CN113840540A - 香料或调味剂混合物 - Google Patents
香料或调味剂混合物 Download PDFInfo
- Publication number
- CN113840540A CN113840540A CN201980096527.XA CN201980096527A CN113840540A CN 113840540 A CN113840540 A CN 113840540A CN 201980096527 A CN201980096527 A CN 201980096527A CN 113840540 A CN113840540 A CN 113840540A
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- Prior art keywords
- formula
- mixture
- acid diester
- compounds
- flavor
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 259
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- -1 (E) -2-methyl-but-2-enedicarboxylic acid diester Chemical class 0.000 claims abstract description 184
- 239000003205 fragrance Substances 0.000 claims abstract description 104
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 54
- YPTLFOZCUOHVFO-VOTSOKGWSA-N diethyl (e)-2-methylbut-2-enedioate Chemical compound CCOC(=O)\C=C(/C)C(=O)OCC YPTLFOZCUOHVFO-VOTSOKGWSA-N 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
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- YPTLFOZCUOHVFO-SREVYHEPSA-N diethyl (z)-2-methylbut-2-enedioate Chemical compound CCOC(=O)\C=C(\C)C(=O)OCC YPTLFOZCUOHVFO-SREVYHEPSA-N 0.000 claims description 27
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 150000005690 diesters Chemical class 0.000 claims description 25
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 claims description 24
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
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- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 5
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- 239000006210 lotion Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
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- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002386 air freshener Substances 0.000 claims description 4
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- 239000002537 cosmetic Substances 0.000 claims description 4
- 230000002951 depilatory effect Effects 0.000 claims description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 4
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- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
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- 150000003077 polyols Chemical class 0.000 claims description 4
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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Images
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
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- C—CHEMISTRY; METALLURGY
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- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C—CHEMISTRY; METALLURGY
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
本发明提供了包含(i)(E)‑2‑甲基‑丁‑2‑烯二羧酸二酯,(ii)(Z)‑2‑甲基‑丁‑2‑烯二羧酸二酯和(iii)2‑亚甲基丁二羧酸二酯的具有果香、类似梨香的味调的香料或调味剂混合物,用于制备这些香料或调味剂或者香料或调味剂混合物的方法,所述香料或调味剂混合物用于产生果香、类似梨香的气味味调或味道味调或者用于制备香味剂混合物或香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品的用途,以及由此制备的以感受有效量包含所述香料或调味剂混合物的产品。
Description
技术领域
本发明涉及香料和调味剂领域,并且涉及具有果香、类似梨香味调的香料或调味剂混合物,一种用于制备具有果香、类似梨香味调的香料或调味剂或者香料混合物或调味剂混合物的方法,这些香料或调味剂混合物用于产生果香、类似梨香的香味味调,或味道味调的用途或者用于制备香味剂混合物、香水油、美妆剂、涂抹剂(Auftragungsmitteln)、洗涤剂和清洁剂、食品或动物饲料,以及由其制备的包含香料或调味剂混合物的产品。
虽然已经存在大量的香料或香味剂或调味剂或芳香物质,但在香水工业中总体上仍然还需要新的香料或调味剂。尤其需要不仅以新的原创香味味调为特征,而且除了其嗅觉特性之外还拥有有利的次要特性的香料或调味剂,例如在某些应用条件下更高的稳定性和充足性、更好的附着能力、更大的传播力度、更低的嗅觉阈值或还有更好的皮肤学或毒理学特性,例如良好的生物可降解性。
特别是,需要与类似物质相比在较低剂量下产生相同或更大的香味或味道贡献,并且由此较少量进入到环境中(低剂量-高影响)的香料或调味剂,或者在相同香味贡献下可以以成本明显更低廉的方式提供的香料或调味剂。在此需要具有复杂的香味特性或味道特性,例如果香、梨型气味特性或味道特性的香料或调味剂。醋酸戊酯(乙酸戊酯),虽然以梨型芳香而闻名,却无法满足这些条件。
此外,考虑到环境保护、能量效率和资源效率,需要由天然的或可再生生产的原料,例如由植物基材料或生物基原料来制备的香料或调味剂。
更需要不含在合成此类香料时可能出现的不希望的且损害健康的副产物的香料或调味剂或者香料混合物或调味剂混合物。
WO 2018/114073 A1公开了香料或香料混合物及其应用,尤其香水油、美妆剂、涂抹剂或洗涤和清洁剂,所述香料或香料混合物包含感受有效量的(i)(E)-2-甲基-丁-2-烯二羧酸-二乙酯,(ii)(Z)-2-甲基-丁-2-烯二羧酸-二乙酯或(iii)2-亚甲基丁二羧酸-二乙酯或这些化合物的混合物或衍生的类似酯的混合物。
这些香料通过使用一系列线性合成来制备。
用于制备中康酸的单酯和/或二酯的方法的第一变体包括以下步骤:
(i)将衣康酸与醋酸酐反应,获得衣康酸酐;
(ii)将衣康酸酐异构化为柠康酸酐;
(iii)将柠康酸酐与具有1至10个碳原子的脂肪族、芳香脂肪族或芳香族醇或者具有1至5个羟基的二醇酯化,获得柠康酸的单酯和/或二酯;以及
(iv)将柠康酸的单酯和/或二酯重排成中康酸的单酯和/或二酯。
用于制备中康酸的单酯和/或二酯的方法的第二变体包括以下步骤:
(i)提供包含至少一种柠康酸单酯和/或二酯以及任选地溶剂的溶液;
(ii)将溶液与碘混合;
(iii)将含碘溶液加热到约170至约200℃;以及
(iv)任选地,以蒸馏方式纯化所获得的产物。
此外,其中优选的是,在首先提及的制备方法中将第二替代性制备方法用作步骤(iv)。因此,最后的重排步骤在第二替代性制备方法之后、也就是在首先提及的制备方法中的步骤(i)至(iii)之后实施。
但是,上述合成方法在扩大规模到工业制备生产中时具有明显的缺点:这些方法需要多个且较长的合成步骤、较长的反应时间并且得到了较低的产率。
此外,在异构化时需要使用更高的量的卤素,尤其是碘,以完成反应。另外,在合成时制备的香料混合物含有副产物。这些副产物中的一些是不希望的,因为它们对香料化合物具有不利的影响。例如,香料或调味剂混合物以明显高于10ppm参考值的量包含合成时使用的卤素、尤其碘。另外,碘(HI)导致香料或调味剂混合物的染色,这是不希望的。因此该方法需要进一步的方法步骤以从香料或调味剂混合物中分离掉碘,例如通过用焦亚硫酸钠来清洗香料或调味剂混合物。此外,卤素的另一个缺点是,它们可能加成到香料或调味剂的双键上。通过加成可能造成香味或风味物质的变化并且由此导致气味特征的劣化。此外,卤素可能引起皮肤刺激,例如皮肤变红。
高纯度的中康酸二酯还可以直接由中康酸制备。但是,中康酸(售卖商品)是非常昂贵的。
因此,本发明的目的在于,基于可再生原料、优选废料来提供具有果香的、类似梨香的芳香的香料和调味剂或者香料混合物或调味剂混合物,并且其克服了所提及的现有技术的缺点,即所述物质或混合物一方面可以在更短的反应时间下并且由此以更低的技术耗费且以更低的成本来制备,并且另一方面其具有高纯度,也就是说不含副产物、尤其不含卤素。
发明内容
本发明的第一个主题涉及一种香料或调味剂混合物,包括感受有效量的通式(I)、式(II)和式(III)的化合物:
其中R1分别为具有1至10个碳原子的直链、支链或环状的烷基残基、芳香脂肪族残基(araliphatischen)或芳香族残基,和/或其中R2分别为具有1至10个碳原子的直链、支链或环状的烷基残基、芳香脂肪族残基或芳香族残基,以及任选地一个或多个另外的组成部分,其中所述香料或调味剂混合物不含卤素、尤其不含碘。
本发明的第二个主题为一种方法,用于制备通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物,所述方法包括以下步骤:
