WO2024162422A1 - 呈味増強用組成物、その製造方法、食品、及び、食品の呈味を増強する方法 - Google Patents

呈味増強用組成物、その製造方法、食品、及び、食品の呈味を増強する方法 Download PDF

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Publication number
WO2024162422A1
WO2024162422A1 PCT/JP2024/003191 JP2024003191W WO2024162422A1 WO 2024162422 A1 WO2024162422 A1 WO 2024162422A1 JP 2024003191 W JP2024003191 W JP 2024003191W WO 2024162422 A1 WO2024162422 A1 WO 2024162422A1
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Prior art keywords
cyclic
glu
pro
leu
ile
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PCT/JP2024/003191
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English (en)
French (fr)
Japanese (ja)
Inventor
絹子 宮崎
瑠乃 小林
久美 坂根
崇 白水
啓子 松原
享宏 鴨井
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House Foods Corp
House Foods Group Inc
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House Foods Corp
House Foods Group Inc
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Priority to JP2024512208A priority Critical patent/JP7787984B2/ja
Priority to CN202480010135.8A priority patent/CN120712025A/zh
Priority to EP24750371.7A priority patent/EP4659591A1/en
Publication of WO2024162422A1 publication Critical patent/WO2024162422A1/ja
Anticipated expiration legal-status Critical
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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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids

Definitions

  • the present invention relates to a flavor enhancing composition, a method for producing the same, a food, and a method for enhancing the flavor of a food.
  • Salt sodium chloride
  • Salt gives food a pleasant taste and is used in food as a source of chlorine and sodium, elements essential for maintaining life.
  • excessive salt intake is known to be the cause of many diseases, including hypertension, and there is a desire to reduce salt intake.
  • Patent Document 1 discloses a spice mix for enhancing saltiness, which contains paprika, yuzu peel and/or dried tangerine peel, ginger, and allspice in a specific ratio, and may further contain at least one spice selected from red chili pepper, cumin, coriander, and celery seed.
  • Patent Document 1 describes that the saltiness enhancing effect can be further enhanced by including smoked spices in the spice mix for enhancing saltiness.
  • Smoked paprika is described as a specific example of a smoked spice.
  • the spice mix for enhancing saltiness has the effect of enhancing the saltiness of food when added to food together with salt.
  • Patent document 2 discloses a salty taste enhancer containing a mixture of pepper, ginger, cloves and cinnamon, and a salty taste enhancer containing a mixture of pepper, ginger, cloves, cinnamon and chili pepper.
  • Patent Document 3 discloses a method for producing spices with enhanced caramel aroma, which includes a step of heating at least one spice selected from the group consisting of coriander, cumin, dried tangerine peel, anise, celery, turmeric, fenugreek, garlic, chili pepper, paprika, fennel, black pepper, ginger, and asafoetida under a gauge pressure of 0.05 MPa or more under conditions such that the heating value is 15 to 170, and a method for producing spices with enhanced almond aroma, which includes a step of heating at least one spice selected from the group consisting of turmeric, chili pepper, fenugreek, cumin, coriander, dried tangerine peel, garlic, paprika, fennel, anise, celery, black pepper, ginger, fenugreek leaves, and cinnamon under conditions of a gauge pressure of less than 0.05 MPa under conditions such that the heating value is 50 to 180.
  • Patent Document 3 further discloses that a spice with enhanced charcoal aroma
  • the present invention provides a taste enhancing composition that can enhance the taste of food by adding it to the food, and a method for producing the same.
  • the present invention also provides a method for enhancing the taste of food.
  • the present inventors have discovered the following means as a taste enhancing composition capable of enhancing the taste of food, a method for producing a taste enhancing composition, a food with enhanced taste, and a method for enhancing the taste of food.
  • a taste enhancing composition containing a cyclic dipeptide may be, for example, a salty taste enhancing composition.
  • cyclic dipeptide contains one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, and alanine.
