公开(公告)号：US5012018A

公开(公告)日：1991-04-30

申请号：US654526

申请日：1984-09-25

申请人： Yasuyuki Tanaka ,  Koichi Ibata ,  Masao Mizuno ,  Yoichi Ninagawa ,  Takashi Nishida

发明人： Yasuyuki Tanaka ,  Koichi Ibata ,  Masao Mizuno ,  Yoichi Ninagawa ,  Takashi Nishida

IPC分类号： C07C69/007 ,  C07C17/00 ,  C07C17/16 ,  C07C21/215 ,  C07C27/00 ,  C07C29/10 ,  C07C29/32 ,  C07C33/02 ,  C07C43/12 ,  C07C43/15 ,  C07C43/16 ,  C07C43/205 ,  C07C43/303 ,  C07C43/313 ,  C07C67/00 ,  C07C67/58 ,  C07C271/12 ,  C07D213/64 ,  C07D213/70 ,  C07D277/16 ,  C07D277/68 ,  C07D309/12 ,  C07F7/18 ,  C07F9/113

CPC分类号： C07D213/64 ,  C07C271/12 ,  C07C29/10 ,  C07C29/32 ,  C07C317/00 ,  C07C321/00 ,  C07C33/02 ,  C07C381/12 ,  C07C43/12 ,  C07C43/15 ,  C07C43/16 ,  C07C43/205 ,  C07C43/303 ,  C07C43/313 ,  C07D213/70 ,  C07D277/16 ,  C07D277/68 ,  C07D309/12 ,  C07F7/1852 ,  C07F9/113

摘要： A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

公开(公告)号：US4886904A

公开(公告)日：1989-12-12

申请号：US081735

申请日：1987-08-05

申请人： Yasuyuki Tanaka ,  Koichi Ibata ,  Masao Mizuno ,  Yoichi Ninagawa ,  Takashi Nishida

发明人： Yasuyuki Tanaka ,  Koichi Ibata ,  Masao Mizuno ,  Yoichi Ninagawa ,  Takashi Nishida

IPC分类号： C07C69/007 ,  C07C17/00 ,  C07C17/16 ,  C07C21/215 ,  C07C27/00 ,  C07C29/10 ,  C07C29/32 ,  C07C33/02 ,  C07C43/12 ,  C07C43/15 ,  C07C43/16 ,  C07C43/205 ,  C07C43/303 ,  C07C43/313 ,  C07C67/00 ,  C07C67/58 ,  C07C271/12 ,  C07D213/64 ,  C07D213/70 ,  C07D277/16 ,  C07D277/68 ,  C07D309/12 ,  C07F7/18 ,  C07F9/113

CPC分类号： C07D213/64 ,  C07C271/12 ,  C07C29/10 ,  C07C29/32 ,  C07C317/00 ,  C07C321/00 ,  C07C33/02 ,  C07C381/12 ,  C07C43/12 ,  C07C43/15 ,  C07C43/16 ,  C07C43/205 ,  C07C43/303 ,  C07C43/313 ,  C07D213/70 ,  C07D277/16 ,  C07D277/68 ,  C07D309/12 ,  C07F7/1852 ,  C07F9/113

摘要： A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

摘要翻译： 一种聚丙烯基组合物，其基本上由下式（I）表示的聚异戊二烯基化合物的混合物组成，其中A1表示羟基或乙酰氧基，IMAMA表示反异戊二烯单元，IMAGE表示顺式 - 异戊二烯单元，n为11至19的整数，所述混合物含有大量至少三种式（I）化合物，其中n表示14,15和16，作为必需成分，总量为至少70 基于混合物重量的重量％; 和衍生自式（I）的聚异戊二烯基化合物的新化合物。 这些组合物和化合物可用于合成哺乳动物多烯醇。 聚乙烯基组合物可以通过用油溶性有机溶剂提取银杏叶或雪松的叶子来制备; 如果需要，水解提取物; 并对提取物进行色谱法，分数溶解，分级冷冻沉淀和分子蒸馏中的一种或多种，​​从而在二氧化硅薄层色谱中分离和回收具有特定Rf值的级分。

公开(公告)号：US5077046A

公开(公告)日：1991-12-31

申请号：US410588

申请日：1989-09-21

申请人： Yasuyuki Tanaka ,  Koichi Ibata ,  Masao Mizuno ,  Yoichi Ninagawa ,  Takashi Nishida

发明人： Yasuyuki Tanaka ,  Koichi Ibata ,  Masao Mizuno ,  Yoichi Ninagawa ,  Takashi Nishida

IPC分类号： C07C69/007 ,  C07C17/00 ,  C07C17/16 ,  C07C21/215 ,  C07C27/00 ,  C07C29/10 ,  C07C29/32 ,  C07C33/02 ,  C07C43/12 ,  C07C43/15 ,  C07C43/16 ,  C07C43/205 ,  C07C43/303 ,  C07C43/313 ,  C07C67/00 ,  C07C67/58 ,  C07C271/12 ,  C07D213/64 ,  C07D213/70 ,  C07D277/16 ,  C07D277/68 ,  C07D309/12 ,  C07F7/18 ,  C07F9/113

CPC分类号： C07D213/64 ,  C07C271/12 ,  C07C29/10 ,  C07C29/32 ,  C07C317/00 ,  C07C321/00 ,  C07C33/02 ,  C07C381/12 ,  C07C43/12 ,  C07C43/15 ,  C07C43/16 ,  C07C43/205 ,  C07C43/303 ,  C07C43/313 ,  C07D213/70 ,  C07D277/16 ,  C07D277/68 ,  C07D309/12 ,  C07F7/1852 ,  C07F9/113

