JPWO2014061734A1 - 塩味増強剤及びその製造方法、並びに、塩味増強方法 - Google Patents
塩味増強剤及びその製造方法、並びに、塩味増強方法 Download PDFInfo
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- JPWO2014061734A1 JPWO2014061734A1 JP2014542170A JP2014542170A JPWO2014061734A1 JP WO2014061734 A1 JPWO2014061734 A1 JP WO2014061734A1 JP 2014542170 A JP2014542170 A JP 2014542170A JP 2014542170 A JP2014542170 A JP 2014542170A JP WO2014061734 A1 JPWO2014061734 A1 JP WO2014061734A1
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- 230000008520 organization Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RMIGTEGRHJUHHM-UHFFFAOYSA-N propan-1-ol;hydrochloride Chemical compound Cl.CCCO RMIGTEGRHJUHHM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000015598 salt intake Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 235000021264 seasoned food Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000012046 side dish Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 208000023516 stroke disease Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- KQNHKQVCQXOKGT-UHFFFAOYSA-N tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-(trifluoromethylsulfonyl)carbamimidoyl]carbamate Chemical compound C(C)(C)(C)OC(=O)NC(=NS(=O)(=O)C(F)(F)F)NC(=O)OC(C)(C)C.C(C)(C)(C)OC(=O)NC(=NS(=O)(=O)C(F)(F)F)NC(=O)OC(C)(C)C KQNHKQVCQXOKGT-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000032895 transmembrane transport Effects 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/02—Guanidine; Salts, complexes or addition compounds thereof
-
- 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
- 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
-
- 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
- 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
-
- 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
- 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
- A23L27/205—Heterocyclic compounds
- A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
-
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/40—Table salts; Dietetic salt substitutes
-
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/40—Table salts; Dietetic salt substitutes
- A23L27/45—Salt substitutes completely devoid of sodium chloride
-
- 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/08—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/18—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/45—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms doubly-bound to the carbon skeleton
