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    Process for the manufacture of gamma-acetoxytiglic aldehyde
    3.
    发明授权
    Process for the manufacture of gamma-acetoxytiglic aldehyde 失效
    制备γ-乙酰氧基乙醛的方法

    公开(公告)号：US5453547A

    公开(公告)日：1995-09-26

    申请号：US316654

    申请日：1994-09-30

    Applicant: Ulriche Zutter

    Inventor： Ulriche Zutter

    IPC: B01J23/44 ,  B01J27/10 ,  C07B61/00 ,  C07C45/40 ,  C07C45/62 ,  C07C47/263 ,  C07C67/40 ,  C07C69/007 ,  C07C69/145 ,  C07C403/12 ,  C07C409/20 ,  C07C45/27 ,  C07C45/28

    CPC classification number: C07C403/12 ,  C07C45/40 ,  C07C45/62 ,  C07C69/007 ,  C07C2101/16

    Abstract: A novel process for the manufacture of .gamma.-acetoxytiglic aldehyde ("C.sub.5 -aldehyde"), which is known as an important starting material for the production of vitamin A acetate from a (.beta.-ionylidenethyl)triphenylphosphonium halide and C.sub.5 -aldehyde, comprises treating a pentenyn-3-ol of the formula HC.tbd.C--C(CH.sub.3)(OH)--CH.dbd.C(R).sub.2 (II), wherein both R's signify either hydrogen or methyl, with ozone, preferably in a lower alkanol R.sup.1 OH, wherein R.sup.1 signifies C.sub.1-4 -alkyl, to obtain an aldehyde 2-hydroxy-2-methyl-3-butynal of the formula HC.tbd.C--C(CH.sub.3)(OH)--CHO (III). The aldehyde III may be converted to the C.sub.5 -aldehyde by conventional means.

    Abstract translation: 用于制造γ-乙酰氧基乙醛（“C5-醛”）的新方法，其被称为从（β-亚硫酰基乙基）三苯基鏻卤化物和C5-醛生产维生素A乙酸酯的重要起始原料，包括处理 式（ⅩⅧ）CC（CH 3）（OH）-CH = C（R）2（II）的戊烯-3-醇，其中R均表示氢或甲基，与臭氧，优选在低级链烷醇R 1 OH中，其中 R1表示C1-4 - 烷基，得到式为HC 3BOND CC（CH3）（OH）-CHO（III）的醛2-羟基-2-甲基-3-丁炔醛。 醛III可以通过常规方法转化成C5醛。

    Process for producing vitamin A derivatives
    4.
    发明授权
    Process for producing vitamin A derivatives 失效
    生产维生素A衍生物的方法

    公开(公告)号：US5424478A

    公开(公告)日：1995-06-13

    申请号：US215813

    申请日：1994-03-22

    Applicant: Mitsutaka Tanaka ,  Tadashi Hanaoka ,  Kunio Takanohashi

    Inventor： Mitsutaka Tanaka ,  Tadashi Hanaoka ,  Kunio Takanohashi

    IPC: C07C69/07 ,  C07C403/12

    CPC classification number: C07C403/12 ,  C07C2101/16

    Abstract: The present specification relates to an industrially advantageous process for producing vitamin A derivatives which are useful as medicaments, feed additives, food additives and the like. The process provides vitamin A derivatives, particularly all-trans vitamin A derivatives in high yield and purity.

    Abstract translation: 本说明书涉及可用作药物，饲料添加剂，食品添加剂等的维生素A衍生物的工业上有利的方法。 该方法以高产率和纯度提供维生素A衍生物，特别是全反式维生素A衍生物。

    Preparation of canthaxanthin and astaxanthin
    5.
    发明授权
    Preparation of canthaxanthin and astaxanthin 失效
    甘氨酸和阿司匹林的制备

    公开(公告)号：US5210314A

    公开(公告)日：1993-05-11

    申请号：US695336

    申请日：1991-04-29

    Applicant: Hansgeorg Ernst ,  Joachim Paust ,  Werner Hoffmann

    Inventor： Hansgeorg Ernst ,  Joachim Paust ,  Werner Hoffmann

    IPC: C07C45/75 ,  C07C49/653 ,  C07C49/743 ,  C07C69/63 ,  C07C403/12 ,  C07C403/24 ,  C07F9/54

    CPC classification number: C07C403/24 ,  C07C403/12 ,  C07F9/54 ,  C07F9/5435 ,  C07C2101/16