摘要： A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mamammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

公开(公告)号：US4668820A

公开(公告)日：1987-05-26

申请号：US722173

申请日：1985-04-10

申请人： Koichi Ibata ,  Tetsuo Takigawa ,  Masafumi Okada ,  Masao Mizuno ,  Takashi Nishida

发明人： Koichi Ibata ,  Tetsuo Takigawa ,  Masafumi Okada ,  Masao Mizuno ,  Takashi Nishida

IPC分类号： C07C69/007 ,  C07C27/00 ,  C07C29/74 ,  C07C29/76 ,  C07C29/88 ,  C07C33/02 ,  C07C67/00 ,  C07C67/54 ,  C07C69/025 ,  C08F8/12 ,  C08F8/14 ,  C07C67/48 ,  C07C67/52

CPC分类号： C07C33/02 ,  C07C29/76

摘要： Polyprenols or esters thereof, which are similar in the trans and cis configurations to dolichol, or mixtures thereof are obtained from the leaves of plants belonging to the genus Pinus L. of the family Pinaceae by extraction, if necessary followed by hydrolysis, esterification or transesterification or a combination thereof. These polyprenyl compounds and mixtures thereof are useful as favorable starting materials for the synthesis of dolichol.

摘要翻译： 通过提取，如果需要，然后进行水解，酯化或酯交换，从属于松果科属松属植物的植物的叶子获得反式和顺式构型与二醇的类似的聚螺旋体或其酯或其混合物 或其组合。 这些聚异戊二烯基化合物及其混合物可用作合成双氯酚的有利原料。

公开(公告)号：US4564477A

公开(公告)日：1986-01-14

申请号：US467253

申请日：1983-02-17

申请人： Tetsuo Takigawa ,  Koichi Ibata ,  Masafumi Okada ,  Masao Mizuno ,  Takashi Nishida

发明人： Tetsuo Takigawa ,  Koichi Ibata ,  Masafumi Okada ,  Masao Mizuno ,  Takashi Nishida

IPC分类号： C07C29/14 ,  C07C29/147 ,  C07C45/29 ,  C07C45/30 ,  C07C45/59 ,  C07C45/67 ,  C07C47/21 ,  C07C49/203 ,  C07C57/03 ,  C07C69/587 ,  C07D295/02 ,  C07D295/03 ,  C07D295/185 ,  C09F5/00

CPC分类号： C07D295/185 ,  C07C255/00 ,  C07C29/14 ,  C07C29/147 ,  C07C45/292 ,  C07C45/298 ,  C07C45/305 ,  C07C45/59 ,  C07C45/676 ,  C07C47/21 ,  C07C49/203 ,  C07C57/03 ,  C07D295/03

摘要： There are provided polyprenyl compounds of the formula ##STR1## wherein ##STR2## represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z.sup.1 and Z.sup.2 combinedly represent .dbd.O, .dbd.CH--COOH,.dbd.CH--COOR.sup.1, .dbd.CH--CN, .dbd.C(CN)COOR.sup.2, .dbd.CH--CO--NH.sub.2, .dbd.CH--CO--N(R.sup.3) (R.sup.4), .dbd.CH--CO--NHR.sup.5, .dbd.CH--CH.sub.2 --N(R.sup.3) (R.sup.4), .dbd.CH--CH.sub.2 --NHR.sup.5 or .dbd.CH--CHO or Z.sup.1 is a hydrogen atom and Z.sup.2 is --CH.sub.2 COOH, --CH.sub.2 COOR.sup.6, --CH(CN)COOR.sup.2, --CH.sub.2 CN, --CH.sub.2 --CO--NH.sub.2, --CH.dbd.CH--N(R.sup.3) (R.sup.4) or --CH.sub.2 --CH.dbd.N--R.sup.5, R.sup.1, R.sup.2 and R.sup.6 each being a lower alkyl group, R.sup.3 and R.sup.4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R.sup.3 and R.sup.4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R.sup.5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group. These polyprenyl compounds can be synthesized starting with a polyprenol obtainable from leaves of a plant such as Ginkgo biloba or Cedrus deodara by extraction and as necessary followed by hydrolysis, or a reactive derivative thereof. The polyprenyl compounds are useful as intermediates for the synthesis of dolichol without the use of an expensive C.sub.5 chain extender.

摘要翻译： 提供下式的聚异戊二烯基化合物：其中，“IMAGE”分别代表异戊二烯单元和顺式异戊二烯单元，n为11-19的整数，Z1和Z2组合表示 = CH 2 COOR 1 = CH-COOR 1 = CH-CN = C（CN）COOR 2 = CH-CO-NH 2 = CH-CO-N（R3）（R4） NHR 5，= CH-CH 2 -N（R 3）（R 4），= CH-CH 2 -NHR 5或= CH-CHO或Z 1是氢原子，Z 2是-CH 2 COOH，-CH 2 COOR 6，-CH（CN）COOR 2，-CH 2 CN ，-CH 2 -CO-NH 2，-CH = CH-N（R 3）（R 4）或-CH 2 -CH = N-R 5，R 1，R 2和R 6各自为低级烷基，R 3和R 4各自独立地为低级 - 烷基，环烷基，芳基或芳烷基或R3和R4组合表示含2-5个碳原子的亚烷基，R5为低级烷基，环烷基，芳基或芳烷基。 这些聚异戊二烯基化合物可以从通过提取从植物如银杏叶或Cedrus deodara的叶获得的聚异戊二烯开始合成，并且根据需要随后进行水解或其活性衍生物合成。 聚异戊二烯基化合物可用作合成Dolichol而不使用昂贵的C5扩链剂的中间体。