  • the cyclic dipeptide is cyclic (Pro-Asn), cyclic (Pro-His), cyclic (Pro-Asp), cyclic (Pro-Pro), cyclic (Pro-Val), cyclic (Pro-Tyr), cyclic (Pro-Leu), cyclic (Pro-Ile), cyclic (Pro-Glu), cyclic (Pro-Gly), cyclic (Pro-Met), cyclic (Arg-Pro), cyclic (Thr-Pro), cyclic (hyPro-Pro), cyclic (Leu-Leu), cyclic (Ile-Leu), cyclic (Ile-Ile), cyclic (Leu-Asp), cyclic (Ile-Asp), cyclic (Leu- Ser), cyclic (Ile-Ser), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Met), cyclic (
  • cyclic dipeptide is one or more selected from the group consisting of cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Thr-Pro), cyclic (Pro-His), cyclic (Ala-Pro), cyclic (Arg-Pro), cyclic (Phe-Pro), cyclic (Phe-Ala), cyclic (Pro-Pro), cyclic (hyPro-Pro), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Gly-Val), cyclic (Ala-Val), cyclic (Pro-Met), cyclic (hyPro-Leu), cyclic (hyPro-Ile), cyclic (Pro-Leu), cyclic (Pro-Ile) and cyclic (Pro-Val).
  • cyclic dipeptide is one or more selected from the group consisting of cyclic (Pro-Met), cyclic (Glu-His), cyclic (Ala-His), cyclic (Gly-His), cyclic (Tyr-His), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Glu-Gly), cyclic (Pro-His) and cyclic (Glu-Phe).
  • the cyclic dipeptide is one or more selected from the group consisting of cyclic (Pro-Met), cyclic (Glu-His), cyclic (Ala-His), cyclic (Gly-His), cyclic (Tyr-His), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Glu-Gly), cyclic (Pro-His
  • the taste enhancing composition according to any one of [1] to [4], further comprising one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acids.
  • the method includes:
  • a taste enhancing composition according to any one of [1] to [7], comprising blending the composition for enhancing taste into a food product.
  • the taste enhancing composition may be, for example, a salty taste enhancing composition.
  • cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acids.
  • organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.
  • a method for enhancing the taste of food comprising adding a cyclic dipeptide to the food.
  • cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and an organic acid.
  • cyclic dipeptide according to [21] or [22], wherein the cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acids.
  • cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acids.
  • organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.
  • the flavor enhancing composition according to one or more embodiments of the present invention can enhance the flavor of food by adding it to the food.
  • the method for producing a composition for enhancing flavor according to one or more embodiments of the present invention can produce the composition for enhancing flavor.
  • the food product according to one or more embodiments of the present invention is a food product with enhanced flavor.
  • the taste of the food can be enhanced by adding the taste enhancing composition to the food.
  • the peak area ratios of several cyclic dipeptides in unheated and heat-treated coriander are shown in the extracted ion chromatograms obtained by LC-MS/MS relative to an internal standard (L-lysine- 13 C 6 monohydrochloride at 47 ⁇ g/g).
  • the peak area ratios of several cyclic dipeptides in unheated and heat-treated coriander are shown in the extracted ion chromatograms obtained by LC-MS/MS relative to an internal standard (L-lysine- 13 C 6 monohydrochloride at 47 ⁇ g/g).
  • taste refers to the taste of a food, and can be, for example, one or more tastes selected from saltiness, sweetness, sourness, bitterness, umami, richness, sweet-umami, spicyness, astringency, flavor spread, and savory taste.
  • “Enhancing” taste refers to enhancing the taste felt when eating a food, and for example, refers to enhancing the weak taste felt when eating a food that contains a reduced amount of flavor components compared to normal (e.g., reduced-salt food).
  • the taste felt when eating food can be divided into three stages: the "top” taste felt first, the “middle” taste felt next, and the “last” taste felt last.
  • enhancing the taste refers to enhancing at least one of these tastes.
  • salty taste refers to the taste felt when eating salt (sodium chloride).
  • Salty taste includes the taste of salt itself and the taste felt when salt is combined with ingredients other than salt.