    Abstract: A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I ##STR1##where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II ##STR2##where R is H (a) or OH (b), with trifluoroacetic acid, reacting the resulting novel trifluoroacetate of the formula III ##STR3##with triphenylphosphine, and reacting the resulting novel triphenylphosphonium trifluoroacetate of the formula IV ##STR4## with 2,7-dimethyl-2,4,6-octatriene-1,8-dial under the conditions of a Wittig synthesis. The present invention also relates to the novel trifluoroacetates of the formula III and the corresponding triphenylphosphonium trifluoroacetates of the formula IV.

    Abstract translation: 制备式I的角黄素（Ia）和虾青素（Ib）的方法，其中R是H（a）或OH（b））包括使式II的叔醇（II）与R （III）的三氟乙酸盐与三苯基膦反应，并使得到的式IV的三氟化三苯基鏻（Ⅳ）与式（Ⅳ）化合物反应，得到新的三氟乙酸盐， 在Wittig合成条件下用2,7-二甲基-2,4,6-辛二烯-1,8-表盘。 本发明还涉及式III的新型三氟乙酸盐和式Ⅳ相应的三苯基三氟乙酸盐。

    Derivatives of 8-dehydro-vitamin A and their preparation
    8.
    发明授权
    Derivatives of 8-dehydro-vitamin A and their preparation 失效
    8-脱氢维生素A的衍生物及其制备方法

    公开(公告)号：US4272456A

    公开(公告)日：1981-06-09

    申请号：US003021

    申请日：1979-01-12

    Applicant: Manfred Baumann ,  Werner Hoffmann

    Inventor： Manfred Baumann ,  Werner Hoffmann

    IPC: A61K31/07 ,  A61K31/23 ,  C07C21/02 ,  C07C22/02 ,  C07C67/00 ,  C07C401/00 ,  C07C403/00 ,  C07C403/02 ,  C07C403/04 ,  C07C403/08 ,  C07C403/12 ,  C07F9/50 ,  C07F9/54

    CPC classification number: C07C403/04 ,  C07C403/08 ,  C07C403/10 ,  C07C403/12 ,  C07C403/14 ,  C07C403/16 ,  C07F9/5428 ,  C07C2101/16

    Abstract: New derivatives of 8-dehydro-vitamin A obtained by vinylating or ethynylating and subsequently partially hydrogenating, 1-[3-methyl-octa-1-yne,3,5,-dien-7-on-1-yl]-2,6-dimethyl-cyclohex-1-ene or its 5- and/or 6-methyl derivatives, converting the resulting alcohols to the corresponding derivatives of 8-dehydro-vitamin A halides by reacting with thionyl chloride or phosgene, and if required converting the resulting alcohols or halides to the corresponding trialkylphosphonium salts or triarylphosphonium salts, or reacting the 8-dehydro-vitamin A halide derivatives with alkali metal salts or alkaline earth metal salts or anhydrides of lower carboxylic acids. The new compounds can be partially hydrogenated to the corresponding polyene compounds, in which case the cis-trans isomer mixtures first obtained can be rearranged in the conventional manner to the physiologically active all-trans compounds. Accordingly, the process provides a method for the total synthesis of vitamin A, and of other compounds of the carotinoid series, which is independent of the Wittig ylide synthesis.

    Abstract translation: 1-脱氧维生素A的新衍生物，其通过乙烯化或乙炔化并随后部分氢化1- [3-甲基 - 辛-1-炔，3,5 - 二烯-7-基-1-基] -2， 6-二甲基 - 环己-1-烯或其5-和/或6-甲基衍生物，通过与亚硫酰氯或光气反应将所得醇转化成8-脱氢 - 维生素A卤化物的相应衍生物，如果需要， 所得醇或卤化物与相应的三烷基鏻盐或三芳基鏻盐反应，或使8-脱氢 - 维生素A卤化物衍生物与低级羧酸的碱金属盐或碱土金属盐或酸酐反应。 新化合物可以部分氢化成相应的多烯化合物，在这种情况下，首先获得的顺反异构体混合物可以以常规方式重新排列到生理活性全反式化合物上。 因此，该方法提供了维生素A和类胡萝卜素系列的其它化合物的总合成方法，其不依赖于维他立叶内酯合成。

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