(a)用选自由以下项组成的组的醇将衣康酸酯化:具有1至10个碳原子的脂肪族、芳香脂肪
族或芳香族醇以及具有2至6个羟基的多元醇,获得衣康酸二酯;以及
(b)用含氮有机碱将所述衣康酸二酯异构化,获得通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物。
在第三方面,本发明涉及一种能够根据本发明方法获得的通式(I)、式(II)或式(III)的香料或调味剂,或者涉及一种包括选自由所述通式(I)、式(II)和式(III)的化合物组成的组中的一种、两种或三种化合物的香料或调味剂混合物,其中所述方法尤其在不使用含卤素、特别是含碘的反应物的情况下进行。
在第四方面,本发明涉及一种用于在香料混合物、香水油、美妆剂、涂抹剂或洗涤剂和清洁剂中赋予、改变和/或增强果香、梨型气味味调或者用于在食物、动物饲料或制药产品中赋予、改变和/或增强果香、梨香味道味调的方法,所述方法包括以下步骤:
(i1)提供本发明的香料或调味剂混合物;以及
(i2)将足以在成品制剂中引起果香、梨型气味味调或味道味调的感受有效量的所述香料或调味剂混合物与至少一种另外的香料或调味剂或与另外的香料或调味剂的混合物混合;
或者
(ii1)提供本发明的香料或调味剂混合物;以及
(ii2)将足以在成品制剂中引起果香、梨型气味味调或味道味调的感受有效量的所述香料或调味剂混合物与香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品混合。
本发明的另一个主题是感受有效量的包括通式(I)、式(II)和式(III)的化合物的本发明的香料或调味剂混合物的用途,用于在香料混合物或香水油、美妆剂、涂抹剂或洗涤和清洁剂中赋予、改变和/或增强果香、梨型气味味调,或者用于在食物、动物饲料或制药产品中赋予、改变和/或增强果香、梨型味道味调,或者用于制备香味剂混合物、香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品。
最后,本发明在另一个方面涉及一种香料混合物或香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品,其包含感受有效量的包括通式(I)、式(II)和式(III)的化合物的本发明的香料或调味剂混合物。
对于本领域技术人员而言,本发明的这些和其他方面、特征和优点可以从对以下详细说明和权利要求书的学习中得出。在此,来自本发明一方面的任何特征可以用在本发明的另一方面中或者进行替换。此外,应当理解,本本申请中包含的实施例描述并说明了本发明,但并不限制本发明,特别是,本发明不限于这些实施例。
如果没有另外提及,所有的百分比数值都是重量%。以“从x到y”形式给出的数值示例包括所提及的值。当然,当以此格式给出多个优选的数值范围时,同样记载了由不同端点的组合产生的所有范围。
附图说明
图1示意性示出用于制备根据本发明的具有果香、类似梨香的味调的通式(I)、(II)和(III)的香料或调味剂或者由其形成的香料或调味剂混合物,与根据现有技术的用于制备具有果香、类似梨香的味调的香料或调味剂或者香料或调味剂混合物的方法的对比。
图2示出本发明的香料或调味剂混合物的1H-NMR谱(400MHz,CDCl3)。标度是f1(ppm)。
图3示出本发明的香料或调味剂混合物的13C-NMR谱(101MHz,CDCl3)。标度是f1(ppm)。
具体实施方式
在第一方面,本发明涉及一种香料或调味剂混合物,包括感受有效量的通式(I)、式(II)和式(III)的化合物:
其中R1分别为具有1至10个碳原子的直链、支链或环状的烷基残基、芳香脂肪族残基或芳香族残基,和/或其中R2分别为具有1至10个碳原子的直链、支链或环状的烷基残基、芳香脂肪族残基或芳香族残基,以及任选地一个或多个另外的组成部分。本发明的香料或调味剂混合物的特征在于,其不含卤素、尤其不含碘。
本发明的香料或调味剂混合物的化合物优选为以下项组成的异构体混合物:
-中康酸((E)-2-甲基-丁-2-烯二羧酸)的衍生物(通式(I)的化合物),
-柠康酸((Z)-2-甲基-丁-2-烯二羧酸)的衍生物(通式(II)的化合物),以及
-衣康酸(2-亚甲基丁二羧酸)的衍生物(通式(III)的化合物)。
出人意料地,已经发现,式(I)的化合物尤其适合用作果香、梨型香料或调味剂,并且同时完全满足了开篇阐述的复杂的要求特征。式(II)和式(III)的化合物在生产过程中同时产生并且同样具有减弱的梨型气味或梨型芳香。
由于其感受特性,本发明的香料或调味剂混合物既适合用作香味物质或香味剂也适合用作味道物质或芳香物质。术语“香味”与“味道”或者“香料混合物”与“调味剂混合物”在本申请的上下文中互相等价地使用,并且因此与所预期的应用目的相关,即为增加香味或者增加芳香。
通式(I)、式(II)和式(III)的化合物为由衣康酸制备的化合物。衣康酸(C5H6O4)是一种有机二元羧酸。它尤其在蒸馏柠檬酸时产生。衣康酸的工艺生产以生物工艺方式通过糖蜜(糖类生产的副产品)和其他带有真菌解乌头酸曲霉(fungi Aspergillusitaconicus)或土曲霉(Aspergillusterreus)菌株物质的液体深层发酵来进行。由此可以从天然或可再生生产的原料来制备通式(I)、式(II)和式(III)的化合物。
还出人意料的是,本发明的香料或调味剂混合物的化合物可以持久且稳定地加入到许多不同配制品中,并且同时在其气味味调或味道味调方面定性且定量地满足或甚至超过癸二烯酸乙酯标准。
感受有效量应理解为通式(I)、式(II)和式(III)的化合物的足以引起果香、类似梨香的气味或味道印象的比例。当在所述香料或调味剂混合物中存在至少0.001重量%的通式(I)、式(II)和式(III)的化合物时,基本上引起这种果香、类似梨香的气味或味道印象。
在第一优选变体中,本发明涉及一种香料或调味剂混合物,其包含感受有效量的选自由中康酸、柠康酸、衣康酸的二酯组成的组的通式(I)、式(II)和式(III)的化合物。
优选地,通式(I)、式(II)或式(III)的化合物中的R1和/或R2分别彼此独立地表示具有1至10个碳原子的直链或支链的烷基残基或者具有1至10个碳原子的环状烷基残基。在此特别优选直链残基,尤其具有1至4个碳原子的烷基残基。替代地,具有这种碳原子数的支链烷基残基是优选的。
残基R1和R2分别可以相同或不同,
通式(I)、式(II)或式(III)的化合物中的具有1至10个碳原子的R1和/或R2优选的直链烷基残基的组由以下基团残基构成:甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基和正癸基。优选的直链烷基残基为甲基、乙基,但是正丙基、正丁基、正戊基和正己基同样适合。直链烷基残基中特别优选的是甲基、乙基、正丙基和正丁基。烷基残基最优选是乙基。
通式(I)、式(II)或式(III)的化合物中具有1至10个碳原子的R1和/或R2的支链烷基残基的组由以下项构成:异丙基、异丁基、仲丁基、叔丁基、异戊基、叔戊基、异己基、叔己基、异庚基、异辛基、叔辛基、异壬基、叔壬基、叔癸基和异癸基。优选的支链烷基残基为异丙基、异丁基、仲丁基和叔丁基。特别优选的支链烷基残基是异丙基和异丁基。
通式(I)、式(II)或式(III)的化合物中具有1至10个碳原子的R1和/或R2的环状烷基残基的组由以下项构成:环丙烷、环丁烷、环戊烷、环己烷、环庚烷和环辛烷、环壬烷和环癸烷。优选的环状烷基残基为环戊烷和环己烷。
在通式(I)、式(II)或式(III)的化合物中R1和/或R2的芳香脂肪族残基的组中,烷基残基应理解为其上的一个或多个氢原子被芳香族残基替代。通式(I)、式(II)或式(III)的化合物中的芳香脂肪族残基的组优选由以下项构成:甲苯、2-甲基呋喃、3-甲基呋喃、甲基吡啶、甲酚、二甲苯、1-甲基萘、2-甲基萘和乙基苯。优选的芳香脂肪族残基是甲苯和乙基苯。
通式(I)、式(II)和式(III)式(I)、式(II)和式(III)的化合物中R1和/或R2的芳香族残基的组优选由以下项构成:嘧啶、呋喃、环硫乙烷(Thiran)、苯、萘、酚、吡啶和苯二氮卓类。优选的芳香族残基为呋喃和苯。
在本发明的一个优选变体中,在上述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的基团R1和/或R2分别彼此独立地代表C1至C4基团,也就是说尤其代表甲基、乙基、丙基或丁基基团。这些化合物可以特别简单地制备并且显示出令人印象非常深刻的气味特征。
在本发明的一个替代的优选变体中,在上述香料或调味剂混合物中的通式(I)、(II)和(III)的化合物中的残基R1为甲基、乙基、丙基和/或丁基残基,并且在上述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的残基R2为甲基残基或乙基残基。
在本发明的另一个替代变体中,在上述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的残基R2为甲基、乙基、丙基和丁基残基,并且在上述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的残基R1为甲基残基或乙基残基。
在本发明的另一个更优选变体中,在上述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的残基R1和R2分别为相同的残基。这简化了制备。
在本发明的另一个变体中,在所述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的残基R1和R2分别彼此独立地选自由以下项构成的组:直链或支链的甲基、乙基、丙基或丁基残基。尤其直链烷基残基和较短的支链烷基残基适合于配合到香味结合袋(Geruchsbindungstaschen)中。
在本发明的另外的优选改进方案中,在上述香料或调味剂混合物中的通式(I)、式(II)或式(III)的化合物中的残基R1和R2分别彼此独立地为甲基、乙基、丙基或丁基残基。
在一个更优选的改进方案中,通式(I)、式(II)和式(III)的化合物中的残基R1和R2分别相同。
在另一个更优选的变体中,本发明涉及一种香料或调味剂混合物,其包含感受有效量的选自由以下项组成的组的化合物(I)、(II)和(III):
(I)中康酸二酯,
(II)柠康酸二酯,以及
(III)衣康酸二酯,其中所述二酯优选地选自由二甲酯、二乙酯、二丁酯或二丙酯、尤其二乙酯组成的组。
本发明香料或调味剂混合物的通式(I)、式(II)或式(III)的化合物中,特别优选的是通式(I)的化合物,因为它们的独特之处在于特别强烈的果香和梨型香味和味道。通式(II)(柠康酸二酯)和(III)(衣康酸二酯)的化合物一般与中康酸二酯一起作为异构体混合物在制备香料或调味剂混合物时获得,但是香味或味道不如中康酸二酯强烈,因此对本发明香料或调味剂混合物的总香味或总味道只具有次要影响。
在另一个最优选的变体中,本发明涉及一种香料或调味剂混合物,其包含感受有效量的选自由以下项组成的组的通式(I)、(II)和(III)的化合物:
(I)(E)-2-甲基丁-2-烯二酸二乙酯(中康酸二乙酯),
(II)(Z)-2-甲基丁-2-烯二酸二乙酯(柠康酸二乙酯),以及
(III)2-亚甲基-丁二酸二乙酯(衣康酸二乙酯)。
先前提及的这三种化合物(I)、(II)和(III)分别形成本发明香料或调味剂混合物的通式(I)、(II)和(III)的最优选变体,但是甲酯、丁酯或丙酯也是有利的。通式(I)、式(II)或式(III)的化合物的乙酯、甲酯和/或丙酯的组合也是可能的。
在本发明香料或调味剂混合物的通式(I)、式(II)或式(III)的化合物中,物质二乙基-(E)-2-甲基丁-2-烯二酸酯或者(E)-2-甲基丁-2-烯二羧酸二乙酯,其中在通式(I)中R1和R2代表乙基残基并且由式(IV)展现
