CN109996778A - 味道调节醛 - Google Patents
味道调节醛 Download PDFInfo
- Publication number
- CN109996778A CN109996778A CN201780055150.4A CN201780055150A CN109996778A CN 109996778 A CN109996778 A CN 109996778A CN 201780055150 A CN201780055150 A CN 201780055150A CN 109996778 A CN109996778 A CN 109996778A
- Authority
- CN
- China
- Prior art keywords
- rebaudioside
- taste
- consumer goods
- compound
- high intensity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 235000019640 taste Nutrition 0.000 title claims abstract description 120
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 149
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 239000000796 flavoring agent Substances 0.000 claims abstract description 99
- 235000019634 flavors Nutrition 0.000 claims abstract description 97
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229930188195 rebaudioside Natural products 0.000 claims description 48
- -1 L- α-aspartyl-L-phenylalanine methyl esters Chemical class 0.000 claims description 46
- 244000228451 Stevia rebaudiana Species 0.000 claims description 44
- 239000000284 extract Substances 0.000 claims description 37
- 235000003599 food sweetener Nutrition 0.000 claims description 35
- 239000003765 sweetening agent Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 29
- 235000006092 Stevia rebaudiana Nutrition 0.000 claims description 27
- 235000009508 confectionery Nutrition 0.000 claims description 27
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 22
- 239000004615 ingredient Substances 0.000 claims description 19
- 244000185386 Thladiantha grosvenorii Species 0.000 claims description 16
- 235000011171 Thladiantha grosvenorii Nutrition 0.000 claims description 16
- 239000000619 acesulfame-K Substances 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 claims description 12
- 239000004384 Neotame Substances 0.000 claims description 12
- 235000010358 acesulfame potassium Nutrition 0.000 claims description 12
- 230000006872 improvement Effects 0.000 claims description 12
- 235000019412 neotame Nutrition 0.000 claims description 12
- 108010070257 neotame Proteins 0.000 claims description 12
- HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- GSGVXNMGMKBGQU-PHESRWQRSA-N rebaudioside M Chemical compound C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSGVXNMGMKBGQU-PHESRWQRSA-N 0.000 claims description 8
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 claims description 8
- 235000019202 steviosides Nutrition 0.000 claims description 8
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 6
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 6
- MZLGFRRNMCCNBB-UHFFFAOYSA-N deca-4,7-dienal Chemical class CCC=CCC=CCCC=O MZLGFRRNMCCNBB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 229940013618 stevioside Drugs 0.000 claims description 6
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 claims description 6
- 150000005846 sugar alcohols Chemical class 0.000 claims description 6
- 235000010447 xylitol Nutrition 0.000 claims description 6
- 239000000811 xylitol Substances 0.000 claims description 6
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 6
- 229960002675 xylitol Drugs 0.000 claims description 6
- CANAPGLEBDTCAF-NTIPNFSCSA-N Dulcoside A Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@]23C(C[C@]4(C2)[C@H]([C@@]2(C)[C@@H]([C@](CCC2)(C)C(=O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC4)CC3)=C)O[C@H](CO)[C@@H](O)[C@@H]1O CANAPGLEBDTCAF-NTIPNFSCSA-N 0.000 claims description 5
- CANAPGLEBDTCAF-QHSHOEHESA-N Dulcoside A Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2O[C@]34CC[C@H]5[C@]6(C)CCC[C@](C)([C@H]6CC[C@@]5(CC3=C)C4)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H](O)[C@H]1O CANAPGLEBDTCAF-QHSHOEHESA-N 0.000 claims description 5
- 229930182478 glucoside Natural products 0.000 claims description 5
- 150000008131 glucosides Chemical class 0.000 claims description 5
- 235000019204 saccharin Nutrition 0.000 claims description 5
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 5
- 229940081974 saccharin Drugs 0.000 claims description 5
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 5
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 4
- 239000001776 FEMA 4720 Substances 0.000 claims description 4
