Process for preparing compositions containing unsaturated lactones,
products produced thereby and organoleptic uses of said products
    1.
    发明授权
    Process for preparing compositions containing unsaturated lactones, products produced thereby and organoleptic uses of said products 失效
    制备含有不饱和内酯的组合物,由此生产的产品和所述产品的感官用途的方法

    公开(公告)号:US4946782A

    公开(公告)日:1990-08-07

    申请号:US228512

    申请日:1988-08-05

    CPC classification number: C12P17/02 A24B15/403 C11B9/0073 C12P7/40 C12P7/42

    Abstract: Described is a process for the preparation of compositions of matter containing unsaturated lactones defined according to the generic structure: ##STR1## wherein R represents C.sub.6 alkyl or alkenyl; and X represents C.sub.2, C.sub.4 or C.sub.6 alkylene or alkenylene; with the provisos that R is C.sub.6 alkyl when X is alkenylene and R is C.sub.6 alkenyl when X is alkylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of:Candida petrophilum, ATCC 20226;Candida oleophila, ATCC 20177;Candida sp., ATCC 20504; andCandida sake, ATCC 28137whereby gamma hydroxydecanoic acid and a mixture of other acids defined according to the generic structure: ##STR2## is formed wherein Y represents an oxo-saturated, oxo-unsaturated or di-unsaturated C.sub.9, C.sub.11 or C.sub.13 moiety according to the reaction: ##STR3## (ii) lactonization of the resulting gamma hydroxydecanoic acid by means of simultaneous acidification and heating according to the reaction: ##STR4## and (iii) lactonization (via distillation) of one or more of the resulting acids defined according to the structure: ##STR5## to form one or more lactones defined according to the generic structure: ##STR6## according to the reaction: ##STR7## wherein the sum of the number of carbon atoms in the X moiety and in the R moiety is equal to the number of carbon atoms in the Y moiety minus 1.Also described are the products produced according to such process as well as their organoleptic utilities for augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos and smoking tobaccos.

    Abstract translation: 描述了根据通用结构定义的含有不饱和内酯的物质组合物的方法:其中R表示C6烷基或烯基; X表示C2,C4或C6亚烷基或亚烯基; 条件是当X是亚烯基时R是C6烷基,当X是亚烷基时,R是C6链烯基,通过以下顺序的步骤:(i)使用选自以下的微生物来蓖麻油或蓖麻油酸发酵:念珠菌 ,ATCC 20226; 嗜油假丝酵母,ATCC 20177; 念珠菌属,ATCC 20504; 和念珠菌,ATCC 28137,由此形成根据通用结构定义的γ-羟基癸酸和其它酸的混合物:其中Y表示氧代饱和的,不饱和的或不饱和的C 9,C 11或C 13部分,根据 (ii)通过根据以下反应的同时酸化和加热来对所得的γ-羟基癸酸进行内酯化:(ⅲ)内酯化(经蒸馏) 根据以下结构定义的一种或多种所得酸:以形成根据通用结构定义的一种或多种内酯:根据该反应:其中,碳原子数 X部分和R部分等于Y部分中的碳原子数减1。还描述了根据这种方法产生的产物以及它们的感官效用,用于增强或增强co的香气或味道 选自香水组合物,古龙水,香料制品,食品,口香糖,药用产品,牙膏,咀嚼烟草和吸烟烟草的可选材料。

    Flavoring with mono-oxomethyl substituted polyhydrodimethanonaphthalene
derivatives

    公开(公告)号:US4470963A

    公开(公告)日:1984-09-11

    申请号:US546383

    申请日:1983-10-28

    CPC classification number: C07C47/347 A24B15/345 C07C47/445

    Abstract: Described are mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives having the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond; wherein R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 '", R.sub.1 "", R.sub.3, R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 '", R.sub.5 "" and R.sub.6 represent hydrogen or methyl with the provisos:(i) at least four of R.sub.1, R.sub.1 ', R.sub.1 ", R.sub.1 '" and R.sub.1 "" are hydrogen; and (ii) at least four of R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 '" and R.sub.5 "" represent hydrogen;and wherein Z represents one of the moieties:(i) carboxaldehyde having the structure: ##STR2## (ii) alkylene dioxy or dialkoxy methyl having the structure: ##STR3## (iii) hydroxy methyl having the structure: ##STR4## (iv) acetoxymethyl having the structure: ##STR5## and wherein R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl or R.sub.7 and R.sub.8 taken together represent C.sub.2 -C.sub.4 alkylene; wherein the line represented by:[++++]is either (i) a carbon-carbon single bond when R.sub.7 and R.sub.8 taken together are C.sub.2 -C.sub.4 alkylene or (ii) no bond at all when R.sub.7 and R.sub.8 taken separately represent C.sub.1 -C.sub.4 lower alkyl. Also described are processes for preparing such mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives, and processes for using the above defined mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives for their organoleptic properties and compositions containing said mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives including perfumes, perfumed articles (such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softeners and cosmetic powders), foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles.

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