

摘要： The invention discloses an intermediate 1-methoxyl-2,6,10-trimethyl-1,3,5, 9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2,6,10-trimethyl-2,5,9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.

摘要翻译： 本发明公开了中间体1-甲氧基-2,6,10-三甲基-1,3,5,9-十一四烯及其制备方法和用途。 在目前番茄红素中间体2-pos双键C-14醛（2,6,10-三甲基-2,5,9-十一碳三烯-1-醛）的合成方法中，昂贵的甲基碘，污染二甲基硫化物和危险的强 需要这种方法，这种方法几乎不适用于工业生产。 本发明提供了一种新的化合物1-甲氧基-2,6,10-三甲基-1,3,5,9-十一四烯，纯的2-位双键C-14醛可以通过水解和精制化合物 。 合成路线简化，实现了工业生产的良好适应性。

公开(公告)号：US20140030419A1

公开(公告)日：2014-01-30

申请号：US13997273

申请日：2011-01-30

申请人： Xinde Xu ,  Bin Shao ,  Xuejun Lao

发明人： Xinde Xu ,  Bin Shao ,  Xuejun Lao

IPC分类号： A23D9/007

CPC分类号： A23D9/007 ,  A23K20/158 ,  A23K20/179 ,  A61K9/10 ,  A61K31/015 ,  A61K47/44

摘要： A carotenoid oil suspension and preparation method thereof are provided. The method includes the following steps: a) mixing carotenoid with organic solvent, heating the mixture to dissolve the carotenoid sufficiently to obtain carotenoid solution; b) introducing the carotenoid solution obtained in step a) into a vegetable oil solution stirred in high speed by spraying, meanwhile recovering the organic solvent generated during spraying under vacuum condition, then, simultaneously completing recycling and spraying, thereafter, obtaining carotenoid oil suspension; wherein, the carotenoid oil suspension comprises a carotenoid crystal with an average particle size of less than 5 μm. The method is applicable in industrial scale with continuous operation and increased efficiency without additional carotenoid crystal grinding processes, and decreases the degradation of carotenoid during the preparation process of carotenoid oil suspension.

摘要翻译： 提供类胡萝卜素油悬浮液及其制备方法。 该方法包括以下步骤：a）将类胡萝卜素与有机溶剂混合，加热混合物以充分溶解类胡萝卜素，得到类胡萝卜素溶液; b）将步骤a）中得到的类胡萝卜素溶液加入到通过喷雾高速搅拌的植物油溶液中，同时在真空条件下回收喷雾过程中产生的有机溶剂，同时完成回收和喷涂，然后获得类胡萝卜素油悬浮液; 其中，类胡萝卜素油悬浮液包含平均粒度小于5um的类胡萝卜素晶体。 该方法适用于工业规模，连续操作，效率高，无需额外的类胡萝卜素晶体研磨工艺，降低类胡萝卜素油悬浮液制备过程中类胡萝卜素的降解。

公开(公告)号：US08536361B2

公开(公告)日：2013-09-17

申请号：US13576659

申请日：2011-01-30

申请人： Runpu Shen ,  Weidong Ye ,  Shiqing Pi ,  Xuejun Lao ,  Luo Liu ,  Xiaohua Song ,  Chunlei Wu ,  Zhigang Wu

发明人： Runpu Shen ,  Weidong Ye ,  Shiqing Pi ,  Xuejun Lao ,  Luo Liu ,  Xiaohua Song ,  Chunlei Wu ,  Zhigang Wu

IPC分类号： C07F9/142

CPC分类号： C07F9/4015 ,  C07C1/34 ,  C07C11/21

摘要： 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4), and preparation method thereof are provided. The preparation method comprises: reacting a pseudo ionone of formula (2) with sulfonium salt to prepare a epoxide of formula (9), and then reacting the epoxide of formula (9) with magnesium bromide to prepare a C-14 aldehyde of formula (3); condensing the C-14 aldehyde of formula (3) with tetra-alkyl methylene diphosphonate to obtain 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4). Furthermore, the preparation method of lycopene via 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4) is also provided. The present method has the advantages of short route, easily obtained raw materials, and low cost.

摘要翻译： 提供式（4）的1,4,6,10-四 - 双十五碳 - 碳膦酸酯及其制备方法。 制备方法包括：使式（2）的假紫罗酮与锍盐反应以制备式（9）的环氧化物，然后使式（9）的环氧化物与溴化镁反应以制备式（C） 3）; 将式（3）的C-14醛缩合成四烷基亚甲基二膦酸盐，得到式（4）的1,4,6,10-四 - 双十五碳酸膦酸酯。 此外，还提供了通式（4）的1,4,6,10-四 - 双十五碳碳酸膦酸酯的番茄红素的制备方法。 本发明方法路线短，原料易得，成本低。