其还被称为中康酸二乙酯,对于本发明具有特殊意义并且本身是从文献中已知的。为此参考以下引用内容:Advanced Synthesis&Catalysis,2012,354(14-15),2859-2864;Organic Letters,2008;10(21),4815-4818;Organic&Biomolecular Chemistry,2010,8(19),4444-4450;Journal of American Chemical Society,2005,127(15),5518-5527;Tetrahedron Letters,1996,37(5),629-632;Tetrahedron Letters,1983,39(9),1475-1485;Journal ofAmerican Chemical Society,2015,137(26),8556-8563;OrganicLetters,2011;13(7),1884-1887;AustralianJournal ofChemistry,1984,37(2),417-424;TetrahedronLetters,1981,22(5),381-384;Synthetic Communications,1977,7(6),375-382;Helvetica Chimica Acta,1974,57(3),856-863。
下文中,名称二乙基-(E)-2-甲基丁-2-烯二酸酯或(E)-2-甲基丁-2-烯二羧酸二乙酯和中康酸二乙酯同义使用。化合物(E)-2-甲基丁-2-烯二酸二乙酯的独特之处在于特别强烈的果香、梨型香味或味道。
对于通式(II)的化合物特别优选的是(E)-2-甲基丁-2-烯二酸二乙酯或(Z)-2-甲基丁-2-烯二羧酸二乙酯(柠康酸二乙酯),并且对于通式(III)的化合物特别优选的是2-亚甲基-丁二酸二乙酯或2-亚甲基丁二羧酸二乙酯(衣康酸二乙酯),它们与(E)-2-甲基丁-2-烯二酸二乙酯或中康酸二乙酯一起产生优选的香料混合物。
先前所述的通式(II)(Z)-2-甲基丁-2-烯二酸二乙酯以及通式(III)2-亚甲基-丁二酸二乙酯的化合物一般与中康酸二乙酯一起在制备香料或调味剂混合物时作为异构体混合物出现,但是香味或味道不如中康酸二酯强烈,因此对本发明香料或调味剂混合物的总香味或总味道只具有次要影响。
优选的是,基于通式(I)、(II)和(III)的化合物的总和或者基于异构体混合物的总重量,本发明的香料或调味剂混合物或异构体混合物,包含至少50至100重量%、更优选60至78重量%、最优选66至72重量%的量的式(I)的化合物,至少2至8重量%、更优选3至7重量%且特别优选4至6重量%的量的式(II)的化合物,和至少18至31重量%、更优选20至29重量%且最优选22至27重量%的量的式(III)的化合物。这还适用于相应的二甲酯、二乙酯、二丙酯和二丁酯的特别优选的化合物,并且尤其适用于中康酸、柠康酸和衣康酸的二乙酯。
因此最优选的是,基于通式(I)、(II)和(III)的化合物的总和或者基于异构体混合物的总重量,本发明的香料或调味剂混合物或异构体混合物包含至少50至100重量%、更优选60至78重量%、最优选66至72重量%的量的(E)-2-甲基丁-2-烯二酸二乙酯(式(I)的化合物),至少2至8重量%、更优选3至7重量%且特别优选4至6重量%的量的(Z)-2-甲基丁-2-烯二酸二乙酯(式(II)的化合物),和至少18至31重量%、更优选20至29重量%且最优选22至27重量%的量的2-亚甲基-丁二酸二乙酯(式(III)的化合物)。
在本发明的一个优选变体中,在香料或调味剂混合物中,式(I)的化合物与的式(II)和式(III)的两种化合物的总和之比为3:1、优选为2.5:1、更优选为1.5:1。这个比率还优选适用于(E)-2-甲基丁-2-烯二酸二乙酯或中康酸二乙酯与(Z)-2-甲基丁-2-烯二酸二乙酯(柠康酸二乙酯)和2-亚甲基-丁二酸二乙酯(衣康酸二乙酯)的化合物混合物。
在本发明的另一个优选变体中,式(I)的化合物与式(II)的化合物之比在66:6至72:4的范围内。在这个范围内实现了特别好的感受结果。
在本发明的香料或调味剂混合物中(E)-2-甲基丁-2-烯二酸二乙酯与(Z)-2-甲基丁-2-烯二酸二乙酯以在66:6至72:4范围内的比率加入时,感受效果是令人印象最深刻的。
在制备本发明的香料或调味剂混合物期间,与式(I)的化合物(中康酸二酯、尤其中康酸二乙酯)一起在制备本发明的香料或调味剂混合物时作为异构体混合物出现的式(II)的化合物(柠康酸二酯、尤其柠康酸二乙酯)和式(III)的化合物(衣康酸二酯、尤其衣康酸二乙酯)的比例对香料或调味剂混合物的香味或味道起到次要作用,因为通式(II)和(III)的化合物比通式(I)的化合物具有较弱的梨型香味或较弱的梨型芳香。因此,在根据本发明的香料或调味剂混合物中的通式(II)和(III)的化合物的比例对香料或调味剂混合物的总香味或总味道仅具有次要影响,所述总香味或总味道尤其由式(I)的化合物的比例决定。式(II)和(III)的化合物相对于式(I)的化合物的比例的变化,也就是说提高,因此也不会导致香味或味道的变化,也就是说变强烈。在最终可以通过制备中的高产率实现的更高的中康酸二酯、尤其中康酸二乙酯(式(I)的化合物)比例下,产生了更强烈的梨香味或梨味道。中康酸二酯、尤其中康酸二乙酯(式(I)的化合物)在本发明混合物中的更高的比例例如还可以通过浓缩来实现。
根据本发明的香料或调味剂混合物的独特之处在于高纯度,也就是说,所述香料或调味剂混合物不包含在合成通式(I)、式(II)或式(III)的化合物时产生的杂质和副产物。
根据本发明,通式(I)、式(II)和式(III)的化合物具有至少98.0%的纯度、优选100%的纯度。中康酸二乙酯尤其具有至少98.0%的纯度,但是更优选100.0%的纯度。具有纯的或几乎纯的中康酸二乙酯的香料或调味剂混合物显示出特别强的梨味调的香味。
根据本的香料或调味剂混合物包含感受有效量的通式(I)、(II)和(III)的化合物或由其组成。
感受有效量是通式(I)、(II)和式(I)的化合物的足以引起果香、类似梨香的气味印象或味道印象的比例。
在本发明的一个优选的改进方案中,在香料或调味剂混合物中,相对于香料或调味剂混合物的总重量包含总共0.001至99.999重量%的通式(I)、式(II)和式(III)的化合物。这尤其适用于通式(I)、式(II)和式(III)的化合物的特别优选的二甲酯、二乙酯、二丙酯或二丁酯。
更优选地,在香料或调味剂混合物中,相对于香料或调味剂混合物的总重量,包含总共0.05至50重量%的通式(I)、式(II)和式(III)的化合物。这尤其适用于通式(I)、式(II)和式(III)的化合物的特别优选的二甲酯、二乙酯、二丙酯或二丁酯。
在本发明的一个替代性优选实施方式中,在香料或调味剂混合物中,相对于香料或调味剂混合物的总重量,包含总共0.5至30重量%的通式(I)、式(II)和式(III)的化合物、尤其二甲酯、二乙酯、二丁酯或二丙酯。
在本发明的一个特别优选的实施方式中,所述香料或调味剂混合物在与(Z)-2-甲基丁-2-烯二酸二乙酯(柠康酸二乙酯)以及2-亚甲基-丁二酸二乙酯(衣康酸二乙酯)的混合物中包含(E)-2-甲基丁-2-烯二酸二乙酯或中康酸二乙酯,具有总计约0.001至约99.999重量%的量,优选地,具有约0.01至约90重量%的量,优选具有约0.05至约50重量%的量,且特别优选具有约0.5至约30重量%的量。
根据本发明的香料或调味剂混合物的独特之处在于强烈的果香、类似梨香的香味味调或味道味调,以及定性且定量地与癸二烯酸乙酯标准相当或甚至超过所述标准的更大容量,如从下表2中突出显示的。
另外有利的是,根据本发明的香料或调味剂混合物不包含卤素杂质或卤素副产物、尤其不包含碘杂质或碘副产物,因为在其制备中不使用现有技术的方法中的采用的卤素反应物、尤其不使用碘反应物。此类杂质或副产物可能导致染色或不利地影响香料,如上文在介绍部分已经详细说明的。由此本发明的香料混合物还是皮肤可接受的并且不造成皮肤变红。
除了上述嗅觉方面的特殊优点之外,另外还可以提及本发明的香料或调味剂混合物的通式(I)、式(II)和式(III)的化合物的突出的材料特性,如在常用美妆溶剂中的可溶性、与此类产品的其他组成部分的相容性以及毒理学上的无害性,这些特性强调了特别适合用于所提及的应用目的。
相对于常规的且类似的香料或调味剂的另一个优点在于其非常便利的可获得性以及简单且由此成本低廉的制备。
除了如上文已经说明的通式(I)、式(II)和式(III)的化合物之外,本发明的香料或调味剂混合物优选还可以包含一种或多种另外的(常见的)有效成分或功能性内含物质,以及一种或多种与通式(I)、(II)和(III)的化合物的标准不对应的其他香料,它们在香料或调味剂混合物中组成将总和补充至100重量%。
本发明的香料或调味剂混合物可以以液态形式在未经稀释的情况下或者在用溶剂稀释的情况下用于增香或芳香化。对此适合的且优选的溶剂尤其为乙醇、甘油、1,2-丙二醇、1,2-丁二醇、二丙二醇、邻苯二甲酸二乙酯、柠檬酸三乙酯、肉豆蔻酸异丙酯和三醋酸甘油酯(Triacetin)。
此类香料或调味剂混合物在此包含最多90重量%、优选约5至约70重量%、尤其约10至约50重量%,并且特别优选约15至约25重量%的所述溶剂。
在一个优选的替代方案中,本发明的香料或调味剂混合物包括合成的或天然的、优选味道中性且气味中性的载体物质、尤其载体油,所述载体油包含呈高度浓缩形式的香味剂以及任选地香水类溶剂和/或助剂。
对于某些应用而言,将本发明的香料或调味剂混合物吸附到载体物质上也是有利的,所述载体物质不仅实现包含在其中的香料在产品中的精细分布还在使用中提供受控的释放。此类载体可以为多孔无机材料,如轻质硫酸盐、硅胶、沸石、石膏、粘土、粘土颗粒、充气混凝土等,或有机材料,如木材、基于纤维素的物质,糖,糊精(例如麦芽糖糊精)或塑料,如PVC、聚乙酸乙烯酯或聚氨酯等。本发明的香料混合物与载体物质的组合代表了根据本发明的示例性产品。
在一个替代的优选实施方式中,本发明的香料或调味剂混合物以微囊封装或喷雾干燥的形式存在,或者作为夹带复合物(包合物)或挤出产品存在,以便在这种形式中添加到例如待香味化或待芳香化的产品。
本发明的香料或调味剂混合物的微囊封装可以例如借助于封装材料,例如由聚氨酯类物质或软明胶形成,通过所谓的凝聚方法来进行。经喷雾干燥的香料组合物或调味剂组合物例如可以通过将包含本发明的香料或调味剂混合物的乳液或分散体喷雾干燥来制备,其中作为载体物质可以优选使用改性的淀粉、蛋白质、糊精和植物胶。夹带复合物例如可以通过向适合的溶剂(例如水)中引入本发明的香料混合物和环糊精或脲衍生物的分散体来制备。挤出产品可以通过将本发明的香料或调味剂混合物与适合的蜡状物质熔融并且通过挤出以及后续的硬化(在适当时在适合的溶剂例如异丙醇中)来获得。
在某些情况下,如此改性的香料或调味剂混合物配制品的特性可以通过用适当材料进行所谓的“涂覆”而在针对性的气味释放方面得以进一步优化,为此优选使用蜡状塑料例如聚乙烯醇。
根据本发明的香料或调味剂混合物有利地包含至少一种另外的香料或调味剂或芳香物,也就是说两种、三种、四种、五种或甚至仍更多种其他香料组分或调味剂组分,或者由本发明的通式(I)、式(II)和式(III)的化合物的异构体混合物(并且在此尤其为(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯)以感受有效量的与至少一种另外的或多种香料或调味剂组成。通常香料或调味剂不用于二元或三元混合物,而是作为可能部分地以非常小量包含两种、三种、四种、五种、十种、但优选仍更大数量的香味物质或味道物质的精巧复杂混合物的组成部分,以获得特别圆润的香味特征。即,在这个意义上,本发明的当前的混合物还应理解为通式(I)、式(II)和式(III)的化合物的异构体混合物与一种、两种、三种、四种、五种、十种、但优选仍更大数量的香料或调味剂的混合物。
