Process for preparing compositions containing unsaturated lactones,
products produced thereby and organoleptic uses of said products

    公开(公告)号:US5110953A

    公开(公告)日:1992-05-05

    申请号:US623522

    申请日:1990-12-07

    摘要: 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, perfumed polymers, foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos and smoking tobaccos.

    Flavoring with mixtures of lactones
    2.
    发明授权
    Flavoring with mixtures of lactones 失效
    用内酯混合调味

    公开(公告)号:US4960597A

    公开(公告)日:1990-10-02

    申请号:US279065

    申请日:1988-12-02

    摘要: 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, perfumed polymers, foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos and smoking tobaccos.

    Process for preparing compositions containing unsaturated lactones,
products produced thereby and organoleptic uses of said products
    3.
    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

    摘要: 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.

    摘要翻译: 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。

    Process for preparing compositions containing unsaturated lactones,
products produced thereby and organoleptic uses of said products

    公开(公告)号:US5023347A

    公开(公告)日:1991-06-11

    申请号:US545610

    申请日:1990-06-29

    摘要: 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 or consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, perfumed polymers, foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos and smoking tobaccos.

    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

    摘要: 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.

    Flavoring with indane alkanols and tricyclic isochromans
    7.
    发明授权
    Flavoring with indane alkanols and tricyclic isochromans 失效
    用二环烷醇和三环异色素调味

    公开(公告)号:US4315951A

    公开(公告)日:1982-02-16

    申请号:US212886

    申请日:1980-12-04

    摘要: Processes and compositions are described for the use in foodstuff flavor and aroma and perfume and perfumed article aroma augmenting, modifying, altering and enhancing compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of certain indane alkanols and tricyclic isochromans defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is C.sub.2 H.sub.5 and the remaining R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents methyl; wherein X is --CH.sub.2 -- or hydrogen and wherein the dashed line represents a carbon-carbon single bond or no bond with the proviso that when X is --CH.sub.2 --, then the dashed line is a carbon-carbon single bond and when X is hydrogen, the dashed line represents no bond.Addition of said indane alkanols or said tricyclic isochromans or mixtures thereof is indicated to produce:A. In food flavorings, a sweet, musky, patchouli-like, and ionone-like aroma and flavor characteristic; (useful for flavor augmentation or enhancement in pear, apricot and peach flavors);B. In perfumes and perfumed articles, a sweet, musky aroma with earthy, minty and sweet nuances.

    摘要翻译: 描述了用于食品香料和香料和香料和香料制品香气增强,改性,改变和增强组合物以及作为食品,口香糖,牙膏,药用产品,香料和香料制品中某些二烷基链烷醇的赋香材料的方法和组合物 和根据通用结构定义的三环异染料:其中R 1,R 2,R 3或R 4中的一个为C 2 H 5,剩余的R 1,R 2,R 3和R 4表示甲基; 其中X是-CH 2 - 或氢,并且其中虚线表示碳 - 碳单键或没有键,条件是当X是-CH 2 - 时,虚线是碳 - 碳单键,当X是氢时 ,虚线表示没有键。 表示添加所述二氢化茚烷醇或所述三环异色素或其混合物以产生:A.在食品调味品中,甜味,麝香,广藿香样和紫罗兰酮样芳香和风味特征; (用于梨,杏和桃味的增味或增强); B.在香水和香水制品中,甜美,麝香的香气与土质,微小和甜美的细微差别。

    Indane alkanols and tricyclic isochromans and organoleptic uses thereof
    8.
    发明授权
    Indane alkanols and tricyclic isochromans and organoleptic uses thereof 失效
    茚烷醇和三环异染料及其感官用途

    公开(公告)号:US4308412A

    公开(公告)日:1981-12-29

    申请号:US212992

    申请日:1980-12-04

    摘要: Processes and compositions are described for the use in foodstuff flavor and aroma and perfume and perfumed article aroma augmenting, modifying, altering and enhancing compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of certain indane alkanols and tricyclic isochromans defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is C.sub.2 H.sub.5 and the remaining R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents methyl; wherein X is --CH.sub.2 -- or hydrogen and wherein the dashed line represents a carbon-carbon single bond or no bond with the proviso that when X is --CH.sub.2 --, then the dashed line is a carbon-carbon single bond and when X is hydrogen, the dashed line represents no bond.Addition of said indane alkanols or said tricyclic isochromans or mixtures thereof is indicated to produce:A. In food flavorings, a sweet, musky, patchouli-like, and ionone-like aroma and flavor characteristic; (useful for flavor augmentation or enhancement in pear, apricot and peach flavors);B. In perfumes and perfumed articles, a sweet, musky aroma with earthy, minty and sweet nuances.

    摘要翻译: 描述了用于食品香料和香料和香料和香料制品香气增强,改性,改变和增强组合物以及作为食品,口香糖,牙膏,药用产品,香料和香料制品中某些二烷基链烷醇的赋香材料的方法和组合物 和根据通用结构定义的三环异染料:其中R 1,R 2,R 3或R 4中的一个为C 2 H 5,剩余的R 1,R 2,R 3和R 4表示甲基; 其中X是-CH 2 - 或氢,并且其中虚线表示碳 - 碳单键或没有键,条件是当X是-CH 2 - 时,虚线是碳 - 碳单键,当X是氢时 ,虚线表示没有键。 表示添加所述二氢化茚烷醇或所述三环异色素或其混合物以产生:A.在食品调味品中,甜味,麝香,广藿香样和紫罗兰酮样芳香和风味特征; (用于梨,杏和桃味的增味或增强); B.在香水和香水制品中,甜美,麝香的香气与土质,微小和甜美的细微差别。