  • the top taste of foods containing salt includes the stimulating taste of salt, the "salty edge,” while middle tastes include “fullness” and “fragrantness,” and end tastes include a “complex metallic taste” and "aftertaste.”
  • Salty taste can also include the taste of "taste boost,” in which the taste of ingredients other than salt is enhanced by salt.
  • enhancing saltiness refers to enhancing at least one of these salty tastes (tastes).
  • the enhancement of taste is more preferably the enhancement of taste derived from one or more taste components selected from salt, sucrose, citric acid, tartaric acid, naringin, glutamic acid or a salt thereof, aspartic acid or a salt thereof, succinic acid or a salt thereof, inosinic acid or a salt thereof, guanylic acid or a salt thereof, glycine or a salt thereof, alanine or a salt thereof, chili pepper, black pepper, animal- or plant-derived extract, and seasoning.
  • the salt in the one or more taste components is exemplified by sodium salt.
  • the animal- or plant-derived extract is exemplified by one or more extracts selected from beef extract, chicken extract, pork extract, seafood extract, garlic extract, and onion extract.
  • the seasoning is exemplified by one or more selected from tomato paste, banana paste, apple paste, honey, soy sauce, miso, ketchup, Worcestershire sauce, mayonnaise, cheese, noodle soup, defatted soybeans, skimmed milk powder, yeast extract, protein hydrolysate, and curry powder.
  • enhanced taste more preferably refers to enhanced taste resulting from one or more flavor components in a food product that contains one or more flavor components, particularly in a food product that contains the one or more flavor components in amounts less than normal.
  • the first embodiment of the present invention comprises: A taste enhancing composition containing a cyclic dipeptide, Regarding.
  • the flavor enhancing composition according to this embodiment can enhance the flavor of a food by blending it with the food.
  • a food containing one or more flavor components as described above in a reduced amount compared to a food that does not contain the flavor enhancing composition according to this embodiment e.g., a reduced-salt food containing a reduced amount of salt compared to a food that does not contain the flavor enhancing composition
  • the cyclic dipeptide in the taste enhancing composition according to the present embodiment preferably contains one or more amino acids selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, alanine, serine, arginine, threonine, asparagine and methionine as constituent amino acids, and particularly preferably contains one or more amino acids selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine and alanine.
  • Cyclic dipeptides containing one or more amino acids selected from the group are preferred because they have a particularly high taste enhancing effect.
  • Specific examples of cyclic dipeptides containing one or more amino acids selected from the above group include preferably cyclic (Pro-Asn), cyclic (Pro-His), cyclic (Pro-Asp), cyclic (Pro-Pro), cyclic (Pro-Val), cyclic (Pro-Tyr), cyclic (Pro-Leu), cyclic (Pro-Ile), cyclic (Pro-Glu), cyclic (Pro-Gly), cyclic (Pro-Met), cyclic (Arg-Pro), cyclic (Thr-Pro), cyclic (hyPro-Pro), cyclic (Leu-Leu), cyclic (Ile-Leu), cyclic (Ile-Ile), cyclic (Leu-Asp), cyclic (Ile-Asp), cyclic (Ile-Ser), cyclic (Ile-Ser
  • cyclic dipeptides are particularly effective at enhancing taste.
  • Another preferred specific example of the cyclic dipeptide having a particularly high taste enhancing effect is one or more selected from the group consisting of cyclic (Pro-Met), cyclic (Glu-His), cyclic (Ala-His), cyclic (Gly-His), cyclic (Tyr-His), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Glu-Gly), cyclic (Pro-His) and cyclic (Glu-Phe), more preferably a mixture of five or more cyclic dipeptides selected from the group, and particularly preferably a mixture of all cyclic dipeptides in the group (wherein cyclic (Leu-His) and cyclic (Ile-His) include at least one of these, and cyclic (Leu-Val) and cyclic (Ile-
  • cyclic (Phe-Phe) and the like refer to a cyclic dipeptide consisting of two amino acids.
  • Leu/Ile refers to a mixture of one or both of leucine (Leu) and isoleucine (Ile).
  • cyclic (Leu/Ile-Val) refers to a mixture of one or both of cyclic (Leu-Val) and cyclic (Ile-Val).