- RLLCWNUIHGPAJY-RYBZXKSASA-N Rebaudioside E Natural products O=C(O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)[C@@H](O)[C@@H](O)[C@H](CO)O1)[C@]1(C)[C@@H]2[C@@](C)([C@@H]3[C@@]4(CC(=C)[C@@](O[C@@H]5[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O6)[C@H](O)[C@@H](O)[C@H](CO)O5)(C4)CC3)CC2)CCC1 RLLCWNUIHGPAJY-RYBZXKSASA-N 0.000 claims description 4
- 239000004376 Sucralose Substances 0.000 claims description 4
- HINSNOJRHFIMKB-DJDMUFINSA-N [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate Chemical compound [H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC(=O)[C@]2(C)CCC[C@@]3(C)[C@]4([H])CC[C@@]5(C[C@]4(CC5=C)CC[C@]23[H])O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O HINSNOJRHFIMKB-DJDMUFINSA-N 0.000 claims description 4
- YILGKTWKKDLHAF-DUXFSIBLSA-M chembl2368344 Chemical compound [Na+].O([C@@H]1[C@H](CO)O[C@H]([C@H]([C@H]1O)O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C([O-])=O)[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O YILGKTWKKDLHAF-DUXFSIBLSA-M 0.000 claims description 4
- LMLPCMPCKSYHQH-UHFFFAOYSA-N deca-7,9-dien-4-one Chemical class CCCC(=O)CCC=CC=C LMLPCMPCKSYHQH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000855 fermentation Methods 0.000 claims description 4
- 230000004151 fermentation Effects 0.000 claims description 4
- 229930189775 mogroside Natural products 0.000 claims description 4
- RLLCWNUIHGPAJY-SFUUMPFESA-N rebaudioside E Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RLLCWNUIHGPAJY-SFUUMPFESA-N 0.000 claims description 4
- QRGRAFPOLJOGRV-UHFFFAOYSA-N rebaudioside F Natural products CC12CCCC(C)(C1CCC34CC(=C)C(CCC23)(C4)OC5OC(CO)C(O)C(OC6OCC(O)C(O)C6O)C5OC7OC(CO)C(O)C(O)C7O)C(=O)OC8OC(CO)C(O)C(O)C8O QRGRAFPOLJOGRV-UHFFFAOYSA-N 0.000 claims description 4
- HYLAUKAHEAUVFE-AVBZULRRSA-N rebaudioside f Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)CO1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HYLAUKAHEAUVFE-AVBZULRRSA-N 0.000 claims description 4
- 235000019408 sucralose Nutrition 0.000 claims description 4
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 claims description 4
- HKPYUQJGQQGZBF-ARQDHWQXSA-N (2r,3s,4s,5r)-2,5-dimethyloxolane-2,3,4-triol Chemical compound C[C@H]1O[C@@](C)(O)[C@@H](O)[C@@H]1O HKPYUQJGQQGZBF-ARQDHWQXSA-N 0.000 claims description 3
- NUFKRGBSZPCGQB-FLBSXDLDSA-N (3s)-3-amino-4-oxo-4-[[(2r)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid;pentahydrate Chemical compound O.O.O.O.O.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C NUFKRGBSZPCGQB-FLBSXDLDSA-N 0.000 claims description 3
- UZFFFFWQKMPLAC-ONEGZZNKSA-N (e)-dec-7-enal Chemical compound CC\C=C\CCCCCC=O UZFFFFWQKMPLAC-ONEGZZNKSA-N 0.000 claims description 3
- CWRKZMLUDFBPAO-SREVYHEPSA-N 4-Decenal Chemical compound CCCCC\C=C/CCC=O CWRKZMLUDFBPAO-SREVYHEPSA-N 0.000 claims description 3
- 239000004377 Alitame Substances 0.000 claims description 3
- 108010011485 Aspartame Proteins 0.000 claims description 3
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
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- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 3
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- LFVPBERIVUNMGV-UHFFFAOYSA-N fasudil hydrochloride Chemical compound Cl.C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCCNCC1 LFVPBERIVUNMGV-UHFFFAOYSA-N 0.000 claims description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
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- A—HUMAN NECESSITIES
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- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
- A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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Abstract
提供了用于味道调节的式(I)的醛(X表示具有至多9个碳原子的烷基或烯基)和/或风味组合物。具体地,本公开主题的化合物提供有效和预料不到的味道调节特性。可以将味道调节和/或风味组合物掺入各种消费成品中,特别是与高强度甜味剂组合。
Description
相关申请的交叉引用
本申请要求2016年9月9日提交的美国临时申请No.62/385,507的优先权,该文献的内容通过引用整体并入本文。
领域
本公开主题涉及能够调节高强度甜味剂的不良味道特征例如与高强度甜叶菊(Stevia)提取物衍生的甜味剂相关的苦味余味的化合物和包含这类化合物的风味组合物。所公开主题还涉及包含这类味道调节化合物和/或风味组合物的消费品。
背景
许多消费者期望甜味食品和饮料。然而,在许多情况下,消费者选择限制其消费的热量糖(例如蔗糖,葡萄糖,果糖)作为减少热量摄入和帮助减轻体重的手段,或者出于需要这种限制的医学原因,例如糖尿病或反应性低血糖。在其他情况下,消费者期望在其饮食中用经过“较少加工”和“更天然”的替代品替代加工过的精制糖。因此,市场对低卡路里或零卡路里的食品和饮料选择存在强烈的需求,所述低卡路里或零卡路里的食品和饮料选择维持与通过使用蔗糖(即糖)和其他传统的热量甜味剂所实现的相似的甜味。
这些传统甜味剂的替代品包括“高强度甜味剂”(“HIS”),其比蔗糖甜数倍但是低热量的或无热量的。HIS为食品和饮料制造商提供额外的益处,因为它们通常比糖更便宜并且贮存更稳定,且可以以低于糖的量使用,同时由于其高甜度强度仍然提供相差无几的甜味特征。
