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    • 2. 发明授权
    • Compounds and process for making a flavorant
    • 化合物和制造香料的方法
    • US5449823A
    • 1995-09-12
    • US234095
    • 1994-04-28
    • Konrad Lerch
    • Konrad Lerch
    • C07C59/215C07D307/60C11B9/00C12P7/42C12P7/62C12P41/00C07C59/147
    • C12P7/42C07C59/215C07D307/60C12P41/006
    • Two optically active forms of 4-hydroxy-3-methyl-2-keto-pentanoic acid of the formula ##STR1## wherein carbon atom 4 has the (S)-configuration, and carbon atom 3 can have the (R)-configuration or the (S)-configuration (compound I) are made using a biotransformation process. Compound I may be manufactured by reacting 4-hydroxy-isoleucine (2S, 3R, 4S) of the formula: ##STR2## with microorganisms which have L-amino acid oxidase activity or with an L-amino acid oxidase. Compound I is a flavor precursor and may also be used as an intermediate for the production of the optically active (5S)-3-hydroxy-4,5-dimethyl-2(5H)-furanone: ##STR3## which is useful as a flavorant.
    • 两种光学活性形式的式(I)的4-羟基-3-甲基-2-酮戊酸其中碳原子4具有(S) - 构型,碳原子3可以具有(R) - 构型 或(S)构型(化合物I)使用生物转化方法制备。 化合物I可以通过使具有下列通式的化合物的4-羟基 - 异亮氨酸(2S,3R,4S)与具有L-氨基酸氧化酶活性的微生物或与L-氨基酸氧化酶反应来制备。 化合物I是风味前体,也可以用作制备光学活性(5S)-3-羟基-4,5-二甲基-2(5H) - 呋喃酮的中间体:其可用作 一种香料。
    • 5. 发明授权
    • Process for the manufacture of known odorants
    • 制造已知气味的方法
    • US5329053A
    • 1994-07-12
    • US111694
    • 1993-08-25
    • Daniel Helmlinger
    • Daniel Helmlinger
    • C07C29/143C07C33/14C07C403/08C07D307/92
    • C07C403/08C07B2200/09C07C2101/16
    • A novel process is described for the manufacture of a mixture of 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol (I) and, respectively, of a mixture of [3a.alpha.,5a.beta.,9a.alpha.,9b.beta.]-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and [3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.]-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan, in which E,E-6-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-4-methyl-hexa-2,4-dien-1-al is reduced either with (a) lithium aluminium hydride or with (b) sodium dithionite in the presence of sodium bicarbonate in aqueous solution and of a phase transfer catalyst or with (c) sodium borohydride or with (d) sodium bis(2-methoxyethoxy)aluminium dihydride and, when reduction agent (c) or (d) is used and optionally in the case when reduction agent (a) is used, the E,E-6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hexa-2,4-dien-1-ol which results as the intermediate is reduced to the desired 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol using a reduction agent (a) or (b) and, if desired, the thus-obtained compounds I are converted in a known manner into a mixture of the aforementioned furans. These furans are suitable as odorants.
    • 描述了一种制备6-(2',6',6'-三甲基 - 环己-1'-烯-1'-基)-4-甲基 - 己-3-烯-1-醇的混合物的新方法 - 醇和4-烯-1-醇(I)和[3aα,5aβ,9aα,9bβ-十氢化-3a,6,6,9a-四甲基萘并[2, 1-b]呋喃和[3aα,5aβ,9aα,9bα]十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃,其中E,E-6- ',6',6'-三甲基环己-1'-烯-1'-基)-4-甲基 - 己-2,4-二烯-1-基还用(a)氢化铝锂或与(b )连二亚硫酸钠在碳酸氢钠存在下在水溶液和相转移催化剂存在下,或与(c)硼氢化钠或(d)双(2-甲氧基乙氧基)二氢化铝二钠反应,当还原剂(c)或(d ),任选在使用还原剂(a)的情况下,E,E-6-(2',6',6'-三甲基 - 环己-1'-烯-1'-基)-4 - 甲基 - 己-1,4-二烯-1-醇,其结果是将中间体还原成所需的6-(2',6',6'-三甲基 - 环 使用还原剂(a)或(b),并且如果需要,使用还原剂(a)或(b),反式-1'-烯-1'-基)-4-甲基 - 己-3-烯-1-醇和-4-烯-1-醇 ,将由此获得的化合物I以已知的方式转化成上述呋喃的混合物。 这些呋喃适合作为气味剂。