  • hyPro refers to ⁇ -hydroxy-proline.
  • the amino acids constituting the cyclic dipeptide may be either L- or D-forms, or a mixture of L- and D-forms.
  • the enhancement of saltiness refers to enhancing one or more of the top, middle, and last tastes.
  • the profile of the enhancement of taste of cyclic dipeptides may differ depending on the difference in the constituent amino acids.
  • one or more cyclic dipeptides having the action of enhancing the top taste can be blended.
  • one or more cyclic dipeptides having the action of enhancing the middle taste can be blended, and in order to impart the action of enhancing the last taste, one or more cyclic dipeptides having the action of enhancing the last taste can be blended.
  • multiple cyclic dipeptides can be blended in combination according to the taste to be enhanced.
  • the taste enhancing composition according to this embodiment contains at least a cyclic dipeptide.
  • the taste enhancing composition according to this embodiment preferably contains, in addition to the cyclic dipeptide, one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and an organic acid.
  • the taste enhancing effect is further enhanced by the combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and an organic acid.
  • the organic acid in the taste enhancing composition according to this embodiment is preferably one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.
  • the cyclic peptide may be blended as a purified product of the cyclic dipeptide that is artificially produced or naturally derived, or may be blended as a naturally derived material containing the cyclic dipeptide.
  • the purified product of the cyclic dipeptide may be in a form containing the cyclic dipeptide at a high concentration, for example, in a form containing the cyclic dipeptide at a concentration of 30% by mass to 100% by mass, preferably 50% by mass to 100% by mass, and more preferably 75% by mass to 100% by mass.
  • Examples of naturally derived materials containing the cyclic dipeptide include spices and extracts thereof obtained by heating one or more spices selected from the group consisting of coriander, paprika, cumin, and asafoetida, and having an increased content of the cyclic dipeptide.
  • a preferred embodiment of the spice will be described with respect to the second embodiment of the present invention.
  • the taste enhancing composition according to this embodiment may consist only of the cyclic dipeptide or a naturally derived material containing the cyclic peptide, or may contain the cyclic dipeptide or a naturally derived material containing the cyclic peptide and other ingredients.
  • examples of other ingredients include one or more ingredients that have a taste enhancing effect, and one or more ingredients that are acceptable as food.
  • the taste enhancing composition according to this embodiment may be in the form of a powder, granules, paste, liquid, etc., and may contain one or more ingredients that are acceptable as food, such as excipients and carriers, as necessary to obtain the desired form.
  • the taste enhancing composition according to this embodiment can contain the cyclic dipeptide in a proportion of preferably 0.1% by mass or more and 100% by mass or less, more preferably 1% by mass or more and 100% by mass or less, even more preferably 5% by mass or more and 100% by mass or less, and particularly preferably 10% by mass or more and 100% by mass or less.
  • the taste enhancing composition according to the present embodiment contains the naturally derived material including the cyclic dipeptide
  • the naturally derived material can be contained in an amount of preferably 30% by mass or more and 100% by mass or less, more preferably 50% by mass or more and 100% by mass or less, even more preferably 80% by mass or more and 100% by mass or less, and most preferably 95% by mass or more and 100% by mass or less.
  • the naturally occurring material containing the cyclic dipeptide in the taste enhancing composition according to this embodiment is preferably in powder form, with a particle size of, for example, 1000 ⁇ m or less.
  • the particle size can be determined from the mesh size of a standard sieve specified in JIS.
  • the naturally occurring material containing the cyclic dipeptide may further contain oils and fats.
  • a second embodiment of the present invention comprises: A method for producing a taste enhancing composition according to a first embodiment of the present invention, comprising the steps of: increasing the cyclic dipeptide in one or more spices selected from the group consisting of coriander, paprika, cumin and asafoetida; A method comprising: Regarding.
  • the inventors have found that when the spices are heated, the amount of cyclic dipeptides in the spices increases.
  • the inventors have also found that when the spices are heated, in addition to the cyclic dipeptides, one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acids also increase.