尽管有这些额外的益处,但由于许多HIS的不良味道特征,HIS的使用通常是有限的。更具体地,HIS通常与苦味,涩味,金属味,酸味,和/或甘草样味道特征相关。因此,持续关注能够增加对具有HIS而没有负面特征的调味品和/或消费品的更像糖味和更均匀甜味的感觉的化合物。
除了HIS之外,还有其他用于食品,饮料,口腔护理产品,非处方药(OTC)和处方药或其他消费品的成分具有不良味道特征如苦味,涩味,金属味,酸味和/或甘草味-样味道特征或其组合。非限制性实例包括单宁,咖啡酸或其酯,萜类化合物,金属盐,活性药物成分(例如布洛芬,右美沙芬,对乙酰氨基酚,愈创甘油醚等),蛋白质和肽,多酚(例如儿茶素,表儿茶素,表儿茶素没食子酸酯,没食子酸,表没食子儿茶素,表没食子儿茶素没食子酸酯等),葎草灵酮,奎宁,天然植物提取物,防腐剂,维生素和矿物质。类似地,一直需要鉴定可调节这些额外味道特征的化合物。
因此,本公开主题的一个目的在于提供能够有效和预料不到地改进HIS的味道特征的新颖的化合物和包含所述化合物的风味组合物。本公开主题的另一个目的在于提供新颖的化合物和包含所述化合物的风味组合物,其能够有效和预料不到地调节包含这类成分的食品、饮料、药物或其他消费品的其他不希望的味道特征的化合物。
发明概述
本公开主题预料不到地和令人惊奇地发现了有效提供有益和期望的味道特征的化合物。
本公开主题提供了由式I表示的风味调节化合物,
其中虚线可以均为单键,或其中一条虚线为双键而另一条为单键,并且
其中X代表C1-C9脂族或支链烷基或包含一个或多个双键的C1-C9脂族或支链烯基。
在某些实施方案中,在式(I)的风味调节化合物中,虚线可以均为单键,或一条虚线为双键而另一条为单键,且其中X代表包含一个或多个非共轭双键的C6-C7烯基。
在某些实施方案中,所述化合物通过发酵和酶反应方法生产。
本公开主题还提供了包含一种或多种式(I)的风味调节化合物的风味组合物。在具体的实施方案中,所述风味调节化合物选自4-癸烯醛;7-癸烯醛;4,7-癸二烯醛;2,4,7-癸三烯醛;2,6-壬二烯醛,3,6-壬二烯醛;6-壬烯醛及其混合物。在其他实施方案中,所述风味调节化合物是两种或更多种4,7-癸二烯醛异构体的混合物,所述4,7-癸二烯醛异构体选自(4Z,7Z)-异构体、(4E,7Z)-异构体、(4Z,7E)-异构体、(4E,7E)-异构体及其混合物。
本公开主题还提供了消费品,其包含:(a)一种或多种风味和/或味道调节组合物;和(b)消费品基料。在某些实施方案中,所述消费品还包含至少一种高强度甜味剂和/或非-HIS甜味剂。在另一个实施方案中,所公开主题提供了消费品,其包含:(a)一种或多种式(I)的化合物;(b)至少一种高强度甜味剂和/或非-HIS甜味剂,和(c)消费品基料。
在某些实施方案中,所述高强度甜味剂选自1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐;L-α-天冬氨酰-L-苯丙氨酸甲酯(阿斯巴甜);乙酰舒泛钾(acesulfamepotassium)(Ace-K或乙酰舒泛K);1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜(三氯蔗糖);(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(爱德万甜(advantame));(3S)-3-(3,3-二甲基丁基氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(纽甜),L-α-天冬氨酰-N-(2,2,4,4-四甲基-3-硫杂环丁烷基)-D-丙氨酰胺(阿力甜);N-环己基氨基磺酸钠(环己基氨基磺酸盐)及其盐(例如环己基氨基磺酸钙,环己基氨基磺酸钠,环己基氨基磺酸镁,环己基氨基磺酸钾)和一些糖醇(例如木糖醇)及其组合。在其他实施方案中,高强度甜味剂来源于甜叶菊(Stevia rebaudiana),其选自全叶和粗甜叶菊(stevia)提取物、改良甜叶菊提取物、一-、二-和多糖基化甜菊醇(steviol)化合物、未经处理的甜叶菊粉末、甜叶菊甙A(Rebaudioside A)(Reb A)、甜叶菊甙B、甜叶菊甙C、甜叶菊甙D、甜叶菊甙D2、甜叶菊甙E和甜叶菊甙F、甜叶菊甙G、甜叶菊甙H、甜叶菊甙I、甜叶菊甙J、甜叶菊甙K、甜叶菊甙L、甜叶菊甙M、甜叶菊甙N、甜叶菊甙O、甜叶菊甙Q、甜叶菊甙R、甜叶菊甙S、甜叶菊甙V、甜叶菊甙W、甜叶菊甙X、甜叶菊甙KA、杜克甙A(Dulcoside A)、悬钩子甙(Rubusoside)、甜菊苷(stevioside)和其他改良甜菊糖苷(stevioside)及其组合。在另外的实施方案中,高强度甜味剂来源于罗汉果(Siraitia grosvenorii),例如选自改良或未改良提取物(即罗汉果(Luo Han Go)提取物或罗汉果(Monk fruit)汁)和罗汉果甙(例如罗汉果甙IV、罗汉果甙V、赛门苷I和11-氧代罗汉果甙V)的那些。在另外的实施方案中,高强度甜味剂选自L-α-天冬氨酰-L-苯丙氨酸甲酯、罗汉果提取物、甜叶菊甙A;及其组合。
本公开主题还提供了调节消费品味道特性的方法,其中将一种或多种式(I)的化合物加入到消费品中,其加入量为能有效调节高强度甜味剂的味道特征的用量。
本发明公开的主题还提供了调节不良味道特征如在消费品中使用高强度甜味剂或其他具有不良味道特征的成分所产生的那些味道特征的方法,所述方法包括将至少一种式(I)的化合物加入到含有高强度甜味剂和/或其他具有不良味道特征的成分的消费品中,其加入量足以为消费品提供更期望的味道或风味特征。
上文已经相当广泛地概述了本公开主题的特征和技术优点,以便可以更好地理解下面的详细描述。在下文中将描述所公开主题的附加特征和优点,其形成所公开主题的权利要求的主题。本领域技术人员应当理解,所公开的理念和具体实施方案可以易于用作修改或设计用于实现本公开主题的相同目的的其他结构的基础。本领域技术人员还应认识到,这种等同构造不脱离所附权利要求中阐述的所公开主题的精神和范围。从以下描述中将更好地理解被认为是所公开主题的特征的新颖特征,关于其构造和操作方法,以及其他目的和优点。
详细描述
如上所述,本领域仍需要调节与HIS和/或其他食品,饮料,口腔护理产品和/或药物产品成分相关的令人不快的苦味,涩味,金属味,酸味和/或甘草样味道特征的化合物。本公开主题通过选自式(I)代表的化合物和/或包含一种或多种所公开化合物的新风味组合物满足了这种需要。
为了清楚而非限制,详细描述分为以下小节:
1.定义;
2.味道调节化合物;
3.高强度甜味剂(HIS)和其他具有不良味道特征的成分;
4.风味组合物;和
5.在消费品中的用途。
1.定义
在本公开的上下文中和在使用各术语的具体上下文中,本说明书中使用的术语通常具有它们在本领域中的普通含义。在以下或本说明书的别处讨论某些术语,从而向从业者提供描述本公开的组合物和方法以及如何制备和使用它们的其他指导。
如本文所使用的,当在权利要求和/或说明书中与术语“包含”结合使用时,使用词语“一个/种(a,an)”可意为“一个/种(one)”,但也与“一个/种或多个/种”、“至少一个/种”和“一个/种或多于一个/种”的含义一致。此外,术语“具有”、“包括”、“包含”和“含有”可互换使用,并且本领域技术人员将会意识到这些术语是开放式术语。
术语“约”或“大约”意为如本领域普通技术人员所确定的对于特定值在可接受的误差范围内,其部分取决于如何测量或确定该值,即,测量系统的限制。例如,“约”可意为给定值的至多20%、至多10%、至多5%和/或至多1%的范围。
如本文所使用的,术语“异构体”指的是具有相同的分子式但原子的排列和构型不同的不同化合物。另外如本文所使用的,术语“立体异构体”指的是本公开主题的给定化合物可存在的任何多种立体异构构型,并且包括几何异构体。应理解,取代基可连接于碳原子的手性中心。因此,本公开主题包括化合物的对映异构体、非对映异构体或外消旋体。此外如本文所使用的,术语“结构异构体”指的是具有相同数量和类型的原子、但原子不同地连接的不同化合物。
如本文所使用的,术语“对映异构体”指的是不可重叠互为镜像的一对立体异构体。一对对映异构体的1:1混合物是“外消旋”混合物。所述术语用于在适合的情况下表示外消旋混合物。
如本文所使用的,术语“非对映异构体”指的是具有至少两个不对称原子,但彼此不互为镜像的立体异构体。绝对立体化学根据Cahn-Ingold-Prelog R-S系统来指定。当化合物是纯对映异构体,各个手性碳处的立体化学可通过R或S来指定。绝对构型未知的拆分的化合物可根据它们在钠D线的波长下使平面偏振光旋转的方向(右旋或左旋)表示为(+)或(-)。本公开主题的化合物含有一个或多个不对称中心,并且可因此产生对映异构体、非对映异构体和其他立体异构形式,就绝对立体化学而言,可定义为(R)-或(S)-。本公开主题意为包括全部这类可能的异构体,包括外消旋混合物、光学纯形式和中间体混合物。光学活性的(R)-和(S)-异构体可使用手性合成子或手性试剂制备,或使用常规技术拆分。如果化合物含有双键,取代基可为E或Z构型。如果化合物含有取代的环烷基,所述环烷基取代基可具有顺式-或反式-构型。所有互变异构形式也旨在包括在内。
如本文所用,术语“调味品”或“风味组合物”可互换使用,并且是指添加到消费产品中的制品,其旨在被吸收或摄取以赋予消费品味道或风味特征,或改进、改变或增强消费品的味道或风味特征。
如本文所用,术语“味道调节”意指改变食品、饮料或其他摄入的消费品的特征以改进消费期间的整体味觉体验,例如,减少苦味,改进甜味特征,或改进整体风味特征和口感。
如本文所用,术语“消费品”是指旨在以其销售形式使用或消费而不是用于随后的商业制造或改性的产品。本文更详细地描述了消费品的非限制性实例。
如本文所用,术语“消费品基料”是指本领域普通技术人员已知的并用于提供消费产品的典型特性的那些成分。
本申请中引用的所有出版物,包括但不限于专利和专利申请,均通过引用并入本文,如同每个单独的出版物被具体和单独地指示通过引用整体并入本文一样。
2.味道调节化合物
本公开的味道调节化合物包括选自式(I)表示的化合物。
其中虚线既可以均为单键,或其中一条虚线为双键而另一条为单键,并且