因此,在本发明的一个优选的改进方案中,所说明的香料或调味剂混合物包含任意数量的选自由以下项构成的组的其他香料或调味剂:(1)烃类;(2)脂肪族醇;(3)脂肪族醛及其缩醛;(4)脂肪族酮及其肟;(5)脂肪族含硫化合物;(6)脂肪族腈;(7)脂肪族羧酸的酯;(8)非环状萜醇;(9)非环状萜醛和萜酮;(10)环状萜醇;(11)环状萜醛和酮;(12)环状醇;(13)环脂肪族醇;(14)环状和环脂肪族醚;(15)环状和大环状酮;(16)环脂肪族醛;(17)环脂肪族酮;(18)环状醇的酯;(19)环脂肪族醇的酯;(20)环脂肪族羧酸的酯;(21)芳香脂肪族醇;(22)芳香脂肪族醇与脂肪族羧酸的酯;(23)芳香脂肪族醚;(24)芳香族和芳香脂肪族醛;(25)芳香族和芳香脂肪族酮;(26)芳香族和芳香脂肪族羧酸及其酯;(27)含氮的芳香族化合物;(28)酚、苯基醚和苯基酯;(29)杂环化合物;(30)内酯;及其任意混合物。
香料或调味剂的选择在此是非常广泛的;可以与通式(I)、式(II)和式(III)的化合物形成的本发明有利组合的对应物质,例如可以在“S.Arctander,PerfumeandFlavorChemicals,Band I und II,Montclair,N.J.,1969,Eigenverlag”或者“H.Surburg und J.Panten,Common Fragrance and Flavor Materials,6.Ausgabe,Wiley-VCH,Weinheim,2016”中找到,并且它们并非已经是由通式(I)、式(II)和式(III)的化合物形成的本发明混合物的组成部分。
具体地可以提及以下内容:
天然原料提取物:这一组代表精油、浸膏、净油、树脂、类树脂、香胶、酊剂,例如龙涎香酊;香树油;当归种子油;当归根油;大茴香油;缬草油;罗勒油;树苔净油(Baummoos-Absolue);月桂叶油;艾草油安息香树脂;佛手柑油;蜂蜡净油;桦焦油;苦杏仁油;香薄荷油;布枯叶油;巴西檀木油杜松油;菖蒲油;樟脑油;依兰油;小豆蔻油;卡藜油;决明子油黑醋栗净油(Cassie-Absolue);海狸香净油(Castoreum-absolue);柏叶油;柏木油;岩蔷薇油;香茅油;柠檬油;苦配巴香膏;苦配巴香膏油;香菜油;木香油;孜然油;奠柏油;茚蒿油;莳萝草油;莳萝籽油;苦橙花叶水净油;橡树苔净油;榄香脂油;龙蒿油;柠檬桉油;桉树油;小茴香油;云杉针油;白松香油;白松香树脂;天竺葵油;葡萄柚油;愈创木油;古云香膏;古云香膏油;永久花净油;永久花油;姜油;鸢尾根净油;鸢尾根油;茉莉净油;菖蒲油;洋甘菊油,蓝色;洋甘菊油,罗马;胡萝卜种子油;苦香树皮油;松针油;留兰香油;葛缕子油;赖百当油;赖百当净油;赖百当树脂;醒目薰衣草净油;醒目薰衣草油;薰衣草净油;薰衣草油;柠檬草油;独活草油;蒸馏酸橙油;压制酸橙油;芳樟油;山苍子油;月桂叶油;肉豆蔻油墨角兰油;橘子油;马尾松油;含羞草净油;麝香颗粒油;麝香酊剂;香紫苏油;肉豆蔻油没药净油;没药油;桃金娘油;康乃馨叶油;康乃馨花油;橙花油;乳香净油;乳香油;金合欢油;橙花净油;橙子油;牛至油;玫瑰草油;广藿香油;紫苏油;秘鲁香膏油;欧芹叶油;欧芹籽油;苦橙叶油;薄荷油;胡椒油;西班牙椒油;松油;波莱油玫瑰净油;玫瑰木油;玫瑰油;迷迭香油;鼠尾草油,达尔马提亚;鼠尾草油,西班牙;檀木油;芹菜籽油;穗华薰衣草油;八角茴香油;安息香油;万寿菊油;冷杉针油;茶树油;松脂油;百里香油;妥卢香膏;零陵香净油;晚香玉净油;香草提取物;紫罗兰叶净油;马鞭草油;香根草油;杜松浆果油;葡萄酒酵母油;苦艾油;冬青油;依兰油;牛膝花油;麝猫净油;肉桂叶油;肉桂皮油及其馏分,或由其中分离出的成分。
单独香料:单独香料可以细分成多个类别,即:
烃,例如3-蒈烯;α-蒎烯;β-蒎烯;α-萜品烯;γ-萜品烯;对伞花烃;红没药烯;莰烯;石竹烯;雪松烯;金合欢烯;柠檬烯;长叶烯;月桂烯;罗勒烯;巴伦西亚桔烯;(E,Z)-1,3,5-十一碳三烯;苯乙烯;二苯基甲烷;
脂肪醇,例如己醇;辛醇;3-辛醇;2,6-二甲基庚醇;2-甲基-2-庚醇;2-甲基-2-辛醇;(E)-2-己烯醇;(E)-和(Z)-3-己烯醇;1-辛烯-3-醇;3,4,5,6,6-五甲基-3/4-庚烯-2-醇和3,5,6,6-四甲基-4-亚甲基庚烷-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛烷-2-醇;9-癸烯醇;10-十一碳烯醇;4-甲基-3-癸烯-5-醇;
脂肪醛及其缩醛,例如己醛;庚醛;辛醛;壬醛;癸醛;十一碳醛;十二碳醛;十三碳醛;2-甲基辛醛;2-甲基壬醛;(E)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一碳烯醛;(E)-4-癸烯醛;2-十二碳烯醛;2,6,10-三甲基-9-十一碳烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛二乙缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅基氧基乙醛;1-(1-甲氧基-丙氧基)-(E,Z)-3-己烯;
脂肪酮及其酮肟,例如2-庚酮;2-辛酮;3-辛酮;2-壬酮;5-甲基-3-庚酮;5-甲基-3-庚酮肟;2,4,4,7-四甲基-6-辛烯-3-酮;6-甲基-5-庚烯-2-酮;
脂肪族含硫化合物,例如3-甲基硫代己醇;3-甲基硫代己基乙酸酯;3-巯基己醇;3-巯基己基乙酸酯;3-巯基己基丁酸酯;3-乙酰基硫代己基乙酸酯;1-薄荷烯-8-硫醇;
脂肪族腈,例如2-壬烯酸腈;2-十一碳烯酸腈;2-十三碳烯酸腈;3,12-十三碳二烯酸腈;3,7-二甲基-2,6-辛二烯酸腈;3,7-二甲基-6-辛烯酸腈;
脂肪族羧酸的酯,例如(E)-和(Z)-3-己烯基甲酸酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;3,5,5-三甲基己基乙酸酯;3-甲基-2-丁烯基乙酸酯;(E)-2-己烯基乙酸酯;(E)-和(Z)-3-己烯基乙酸酯;乙酸辛酯;3-辛基乙酸酯;1-辛烯-3-基乙酸酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)-和(Z)-3-己烯基异丁酸酯;巴豆酸己酯;异戊酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;(E,Z)-2,4-癸二烯酸乙酯;2-辛炔酸甲酯;2-壬炔酸甲酯;2-异戊氧基乙酸烯丙酯;3,7-二甲基-2,6-辛二烯酸甲酯;4-甲基-2-戊基-巴豆酸酯;
非环状萜烯醇,例如香茅醇;香叶醇;橙花醇;芳樟醇;薰衣草醇;橙花叔醇;金合欢醇;四氢芳樟醇;四氢香叶醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛烷-2-醇;2-甲基-6-亚甲基-7-辛烯-2-醇;2,6-二甲基-5,7-辛二烯-2-醇;2,6-二甲基-3,5-辛二烯-2-醇;3,7-二甲基-4,6-辛二烯-3-醇;3,7-二甲基-1,5,7-辛三烯-3-醇;2,6-二甲基-2,5,7-辛三烯-1-醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸酯和3-甲基-2-丁烯酸酯;
非环状萜醛和萜酮,例如香叶醛;橙花醛;香茅醛;7-羟基-3,7-二甲基辛醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一碳烯醛;香叶基丙酮;以及香叶醛、橙花醛、7-羟基-3,7-二甲基辛醛的二甲基缩醛和二乙基缩醛;
环状萜烯醇,例如薄荷醇;异胡薄荷醇;α-萜品醇;萜品烯醇-4;薄荷烷-8-醇;薄荷烷-1-醇;薄荷烷-7-醇;冰片;异冰片醇;芳樟醇氧化物;诺普醇;雪松醇;龙涎醇;香根草醇;愈创醇;及其甲酸酯、乙酸酯、丙酸酯、异丁酸酯、丁酸酯、异戊酸酯、戊酸酯、己酸酯、巴豆酸酯、惕各酸酯和3-甲基-2-丁烯酸酯;
环状萜烯醛和酮,例如薄荷酮;异薄荷酮;8-巯基薄荷烷-3-酮;香芹酮;樟脑;葑酮;α-紫罗兰酮;β-紫罗兰酮;α-正甲基紫罗兰酮;β-正甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-鸢尾酮;α-二氢大马酮;β-二氢大马酮;β-大马酮;δ-二氢大马酮;γ-二氢大马酮;1-(2,4,4-三甲基-2-环己烯-1-基)-2-丁烯-1-酮;1,3,4,6,7,8a-六氢-1,1,5,5-四甲基-2H-2,4a-桥亚甲基萘-8(5H)-酮;2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-2-丁烯醛;诺卡酮;二氢诺卡酮;4,6,8-巨豆三烯-3-酮;α-甜橙醛;β-甜橙醛;酰基化的柏木油(甲基柏木基酮);
环状醇,例如4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异莰基环己醇;2,6,9-三甲基-Z2,Z5,E9-环十二碳三烯-1-醇;2-异丁基-4-甲基四氢-2H-吡喃-4-醇;
环脂肪族醇,例如α,3,3-三甲基环己基甲醇;1-(4-异丙基环己基)乙醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;2-乙基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-戊-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;1-(2,2,6-三甲基环己基)戊-3-醇;1-(2,2,6-三甲基环己基)己-3-醇;
环状和环脂肪族醚,例如桉叶素(桉油醇);柏木基甲基醚;环十二烷基甲基醚;1,1-二甲氧基环十二烷;(乙氧基甲氧基)环十二烷;α-环氧柏木烷(α-环庚烯环氧化物);3a,6,6,9a-四甲基十二氢萘并[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基十二氢萘并[2,1-b]呋喃;1,5,9-三甲基-13-氧杂二环[10.1.0]三癸-4,8-二烯;玫瑰醚(氧化玫瑰);2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二噁烷(二氧杂环己烷);
环状的和大环状的酮,例如4-叔丁基环己酮;2,2,5-三甲基-5-戊基环戊酮;2-庚基环戊酮;2-戊基环戊酮;2-羟基-3-甲基-2-环戊烯-1-酮;3-甲基-顺式-2-戊烯-1-基-2-环戊烯-1-酮;3-甲基-2-戊基-2-环戊烯-1-酮;3-甲基-4-环十五烯酮;3-甲基-5-环十五烯酮;3-甲基环十五碳酮;4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮;4-叔戊基环己酮;5-环十六烯-1-酮;6,7-二氢-1,1,2,3,3-五甲基-4(5H)-茚酮;8-环十六烯-1-酮;9-环十七烯-1-酮;环十五碳酮;环十六碳酮;
环脂肪族醛,例如2,4-二甲基-3-环己烯甲醛;2-甲基-4-(2,2,6-三甲基-环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
环脂肪族酮,例如1-(3,3-二甲基环己基)-4-戊烯-1-酮;2,2-二甲基-1-(2,4-二甲基-3-环己烯-1-基)-1-丙酮;1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢-2-萘烯基甲基酮;甲基-2,6,10-三甲基-2,5,9-环十二碳三烯基酮;叔丁基-(2,4-二甲基-3-环己烯-1-基)酮;
