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    Process for Synthesis of (3S)- and (3R)-3-Hydroxy-Beta-Ionone, and Their Transformation to Zeaxanthin and Beta-Cryptoxanthin
    1.
    发明申请
    Process for Synthesis of (3S)- and (3R)-3-Hydroxy-Beta-Ionone, and Their Transformation to Zeaxanthin and Beta-Cryptoxanthin 有权

    公开(公告)号：US20090311761A1

    公开(公告)日：2009-12-17

    申请号：US12484703

    申请日：2009-06-15

    Applicant: Frederick Khachik ,  An-Ni Chang

    Inventor： Frederick Khachik ,  An-Ni Chang

    IPC: C12P7/26 ,  C07C45/67

    CPC classification number: C12P41/004 ,  C07C45/67 ,  C12P7/26 ,  C07C49/242

    Abstract: (3R)-3-Hydroxy-β-ionone and (3S)-3-hydroxy-β-ionone are two important intermediates in the synthesis of carotenoids with β-end group such as lutein, zeaxanthin, β-cryptoxanthin, and their stereoisomers. Among the various stereoisomers of these carotenoids, only (3R,3′R,6′R)-lutein, (3R,3′R)-zeaxanthin, and (3R)-β-cryptoxanthin are present in commonly consumed fruits and vegetables. There are 3 possible stereoisomers for zeaxanthin, these are: dietary (3R,3′R)-zeaxanthin (1), non-dietary (3S,3′S)-zeaxanthin (2), and non-dietary (3R,3′S;meso)-zeaxanthin (3) which is a presumed metabolite of dietary lutein. Dietary lutein as well as 1 and 3 are accumulated in the human macula and have been implicated in the prevention of age-related macular degeneration. (3R)-β-Cryptoxanthin (4) is also present in selected ocular tissues at a very low concentration whereas its enantiomer (3S)-β-cryptoxanthin (5) is absent in foods and human plasma.The present invention relates to a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydroxy-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)—C15-Wittig salt] and its (3S)-enantiomer [(3S)—C15-Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercially available 2,5-dimethylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin (1-3). Similarly, (3R)—C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal to yield 4 and 5.

    Process for making intermediates for fragrance components from α-campholenic aldehyde
    8.
    发明授权
    Process for making intermediates for fragrance components from α-campholenic aldehyde 失效
    从α-樟脑醛制备香料成分的中间体的方法

    公开(公告)号：US07262329B1

    公开(公告)日：2007-08-28

    申请号：US11604431

    申请日：2006-11-27

    Applicant: Gennadiy G. Kolomeyer ,  Jacob Oyloe ,  Douglas A. Ferone

    Inventor： Gennadiy G. Kolomeyer ,  Jacob Oyloe ,  Douglas A. Ferone

    IPC: C07C45/67 ,  C07C45/72 ,  C07C45/74

    CPC classification number: C07C45/66 ,  C07C45/72 ,  C07C45/74 ,  C07C45/82 ,  C07C49/21 ,  C07C49/242

    Abstract: A two-step aldol condensation process is disclosed. α-Campholenic aldehyde (ACA) and methyl ethyl ketone (MEK) react in the presence of a base under conditions effective to produce a mixture comprising a high yield of ketol condensation products. Dehydration of the ketols in the presence of an organic sulfonic acid provides unsaturated ketones that are valuable intermediates for fragrance components for synthetic sandalwood products. Compared with the usual one-step, base-catalyzed approach, the two-step process increases the yield of all condensation products and maximizes production of the most valuable ketone isomers.

    Abstract translation: 公开了两步醛醇缩合方法。 α-烷基醛（ACA）和甲基乙基酮（MEK）在碱的存在下在有效产生包含高产量的酮缩醇产物的混合物的条件下反应。 在存在有机磺酸的情况下，酮基的脱水提供不饱和酮，其是用于合成檀香产品的香料组分的有价值的中间体。 与通常的一步，碱催化方法相比，两步法提高了所有缩合产物的产率，并最大限度地提高了最有价值的酮异构体的生产。

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