其中X代表C1-C9脂族或支链烷基或包含一个或多个双键的C1-C9脂族或支链烯基。
在某些实施方案中,所述化合物是式(I),其中虚线可以均为单键,或一条虚线为双键而另一条为单键,且其中X代表包含一个或多个非共轭双键的C6-C7烯基。照此,在某些实施方案中,所述化合物是具有至少一个双键的C9-C10醛。
在其中化合物包含一个或多个双键的那些实施方案中,每个化合物可以是E-或Z-构型,从而产生各种立体异构形式。所有这些可能的异构体,包括异构体混合物,纯形式和中间体混合物都包括在本发明公开的主题中。
在某些非限制性实施方案中,式(I)的醛化合物是4-癸烯醛;7-癸烯醛;4,7-癸二烯醛;2,4,7-癸三烯醛;6-壬烯醛,2,6-壬二烯醛,或3,6-壬二烯醛。在某些实施方案中,式(I)的醛是两种或更多种4,7-癸二烯醛异构体的混合物,所述4,7-癸二烯醛异构体选自(4Z,7Z)-异构体、(4E,7Z)-异构体、(4Z,7E)-异构体、(4E,7E)-异构体及其混合物。在另一个实施方案中,所述醛限于(4Z,7Z)-异构体。
本公开的化合物可以是合成的或天然衍生的。合成形式的化合物包括通过化学合成或通过化学方法分离得到的那些,无论是人工的还是天然相同的,例如美国专利No.4,687,599中所述的那些,该专利全文以引用的方式并入本文。在一个实施方案中,式(I)的化合物的合成形式可如实施例9中所述制备。
天然形式的化合物包括通过物理、酶和/或微生物方法例如发酵由植物或动物来源的材料获得的那些。在一个实施方案中,式(I)的化合物的天然形式可通过提取植物或动物来源的材料而获得。例如,通过提取物种菖蒲(Acorus calamus)的植物材料可以获得4,7-癸二烯醛的天然形式。在另一个实施方案中,式(I)的化合物的天然形式通过发酵方法获得,包括但不限于实施例10中描述的方法。
3.高强度甜味剂(HIS)和具有不良味道特性的其他成分
本公开主题的化合物可以与可以为调节目标的高强度甜味剂(HIS)或具有不良味道特性的其他成分联用。
本公开主题的HIS可以是合成的(本文也称作“人造的”)或天然来源的。合成HIS的非限制性实例包括1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐;L-α-天冬氨酰-L-苯丙氨酸甲酯(阿斯巴甜);乙酰舒泛钾(Ace-K或乙酰舒泛K);1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜(三氯蔗糖);(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(爱德万甜);(3S)-3-(3,3-二甲基丁基氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(纽甜),L-α-天冬氨酰-N-(2,2,4,4-四甲基-3-硫杂环丁烷基)-D-丙氨酰胺(阿力甜);N-环己基氨基磺酸钠(环己基氨基磺酸盐)及其盐(例如环己基氨基磺酸钙,环己基氨基磺酸钠,环己基氨基磺酸镁,环己基氨基磺酸钾)和一些糖醇(例如木糖醇)。
天然衍生的HIS可以包括、但不限于二萜糖苷,如来源于植物甜叶菊属如甜叶菊的成员(本文也称作“甜叶菊来源的甜味剂”)或来源于罗汉果(Siraitia grosvenorii)(通常也称作罗汉果(Luo Han Go)或罗汉果(Monk fruit))的那些甜味剂。甜叶菊来源的甜味剂的非限制性实例包括全叶和粗甜叶菊提取物、改良甜叶菊提取物、一-、二-和多糖基化甜菊醇化合物、未经处理的甜叶菊粉末、甜叶菊甙A(Reb A)、甜叶菊甙B、甜叶菊甙C、甜叶菊甙D、甜叶菊甙D2、甜叶菊甙E和甜叶菊甙F、甜叶菊甙G、甜叶菊甙H、甜叶菊甙I、甜叶菊甙J、甜叶菊甙K、甜叶菊甙L、甜叶菊甙M、甜叶菊甙N、甜叶菊甙O、甜叶菊甙Q、甜叶菊甙R、甜叶菊甙S、甜叶菊甙V、甜叶菊甙W、甜叶菊甙X、甜叶菊甙KA、杜克甙A、悬钩子甙、甜菊苷和其他改良甜菊糖苷。罗汉果来源的HIS的非限制性实例包括改良或未改良提取物(即罗汉果提取物或罗汉果汁)和罗汉果甙(例如罗汉果甙IV、罗汉果甙V、赛门苷I和11-氧代罗汉果甙V)。
天然来源的HIS的其他非限制性实例包括甜蛋白(例如莫纳甜,仙茅甜蛋白,奇异果甜蛋白,莫内甜蛋白,马槟榔甜蛋白,潘塔亭(pentadin),甜味蛋白,赫南德辛(hernandulcin),甜茶内酯,二羟丙茶碱,根皮苷,三叶甙,根皮素),新橙皮甙二氢查尔酮,柚皮甙二氢查尔酮,甘草酸及其盐,聚波朵苷(polypodoside)A和天然提取物如甘草根提取物,柑橘馏出物提取物和卡特莫夫果(katemfe)提取物。
本领域技术人员将认识到,存在用于食品,饮料,非处方药(OTC)和处方药或其他消费品的具有不良味道特征如苦味,涩味,金属味,酸味和/或甘草样-味道特性或其组合的其他成分,其引起与上述HIS相似的异味并且对于调味师呈现类似的问题。在一个实施方案中,本发明公开的化合物可用于为这种非-HIS材料提供味道调节益处。这种非-HIS调节目标材料的非限制性实例包括可可,咖啡,咖啡碱,可可碱,二酮哌嗪,氨基酸,苦味肽,蛋白质(例如,植物蛋白,酪蛋白,大豆,乳清),水解蛋白,柚皮甙,牛磺酸,瓜拉那,绿原酸,防腐剂(例如钾盐,钠盐),锌盐,异黄酮,多酚,薄荷醇,奎宁,某些精油(如薄荷油),美拉德反应产物,啤酒,蛇麻子(hops),葎草酮,异葎草酮,葎草灵酮,蛇麻酮,希鲁酮,单宁,咖啡酸或其酯,萜类化合物,金属盐,某些活性药物成分(例如对乙酰氨基酚,布洛芬,水杨酸,右美沙芬,愈创甘油醚,乙酰水杨酸,西咪替丁,雷尼替丁,阿莫西林,洛哌丁胺),奎尼丁,奎宁,龙胆根提取物,金鸡纳树皮提取物,多酚(例如儿茶素,表儿茶素,表儿茶素没食子酸酯,没食子酸,表没食子儿茶素,表没食子儿茶素没食子酸酯),ω-3-脂肪酸,醇,维生素(例如B族维生素)和矿物质。
4.风味和风味调节组合物
在某些实施方案中,本公开的式(I)的味道调节化合物可以配制成“味道调节组合物”,以提供味道调节,但不是特定的风味特征。这种味道调节组合物可以加入到其他调味品或风味组合物中。在另外的实施方案中,本公开的式(I)的味道调节化合物可以配制成“风味组合物”,除了味道调节之外,其可以用于提供特定的风味特征。在某些实施方案中,风味组合物可进一步含有其他风味成分和/或甜味组分或甜味剂。
在某些实施方案中,本公开主题的味道调节组合物可包含另外的味道调节化合物,以进一步改变风味组合物的味道调节能力。这种味道调节化合物的非限制性实例包括萜烯(例如倍半萜,二萜,三萜等),类黄酮,有机酸(如酒石酸,乙酸,柠檬酸,苹果酸等),无机酸,有机盐,核苷酸单磷酸酯、二磷酸盐和三磷酸酯,羟基黄烷酮,羟基苯甲酰胺,羟基脱氧苯偶姻,羟基苯基烷二酮,二乙酰三聚体,γ-氨基丁酸,香草醛,香草提取物,联香草醛(divanillins),羟基黄烷,lactisoles,2,4-二羟基苯甲酸,麦芽酚,乙基麦芽酚,甲基环戊烯醇酮(cyclotene),甲基环戊烯醇酮水合物,4-羟基-2,5-二甲基呋喃-3(2H)-酮(furanol),葫芦巴内酯(sotolone),枫树呋喃酮,mesifurane,天然馏出物和提取物(如蜂蜜,糖蜜,角豆,红糖,糖,姜,生咖啡),脂肪酸,脂肪酸酯,脂肪,油,3-(1-((3,5-二甲基异噁唑-4-基)甲基)-1H-吡唑-4-基)-1-(3-羟基苄基)-咪唑烷-2,4-二酮,内酯,1-十六烷醇,薄荷醇,薄荷酮,樟脑,长叶薄荷醇,异胡薄荷醇,桉树脑,2-异丙基-N-2,3-三甲基丁酰胺,N-乙基-2-异丙基-5-甲基环己烷甲酰胺,3-(对薄荷烷-3-甲酰氨基)乙酸乙酯,N-(4-甲氧基苯基)-对薄荷烷甲酰胺,N-乙基-2,2-二异丙基丁酰胺,N-环丙基-5-甲基-2-异丙基环己烷甲酰胺,N-(1,1-二甲基-2-羟基乙基)-2,2-二乙基丁酰胺,N-(4-氰基甲基苯基)-对薄荷烷甲酰胺,N-(2-(吡啶-2-基)乙基)-3-对薄荷烷甲酰胺,N-(2-羟基乙基)-2-异丙基-2,3-二甲基丁酰胺,环丙烷甲酸(2-异丙基-5-甲基-环己基)-酰胺,N-[4-(2-氨基-2-氧代乙基)苯基]-对薄荷烷甲酰胺,吡咯烷酮甲酸薄荷酯,荜澄茄醇(cubebol),冰素(icilin),1-(2-羟基-4-甲基环己基)乙酮,N-(4-(氰基甲基)苯基)-2-异丙基-5,5-二甲基环己烷-1-甲酰胺,4-(二甲基氨基)-4-氧代丁酸2-异丙基-5-甲基环己酯,N-苯并[1,3]二氧杂环戊烯-5-基-3-对薄荷烷甲酰胺,N-苯并噁唑-4-基-3-对薄荷烷甲酰胺,N-4-([1,2,4]三唑-1-基)-苯基-3-对薄荷烷甲酰胺,N-4-(吡唑-1-基)-苯基-3-对薄荷烷甲酰胺,N-(1-异丙基-1,2-二甲基丙基)-1,3-苯并间二氧杂环戊烯-5-甲酰胺,N-(1-甲基-1-异丙基丁基)苯甲酰胺,葑基-N,N-二甲基琥珀酰胺,单琥珀酸葑基酯,丙二酸乙基葑基酯,单琥珀酸冰片酯,单琥珀酸异冰片酯,3-氧代丁酸薄荷酯,3-氧代戊酸薄荷酯,3-l-薄荷氧基丙-1,2-二醇,3-l-薄荷氧基-2-甲基丙-1,2-二醇,对薄荷烷-3,8-二醇,2-l-薄荷氧基乙-1-醇,3-l-薄荷氧基丙-1-醇,4-l-薄荷氧基丁-1-醇,3-羟基丁酸薄荷酯,6-异丙基-9-甲基-1,4-二氧杂螺-(4,5)-癸烷-2-甲醇,2-[(2-对薄荷氧基)乙氧基]乙醇,琥珀酸薄荷酯,戊二酸薄荷酯,琥珀酸二薄荷酯,戊二酸二薄荷酯,乳酸薄荷酯,薄荷酮甘油缩酮,薄荷油,椒样薄荷油,留兰香油,桉树油,千日菊酰胺,山椒醇,羟基γ-山椒醇,羟基-山椒醇,山椒醇-I,山椒醇II,山椒酰胺,日本辣椒提取物,佳味碱,紫锥菊(echinacea)提取物,北方花椒提取物,尼泊尔香料帖木儿(timur)提取物,4-(1-薄荷氧基甲基)-2-苯基-1,3-二氧戊环,N-异丁基癸-(2,4)-二烯酰胺,N-环丙基-(2E,6Z)-壬二烯酰胺,N-乙基-(2E,6Z)-壬二烯酰胺,金纽扣(jambu)油树脂,烯丙基-异硫氰酸酯,异硫氰酸4-羟基苄基酯,芥子油,日本辣根提取物,榄香醇,榄香素(elimicin),白柠檬醚,榄香脂油,罗勒烯五氧化物(ocimene quintoxide),2-异丙烯基-5-甲基-5-乙烯基四氢呋喃,香草基乙基醚,香草基丙基醚,香草醛丙二醇缩醛,乙基香草醛丙二醇缩醛,辣椒素,姜醇,香草基丁基醚,4-(1-薄荷氧基-甲基)-2-苯基-1,3-二氧戊环,4-(1-薄荷氧基-甲基)-2-(3',4'-二羟基-苯基)-1,3-二氧戊环,4-(1-薄荷氧基-甲基)-2-(2'-羟基-3'-甲氧基-苯基)-1,3-二氧戊环,4-(1-薄荷氧基-甲基)-2-(4'-甲氧基苯基)-1,3-二氧戊环,4-(1-薄荷氧基-甲基)-2-(3',4'-亚甲二氧基-苯基)-1,3-二氧戊环,黑胡椒提取物,肉桂醛,胡椒碱,辣椒油,红辣椒油树脂,辣椒油树脂,姜油树脂,壬基酸香草基酰胺,4-(1-薄荷氧基甲基)-2-(3'-甲氧基-4'-羟基苯基)-1,3-二氧戊环,香草醛-1,2-己二醇缩醛,香草醛-1,2-丁二醇缩醛,香草醛-1-丁氧基甘油缩醛,乙基香草醛,乙基香草醇(3-乙氧基-4-羟基苄醇),高香草酸乙酯,香草基异丙基醚,及其所有的立体异构体和混合物。