  • Coriander refers to the seeds of Coriander (Coriandrum sativum), an annual plant in the Umbelliferae family.
  • the coriander to be heated may be whole coriander seeds or a pulverized product obtained by pulverizing whole seeds, but whole seeds are preferred.
  • Paprika refers to a spice (paprika powder) made by drying and powdering the skin and flesh of the fruit of Capsicum annuum var. grossum, a perennial plant of the Solanaceae family.
  • paprika refers to paprika powder that can be used as a spice, unless otherwise specified. Paprika powder can be heated.
  • Cumin refers to the seeds of Cuminum cyminum, an annual plant of the Apiaceae family.
  • the cumin to be heated may be whole cumin seeds or a ground product obtained by crushing whole seeds, but whole seeds are preferred.
  • asafoetida refers to a dried resin extracted from asafoetida (Ferula assa-foetida), a plant of the Umbelliferae family, which is used as a spice.
  • Asafoetida used as a spice may further contain additives such as gum arabic and rice flour in addition to asafoetida resin.
  • powdered asafoetida containing asafoetida resin and additives is commercially available as a spice.
  • asafoetida refers to asafoetida used as a spice, which may contain the additives, unless otherwise specified.
  • the mass of asafoetida used in each embodiment described below is expressed as a mass converted assuming that the content of asafoetida resin is 12% by mass. For example, if the asafoetida resin content of the asafoetida used is 6% by mass, then "200 mg of heat-treated asafoetida" is 400 mg in mass when calculated assuming that the asafoetida resin content is 12% by mass.
  • the process of heating one or more selected from the group consisting of coriander, paprika, and cumin is preferably a heat treatment including heating one or more selected from the group consisting of coriander, paprika, and cumin without adding fats or oils (hereinafter sometimes referred to as "first heat treatment"), or a heat treatment including heating one or more selected from the group consisting of coriander, paprika, and cumin together with fats or oils (hereinafter sometimes referred to as "second heat treatment").
  • the preferred embodiment of the first heat treatment for one or more selected from the group consisting of coriander, paprika, and cumin is described below.
  • the amount of water to be blended is not particularly limited, but preferably, the amount of water to be blended can be appropriately set so that the water activity after heating falls within the range described below.
  • the temperature and time are preferably set so that the heating value is preferably 100 or more, more preferably 1000 or more, even more preferably 5000 or more, and furthermore, the heating value is preferably 100 or more and 20000 or less.
  • the temperature and time are preferably set so that the heating value is preferably 15 or more, preferably 50 or more, preferably 60 or more, preferably 100 or more, preferably 130 or more, even more preferably 190 or more, and most preferably 200 or more, and furthermore, the heating value is preferably 15 or more and 1000 or less, preferably 15 or more and 600 or less, more preferably 60 or more and 500 or less, even more preferably 100 or more and 410 or less, and particularly preferably 190 or more and 410 or less.
  • One or more selected from the group consisting of coriander, paprika, and cumin that are heat-treated under conditions in which the heating value falls within the above range is particularly preferred because it contains a large amount of cyclic dipeptides.
  • Heating conditions that result in a heating value within the above range preferably include heating at the temperature and time described below.
  • the heating value is calculated by integrating the value expressed by the formula (hereinafter referred to as the "CV value") over the heating time (minutes).
  • the heating of one or more selected from the group consisting of coriander, paprika, and cumin can be performed at a temperature of, for example, 110°C or higher, preferably 120°C or higher, more preferably 125°C or higher, and particularly preferably 128°C or higher, for example, 110°C or higher and 300°C or lower, preferably 120°C or higher and 250°C or lower, preferably 125°C or higher and 200°C or lower, preferably 128°C or higher and 180°C or lower, preferably 128°C or higher and 160°C or lower, and more preferably 128°C or higher and 150°C or lower.
  • the heating of one or more selected from the group consisting of coriander, paprika, and cumin can be performed so that the heating time in the above temperature range is, for example, 5 minutes or more, preferably 10 minutes or more, preferably 20 minutes or more, more preferably 30 minutes or more, for example, 5 minutes or more and 120 minutes or less, preferably 10 minutes or more and 90 minutes or less, and more preferably 20 minutes or more and 75 minutes or less.