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Abstract
Description
本出願は、2012年10月18日に出願された、日本国特許出願第2012−230673号明細書(その開示全体が参照により本明細書中に援用される)に基づく優先権を主張する。
(i)へテロ原子によって中断されてもよい炭素数1〜5の直鎖または分岐の炭化水素基であって、
カルボキシル基及び水酸基からなる群から選択される少なくとも1個の基を有してもよい炭化水素基、または
(ii)水素原子を示す。]
m及びnは1〜4の整数をそれぞれ表し、m+nは3〜5の整数である。
m’及びn’は1〜3の整数をそれぞれ表し、m’+n’は2〜4の整数である。
kは0〜3の整数を表す。]
(i)へテロ原子によって中断されてもよい炭素数1〜5の直鎖または分岐の炭化水素基であって、
カルボキシル基及び水酸基からなる群から選択される少なくとも1個の基を有してもよい炭化水素基、または
(ii)水素原子
を示す。]
S−メチルイソチオ尿素またはその塩と
を反応させる工程を含む、
下記一般式(1)で表される化合物またはその塩からなる塩味増強剤の製造方法。
m及びnは1〜4の整数をそれぞれ表し、m+nは3〜5の整数である。
m’及びn’は1〜3の整数をそれぞれ表し、m’+n’は2〜4の整数である。
kは0〜3の整数を表す。]
S−メチルイソチオ尿素またはその塩と
を反応させる工程を含む、
下記一般式(2)〜(6)のいずれかで表される化合物またはその塩からなる塩味増強剤の製造方法。
本発明は塩味増強剤に関する。ここで、塩味増強剤とは、自身は実質的に塩味を有しないが、食塩(塩化ナトリウム)と併用することで、食塩の塩味を強く感じさせる物質を指す。具体的には、例えば、閾値以下の塩味物質に共存させることで感じることができなかった塩味を感じさせる効果を持つ物質や、添加することにより強い塩味を誘導するような効果を有する物質などが含まれる。
(i)ヘテロ原子で中断されてもよい炭素数1〜5の直鎖または分岐の炭化水素基であって、
カルボキシル基及び水酸基からなる群から選択される少なくとも1個の基を有してもよい炭化水素基、または
(ii)水素原子
を示す。]
m及びnは1〜4の整数をそれぞれ表し、m+nは3〜5の整数である。
m’及びn’は1〜3の整数をそれぞれ表し、m’+n’は2〜4の整数である。
kは0〜3の整数を表す。]
q=0の場合:
本発明の一般式(1)で表される化合物またはその塩は、例えば、下記のReaction Scheme-1(反応式−1)に準じて、1級アミン化合物(X)に、グアニジル化試薬(guanidinylation reagents)を反応させることにより合成することができる。
本発明は、上記化合物またはその塩(本発明の塩味増強剤)を含む調味料をも提供する。
本発明は、飲食品の塩味増強方法をも提供する。本発明の方法は、飲食品に、上記化合物またはその塩を添加する工程を含む。
1H−NMRおよび13C−NMR測定:Varian社製、Inova 500
MS−ESI測定:日本電子社製、JMS-T100LC AccuTOF。
13C-NMR(CD3OD, 125MHz):δ=26.5, 30.4, 42.3, 62.3, 158.5
MS-ESI(C5H14ON3Cl):2M+HCl+H : 299.21 (計算値: 299.20)。
13C-NMR(CD3OD, 125MHz): δ=32.4, 39.5, 59.7, 158.8
MS-ESI(C4H12ON3Cl):2M+HCl+H : 271.17 (計算値: 271.17)。
13C-NMR(CD3OD, 125MHz): δ=24.0, 29.6, 33.0, 42.4, 62.6, 158.6
MS-ESI(C6H16ON3Cl):2M+HCl+H : 327.24 (計算値: 327.23)。
13C-NMR(CD3OD, 125MHz): δ=45.1, 61.4, 159.3
MS-ESI(C3H10ON3Cl):2M+HCl+H : 243.13 (計算値: 243.13)。
13C-NMR(CD3OD, 125MHz): δ=26.5, 27.5, 29.8, 33.4, 42.4, 62.8, 158.6
MS-ESI(C7H18ON3Cl):2M+HCl+H : 355.26 (計算値: 355.26)。
13C-NMR(CD3OD, 125MHz): δ=20.7, 49.7, 67.1, 159.3。
13C-NMR(CD3OD, 125MHz): δ=17.1, 51.3, 66.3, 158.6。
13C-NMR(CD3OD, 125MHz):δ=22.6(×2), 37.4, 49.7, 68.8, 159.4
MS-ESI(C6H16ON3Cl):2M+HCl+H : 327.20 (計算値: 327.23)。
13C-NMR(CD3OD, 125MHz):δ=43.0, 62.1, 70.5, 73.6, 159.2。
13C-NMR(CD3OD, 125MHz):δ=32.2, 35.3, 42.3, 62.7, 158.7。