在某些实施方案中,另外的味道调节化合物可以是本领域已知作为甜味剂(例如甜蛋白)的化合物,但是以低于提供甜味效果所必需的阈值水平的水平使用。
在某些实施方案中,本公开的式(I)的味道调节化合物可用于包含至少一种HIS和/或至少一种非-HIS甜味剂的味道调节组合物中。在另外的实施方案中,风味组合物不含HIS和/或非-HIS甜味剂。在其他实施方案中,可以单独添加HIS和/或非-HIS甜味剂。
存在于本公开主题的风味组合物中的一种或多种式(I)的化合物的量可以基于风味组合物的其他调节剂的量而变化,但典型地存在量为风味组合物总重的约0.001份/万亿份(ppt)至10%重量,或约1份/万亿份至约10%重量,或约0.001%-约5%重量,和在它们间的值。在另外的实施方案中,式(I)的化合物可以以占风味组合物重量约0.00001%-约10%重量,或约0.00001%-约5%重量,或约0.00001%-约1%重量,或约0.00001%-约0.1%重量的量存在。在另外的实施方案中,式(I)的化合物可以以占风味组合物重量约0.00001%-约10%重量,或约0.0001%-约10%重量,或约0.001%-约10%重量,或约0.01%-约510%重量,或约0.1%-约10%重量,或约1.0%-约10%重量,或约5%-约10%重量的量存在。在某些实施方案中,式(I)的化合物可以以占风味组合物重量约0.00001%-约10%重量,或约0.1%-约5%重量,或约0.5%-约2%重量,或约0.5%-约1%重量的量存在。
在本公开主题的一个实施方案中,所述味道调节组合物或风味组合物包含一种或多种式(I)的化合物和一种或多种非-HIS材料。这类非-HIS调节目标材料的非限制性实例包括可可,咖啡,咖啡碱,可可碱,二酮哌嗪,氨基酸,苦味肽,蛋白质(例如,植物蛋白,酪蛋白,大豆,乳清),水解蛋白,柚皮甙,牛磺酸,瓜拉那,绿原酸,防腐剂(例如钾盐,钠盐),锌盐,异黄酮,多酚,薄荷醇,奎宁,某些精油(如薄荷油),美拉德反应产物,啤酒,蛇麻子(hops),葎草酮,异葎草酮,葎草灵酮,蛇麻酮,希鲁酮,单宁,咖啡酸或其酯,萜类化合物,金属盐,某些活性药物成分(例如对乙酰氨基酚,布洛芬,水杨酸,右美沙芬,愈创甘油醚,乙酰水杨酸,西咪替丁,雷尼替丁,阿莫西林,洛哌丁胺),奎尼丁,奎宁,龙胆根提取物,金鸡纳树皮提取物,多酚(例如儿茶素,表儿茶素,表儿茶素没食子酸酯,没食子酸,表没食子儿茶素,表没食子儿茶素没食子酸酯),ω-3-脂肪酸,醇,维生素(例如B族维生素)和矿物质。
在其他实施方案中,本公开的味道调节组合物或风味组合物可以掺入含有一种或多种风味成分或风味组合物的更复杂的调味品中,以增强或补充这些调味品的总体味道特征。这种风味成分或风味组合物包括例如天然或合成香精,即水果香精(例如柠檬,酸橙,橙子,葡萄柚;樱桃,草莓,覆盆子,酸果蔓;苹果,葡萄,菠萝,香蕉,番茄);天然或合成植物香精(如茶香精,咖啡香精,榛子,杏仁,山核桃或其他坚果香精,香草香精)和其他复杂的风味特性(例如可乐风味或想象的风味,如“生日蛋糕”或“冰淇淋圣代”)。
本公开主题的味道调节或风味组合物可进一步包含一种或多种支持材料。作为非限制性实例,支持材料可包括稀释剂,例如乙醇,纯净水,甘油:溶剂;载体,例如一缩二丙二醇,三醋精;防腐剂,例如亚硫酸盐,亚硝酸钠,丙酸,山梨酸,苯甲酸,乙二胺四乙酸二钠(EDTA);调味剂,例如醇类,酯类,醛类,酮类,内酯类,酚类;风味增强剂,例如谷氨酸一钠(MSG),谷氨酸一钾,双谷氨酸钙(CDG),鸟苷一磷酸鸟苷酸二钠,鸟苷酸钠,肌苷酸及其盐,L-亮氨酸;抗氧化剂,例如抗坏血酸,抗坏血酸钠,抗坏血酸钙,抗坏血酸的脂肪酸酯,生育酚,α-生育酚,γ-生育酚,δ-生育酚,棓酸丙酯,棓酸辛酯,异抗坏血酸,异抗坏血酸钠,没食子酸十二酯,叔丁基氢醌(TBHQ),丁羟茴醚(BHA),丁羟甲苯(BHT),柠檬酸,4-己基间苯二酚;保色剂;染料或色淀;螯合剂,乳化剂,例如卵磷脂,酸单甘油酯,乙酰单酸甘油酯,乳酰化单酸甘油酯,糖酯,山梨坦酯,聚甘油酯,硬脂酰二乙酸钙;稳定剂;酸、碱和/或消结块剂,例如硅酸钙,碳酸镁,铝矽酸钠。可安全用于消费品的其他已知风味成分可为本领域技术人员所知,例如参考教科书S.Arctander,Perfume and Flavor Chemicals,1969,Montclair,New Jersey,USA中列出的那些成分,该文献作为用于整体并入本文。
本公开的味道调节和/或风味组合物可以是单一成分或调味成分的简单混合物形式或包囊形式,例如包埋在固体基质中的组合物形式,所述固体基质可包括成壁和增塑材料,例如单糖,二糖或三糖,天然或改性淀粉,水胶体,纤维素衍生物,聚乙酸乙烯酯,聚乙烯醇,蛋白质或果胶。特别有用的基质材料的实例包括,例如,蔗糖,葡萄糖,乳糖,左旋糖,果糖,麦芽糖,核糖,右旋糖,异麦芽酮糖醇,山梨醇,甘露糖醇,木糖醇,拉克替醇,麦芽糖醇,戊糖醇(pentatol),阿拉伯糖,戊糖,木糖,半乳糖,麦芽糖糊精,糊精,化学改性淀粉,氢化淀粉水解物,琥珀酰化或水解淀粉,琼脂,角叉菜胶,阿拉伯树胶,阿拉伯胶,黄蓍胶,藻酸盐,甲基纤维素,羧甲基纤维素,羟基乙基纤维素,羟丙基甲基纤维素,衍生物,明胶,琼脂,藻酸盐及其混合物。包封是本领域技术人员众所周知的,并且可以例如使用诸如喷雾干燥,附聚或挤出,或包衣包封的技术进行,包括凝聚和复合凝聚技术。在一些实施方案中,味道调节和/或风味组合物可以是上述形式的一种或多种。
5.在消费品中的用途
如上所述的本公开主题的味道调节组合物或风味组合物可以有利地用于预期食用、吸收否则就是消耗的各种消费品中。
在某些实施方案中,本公开主题还提供了消费品,其包含:(i)含有至少一种式(I)的化合物的味道调节或风味组合物;和(ii)消费品基料。
在某些实施方案中,所述风味组合物包含至少一种HIS和/或其他非-HIS甜味剂。在其他实施方案中,所述风味组合物不含HIS和/或非-HIS甜味剂。在这类实施方案中,所述HIS或非-HIS甜味剂可以单独地加入到消费品中。
本公开主题还提供了调节消费品的味道特征的方法,这类方法包括:(i)混合至少一种式(I)的化合物,形成味道调节或风味组合物;和(ii)将味道调节或风味组合物与消费品基料混合。
本文所述的式(I)的化合物可用于其味道调节特性以有益于消费品制品,其可任选地包括具有不良味道特征的HIS或其他成分(即具有HIS的消费品基料或具有不良味道特征的其他成分和任选地另外的制品成分,即支持材料,香料,热量甜味剂),简单地通过使用常规技术和方法将一种或多种式(I)的化合物加入到消费品制品中来进行。因此,在一个替代实施方案中,本公开主题还提供改进、增强或改变包含HI S或其他具有不良味道特征的成分的消费品制品的味道特性的方法,其中将至少一种式(I)的化合物以能有效调节消费品异味的量添加到消费品制品中。
在一些实施方案中,式(I)的化合物在消费品中的存在量小于约0.1份/百万份(ppm),任选地小于或等于约0.01ppm,任选地小于或等于约0.001ppm,按重量计算。在一些实施方案中,式(I)的化合物在消费品中的存在量小于约0.1份/十亿份(ppb)。在其他实施方案中,式(I)的化合物在消费品中的存在量小于或等于约0.10份/万亿份(ppt)重量。在具体的实施方案中,在食品和饮料消费品中,式(I)的化合物的存在量为约0.0001ppt至约1%重量。
在其他实施方案中,式(I)的化合物以低于其气味检测阈值的量存在于消费品中。在某些实施方案中,式(I)的化合物在消费品中的存在量小于品尝师检测到化合物特有的风味特征的量。
消费品中HIS和/或非-HIS甜味剂的量变化很大,并且取决于消费品的类型和消费品的期望的甜味印象。在某些实施方案中,除了HIS之外,消费品还可包含一种或多种天然或合成甜味剂(例如全热量甜味剂和/或低热量糖替代品)。这种天然甜味剂的非限制性实例包括单糖(例如果糖,葡萄糖,甘露糖,鼠李糖,木糖,D-塔格糖,塔格糖,半乳糖,阿洛酮糖),二糖(例如蔗糖,乳糖,麦芽糖),海藻糖,半乳糖,核酮糖,苏糖,阿拉伯糖,来苏糖,阿洛糖,阿卓糖,转化糖,半乳低聚糖,丙醛糖,果糖寡聚体,四糖,甘露聚糖-寡糖,麦芽低聚糖,糊精,棉子糖,糖醇(如赤藓醇,甘油,拉克替醇,麦芽糖醇,甘露糖醇,山梨醇,木糖醇,半乳糖醇)玉米糖浆,糙米糖浆,椰子晶体,椰子糖,椰子糖浆,椰枣糖,果聚糖,生蜂蜜,枫树汁,槭糖浆,槭糖,核桃汁,桦树汁,梧桐汁,铁木汁,糖蜜,糖蜜糖,蔗糖,棕榈糖,原糖,大米糖浆,高粱,高粱糖浆,木薯糖浆,麦芽糖浆,大麦麦芽糖浆,大麦麦芽粉,甜菜糖,焦糖,角豆糖浆,龙舌兰属胰岛素,龙舌兰属花蜜,龙舌兰属糖浆或其混合物。
因此,消费品中本公开主题的一种或多种化合物和/或味道调节组合物和/或风味组合物的量将相应地根据消费品中HIS甜味剂的量以及消费品的其他组分成分(包括任何额外的甜味剂)的类型和用量而变化。这些和其他因素将影响包含HIS的消费品中本发明公开化合物用量的确定,所述化合物的用量能有效调节HIS的令人不快的味道特征。基于这些因素和本公开的教导,配制调味品和/或消费品的领域的技术人员可以确定本公开主题的一种或多种化合物和/或一种或多种味道调节组合物和/或一种或多种风味组合物的适当和有效量,用于调节消费品中HIS的异味。