环状醇的酯,例如2-叔丁基环己基乙酸酯;4-叔丁基环己基乙酸酯;2-叔戊基环己基乙酸酯;4-叔戊基环己基乙酸酯;3,3,5-三甲基环己基乙酸酯;十氢-2-萘基乙酸酯;2-环戊基环戊基巴豆酸酯;3-戊基四氢-2H-吡喃-4-基乙酸酯;十氢-2,5,5,8a-四甲基-2-萘基乙酸酯;4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6茚基乙酸酯;4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6茚基丙酸酯;4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6茚基异丁酸酯;4,7-桥亚甲基-八氢-5或6-茚基乙酸酯;
环脂肪族醇的酯,例如1-环己基乙基巴豆酸酯;
环脂肪族羧酸的酯,例如烯丙基-3-环己基丙酸酯;烯丙基环己氧基乙酸酯;顺式和反式甲基二氢茉莉酮酸甲酯;顺式和反式甲基茉莉酸甲酯;甲基-2-己基-3-氧代环戊烷羧酸酯;乙基-2-乙基-6,6-二甲基-2-环己烯羧酸酯;乙基-2,3,6,6-四甲基-2-环己烯羧酸酯;乙基-2-甲基-1,3-二氧戊环-2-乙酸酯;
芳香脂肪族醇,例如苄醇;1-苯基乙基醇;2-苯基乙基醇;3-苯基丙醇;2-苯基丙醇;2-苯氧基乙醇;2,2-二甲基-3-苯基丙醇;2,2-二甲基-3-(3-甲基苯基)丙醇;1,1-二甲基-2-苯基乙基醇;1,1-二甲基-3-苯基丙醇;1-乙基-1-甲基-3-苯基丙醇;2-甲基-5-苯基戊醇;3-甲基-5-苯基戊醇;3-苯基-2-丙烯-1-醇;4-甲氧基苄基醇;1-(4-异丙基苯基)乙醇;
芳香脂肪族醇与脂肪族羧酸的酯,例如乙酸苄酯;丙酸苄酯;异丁酸苄酯;异戊酸苄酯;2-苯基乙基乙酸酯;2-苯基乙基丙酸酯;2-苯基乙基异丁酸酯;2-苯基乙基异戊酸酯;1-苯基乙基乙酸酯;α-三氯甲基苄基乙酸酯;α,α-二甲基苯基乙基乙酸酯;α,α-二甲基苯基乙基丁酸酯;乙酸肉桂酯;2-苯氧基乙基异丁酸酯;4-甲氧基苄基乙酸酯;
芳香脂肪族醚,例如2-苯基乙基甲基醚;2-苯基乙基异戊基醚;2-苯基乙基-1-乙氧基乙基醚;苯基乙醛二甲基缩醛;苯基乙醛二乙基缩醛;氢化阿托醛二甲基缩醛;苯基乙醛甘油缩醛;2,4,6-三甲基-4-苯基-1,3-二噁烷;4,4a,5,9b-四氢茚并[1,2-d]-m-二噁英;4,4a,5,9b-四氢-2,4-二甲基茚并[1,2-d]-m-二噁英;
芳香族和芳香脂肪族醛,例如苯甲醛;苯乙醛;3-苯基丙醛;氢化阿托醛(龙葵醛);4-甲基苯甲醛;4-甲基苯基乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)丙醛;2-甲基-3-(4-叔丁基苯基)丙醛;2-甲基-3-(4-异丁基苯基)丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛;α-戊基肉桂醛;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧苯甲醛;3,4-二甲氧基苯甲醛;2-甲基-3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧苯基)丙醛;
芳香族和芳香脂肪族酮,例如苯乙酮;4-甲基苯乙酮;4-甲氧基苯乙酮;4-叔丁基-2,6-二甲基苯乙酮;4-苯基-2-丁酮;4-(4-羟基苯基)-2-丁酮;1-(2-萘基)乙酮;2-苯并呋喃基乙酮;(3-甲基-2-苯并呋喃基)乙酮;二苯甲酮;1,1,2,3,3,6-六甲基-5-茚满基甲基酮;6-叔丁基-1,1-二甲基-4-茚满基甲基酮;1-[2,3-二氢-1,1,2,6-四甲基-3-(1-甲基乙基)-1H-5-茚基]乙酮;5',6',7',8'-四氢-3',5',5',6',8',8'-六甲基-2-萘乙酮;
芳香族和芳香脂肪族羧酸及其酯,例如苯甲酸;苯基乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄酯;甲基苯基乙酸酯;乙基苯基乙酸酯;香叶基苯基乙酸酯;苯基乙基-苯基乙酸酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄酯;肉桂酸苯乙酯;肉桂酸肉桂酯;烯丙基苯氧基乙酸酯;水杨酸甲酯;水杨酸异戊酯;水杨酸己酯;水杨酸环己酯;顺式-3-己烯基水杨酸酯;水杨酸苄酯;水杨酸苯乙酯;甲基-2,4-二羟基-3,6-二甲基苯甲酸酯;乙基-3-苯基甘油酸酯;乙基-3-甲基-3-苯基甘油酸酯;
含氮的芳香族化合物,例如2,4,6-三硝基-1,3-二甲基-5-叔丁基苯;3,5-二硝基-2,6-二甲基-4-叔丁基苯乙酮;肉桂酸腈;3-甲基-5-苯基-2-戊烯酸腈;3-甲基-5-苯基戊酸腈;邻氨基苯甲酸甲酯;N-甲基氨基苯甲酸甲酯;邻氨基苯甲酸甲酯与7-羟基-3,7-二甲基辛醛、2-甲基-3-(4-叔丁基苯基)丙醛或2,4-二甲基-3-环己烯甲醛的席夫碱;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;2-(3-苯基丙基)吡啶;吲哚;粪臭素;2-甲氧基-3-异丙基吡嗪;2-异丁基-3-甲氧基吡嗪;
酚、苯基醚和苯基酯,例如草蒿脑;茴香脑;丁香酚;丁香基甲基醚;异丁香酚;异丁香基甲基醚;百里香酚;香芹酚;二苯醚;β-萘基甲基醚;β-萘基乙基醚;β-萘基异丁基醚;1,4-二甲氧基苯;乙酸丁香酚酯;2-甲氧基-4-甲基苯酚;2-乙氧基-5-(1-丙烯基)苯酚;对甲苯基苯基乙酸酯;
杂环化合物,例如2,5-二甲基-4-羟基-2H-呋喃-3-酮;2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮;3-羟基-2-甲基-4H-吡喃-4-酮;2-乙基-3-羟基-4H-吡喃-4-酮;
内酯,例如1,4-辛内酯;3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸烯-1,4-内酯;1,4-十一碳内酯;1,4-十二碳内酯;1,5-癸内酯;1,5-十二碳内酯;4-甲基-1,4-癸内酯;1,15-十五碳内酯;顺式和反式-11-十五碳烯-1,15-内酯;顺式和反式-12-十五碳烯-1,15-内酯;1,16-十六碳内酯;9-十六碳烯-1,16-内酯;10-氧杂-1,16-十六碳内酯;11-氧杂-1,16-十六碳内酯;12-氧杂-1,16-十六碳内酯;1,12-十二碳二酸乙烯酯;1,13-十三碳二酸乙烯酯;香豆素;2,3-二氢香豆素;八氢香豆素;
以及上述香料或调味剂的任意混合物。
在第二方面,本发明涉及一种方法,用于制备通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物,所述方法包括以下步骤:
(a)用选自由以下项组成的组的醇:具有1至10个碳原子的脂肪族、芳香脂肪族或芳香族醇或具有2至6个羟基的多元醇,将衣康酸酯化,获得衣康酸二酯;以及
(b)用含氮有机碱将所述衣康酸二酯异构化,获得通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物。
将参考图1中对方法执行方式的展示来详细说明用于制备通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物的所述方法。
在本发明方法的第一反应步骤(步骤(a))中,使衣康酸与大约等摩尔量的或过量的醇酯化。该反应是酸催化的,优选在使用硫酸或对甲苯磺酸的情况下在回流下进行。然后将未转化的醇蒸馏掉。在此获得衣康酸的二酯。酸催化的衣康酸酯化步骤在本领域技术人员已知的常规工艺条件下进行。
在本发明方法的第二步骤(步骤(b))中,在使用含氮有机碱的情况下进行第一步骤中获得的衣康酸二酯的异构化,一般而言获得选自由通式(I)、式(II)和式(III)的化合物组成的组的化合物中的一种或多种,或者具体而言获得选自由中康酸、柠康酸和/或衣康酸的二酯组成的组的化合物中的一种或多种。
这个异构化反应优选在溶剂中进行并且要求100至150℃的温度。在此随后也将溶剂去除。
在此根据本发明的一个改进方案特别优选的是如下的制备方法,其中在步骤(b)中使用高沸点溶剂。
高沸点溶剂优选包含具有高于250℃、更优选高于300℃的沸点的溶剂。在此,基于聚亚烷基二醇(PAG)的产品已经证实为有用的。此类产品例如为作为润滑物质已知的50-B SYNALOXTM 50-xB,以及包含结构为RO-[CH2-C(CH3)HO]n-[CH2CH2O]m-H的具有单一末端羟基的氧化乙烯和氧化丙烯基团的含醇材料。
在本发明的替代性的且优选的改进方案中,在步骤(b)中使用如下溶剂体系作为保护溶剂,该溶剂体系包括具有高于150℃的沸点的高沸点溶剂并且另外包括具有介于90℃与120℃之间沸点的共溶剂。这种体系明显提高了产率,因为在没有保护溶剂的情况下,经蒸馏的产物倾向于在较长的蒸馏路线上使用较大反应容器进行大规模聚合。可能显示出,当保护溶剂具有如下沸点,即,使其还可以与产物一起蒸馏以防止在蒸馏时的产物聚合,则即使在较大的批次下也可能提高产率或保持较高产率。特别优选地,共溶剂具有介于95℃与110℃之间、特别优选100℃至105℃的沸点。
保护溶剂或共溶剂可以在蒸馏步骤之后通过常用方法分离掉。
适合的保护溶剂或共溶剂为:
·脂肪族烃,并且尤其链烷烃,优选辛烷、异辛烷、壬烷、癸烷、十一烷或十四烷;
·氯化的脂肪族烃,优选1,1,2-三氯乙烷、五氯乙烷、1-碘-2-甲基丙烷、1-氯己烷或1-氯-2-乙基己烷;
·氯化的芳香族烃,优选氯苯或氯甲苯;
·醚,尤其脂肪族醚,优选丁醚、异丁醚、乙基己基醚、1-丁氧基-2-甲氧基乙烷、1,1-二乙氧基丁烷、戊醚、异戊醚或二丙氧基甲烷;
·芳香族醚,优选苯基丙基醚或异亚丙基丙酮;
·硝化化合物,优选硝基丙烷或硝基苯;
·脂肪族、环脂肪族或芳香族酮,优选甲基乙基酮、甲基异丁基酮、二异丁基酮、甲基正戊基酮、甲基异戊基酮、环己酮、甲基环己酮或双丙酮醇。
保护溶剂或共溶剂还可以作为单独的混合物使用。
由高沸点溶剂聚亚烷基二醇(PAG)和共溶剂二噁烷形成的溶剂体系已经被证实为是特别有利的。
为了进行酯化,也就是说为了制备衣康酸二酯,在本发明方法的步骤(a)中使用具有1至10个碳原子的脂肪族、芳香脂肪族或芳香族醇或者具有2至6个羟基的多元醇,其中优选二醇。
优选地,使用甲醇、异丙醇、异构丁醇、乙二醇、二甘醇、丙二醇、二丙二醇或甘油来制备衣康酸二酯。最优选地,使用甲醇、乙醇或丙醇来将衣康酸酯化。同样可以使用甲醇、乙醇和/或丙醇的组合(也就是说混合物)来进行酯化。
在使用含氮有机碱作为催化剂的情况下,在本发明的方法的步骤(b)中,将衣康酸二酯异构化成通式(I)、(II)和(III)的化合物,尤其中康酸、柠康酸和衣康酸的二酯。
含氮有机碱选自由以下项组成的组:TMEDA(N,N,N',N'-四甲基乙二胺)(沸点:121℃)、TEA(四乙基铵)(沸点:89℃)、二丁基胺(沸点:159.6℃)、吡啶(沸点:115℃)、NMP(N-甲基-2-吡咯烷酮)(沸点:202℃)、三辛基胺(沸点:365℃)及其混合物。
用含氮有机碱进行异构化的优点是,由于异构化之后不同的沸点,N-碱可以很好地与产物(也就是说通式(I)、式(II)和式(III)的化合物)分离。在本发明方法中N-碱与产物的分离或者N-碱的回收以蒸馏方式进行。在蒸馏之后,N-碱可以重新用在本发明方法中。在本发明方法中使用的含氮有机碱具有另外的优点,即,它们不会不利地影响所获得的产物的香味特征或味道特征。
在使用TMEDA或三乙基胺的情况下将衣康酸二酯异构化已经证实为是特别有利的。如异构化对比所示出的,与用经典钌催化剂进行异构化相比,用这两种含氮有机碱之一进行异构化产生了特别高的产率而同时降低了反应时间,如从下表1中可以看出的:
表1:
如从表1中另外可以看出的,由于TMEDA的不同沸点以及由于其容易与通式(I)、式(II)或式(III)的化合物分离,在使用TMEDA的情况下使衣康酸二酯异构化已经证实为特别有利的。通过使用TMEDA,还可以显著降低衣康酸二酯的异构化的反应时间并且此外产生最好的结果,这涉及通式(I)、(II)和(III)的化合物相互之间的混合比,如下文将详细说明的。
在本发明方法的步骤(b)中,衣康酸二酯的异构化持续进行1至5小时的时长,以便获得衣康酸二酯向通式(I)、(II)和(III)的化合物的最优的异构化。异构化优选进行2至3小时的时间。
根据本发明的方法产生了如下的异构体混合物或香料或调味剂混合物,其中相对于通式(I)、式(II)和式(III)的化合物的总和或者相对于异构体混合物的总重量以至少50至100重量%、更优选60至78重量%且特别优选66至72重量%的量包含式(I)的化合物,以至少2至8重量%、更优选3至7重量%且特别优选4至6重量%的量包含式(II)的化合物,并且以至少18至31重量%、更优选20至29重量%且最优选22至27重量%的量包含式(III)的化合物。
上述混合比还适用于中康酸、柠檬酸和衣康酸的分别特别优选的二甲酯、二乙酯、二丙酯或二丁酯、尤其二乙酯的化合物混合物。
在根据本发明的方法的一个优选变体中,式(I)的化合物以与香料或调味剂混合物中的式(II)和式(III)的两种化合物的总和之比3比1、优选2.5比1、更优选1.5比1存在。这些混合比还适用于中康酸、柠康酸和衣康酸的相应优选的二甲酯、二乙酯、二丙酯或二丁酯,尤其二乙酯的化合物混合物。在更高的中康酸酯比例下产生了更强烈的梨香味。
本发明的方法另外还产生了通式(I)的化合物,或者包括纯度至少为98.0%的、但优选纯度还为100.0%的通式(I)的化合物,尤其中康酸的相应二甲酯、二乙酯、二丙酯或二丁酯的香料或调味剂混合物。此类具有纯的或几乎纯的中康酸二酯,尤其中康酸二乙酯的香料或调味剂混合物显示出具有梨味调的特别强的香味。
根据本发明的方法的一个优选的实施方式还涉及一种用于制备化合物(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)或2-亚甲基丁二羧酸二酯(衣康酸二酯)或者用于制备包括选自由(E)-2-甲基丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基丁-2-烯二羧酸二酯(柠康酸二酯)和2-亚甲基丁二羧酸二酯(衣康酸二酯)组成的组的一种、两种或三种化合物的混合物的方法,所述方法包括以下步骤:
(a)用选自由以下项组成的组的醇将衣康酸酯化:甲醇、乙醇、丙醇和丁醇,获得衣康酸二酯;以及
(b)用含氮有机碱将所述衣康酸二酯异构化,获得化合物(E)-2-甲基丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基丁-2-烯二羧酸二酯(柠康酸二酯)或2-亚甲基丁二羧酸二酯(衣康酸二酯)或者包括选自由(E)-2-甲基丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基丁-2-烯二羧酸二酯(柠康酸二酯)和2-亚甲基丁二羧酸二酯(衣康酸二酯)组成的组的一种、两种或三种化合物的混合物。
在一个最优选的变体中,在上述方法中包含的根据通式(I)、(II)和(III)的中康酸、柠康酸和/或衣康酸的二酯为二乙酯,即(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯或2-亚甲基-丁二酸二乙酯或者包括选自由(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯组成的组的一种、两种或三种化合物的混合物。
在这种变体中,本发明的方法产生了如下的异构体混合物或香料或调味剂混合物,其中相对于通式(I)、式(II)和式(III)的化合物的总和或者相对于异构体混合物的总重量以至少50至100重量%、更优选60至78重量%、最优选66至72重量%的量包含(E)-2-甲基丁-2-烯二酸二乙酯或中康酸二乙酯(式(I)的化合物),以至少2至8重量%、更优选3至7重量%且特别优选4至6重量%的量包含(Z)-2-甲基丁-2-烯二酸二乙酯(式(II)的化合物),并且以至少18至31重量%、更优选20至29重量%且最优选22至27重量%的量包含2-亚甲基-丁二酸二乙酯(式(III)的化合物)。
与根据WO 2018/114073 A1的方法相比,根据本发明的方法的独特之处在于所述方法包括更少的(也就是说仅两个)且更短的合成步骤,也就是说总反应时间更短。
本发明方法的另一个优点是,在没有使用卤素、尤其碘的情况下而是在使用含氮有机碱的情况下使衣康酸二酯异构化。另外,使用含氮有机碱没有产生气味污染。
相反,在根据现有技术的方法中在柠檬酸酯异构化成中康酸酯和衣康酸酯时使用碘作为催化剂要求大量的碘来完全完成异构化反应。这进而要求纯化所得产物的附加步骤,以便将过量的碘从反应混合物中分离出来。使用碘另外还导致双键的加成,这进而要求随后的脱卤化氢。
如从以下的实施例1中可以看出的,在大规模制备香料或调味剂混合物时它们在最终产物中具有更高的碘含量,这是由于更大量的碘造成的。与此不同,在大规模制备本发明的香料或调味剂混合物产生了不含碘的最终产物。因此,根据本发明的方法是特别有利的。
此外,用现有技术的方法制备的香料或调味剂混合物含有杂质和副产物。这些杂质和副产物中的一些是不希望的,因为它们对香料具有不利的影响。例如,这些香料或调味剂混合物含有在合成时使用的卤素、尤其碘。
根据本发明方法制备的香料或调味剂混合物不具有此类碘杂质,因为合成在没有使用卤素、尤其碘的情况下完成。
根据本发明的方法另外具有如下优点,即所述方法与根据WO 2018/114073 A1的方法相比提供了更高的产率。在本发明方法中的产率为>90%、优选>97%。相反,在根据WO2018/114073A1的方法中产率为约60%。此外,未反应的初始原料可以用在进一步的合成过程中。
本发明方法的上述优点因此有助于以下事实:以更低的技术耗费(也就是说以更少的合成步骤)制备具有果香、类似梨香的芳香的香料或调味剂或香料或调味剂混合物,并且因此成本更低且具有高纯度。
在另外的第三方面,本发明涉及能够根据本发明方法获得的通式(I)、式(II)或式(III)的香料或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的香料或调味剂混合物,其中所述方法的独特之处尤其在于所述方法在不使用含卤素、尤其含碘的反应物的情况下进行。
出人意料地,已经证实,一般而言式(I)、式(II)和/或式(III)的化合物的异构体混合物并且具体而言通式(I)的中康酸二酯、优选中康酸二乙酯特别适合于赋予、改和/或增强梨型香味或味道。
因此,本发明的第四方面涉及一种用于在香味剂混合物、香水油、美妆剂、涂抹剂或洗涤和清洁剂中赋予、改变和/或增强果香、梨型气味味调或者用于在食物、动物饲料或制药产品中赋予、改变和/或增强果香、梨型味道味调的方法,所述方法包括以下步骤:
(i1)提供包括通式(I)、式(II)和式(III)的化合物的本发明香料或调味剂混合物;以及
(i2)将足以在成品制剂中引起果香、梨型气味味调或味道味调的感受有效量的所述香料或调味剂混合物与至少一种另外的香料或调味剂或与另外的香料或调味剂的混合物混合;
或者
(ii1)提供包括通式(I)、式(II)和式(III)的化合物的本发明香料或调味剂混合物;以及
(ii2)将足以在成品制剂中引起果香、梨香气味味调或味道味调的感受有效量的所述香料或调味剂混合物与香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品混合。
在此优选的是由(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)和2-亚甲基丁二羧酸二酯(衣康酸二酯)形成的混合物。这尤其适用于特别优选的二甲酯、二乙酯、二丙酯或二丁酯的相应混合物。
因此,在用于赋予、改变和/或增强果香、梨型香味味调或味道味调的方法中最优选的是由(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯形成的混合物。
本发明的另一个方面涉及感受有效量的本发明香料或调味剂混合物的用途,所述香料或调味剂混合物一般而言包括式(I)、式(II)和式(III)的化合物或者具体而言包括(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯,用于在香味剂混合物或芳香油、美妆剂、涂抹剂或洗涤和清洁剂中赋予、改变和/或增强果香、梨型气味味调,或者用于在食物、动物饲料或制药产品中赋予、改变和/或增强果香、梨型味道味调,或者用于制备香味剂混合物、芳香油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品。
由于其有利的嗅觉特性,本发明的香料或调味剂混合物突出地适合用于以梨香味调对产品增加香味或增香或芳香化。
关于优选的加入物质和加入量,参考前文的实施方案,这些实施方案在此同样适用,因而不再重复。
一般而言包括通式(I)、式(II)和式(III)的化合物的香料或调味剂混合物对此是优选的。更优选的是由(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)和2-亚甲基丁二羧酸二酯(衣康酸二酯)形成的香料或调味剂混合物。这尤其适用于中康酸、柠康酸和衣康酸的相应的二甲酯、二乙酯、二丙酯或二丁酯的混合物。
用由(E)-2-甲基-丁-2-烯二羧酸二乙酯或中康酸二乙酯与(Z)-2-甲基-丁-2-烯二羧酸二乙酯和2-亚甲基丁二羧酸二乙酯形成的香料或调味剂混合物获得了对产品增加香味或芳香化的最佳结果。
尤其要再次强调,本发明的任一设计方案的相应特别优选的变体和改进方案涉及到由(E)-2-甲基-丁-2-烯二羧酸二乙酯(中康酸二乙酯)、(Z)-2-甲基-丁-2-烯二羧酸二乙酯(柠康酸二乙酯)和2-亚甲基丁二羧酸二乙酯(衣康酸二乙酯)形成的异构体混合物,所述混合物以总共至少50重量%的量包含这些化合物。
最后,本发明涉及以感受有效量包含本发明的香料或调味剂混合物的香味剂混合物、香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品。
这些香味剂混合物或香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物或动物饲料或其其他组成部分或组合物优选为如在WO 2018/114073 A1的第[0074]至[0204]段中详细说明的那些。此公开内容通过指定的引用整体并入到本申请中。
涂抹剂应理解为不属于香水油、美妆剂或洗涤和清洁剂的组中的所有在此提及的试剂。
根据本发明的一个优选的改进方案,在这些香味剂混合物、试剂和食物中,相对于所述香味剂混合物、试剂和食物以0.05至5重量%的量包含根据本发明的香料或调味剂混合物。
因此本发明不仅涉及香味剂混合物或香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物还涉及动物饲料,其包含本发明的香料或调味剂混合物,所述香料或调味剂混合物一般而言包括式(I)、式(II)和式(III)的化合物或者具体而言包括(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯。
优选将本发明的香料或调味剂混合物与其他组成部分组合。优选的其他组成部分选自由以下项组成的组:
防腐剂,优选在US 2006/0089413中所述的那些,磨料、抗粉刺剂和用于控制皮脂的试剂,优选在WO 2008/046791中所述的那些,抗皮肤老化剂,优选在WO 2005/123101中所述的那些,抗菌剂、抗蜂窝炎剂、去屑剂,优选在WO2008/046795中所述的那些,消炎剂、刺激抑制剂、防刺激剂(抗炎症的、抑制刺激的和防止刺激的试剂),优选在WO 2007/042472和US2006/0089413中所述的那些,抗微生物剂,优选在WO 2005/123101中所述的那些,抗氧化剂,优选在WO 2005/123101中所述的那些,收敛剂、汗液抑制剂、抗静电剂、粘合剂、缓冲剂、载体材料,优选在WO 2005/123101中所述的那些,螯合剂,优选在WO 2005/123101中所述的那些,细胞兴奋剂、清洁剂、护理剂、脱毛剂、表面活性物质、除臭剂和止汗剂,优选在WO2005/123101中所述的那些,增塑剂、乳化剂,优选在WO 2005/123101中所述的那些,酶、精油,优选在US 2008/0070825中所述的那些,驱虫剂,优选在WO 2005/123101中所述的那些,纤维、成膜剂、固定剂、发泡剂、泡沫稳定剂、用于防止发泡的物质、增泡剂、杀真菌剂、凝胶化剂、凝胶形成剂,优选在WO 2005/123101中所述的那些,毛发护理剂、毛发变形剂、直发剂、湿度调节剂(助湿物质、润湿物质和/或保湿物质),优选在WO 2005/123101中所述的那些,渗透质,优选在WO 2005/123101中所述的那些,相容性溶质,优选在WO 01/76572和WO02/15686中所述的那些,漂白剂、增强剂、去污剂、光学增亮剂、浸泡剂、防污剂、减摩擦剂、增滑剂、保湿霜、膏剂、遮光剂、塑化剂、遮盖剂、亮光剂、增亮剂、聚合物,优选在WO 2008/046676中所述的那些,粉末、蛋白质和蛋白水解液,优选在WO 2005/123101和WO 2008/046676中所述的那些,补油剂、打磨剂、皮肤舒缓剂、皮肤清洁剂、皮肤护理剂、皮肤治愈剂(皮肤修复剂),优选包含胆甾醇和/或脂肪酸和/或神经酰胺和/或伪神经酰胺,在此优选在WO 2006/053912中所述的那些,皮肤提亮剂,优选在WO 2007/110415中所述的那些,护肤剂、皮肤软化剂、皮肤冷却剂,优选在WO 2005/123101中所述的那些,皮肤加热剂,优选在WO2005/123101中所述的那些,稳定剂、UV吸收剂、UV过滤剂,优选在WO 2005/123101中所述的那些,亚苄基-β-二羰基化合物,优选在WO 2005/107692中所述的那些,α-苯甲酰肉桂酸腈,优选在WO 2006/015954中所述的那些,AhR受体对抗药,优选在WO 2007/128723和WO 2007/060256中所述的那些,清洗剂、柔软剂、悬浮剂、皮肤美黑剂,优选在WO 2006/045760中所述的那些,增稠剂、维生素,优选在WO 2005/123101中所述的那些,油、蜡和脂肪,优选在WO2005/123101中所述的那些,磷脂,优选在WO 2005/123101中所述的那些,脂肪酸(饱和脂肪酸,单或多不饱和脂肪酸,α-羟基酸,多羟基脂肪酸),优选在WO 2005/123101所述的那些,液化剂、着色剂、颜色保护剂以及颜料,优选在WO 2005/123101中所述的那些,抗腐蚀剂、芳香剂和调味剂以及其他附加的香料,优选在S.Arctander,Perfume andFlavorChemicals,Eigenverlag,Montclair,N.J.,1969和Surburg,Panten,Common Fragrance and FlavorMaterials,5th Edition,Wiley-VCH,Weinheim 2006中详述的,尤其在US 2008/0070825中明确提及的、并非已经是本发明香水油的香味剂混合物的组成部分的另外香料,醇和多元醇,优选在WO 2005/123101中所述的那些,表面活性剂,优选在WO 2005/123101中所述的那些,动物提取物、酵母提取物、藻类或微藻提取物、电解质、塑化剂、有机溶剂,优选在WO2005/123101中所述的那些,或者硅酮和硅酮衍生物,优选在WO 2008/046676中所述的那些。
在本发明的意义上,包含由通式(I)、式(II)和式(III)的化合物形成的本发明香料或调味剂混合物或者由(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯形成的香料或调味剂混合物的洗涤和清洁剂(简称为WSR剂)可以以作为粉末、颗粒、片剂等的固态形式,但还可以以液态、凝胶状或糊状形式存在。优选涉及不仅适合于手洗衣物还适合于机洗衣物、尤其纺织品的洗涤剂。还可以涉及用于工业领域或用于家用领域的洗涤和清洁剂。清洁剂例如还可以用于清洁硬质表面。在此例如涉及用于手动清洁或机洗清洁餐具的餐具清洁剂。还可以涉及用于清洁硬质表面(如家具表面、瓷砖、花砖、墙壁和底板覆盖物)常见的工业清洁剂或家用清洁剂。除了餐具之外,硬质表面还可以考虑家用和商用的所有其余的硬质表面,尤其由玻璃、陶瓷、塑料或金属形成的表面。
WSR剂可以具有其他可商购的组成部分,例如表面活性剂、骨架材料、漂白剂、漂白剂活化剂、增稠剂、酶、电解质、pH调节剂、着色剂和香味剂、泡沫抑制剂、抗再沉积剂、光学增亮剂、灰化抑制剂、抗皱剂、抗微生物有效物质、防腐剂、抗氧化剂、抗静电剂、UV吸附剂、重金属络合剂等。
在本发明的一个优选变体中,用本发明的香料或调味剂混合物(包括感受有效量的通式(I)、式(II)和式(III)的化合物)或优选用香料混合物(包括感受有效量的(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯)增香或增加香味的香味剂混合物或香水油、美妆剂、涂抹剂以及还有洗涤和清洁剂选自由以下项组成的组:香水净油,香水,淡香水,须后水,古龙水,须前产品,喷洒古龙水,有香味的湿纸巾,酸性、碱性和中性清洁剂,例如地板清洁剂,窗玻璃清洁剂,餐具清洗剂,浴室和卫生间清洁剂,清洗乳,固态和液态的厕所清洁剂,粉末和泡沫状的地毯清洁剂,液态洗涤剂,粉末状洗涤剂,洗涤预处理剂如漂白剂,柔顺剂和去污剂,织物软化剂,清洗皂,清洗片剂,消毒剂,表面消毒剂,呈液态、凝胶状或施加在固态载体上的形式的空气清新剂,气溶胶喷雾,蜡和抛光剂如家具抛光剂,地板蜡,鞋油以及个人护理剂例如固态和液态的皂,沐浴露,洗发水,剃须皂,剃须泡沫,浴油,水包油、油包水和水包油包水类型的化妆乳液例如皮肤霜和皮肤乳液,面霜和乳液,防晒霜和乳液,晒后霜和乳液,手霜和乳液,足霜和乳液,脱毛霜和乳液,须后霜和乳液,美黑霜和乳液,护发产品例如发胶,啫喱,发乳液,护发素,永久和半永久的染发剂,发变形剂如冷烫剂和直发剂,发根营养液,发霜和乳液,除臭剂和止汗剂例如腋窝喷雾,滚擦剂(Roll-ons),除臭棒,除臭霜,装饰性化妆产品,蜡烛,灯油,线香,杀虫剂,驱虫剂和燃料。
包含本发明的香料或调味剂混合物的特别优选的香水油或试剂选自由以下项组成的组:-香水,淡香水,须后水,古龙水,须前产品,喷洒古龙水;
-酸性、碱性和中性清洁剂,尤其在家用领域中,优选地板清洁剂,窗玻璃清洁剂,餐具清洗剂,浴室和卫生间清洁剂,清洗乳,固态和液态的厕所清洁剂,粉末和泡沫状的地毯清洁剂,液态洗涤剂,粉末状洗涤剂,织物软化剂,表面消毒剂、尤其用于硬质表面(硬质表面清洁剂);
-个人护理剂,优选固态和液态的皂,沐浴露,洗发水,剃须皂,剃须泡沫;
-水包油、油包水和水包油包水类型的化妆乳液、优选皮肤霜和乳液,面霜和乳液,防晒霜和乳液,晒后霜和乳液,手霜和乳液,足霜和乳液,脱毛霜和乳液,须后霜和乳液,美黑霜和乳液,亮肤霜和乳液;
-护发产品,优选发胶,啫喱,固定用发乳液,护发素,永久和半永久的染发剂,发根营养液,发霜和乳液;
-除臭剂和止汗剂,优选腋窝喷雾,滚擦剂(优选作为醇溶剂或非醇溶剂,作为凝胶或(微)乳液),除臭棒(Deo棒),除臭霜。
本发明的特别优选的增香剂为洗涤和清洁剂,卫生或护理产品、尤其在身体和头发护理、美妆用品和家用品领域中。
在本发明的一个优选变体中,用本发明的调味剂混合物(包括感受有效量的通式(I)、式(II)和式(III)的化合物)或优选用由(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯形成的香料混合物芳香化的食物选自由以下项组成的组:乳制品、饮料、糖果、营养补充剂、膳食食物、代餐食物和半成品。
此外,包括感受有效量的通式(I)、式(II)和式(III)的化合物的本发明调味剂混合物或优选包括感受有效量的(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯形成的香料混合物还用于使制药产品芳香化。
优选的产品是其中相对于增香的或芳香化的最终产品的总重量本发明的香料或调味剂混合物在产品中的比例为0.01至10重量%、优选0.1至5重量%且特别优选0.25至3重量%的那些产品。
实施例
实施例1:根据WO 2018/114073制备的香料或调味剂混合物的碘含量的测定
根据EN 1511,CON-PV 01187,ICP-MS测定样品的碘含量。
样品1: 碘含量:23±4.6mg/kg
样品2: 碘含量:69±14mg/kg
样品1涉及3kg的批次过程。相反,样品2涉及50kg的批次过程。批次过程中的混合物量越高,就需要越多的碘,这造成最终产物中的更高的碘含量。
实施例2:(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯的制备
步骤1:2-亚甲基-丁二酸二乙酯(衣康酸二乙酯)的制备
在5升的双夹套烧瓶中放入乙醇(2250ml,3体积%)并且加热到50℃。然后分分批加入2-亚甲基丁酸(衣康酸)(750g,5.76mol,1.0当量),直到全部溶解。随后滴加硫酸(126ml,0.4当量)并且在回流下煮沸5小时。反应结束后,在旋转蒸发器上蒸出过量的乙醇并且将残留物用MTBE(甲基叔丁基醚)(150ml)稀释,并依次用5%的NaCl溶液(250mlx 2)和5%的Na2CO3溶液清洗(250ml)。所获得的溶液通过硫酸钠干燥。将此时获得的溶液在60℃的温度和500-10mbar的压力下蒸发。产量:965.8g;GC纯度=99.9%。
2-亚甲基-丁二酸二乙酯的谱图数据:
1H NMR(400MHz,CDCl3)δ6.32(d,J=1.0Hz,1H),5.70(q,J=1.2Hz,1H),4.22(q,J=7.1Hz,2H),4.16(q,J=7.1Hz,2H),3.33(d,J=1.1Hz,2H),1.30(t,J=7.2Hz,3H),1.26(t,J=7.4Hz,3H)。13C NMR(101MHz,CDCl3)δ170.8,166.2,134.2,128.1,61.0,60.1,37.8,14.2,14.2。
步骤2:(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯的制备
将衣康酸二乙酯(500g;2.68mol)与含氮碱TMEDA(约10重量%;50g;0.43mol)的混合物在2升三口烧瓶中在130至135℃的温度下在大气压力下加热2至4小时。气相色谱分析得到了72%的(E)-2-甲基丁-2-烯二酸二乙酯和(Z)-2-甲基丁-2-烯二酸二乙酯的组合物。然后通过蒸馏纯化反应混合物。首先将TMEDA在120℃的温度和1013mbar的压力下蒸馏掉(蒸馏掉93%的TMEDA,其可以重复利用)。然后在约224℃的温度和1013mbar的压力下继续蒸馏所获得的产物混合物((E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯和2-亚甲基-丁二酸二乙酯)。产量(混合物):451g;纯度(混合物):>99%。
主要异构体(E)-2-甲基丁-2-烯二酸二乙酯的谱图数据:
1H-NMR(400MHz,CDCl3):δ=1.31(t,J=7.1Hz,3H),1.32(t,J=7.2Hz,3H),2.29(d,J=1.5Hz,3H),4.16(q,J=7.5Hz,2H),4.24(m,2H),6.78(d,J=1.6Hz,1H)。
13C NMR(101MHz,CDCl3):δ=167.2,165.9,143.8,126.7,61.6,60.6,14.3,14.2,14.1。
实施例3:本发明的香料或调味剂混合物的感受评分
表2:香料-对比
如从表2中的感受评分结果可以看出的,本发明的香料或调味剂混合物在不同的载体中的独特之处在于完全的、强烈的且新鲜的梨香味或梨味道,所述梨香味或梨味道取决于基础材料而可以定性且定量地与癸二烯酸乙酯标准相当或者甚至超过该标准。
实施例4:以嗅觉计量方式测定本发明的香料或调味剂混合物的香味强度
表3:香味阈值(ODT;气味检测阈值)-对比
使用名称为TO8的动态嗅觉计测定上述样品的香味阈值(ODT;气味检测阈值),其中用清洁空气稀释有气味的空气样品。将稀释物呈现给测试者(试嗅员)进行评估。用来自钢瓶的合成空气或用经处理的压缩空气来运行设备。用这种纯空气来运行两个气体喷射泵,所述气体喷射泵直接从样品袋中抽吸样品空气。在气体喷射泵中,样品空气与纯空气充分混合。这个混合物经由转向阀流到各个测试者的位置。样品空气的体积流量借助于经校准的测试板通过控制程序来自动设定。气味浓度的测定是最常见的应用情况。在此,样品空气以逐渐升高的浓度呈现以进行评估,直到测试人员感受到香味。在首次可辨识的气味印象下按下应答按键(“是的,闻到了”),达到了气味阈值浓度。用嗅觉计和在测试者参与下进行的测量按照固定的标准进行。这些嗅觉计量测量方法在欧洲标准DINEN 13725中进行了规定。嗅觉计TO8和用其实现的测量方法符合这些指南,并使嗅觉计量成为客观、普遍认可且经过验证的测量方法。
嗅觉评价结果表明,根据本发明的香料或调味剂混合物具有与癸二烯酸乙酯标准的香味阈值相当的香味阈值,但是比根据现有技术的香料或调味剂混合物的香味阈值低得多。
由此,本发明的香料或调味剂混合物非常适合用于增加香味或调味。由于更低的香味阈值,更小的剂量的香料或调味剂混合物足以产生可感知的香味或芳香化。
Claims (18)
2.根据权利要求1所述的香料或调味剂混合物,其中在通式(I)、(II)和(III)的化合物中R1和/或R2分别彼此独立地选自由直链或支链的甲基、乙基、丙基和丁基残基组成的组。
3.根据权利要求1或权利要求2所述的香料或调味剂混合物,其中在通式(I)、(II)和(III)的化合物中R1和R2分别是相同的。
4.根据权利要求1至3之任一所述的香料或调味剂混合物,其中通式(I)、(II)和(III)的化合物为如下化合物:
(I)(E)-2-甲基丁-2-烯二酸二乙酯,
(II)(Z)-2-甲基丁-2-烯二酸二乙酯,以及
(III)2-亚甲基-丁二酸二乙酯。
5.根据权利要求1至4之任一所述的香料或调味剂混合物,其特征在于,基于所述通式(I)、(II)、(III)的化合物的总和,所述香料或调味剂混合物以至少50至100重量%、尤其60至78重量%的量包括所述通式(I)的化合物,以至少2至8重量%、尤其3至7重量%的量包括所述通式(II)的化合物,并且以至少18至31重量%、尤其20至29重量%的量包括所述通式(III)的化合物。
6.根据权利要求1至5之任一所述的香料或调味剂混合物,其特征在于,基于所述香料或调味剂混合物的总重量,所述香料或调味剂混合物以总共0.001至99.999重量%、优选0.05至50重量%的量包括通式(I)、(II)、和(III)的化合物。
7.根据权利要求1至6之任一所述的香料或调味剂混合物,其特征在于,所述香料或调味剂混合物包含一种或多种香料或调味剂,所述香料或调味剂选自由以下项组成的组:
(1)烃类;
(2)脂肪族醇
(3)脂肪族醛及其缩醛
(4)脂肪族酮及其肟
(5)脂肪族含硫化合物
(6)脂肪族腈
(7)脂肪族羧酸酯
(8)非环状萜烯醇
(9)非环状萜烯醛和萜烯酮;
(10)环状萜烯醇;
(11)环状萜烯醛和萜烯酮
(12)环状醇;
(13)环脂肪族醇;
(14)环状和环脂肪族醚;
(15)环状和大环状酮;
(16)环脂肪族醛;
(17)环脂肪族酮;
(18)环状醇的酯;
(19)环脂肪族醇的酯;
(20)环脂肪族羧酸的酯;
(21)芳香脂肪族醇;
(22)芳香脂肪族醇与脂肪族羧酸的酯;
(23)芳香脂肪族醚;
(24)芳香族和芳香脂肪族醛;
(25)芳香族和芳香脂肪族酮;
(26)芳香族和芳香脂肪族羧酸及其酯;
(27)含氮的芳香族化合物;
(28)酚、苯基醚和苯基酯;
(29)杂环化合物;
(30)内酯;
以及上述香味物质的混合物。
8.一种方法,用于制备通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物,所述方法包括以下步骤:
(a)用选自由以下项组成的组的醇将衣康酸酯化:具有1至10个碳原子的脂肪族、芳香脂肪族或芳香族醇以及具有2至6个羟基的多元醇,获得衣康酸二酯;以及
(b)用含氮有机碱将所述衣康酸二酯异构化,获得通式(I)、式(II)或式(III)的化合物或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的混合物。
9.根据权利要求8所述的方法,其中所述醇选自由以下项组成的组:甲醇、异丙醇、异构丁醇、乙二醇、二乙二醇、丙二醇、二丙二醇、甘油及其混合物,尤其甲醇、乙醇、丙醇及其混合物;和/或
所述含氮有机碱选自由以下项组成的组:TMEDA(N,N,N',N'-四甲基乙二胺)、TEA(四乙基铵)、二丁基胺、吡啶、NMP(N-甲基-2-吡咯烷酮)、三辛基胺及其混合物,尤其TMEDA。
10.根据权利要求8或权利要求9所述的方法,其中步骤(b)的反应时长介于1至5小时之间、优选2至3小时之间。
11.根据权利要求8至10之任一所述的方法,其中基于所述通式(I)、(II)和(III)的化合物的总和,以至少50至100重量%、尤其60至78重量%的量包含所述通式(I)的化合物,以至少2至8重量%、尤其3至7重量%的量包含所述通式(II)的化合物,并且以至少18至31重量%、尤其20至29重量%的量包含所述通式(III)的化合物。
12.根据权利要求8至11之任一所述的方法,用于制备化合物(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)或2-亚甲基丁二羧酸二酯(衣康酸二酯)或者用于制备包括选自由(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)和2-亚甲基丁二羧酸二酯(衣康酸二酯)组成的组的一种、两种或三种化合物的混合物,其特征在于,所述方法包括以下步骤:
(a)用选自由以下项组成的组的醇将衣康酸酯化:甲醇、乙醇、丙醇和丁醇,获得衣康酸二酯;以及
(b)用含氮有机碱将所述衣康酸二酯异构化,获得化合物(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)或2-亚甲基丁二羧酸二酯(衣康酸二酯)或者包括选自由(E)-2-甲基-丁-2-烯二羧酸二酯(中康酸二酯)、(Z)-2-甲基-丁-2-烯二羧酸二酯(柠康酸二酯)和2-亚甲基丁二羧酸二酯(衣康酸二酯)组成的组的一种、两种或三种化合物的混合物。
13.根据权利要求8至12之任一所述的方法,其特征在于,所述中康酸酯、柠康酸酯和/或衣康酸酯的二酯为二乙酯、尤其(E)-2-甲基丁-2-烯二酸二乙酯、(Z)-2-甲基丁-2-烯二酸二乙酯或2-亚甲基丁二酸二乙酯。
14.能够根据权利要求8至13之任一所述的方法获得的通式(I)、式(II)或式(III)的香料或调味剂或者包括选自由通式(I)、式(II)和式(III)的化合物组成的组的一种、两种或三种化合物的香料或调味剂混合物,尤其其中所述方法在不使用含卤素、尤其含碘的反应物的情况下进行。
15.一种用于在香料混合物、香水油、美妆剂、涂抹剂或洗涤和清洁剂中赋予、改变和/或增强果香、梨型气味味调或者用于在食物、动物饲料或制药产品中赋予、改变和/或增强果香、梨香味道味调的方法,所述方法包括以下步骤:
(i1)提供根据权利要求1至7之任一或权利要求14所述的香料或调味剂混合物;以及
(i2)将足以在成品制剂中引起果香、梨型气味味调或味道味调的感受有效量的所述香料或调味剂混合物与至少一种另外的香料或调味剂或与另外的香料或调味剂的混合物混合;
或者
(ii1)提供根据权利要求1至7之任一或权利要求14所述的香料或调味剂混合物;以及
(ii2)将足以在成品制剂中引起果香、梨型气味味调或味道味调的感受有效量的所述香料或调味剂混合物与香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品混合。
16.感受有效量的根据权利要求1至7之任一或权利要求14所述的香料或调味剂混合物的用途,用于在香料混合物或香水油、美妆剂、涂抹剂或洗涤和清洁剂中赋予、改变和/或增强果香、梨型气味味调或者用于在食物、动物饲料或制药产品中赋予、改变和/或增强果香、梨型味道味调或者用于制备香味剂混合物、香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品。
17.一种香料混合物或香水油、美妆剂、涂抹剂、洗涤和清洁剂、食物、动物饲料或制药产品,包含感受有效量的根据权利要求1至7之任一或权利要求14所述的香料或调味剂混合物。
18.根据权利要求17所述的香水油或试剂,其中所述香水油、美妆剂、涂抹剂或洗涤和清洁剂选自由以下项组成的组:香水净油,香水,淡香水,须后水,古龙水,须前产品,喷洒古龙水,有香味的湿纸巾,酸性、碱性和中性清洁剂,例如地板清洁剂,窗玻璃清洁剂,餐具清洗剂,浴室和卫生间清洁剂,清洗乳,固体和液体的厕所清洁剂,粉末和泡沫状的地毯清洁剂,液体洗涤剂,粉末状洗涤剂,洗涤预处理剂如漂白剂,柔顺剂和去污剂,织物软化剂,清洗皂,清洗片剂,消毒剂,表面消毒剂,呈液态、凝胶状或施加在固态载体上的形式的空气清新剂,气溶胶喷雾,蜡和抛光剂如家具抛光剂,地板蜡,鞋油以及个人护理剂例如固体和液体的皂,沐浴露,洗发水,剃须皂,剃须泡沫,浴油,水包油、油包水和水包油包水类型的化妆乳液,例如皮肤霜和皮肤乳液,面霜和乳液,防晒霜和乳液,晒后霜和乳液,手霜和乳液,足霜和乳液,脱毛霜和乳液,须后霜和乳液,美黑霜和乳液,护发产品例如发胶,啫喱,发乳液,护发素,永久和半永久的染发剂,发变形剂如冷烫剂和直发剂,发根营养液,发霜和乳液,除臭剂和止汗剂例如腋窝喷雾,滚擦剂,除臭棒,除臭霜,装饰性化妆产品,蜡烛,灯油,线香,杀虫剂,驱虫剂和燃料,并且其中所述食物选自由以下项组成的组:乳制品、饮料、糖果、营养补充剂、膳食食物、代餐食物和半成品。
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JPH01104030A (ja) * | 1987-10-17 | 1989-04-21 | Nippon Oil & Fats Co Ltd | メサコン酸ジエステルの製造法 |
WO2018114073A1 (de) * | 2016-12-21 | 2018-06-28 | Symrise Ag | Riechstoffmischung |
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JPH01104030A (ja) * | 1987-10-17 | 1989-04-21 | Nippon Oil & Fats Co Ltd | メサコン酸ジエステルの製造法 |
WO2018114073A1 (de) * | 2016-12-21 | 2018-06-28 | Symrise Ag | Riechstoffmischung |
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