  • the first heat treatment of coriander may be a heat treatment in an open system that is not sealed, or a heat treatment under pressurized sealed conditions, but is preferably a heat treatment in an open system that is not sealed.
  • Heat treatment of coriander in an open system can be performed by heating using superheated steam or heating using an oven.
  • heating devices used for heat treatment of coriander include a superheated steam vortex mixer, an oven, a flat-bottom roaster, a vertical heating mixer, a microwave heating device, etc.
  • the first heat treatment of one or more selected from the group consisting of paprika and cumin can be carried out under pressure conditions with a gauge pressure of preferably 0.05 MPa or more, more preferably 0.2 MPa or more. There is no particular upper limit to the pressure during heating, but from the standpoint of the equipment, a gauge pressure of 0.6 MPa or less is preferred.
  • the first heating treatment for one or more selected from the group consisting of paprika and cumin can be performed using various means such as pressurized sealed heating, superheated steam heating, oven heating, etc., but pressurized sealed heating is preferably used.
  • heating devices used for pressurized sealed heating include pressurized sealed kettles and retort sterilizers. When using heating other than pressurized sealed heating, ovens, flat-bottom roasters, vertical heating mixers, microwave heating devices, superheated steam vortex mixers, superheated steam sterilizers, etc. can be used as appropriate.
  • one or more spices selected from the group consisting of coriander, paprika, and cumin are heated together with fats and oils.
  • the heat-treated spices obtained by the second heat treatment are preferable because they have a particularly strong effect of enhancing flavor.
  • the amount of fats and oils used in the second heat treatment is not particularly limited, but for example, 10 parts by mass or more and 500 parts by mass or less, preferably 50 parts by mass or more and 200 parts by mass or less of fats and oils can be used per 100 parts by mass of the spices.
  • the fats and oils are not particularly limited as long as they are edible fats and oils derived from plants, animals, etc. that are acceptable as foods.
  • the fats and oils may have their melting points adjusted by techniques such as transesterification of fatty acids and hydrogenation.
  • the temperature and time of the second heat treatment are preferably set so that the heating value defined above is preferably 0.3 or more, more preferably 0.3 or more and 6000 or less.
  • the range of heating value in the second heat treatment for paprika is, for example, 0.3 or more and 6000 or less, preferably 2.5 or more and 450 or less, more preferably 30 or more and 110 or less.
  • the range of heating value in the second heat treatment for coriander or cumin is, for example, 1 or more and 6000 or less, preferably 20 or more and 4000 or less, more preferably 100 or more and 1000 or less, particularly preferably 200 or more and 600 or less.
  • the spices heat-treated under conditions in which the heating value falls within the above range are particularly preferred because they contain a large amount of cyclic dipeptides.
  • the heating conditions in which the heating value falls within the above range can preferably include heating at the temperature and time described below.
  • a mixture of one or more spices selected from the group consisting of coriander, paprika, and cumin and fats and oils can be heated at a temperature of, for example, 90°C or higher, preferably 100°C or higher, more preferably 120°C or higher, more preferably 130°C or higher, more preferably 140°C or higher, more preferably 150°C or higher, for example, 90°C or higher and 230°C or lower, preferably 100°C or higher and 220°C or lower, more preferably 120°C or higher and 220°C or lower, more preferably 130°C or higher and 210°C or lower, more preferably 150°C or higher and 210°C or lower, particularly preferably 160°C or higher and 210°C or lower.
  • the second heat treatment can be performed such that the heating time in the temperature range is, for example, 1 minute or higher, preferably 2 minutes or higher, preferably 3 minutes or higher, for example, 1 minute or higher and 10 minutes or less, preferably 2 minutes or higher and 7 minutes or less, more preferably 3 minutes or higher and 7 minutes or less.
  • the spices obtained by the second heat treatment under these conditions are preferable because they contain a particularly large amount of cyclic dipeptides.