在本公开主题的一个实施方案中,包含具有一种或多种式(I)的化合物的味道调节组合物或风味组合物的消费品还可以包含一种或多种高强度甜味剂,其选自:1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐;L-α-天冬氨酰-L-苯丙氨酸甲酯(阿斯巴甜);乙酰舒泛钾(Ace-K或乙酰舒泛K);1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜(三氯蔗糖);(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(爱德万甜);(3S)-3-(3,3-二甲基丁基氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(纽甜),L-α-天冬氨酰-N-(2,2,4,4-四甲基-3-硫杂环丁烷基)-D-丙氨酰胺(阿力甜);N-环己基氨基磺酸钠(环己基氨基磺酸盐)及其盐(例如环己基氨基磺酸钙,环己基氨基磺酸钠,环己基氨基磺酸镁,环己基氨基磺酸钾)和一些糖醇(例如木糖醇)及其组合。
在本公开主题的另一个实施方案中,包含具有一种或多种式(I)的化合物的味道调节组合物或风味组合物的消费品还可以包含一种或多种二萜糖苷化合物,例如甜叶菊来源的甜味剂,其选自全叶和粗甜叶菊提取物、改良甜叶菊提取物、一-、二-和多糖基化甜菊醇化合物、未经处理的甜叶菊粉末、甜叶菊甙A(Reb A)、甜叶菊甙B、甜叶菊甙C、甜叶菊甙D、甜叶菊甙D2、甜叶菊甙E和甜叶菊甙F、甜叶菊甙G、甜叶菊甙H、甜叶菊甙I、甜叶菊甙J、甜叶菊甙K、甜叶菊甙L、甜叶菊甙M、甜叶菊甙N、甜叶菊甙O、甜叶菊甙Q、甜叶菊甙R、甜叶菊甙S、甜叶菊甙V、甜叶菊甙W、甜叶菊甙X、甜叶菊甙KA、杜克甙A、悬钩子甙、甜菊苷和其他改良甜菊糖苷;或来源于罗汉果的高强度甜味剂,例如选自改良或未改良提取物(即罗汉果提取物或罗汉果汁)和罗汉果甙(例如罗汉果甙IV、罗汉果甙V、赛门苷I和11-氧代罗汉果甙V)的那些。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含罗汉果提取物,任选地包含(4Z,7Z)-癸二烯醛和罗汉果提取物。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含L-α-天冬氨酰-L-苯丙氨酸甲酯,并且任选地包含(4Z,7Z)-癸二烯醛和L-α-天冬氨酰-L-苯丙氨酸甲酯。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐,任选地包含(4Z,7Z)-癸二烯醛和1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含乙酰舒泛钾,任选地包含(4Z,7Z)-癸二烯醛和乙酰舒泛钾。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜,任选地包含(4Z,7Z)-癸二烯醛和1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸,任选地包含(4Z,7Z)-癸二烯醛和(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸。
在本公开主题的另一个实施方案中,所述消费品包含具有至少一种本公开的式(I)化合物的味道调节组合物或风味组合物且还包含(3S)-3-(3,3-二甲基丁基氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(纽甜),任选地包含(4Z,7Z)-癸二烯醛和(3S)-3-(3,3-二甲基丁基氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸。
在某些另外的实施方案中,所述消费品包含至少一种具有不良味道特征的非-HIS成分。在另一个实施方案中,具有不良味道特征的非-HIS成分可以单独地加入到消费品中。这类具有不良味道特征的非-HIS成分包括、但不限于可可,咖啡,咖啡碱,可可碱,二酮哌嗪,氨基酸,苦味肽,蛋白质(例如,植物蛋白,酪蛋白,大豆蛋白),水解蛋白,柚皮甙,牛磺酸,瓜拉那,绿原酸,防腐剂(例如钾盐,钠盐),锌盐,异黄酮,多酚,薄荷醇,奎宁,某些精油(如薄荷油),美拉德反应产物,啤酒,蛇麻子(hops),葎草酮,异葎草酮,葎草灵酮,蛇麻酮,希鲁酮,单宁,咖啡酸或其酯,萜类化合物,金属盐,某些活性药物成分(例如对乙酰氨基酚,布洛芬,水杨酸,右美沙芬,愈创甘油醚,乙酰水杨酸,西咪替丁,雷尼替丁,阿莫西林,洛哌丁胺),奎尼丁,奎宁,龙胆根提取物,金鸡纳树皮提取物,多酚(例如儿茶素,表儿茶素,表儿茶素没食子酸酯,没食子酸,表没食子儿茶素,表没食子儿茶素没食子酸酯),ω-3-脂肪酸,醇,维生素(例如B族维生素)和矿物质。
在消费品中的本公开主题的一种或多种化合物和/或味道调节组合物和/或风味组合物的量将相应地根据消费品中具有不良味道特征的成分的量以及消费品的其他组分成分的量和类型而变化。这些和其他因素将影响消费品中本公开的化合物的量的确定,所述消费品包含具有不良味道特征的成分,所述量的确定能有效调节消费品的味道特征。基于这些因素和本公开的教导,配制调味品和/或消费品的领域的技术人员可以确定本公开主题的一种或多种化合物和/或一种或多种味道调节组合物和/或一种或多种风味组合物的适当和有效量,以用于调节消费品的味道特性。
本公开主题的示例性消费品包括食品,例如烘焙食品,酱油,汤,快餐食品,糖果产品,乳制品,婴儿食品,调味品和蜜饯;饮料;口腔护理产品;药品;宠物食品;和动物饲料。该产品列表是以举例说明的方式给出的,并且不应视为以任何方式限制。
饮料的非限制性实例,例如即饮饮料,饮料浓缩物,包括碳酸和非碳酸软饮料,冷冻即饮饮料,咖啡饮料,茶饮料,乳品饮料,粉状软饮料,加香水,强化水,运动饮料,果汁和果汁加香饮料,葡萄酒冷却剂,含酒精和不含酒精的即饮鸡尾酒和加香酒精饮料。这些饮料可任选地含有天然或合成的香料。本组合物和方法可用于的特定类别的饮料是膳食软饮料(或苏打水),例如可乐,柑橘和水果味饮料等。在一些实施方案中,消费品是消费者用于加香水或另一种饮料的浓缩调味产品,例如调味包,调味片或增味剂滴剂。
在某些实施方案中,本公开主题的消费品是烘焙食品。如本文所用的“烘焙食品”包括方便食品,即食产品,面粉和混合物,其需要在食用前进行制备。烘焙食品的非限制性实例包括蛋糕,薄脆饼干,小甜点,布朗尼蛋糕,松饼,面包卷,圈饼,甜甜圈,派,馅饼,面粉糕饼,新月形面包,饼干,面包,面包产品和小面包。
糖食产品的非限制性实例包括口香糖,硬糖,耐嚼糖果,焦糖,软糖和巧克力。乳制品的非限制性实例包括冰淇淋,布丁和酸奶。调味品和蜜饯的非限制性实例包括糖浆,腌泡汁,蘸料,调味料,番茄酱,沙拉酱和水果蜜饯和制品。谷物和棒的非限制性实例包括早餐谷物,早餐棒,蛋白棒,燕麦棒,谷物涂覆衣料和燕麦片。
在某些实施方案中,本公开主题的组合物可以用于药物产品,例如咳嗽糖浆或其他液体药物制剂,可咀嚼片剂或吸入雾剂形式的药物剂型,“糖果”,可咀嚼的口香糖或硬锭剂。口腔护理产品的非限制性实例包括药物,例如咽喉锭剂,维生素,咀嚼片,喷雾器,药用滴剂,牙膏,牙胶,口腔洗剂,口腔清洗剂,漱口药,口腔膜条和口气薄荷糖。药物的非限制性实例包括减充血剂,止咳混合物,咽喉用锭剂,消化不良用制剂,口服镇痛药,片剂,胶囊,滴剂等。在一些实施方案中,本公开主题的组合物可直接或间接加入药物剂型中。例如片剂,胶囊,滴剂或锭剂,其还含有治疗活性剂。可以添加本公开主题的组合物以改进国际公开申请No.WO2007/089652中公开的制剂的味道特性,该申请通过引用整体并入本文。
在另一个实施方案中,将本公开主题的组合物直接或间接加入含有治疗活性剂(例如,诸如右美沙芬或其他镇咳药的药剂)的药物剂型(例如片剂,胶囊,滴剂,锭剂或糖浆)中。例如,本公开主题的一个实施方案提供含有本公开主题的组合物的止咳滴剂或锭剂。
在某些实施方案中,本公开主题的组合物可以与治疗活性剂组合,所述治疗活性剂包括例如镇痛药,例如布洛芬和对乙酰氨基酚;轻泻剂,例如酚酞二辛基磺基琥珀酸钠;减食欲剂,例如安非他明和苯丙醇胺;抗酸剂,例如碳酸钙;抗哮喘药例如茶碱;止泻药,如盐酸地芬诺酯;抗气胀药,如二甲硅油(simethecon);抗偏头痛药,如麦角胺酒石酸盐;抗精神病药,如氟哌啶醇;镇痉药或镇静剂,如苯巴比妥(含或不含阿托品);抗过敏药,如甲基多巴和哌醋甲酯;安神药,如苯二氮卓类,羟嗪甲丙氨酯类和吩噻嗪类;抗组胺药,如马来酸氯苯那敏,马来酸吡拉明,琥珀酸多西拉敏,马来酸溴苯那敏,枸橼酸苄苯醇胺,盐酸氯环利嗪和马来酸吡拉明;减充血剂,如苯丙醇胺盐酸盐,盐酸去氧肾上腺素,苯丙醇胺酒石酸氢盐和伪麻黄碱的硫酸盐或盐酸盐;β阻滞剂,如普萘洛尔;抗酗酒剂,如双硫仑;咳嗽抑制剂,如苯佐卡因和右美沙芬;氟化物补充剂,如氟化钠等;局部抗生素,如四环素和克林霉索;皮质类固醇供应者,如泼尼松/泼尼松龙;抗甲状腺肿药,如秋水仙碱和别嘌呤醇;抗癫痫药,如苯妥英钠;抗脱水剂,如电解质补充剂;防腐材料,例如,十六烷基吡啶鎓氯化物;抗菌剂,例如脲等。
在某些实施方案中,所公开主题的组合物包含在含有尼古丁的药物剂型(例如口香糖或锭剂)中,以调节尼古丁的苦味和刺激性味道。在许多设计用于戒烟的商业产品中,尼古丁以尼古丁polacrilex的形式存在。尼古丁polacrilex是与离子交换树脂如弱酸结合的尼古丁,具有聚甲基丙烯酸/二乙烯基苯聚合物基质并具有氢离子形式的polacrilex树脂。离子交换树脂的商业实例包括AmberliteTM IRP64(可从Rohm and Haas,现在DowChemical Co.,Midland,MI获得)和PuroliteTM C115HMR(可从The Purolite Co.,BalaCynwyd,PA获得)。示例性商业产品,可从GlaxoSmithKline(Middlesex UK)商购获得,作为含有2mg或4mg尼古丁的可溶性锭剂。