13C-NMR(CD3OD, 125MHz):δ=11.5, 23.2, 44.0, 158.6
MS-ESI(C4H12N3Cl):2M+HCl+H : 239.14 (計算値: 239.18)。
粗3-グアニジノ-1-プロパノール硫酸塩(m) 344mg、にメタノール10mlを加え、さらにシリカゲル(ワコーゲルC-200)2.0gを加えたのち、エバポレーターを用いて溶媒を除きシリカゲルに試料を吸着させサンプルゲルとした。分離ゲル(ワコーゲルC-200)14.1gをアセトンに懸濁してガラスカラムに充填のカラムの上に上述のサンプルゲルを重層しアセトン50ml、エタノール50mlを流したのちメタノール200mlを流すことで溶出したメタノール層をエバポレーターで乾固することで、3-グアニジノ-1-プロパノール硫酸塩(m)を無色油状物質として235mg(1.41mmol,70.5%)を得た。
13C-NMR (CD3OD、125MHz) :δ=32.5, 39.2, 59.6, 158.9
合成例1〜11及び合成例14で合成した化合物、並びに、市販品を入手したグアニジン塩酸塩、β-グアニジノプロパン酸、γ-グアニジノ酪酸及び6-グアニジノカプロン酸を評価試料として、塩味増強作用を評価した。
+++:0.805重量%の食塩水と同等またはこれ以上の塩味を呈する(15%以上の塩味増強効果を示す);
++:0.770重量%の食塩水と同等またはこれ以上の塩味を呈する(10%以上の塩味増強効果を示す);
+:0.735重量%の食塩水と同等またはこれ以上の塩味を呈する(5%以上の塩味増強効果を示す);
±:0.735重量%の食塩水以下の塩味を呈する(塩味増強効果は5%未満)、または、苦味等により評価不能。
合成例2で得た3-グアニジノ-1-プロパノール塩酸塩について、添加濃度と塩味増強作用の関係を評価した。
++++:0.840重量%の食塩水と同等またはこれ以上の塩味を呈する(20%以上の塩味増強効果を示す);
+++:0.805重量%の食塩水と同等またはこれ以上の塩味を呈する(15%以上の塩味増強効果を示す);
++:0.770重量%の食塩水と同等またはこれ以上の塩味を呈する(10%以上の塩味増強効果を示す);
+:0.735重量%の食塩水と同等またはこれ以上の塩味を呈する(5%以上の塩味増強効果を示す);
±:0.735重量%の食塩水以下の塩味を呈する(塩味増強効果は5%未満)。
合成例2で得た3-グアニジノ-1-プロパノール塩酸塩について、飲食品中での塩味増強効果を評価した。
Claims (14)
- 請求項1〜3のいずれか1項に記載の化合物またはその塩からなる食品添加物。
- 請求項1〜3のいずれか1項に記載の化合物またはその塩を含む調味料。
- さらに塩化ナトリウムを含む、請求項5に記載の調味料。
- 請求項1〜3のいずれか1項に記載の化合物またはその塩を含む飲食品。
- 請求項1〜3のいずれか1項に記載の化合物またはその塩を10ppm以上含む飲食品。
- 請求項1〜3のいずれか1項に記載の化合物またはその塩が、添加されたものである、請求項10または11に記載の飲食品。
- さらに塩化ナトリウムを含む、請求項10〜12のいずれか1項に記載の飲食品。
- 飲食品に、請求項1〜3のいずれか1項に記載の化合物またはその塩を添加する工程を含む、飲食品の塩味増強方法。
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BR112015008523A2 (pt) | 2017-07-04 |
KR20150068972A (ko) | 2015-06-22 |
TWI632861B (zh) | 2018-08-21 |
HUE039797T2 (hu) | 2019-02-28 |
WO2014061734A1 (ja) | 2014-04-24 |
RU2015118383A (ru) | 2016-12-10 |
MX2015004854A (es) | 2015-07-21 |
IN2015DN03243A (ja) | 2015-10-02 |
SG11201502822SA (en) | 2015-05-28 |
TR201815279T4 (tr) | 2018-11-21 |
KR101912494B1 (ko) | 2018-10-26 |
EP2910130B1 (en) | 2018-08-15 |
HK1206562A1 (en) | 2016-01-15 |
TW201427608A (zh) | 2014-07-16 |
PH12015500799A1 (en) | 2015-06-08 |
EP2910130A1 (en) | 2015-08-26 |
US20150250217A1 (en) | 2015-09-10 |
EP2910130A4 (en) | 2016-05-25 |
BR112015008523B1 (pt) | 2020-11-10 |
SG10201702809XA (en) | 2017-05-30 |
RU2653735C2 (ru) | 2018-05-14 |
CN104736000A (zh) | 2015-06-24 |
CN104736000B (zh) | 2018-07-06 |
JP6352190B2 (ja) | 2018-07-04 |
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