  • the second heat treatment of one or more spices selected from the group consisting of coriander, paprika, and cumin can be carried out in an open or closed system.
  • the second heat treatment of one or more spices selected from the group consisting of coriander, paprika, and cumin can be performed by heating using superheated steam or heating using an oven.
  • heating devices used in the second heat treatment include ovens, flat-bottom roasters, vertical heating mixers, microwave heating devices, etc.
  • the one or more spices selected from the group consisting of coriander, paprika, and cumin heated by the first heating process or the second heating process may be subjected to a further aging process after the heating process.
  • the aging process is a process of storing the spices in an air atmosphere at a temperature higher than room temperature, for example, in a sealed container filled with air, at 30°C to 50°C, preferably 35°C to 45°C, for example, for 5 to 15 days, preferably 7 to 10 days.
  • the water activity of one or more spices selected from the group consisting of coriander, paprika, and cumin heated by the first heat treatment or the second heat treatment, measured at 25°C, is preferably 0.85 or less, more preferably 0.81 or less, and particularly preferably 0.80 or less.
  • the treatment for heating asafoetida is also preferably a heating treatment including heating asafoetida without adding fats or oils (hereinafter sometimes referred to as the "first heating treatment"), or a heating treatment including heating asafoetida together with fats or oils (hereinafter sometimes referred to as the "second heating treatment").
  • first heating treatment a heating treatment including heating asafoetida without adding fats or oils
  • second heating treatment a heating treatment including heating asafoetida together with fats or oils
  • the temperature and time of the first heat treatment of Asafoetida are preferably set so that the heating value defined above is preferably 15 or more, more preferably 50 or more, even more preferably 100 or more, and further preferably so that the heating value is preferably 15 or more and 1000 or less, more preferably 50 or more and 500 or less, even more preferably 100 or more and 410 or less, and most preferably 100 or more and 300 or less.
  • a preferred range of the heating value is, for example, 50 or more and 300 or less.
  • Asafoetida heat-treated under conditions in which the heating value falls within the above range is particularly preferred because it contains a large amount of cyclic dipeptides.
  • the heating conditions in which the heating value falls within the above range may preferably include heating at the temperature and time described below.
  • heating can be performed at a temperature of, for example, 110°C or higher, preferably 120°C or higher, more preferably 125°C or higher, and particularly preferably 128°C or higher, and for example, 100°C or higher and 180°C or lower, preferably 120°C or higher and 160°C or lower, more preferably 125°C or higher and 150°C or lower, and particularly preferably 128°C or higher and 150°C or lower.
  • the first heat treatment can be performed so that the heating time in the above temperature range is, for example, 20 minutes or higher, preferably 30 minutes or higher, for example, 20 minutes or higher and 120 minutes or lower, preferably 30 minutes or higher and 90 minutes or lower, and more preferably 30 minutes or higher and 60 minutes or lower.
  • Asafoetida obtained by the first heat treatment under these conditions is preferable because it contains a large amount of cyclic dipeptides.
  • the first heating process can be carried out under pressure conditions where the gauge pressure is preferably 0.05 MPa or more, and more preferably 0.2 MPa or more. There is no particular upper limit to the pressure during heating, but from the standpoint of the equipment, a gauge pressure of 0.6 MPa or less is preferable.
  • asafoetida alone may be used, or a mixture of asafoetida and water may be used.
  • the amount of water in the mixture of asafoetida and water is not particularly limited, but preferably, the amount of water can be appropriately set so that the water activity after heating falls within the range described below.
  • pressurized sealed heating For the first heating treatment, various means such as pressurized sealed heating, superheated steam heating, oven heating, etc. can be used, but pressurized sealed heating is preferably used.
  • heating devices used for pressurized sealed heating include pressurized sealed kettles and retort sterilizers. When using heating other than pressurized sealed heating, ovens, flat-bottom roasters, vertical heating mixers, microwave heating devices, superheated steam vortex mixers, superheated steam sterilizers, etc. can be used as appropriate.
  • asafoetida is heated together with fats and oils.