含有烟碱的口香糖和锭剂也可以商品名(例如WhiteIceTM Mint),和非品牌的通用版本商购获得。这些制品典型地每单位份含有2mg或4mg烟碱。本公开主题的组合物可用于改进美国公开申请No.2007/0014887或EP公开申请EP1107730中公开的制品的性质,其各自通过引用整体并入本文。
在某些实施方案中,消费品是浓缩甜味剂。适合的浓缩物组合物的非限制性实例包括粉末或片剂形式的糖浆和餐桌甜味剂。在一个示例性实施方案中,消费品以多个单份包装或包装的形式提供,其中甜味剂可以储存,分配和使用。任选地,浓缩甜味剂组合物可包括一种或多种天然调味品。
在某些其他实施方案中,消费品是动物饲料或家庭宠物食品,包括动物健康和营养产品。这种动物饲料和宠物食品的非限制性实例包括配合饲料,液体饲料,饲料(例如预混合物,饲料口粮,蛋白质或矿物质补充剂),湿或干犬粮,饲狗的硬饼干或零食和湿或干猫科动物食品。
所本公开主题还提供了调节高强度甜味剂的味道特征的方法,所述方法包括向甜味剂中加入至少一种本公开主题的化合物,其量足以提供比通过使用蔗糖提供的味道特征更接近的味道特征。
在本公开主题的一个实施方案中,消费品包含至少一种本发明公开的化合物和阿斯巴甜。这种消费品的非限制性实例包括餐饮苏打水和其他软饮料,果汁,葡萄酒冷却剂,可可混合物,茶,速溶咖啡,牛奶饮料,摇匀混合物,酸奶,餐桌甜味剂,速溶早餐,早餐谷物,冷冻甜点,明胶甜点,布丁,打顶混合物,口香糖,薄荷糖,轻泻药和咀嚼维生素补充剂。
在本公开主题的另一个实施方案中,消费品包含至少一种本公开的化合物和一种或多种甜叶菊衍生的甜味剂。在本公开主题的又一个实施方案中,消费品包含(4Z,7Z)-癸二烯和甜叶菊甙A。该实施方案特别适合的消费品的非限制性实例包括饮料产品(餐饮苏打水和其他软饮料,加香水),酸奶,谷物,口香糖,软糖和硬糖,餐桌甜味剂和药品。在本公开主题的另一个实施方案中,消费品包含至少一种本公开的化合物和罗汉果的提取物。
在本公开主题的又一个实施方案中,消费品包含至少一种本公开的化合物和L-α-天冬氨酰-L-苯丙氨酸甲酯,任选地包含(4Z,7Z)-癸二烯醛和L-α-天冬氨酰-L-苯丙氨酸甲酯。适合的消费品的非限制性实例包括餐饮苏打水和其他软饮料,果汁,葡萄酒冷却剂,可可混合物,茶,速溶咖啡,牛奶饮料,摇匀混合物,酸奶,餐桌甜味剂,速溶早餐,早餐谷物,冷冻甜点,明胶甜点,布丁,打顶混合物,口香糖,薄荷糖,轻泻药和咀嚼维生素补充剂。
在本公开主题的又一个实施方案中,消费品包含至少一种本发明公开的化合物和1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐,任选地包含(4Z,7Z)-癸二烯醛和1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐。适合的消费品的非限制性实例包括饮料,餐桌甜味剂,
在本公开主题的又一个实施方案中,消费品包含至少一种本公开的化合物和乙酰舒泛钾,任选地包含(4Z,7Z)-癸二烯醛和乙酰舒泛钾。适合的消费品的非限制性实例包括烘焙食品,冷冻甜点,糖果和饮料。
在公开主题的又一个实施方案中,消费品包含至少一种本公开的化合物和1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜,任选地包含(4Z,7Z)-癸二烯醛和1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜。适合的消费品的非限制性实例包括烘焙食品,饮料,口香糖,明胶和冷冻乳制甜点。
在公开主题的另一个实施方案中,消费产品包含至少一种本公开的化合物和(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸,任选地包含(4Z,7Z)-癸二烯醛和(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸。特别适合的消费品的非限制性实例包括烘焙食品。
在本公开主题的另一个实施方案中,消费产品包含至少一种本公开的化合物和(3S)-3-(3,3-二甲基丁氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸,任选地包含(4Z,7Z)-癸二烯醛和(3S)-3-(3,3-二甲基丁氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸。特别适合的消费品的非限制性实例包括烘焙食品。
在另一方面,本公开主题提供了一种调节消费品味道特征的方法,所述消费品包含一种或多种苦味,涩味,金属味或其他不良味道特征,所述方法通过向消费品的基料中添加有效量的至少一种式(I)的化合物和/或包含至少一种式(I)的化合物的风味组合物来进行。如本文所用,术语“有效量”是指在消费品中所述式(I)的化合物和/或包含至少一种式(I)的化合物的味道调节组合物和/或包含至少一种式(I)的化合物的风味组合物能够赋予所述产品较少的令人不愉快的味道特征的用量。有效量将根据存在的其他成分,它们的相对量和期望的效果的不同而广泛变化。
实施例
本公开主题通过参照下列实施例得到更好理解,提供这些实施例作为对本公开主题的示例,而绝非限制。
实施例1:风味组合物(甜叶菊甙A)的味道改进
根据下表制备用于味道比较的两种风味组合物:
表1.
显示的百分比按重量计。三名训练有素的专家小组成员评估了两种增甜的风味组合物。所有三种风味组合物A都比对照更清洁,具有明显更好的余味。
实施例2:风味组合物(L-α-天冬氨酰-L-苯丙氨酸甲酯)的味道改进
根据下表制备两种用于味道比较的风味组合物:
表2.
对照 | A | |
水 | 99.98% | 99.97% |
L-α-天冬氨酰-L-苯丙氨酸甲酯 | 0.02% | 0.02% |
10ppb的(4Z,7Z)-癸二烯醛在乙醇中的溶液 | - | 0.01% |
显示的百分比按重量计。三名训练有素的专家小组成员评估了两种增甜的风味组合物。所有三种风味组合物A都具有比对照明显更好的余味。
实施例3:风味组合物(罗汉果提取物)的味道改进
根据下表制备两种用于味道比较的风味组合物:
表3.
对照 | A | |
水 | 98.5% | 98.4% |
罗汉果(“罗汉果”)汁 | 1.5% | 1.5% |
10ppb的(4Z,7Z)-癸二烯醛在乙醇中的溶液 | - | 0.10% |
显示的百分比按重量计。三名训练有素的专家小组成员评估了两种增甜的风味组合物。所有三种显示的风味组合物A都具有比对照明显更好的余味。
实施例4:口香糖味道改进
制备三种口香糖样品用于味道比较:(1)没有任何味道调节成分的对照样品;(2)样品A,其包含用于调节不良HIS味道特征的商品化味道调节组合物;和(3)样品B,其中用0.1%的(4Z,7Z)-癸二烯醛代替样品A的商品化味道调节组合物中的0.1%溶剂,得到“包括味道调节化合物的调节调味品”,全部如表4所示。“口香糖基质成分”是本领域普通技术人员已知的成分并且用于提供典型的口香糖性质并且包括弹性体(例如聚异丁烯,聚丁烯,异丁烯-异戊二烯共聚物,苯乙烯-丁二烯共聚物,聚乙酸乙烯酯,天然橡胶,节路顿胶,lechicaspi,perillo);弹性体增塑剂(例如部分氢化松香的甘油酯,浮油松香的甘油酯,松香的甲基和部分氢化甲酯);蜡(例如聚乙烯,蜜蜂蜡,巴西棕榈蜡,石蜡);脂肪,油,乳化剂,填料(例如碳酸钙,碳酸镁,氢氧化铝,硅酸镁和硅酸铝,粘土,氧化铝,纤维素聚合物);组织形成剂(例如氢化和部分氢化的植物油,甘油单硬脂酸酯,可可脂,棕榈酸,油酸,亚麻酸)。
表4.
显示的百分比按重量计。在单独的品尝期间,共有20名经过培训的专家小组成员对三种口香糖样品进行了评估,并且发现样品B提供了比对照或样品A更好的余味。
实施例5:酸奶改进
制备样品以评价含有(4Z,7Z)-癸二烯醛的调节组合物与还原糖甜叶菊增甜的酸奶的效果。
用7.5%糖、68ppm Reb A 97和脱脂原味酸奶制备还原糖酸奶基料(对照)。测试样品是对照加0.05%的调节组合物。调节组合物含有0.0001%的0.01%部分(cut)的(4Z,7Z)-癸二烯醛以及其他调节剂。感官评估由5人的专家小组进行。
所有5名专门小组成员都表示测试样品逗留不去的异味比对照品少。两位小组成员表示测试样品比对照是更似奶油的。一名专家小组成员指出,甜味得到改进。
实施例6:罗汉果汁味道改进
通过在乙酸乙酯中组合并混合0.000001%部分(cut)的1%2,6-壬二烯醛(在乙醇中1%)进行味道比较,并使用在水中的罗汉果饮料中0.10%的稀释度,其中罗汉果汁浓缩物以0.15%存在。三名训练有素的专家评估了这种组合与没有味道调节化合物的罗汉果汁的对照品。得到的组合显示了对罗汉果汁的异味、即不良味道特性的调节。
实施例7和8提供了本公开主题的另外的低卡路里食品和饮料产品的示例性实施方案。
实施例7:加香水饮料
合并AceK和1份/万亿份的(4Z,7Z)-癸二烯醛在乙醇中的稀释液,且然后混合天然草莓香精。将得到的混合物加入到处理过的水中。
实施例8:具有浓甜味剂的低卡路里烘焙食品(小甜点)
混合甜叶菊甙A 97%和(4Z,7Z)-癸二烯醛,形成浓甜味剂。通过配混浓甜味剂与盐、糖、小苏打、香料和起酥油/黄油制备小甜点。将鸡蛋且然后将面粉加入到该混合物中,制成小甜点生面团。将测量量(约一茶匙量)的小甜点滴落在小甜点薄板上并且在420华氏度数下烘烤8分钟。
实施例9:4Z,7Z-癸二烯醛的合成
顺式-3-己烯基三苯基溴化鏻的合成(由顺式-3-己烯醇的2步):在N2气氛下,合并顺式-3-己烯醇(.4mol),THF(s/s=10)和三乙胺(2eq.)并冷却至0℃。通过加料漏斗逐滴加入甲磺酰氯(1.5eq.)。加入氯化物后30分钟,反应混合物的GC显示没有原料。将反应混合物倾入乙醚中,用10%HCl洗涤,然后用盐水洗涤,然后用饱和NaHCO3洗涤,再用盐水洗涤。将有机物质用MgSO4干燥并浓缩,得到橙色油状物。将未经进一步纯化的粗顺式-3-己烯基甲磺酸酯在乙醚(s/s=10)中稀释,并在室温下逐滴加入溴化锂(1.5eq.)和乙醚(s/s=4)的溶液中。搅拌过夜后,将反应混合物倾入盐水中。分离有机相,水相用乙醚萃取3次。乙醚萃取液用MgSO4干燥,浓缩成粗顺式-3-己烯基溴,可用于下一步骤。
用乙腈(s/s=10)稀释顺式-3-己烯基溴,与PPh3(1.5eq.)合并并回流36小时。在减压除去乙腈后,将1:1己烷:乙醚的混合物加入到反应烧瓶中并冷藏过夜。过滤所得固体,用乙醚洗涤,直至固体样品通过1H NMR显示不再有PPh3。真空干燥后,收集纯的顺式-3-己烯基三苯基溴化鏻。
3-(1,3-二氧戊环-2-基)丙醛的合成:将丙烯醛乙烯缩醛与甲苯(s/s=1)、Rh(CO)2Acac(.0015eq.)和PPh3(.0078eq.)在高压釜中合并。在250psi下将CO/H2(1:1)加入反应器中,并在65℃下搅拌容器内容物。48小时后,反应完成,得到约50/50的支链/直链产物的混合物。通过蒸馏(20T,35℃浴,24℃蒸馏球(bulb))除去甲苯和低沸点杂质。分馏(3-ft柱,r/r=12/1,.78T,65℃浴,52℃蒸馏球)除去大部分支化产物。然后,短程蒸馏(.88T,65℃浴,36℃蒸馏球)得到纯的直链产物3-(1,3-二氧戊环-2-基)丙醛。
2-((3Z,6Z)壬-3,6-二烯基)-1,3-二氧戊环的合成:然后将3-(1,3-二氧戊环-2-基)丙醛用于维蒂希反应。具体而言,将顺式-3-己烯基三苯基溴化鏻(1eq.)加入到配有加料漏斗的圆底烧瓶中。抽真空烧瓶并用N2吹扫后,加入乙醚(s/s=2)与盐形成浆液。在室温下,在1小时内将n-BuLi(1.6M己烷溶液,1当量)滴加到浆料中并再搅拌1小时以形成内鎓盐。用丙酮与干冰浴将反应冷却至-35℃。然后将3-(1,3-二氧戊环-2-基)丙醛(1eq.)的乙醚溶液(s/s=10)逐滴加入到内鎓盐中。使反应温热至室温并搅拌过夜。将饱和NH4Cl加入到反应混合物中并搅拌直至所有固体溶解。将混合物用乙醚萃取3次,用5%HCl洗涤,然后用饱和NaHCO3洗涤,然后用盐水洗涤。用MgSO4干燥乙醚萃取液并浓缩。浓缩的萃取液用1:1乙醚:己烷的混合物过滤。浓缩滤液,并在短程蒸馏(.5T,至多110℃)后,获得产物。
2-((3Z,6Z)壬-3,6-二烯基)-1,3-二氧戊环脱保护得到4Z,7Z-癸二烯醛:将2-((3Z,6Z)壬-3,6-二烯基)-1,3-二氧戊环与50%乙醛酸(s/s=2)和1,4-二噁烷(s/s=2)一起加热至75℃过夜。冷却后,用5%Na2CO3处理该反应混合物,用乙醚萃取,用水洗涤,干燥,浓缩,得到粗4Z,7Z-癸二烯醛。分馏(.44T,35-36℃)得到4Z,7Z-癸二烯醛。
实施例10:用于4Z,7Z-癸二烯醛合成的发酵方法
通过首先用Thalassiosira rotula硅藻(其在20℃下在二氧化碳下使用13:11光照:黑暗循环在L1培养基中生长3周)处理二十碳五烯酸(EPA)获得4,7-癸二烯醛的天然形式。收获细胞并冷冻,然后在另外的L1培养基中研磨。然后在室温下将EPA加入到中性缓冲液中的这些研磨细胞中并搅拌3小时。用乙酸乙酯萃取样品并通过气相色谱分析,证实存在2,4,7-癸三烯醛。然后将该产物用酿酒酵母(Saccharomyces cerevisiae)酵母和D-葡萄糖在pH 7.5缓冲液中于30℃下处理10分钟。用乙酸乙酯萃取粗发酵产物,并通过气相色谱分析,证实存在期望的4,7-癸二烯醛。
尽管已经详细描述了本公开主题及其优点,但是应当理解,在不脱离由所附权利要求限定的所公开主题的精神和范围的情况下,可以在本文中进行各种改变、替换和更改。此外,本公开的范围不旨在限于说明书中描述的过程,装置,制造方法,物质组成,方式,方法和步骤的特定实施方案。正如本领域普通技术人员从本公开主题,过程,装置,制造方法,物质组成,方式,方法或步骤的公开内容所理解的,可以根据本公开主题使用目前存在或稍后开发的内容,它们基本上具有与本文所述相应实施方案相同的功能或可以实现基本上相同的效果。因此,所附权利要求旨在在其范围内包括这样的过程,装置,制造方法,物质组成,方式,方法或步骤。
根据前面的描述,本领域技术人员将想到组合物和方法的各种修改和变化。属于所附权利要求范围内的所有这些修改旨在包括在其中。
在本申请全文中引用了专利,专利申请出版物产品描述和方案,其公开内容出于所有目的通过引用整体并入本文。
Claims (15)
1.式I表示的风味调节化合物,
其中虚线可以均为单键,或其中一条虚线为双键而另一条为单键,并且
其中X代表C1-C9脂族或支链烷基或包含一个或多个双键的C1-C9脂族或支链烯基。
2.权利要求1的风味调节化合物,其中虚线可以均为单键,或一条虚线为双键而另一条为单键,且其中X代表包含一个或多个非共轭双键的C6-C7烯基。
3.权利要求1的调节化合物,其中所述化合物通过发酵和酶反应方法生产。
4.风味组合物,包含一种或多种权利要求1的风味调节化合物。
5.权利要求4的风味组合物,其中该风味调节化合物选自4-癸烯醛;7-癸烯醛;4,7-癸二烯醛;2,4,7-癸三烯醛;2,6-壬二烯醛,3,6-壬二烯醛;6-壬烯醛及其混合物。
6.权利要求4或5的风味组合物,其中该风味调节化合物是两种或更多种4,7-癸二烯醛异构体的混合物,所述4,7-癸二烯醛异构体选自(4Z,7Z)-异构体、(4E,7Z)-异构体、(4Z,7E)-异构体、(4E,7E)-异构体及其混合物。
7.消费品,包含:(a)一种或多种权利要求4-6任一项的风味组合物;和(b)消费品基料。
8.权利要求7的消费品,还包含至少一种高强度甜味剂和/或非-HIS甜味剂。
9.消费品,包含:(a)一种或多种权利要求1或2的化合物;(b)至少一种高强度甜味剂和/或非-HIS甜味剂,和(c)消费品基料。
10.权利要求7-9之一的消费品,其中所述高强度甜味剂选自1,2-苯并噻唑-3(2H)-酮1,1-二氧化物(糖精)或其钠盐;L-α-天冬氨酰-L-苯丙氨酸甲酯(阿斯巴甜);乙酰舒泛钾(Ace-K或乙酰舒泛K);1,6-二氯-1,6-二脱氧-β-D-呋喃果糖基-4-氯-4-脱氧-α-D-吡喃半乳糖苷纽甜(三氯蔗糖);(3S)-3-[3-(3-羟基-4-甲氧基苯基)丙基氨基]-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(爱德万甜);(3S)-3-(3,3-二甲基丁基氨基)-4-[[(2S)-1-甲氧基-1-氧代-3-苯基丙-2-基]氨基]-4-氧代丁酸(纽甜),L-α-天冬氨酰-N-(2,2,4,4-四甲基-3-硫杂环丁烷基)-D-丙氨酰胺(阿力甜);N-环己基氨基磺酸钠(环己基氨基磺酸盐)及其盐(例如环己基氨基磺酸钙,环己基氨基磺酸钠,环己基氨基磺酸镁,环己基氨基磺酸钾)和一些糖醇(例如木糖醇)及其组合。
11.权利要求7-9任一项的消费品,其中所述高强度甜味剂来源于甜叶菊(Steviarebaudiana),其中所述高强度甜味剂选自全叶和粗甜叶菊提取物、改良甜叶菊提取物、一-、二-和多糖基化甜菊醇化合物、未经处理的甜叶菊粉末、甜叶菊甙A(Reb A)、甜叶菊甙B、甜叶菊甙C、甜叶菊甙D、甜叶菊甙D2、甜叶菊甙E和甜叶菊甙F、甜叶菊甙G、甜叶菊甙H、甜叶菊甙I、甜叶菊甙J、甜叶菊甙K、甜叶菊甙L、甜叶菊甙M、甜叶菊甙N、甜叶菊甙O、甜叶菊甙Q、甜叶菊甙R、甜叶菊甙S、甜叶菊甙V、甜叶菊甙W、甜叶菊甙X、甜叶菊甙KA、杜克甙A、悬钩子甙、甜菊苷和其他改良甜菊糖苷及其组合。
12.权利要求7-9任一项的消费品,其中所述高强度甜味剂来源于罗汉果(Siraitiagrosvenorii),其中所述高强度甜味剂选自改良或未改良提取物、罗汉果甙及其组合。
13.权利要求7-9任一项的消费品,其中所述高强度甜味剂选自L-α-天冬氨酰-L-苯丙氨酸甲酯、罗汉果提取物、甜叶菊甙A;及其组合。
14.调节消费品味道特性的方法,其中将一种或多种权利要求1或2的化合物加入到消费品中,其加入量能有效调节高强度甜味剂的味道特征。
15.用于调节消费品中不良味道特征的方法,包含将至少一种权利要求1或2的化合物加入到消费品中,所述消费品包含高强度甜味剂和/或其他具有不良味道特征的成分,所述化合物的加入量足以为所述消费品提供更理想的味道或风味特征。
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Also Published As
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EP3510010A1 (en) | 2019-07-17 |
CN109996778B (zh) | 2022-12-13 |
BR112019003346B1 (pt) | 2022-12-27 |
KR20230114334A (ko) | 2023-08-01 |
AU2017322677B2 (en) | 2020-12-17 |
MX2019002771A (es) | 2019-05-27 |
EP3510010B1 (en) | 2023-09-06 |
CA3033329A1 (en) | 2018-03-15 |
JP7021199B2 (ja) | 2022-02-16 |
KR20190050984A (ko) | 2019-05-14 |
SG11201901699TA (en) | 2019-03-28 |
WO2018049352A1 (en) | 2018-03-15 |
JP2019529629A (ja) | 2019-10-17 |
US11540542B2 (en) | 2023-01-03 |
AU2017322677A1 (en) | 2019-02-28 |
US20190208806A1 (en) | 2019-07-11 |
PH12019500469A1 (en) | 2019-11-11 |
MY193151A (en) | 2022-09-26 |
BR112019003346A2 (pt) | 2019-06-11 |
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