  • the heat-treated asafoetida obtained by the second heating process is particularly preferred because it has a strong effect of enhancing flavor.
  • the amount of fats and oils used in the second heating process is not particularly limited, but for example, 10 parts by mass or more and 500 parts by mass or less, preferably 50 parts by mass or more and 200 parts by mass or less of fats and oils can be used per 100 parts by mass of asafoetida.
  • the fats and oils are not particularly limited as long as they are edible fats and oils derived from plants, animals, etc. that are acceptable as foods.
  • the fats and oils may have their melting points adjusted by techniques such as transesterification of fatty acids and hydrogenation.
  • the temperature and time of the second heat treatment are preferably set so that the heating value defined above is preferably 5 or more, more preferably 10 or more, and even more preferably 20 or more.
  • the upper limit of the heating value in the second heat treatment is, for example, 100 or less, preferably 50 or less, and more preferably 40 or less. That is, the heating value is preferably 5 or more and 100 or less, more preferably 10 or more and 50 or less, and even more preferably 20 or more and 40 or less.
  • Asafoetida heat-treated under conditions in which the heating value falls within the above range is particularly preferred because it contains a large amount of cyclic dipeptides.
  • the heating conditions in which the heating value falls within the above range can preferably include heating at the temperature and time described below.
  • the mixture of asafoetida and fats and oils can be heated at a temperature of, for example, 90°C or higher, preferably 100°C or higher, more preferably 110°C or higher, more preferably 120°C or higher, and particularly preferably 125°C or higher, for example, 30 minutes or longer and 180°C or lower, preferably 100°C or higher and 160°C or lower, more preferably 110°C or higher and 150°C or lower.
  • the second heating treatment can be performed such that the heating time in the above temperature range is, for example, 2 minutes or longer, preferably 3 minutes or longer, for example, 2 minutes or longer and 10 minutes or less, preferably 3 minutes or longer and 7 minutes or less.
  • Asafoetida obtained by the second heating treatment under these conditions is preferable because it contains a particularly large amount of cyclic dipeptides.
  • the second heat treatment can be carried out in either an open or closed system.
  • the second heating treatment can be carried out by heating using superheated steam or heating using an oven.
  • heating devices used in the second heating treatment include ovens, flat-bottom roasters, vertical heating mixers, microwave heating devices, etc.
  • the water activity of the asafoetida obtained by heat treatment, measured at 25°C, is preferably 0.70 or less, more preferably 0.60 or less, and particularly preferably 0.50 or less.
  • one or more selected from the group consisting of the cyclic dipeptide, sulfurol, sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acid described in relation to the flavor enhancing composition according to the first embodiment of the present invention are increased.
  • the cyclic dipeptide is preferably a cyclic dipeptide containing one or more constituent amino acids selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, alanine, serine, arginine, threonine, asparagine, and methionine, and is particularly preferably a cyclic dipeptide containing one or more constituent amino acids selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, and alanine, and preferred specific examples thereof are as described above.
  • Cyclic dipeptides that increase when coriander is heated typically include one or more selected from the cyclic dipeptides assigned coriander IDs: 1 to 60 in the table at the end of the examples. Furthermore, heating coriander increases one or more selected from sulfurol, sulfurol acetate, and organic acids, and in particular increases one or more selected from sulfurol, sulfurol acetate, tartaric acid, malic acid, and trans-aconitic acid.
  • Cyclic dipeptides that increase when paprika is heated include typically one or more selected from the cyclic dipeptides assigned paprika IDs: 1 to 48 in the table at the end of the examples. Furthermore, heating paprika increases one or more selected from sulfurol, sulfurol acetate, and organic acids, and in particular increases one or more selected from sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, trans-aconitic acid, and tartaric acid.
  • Cyclic dipeptides that increase when cumin is heated typically include one or more selected from the cyclic dipeptides assigned cumin IDs: 1 to 32 in the table at the end of the examples. Furthermore, heating cumin increases one or more selected from sulfurol, sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and organic acids, and in particular increases one or more selected from sulfurol, sulfurol acetate, cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.
  • Cyclic dipeptides that increase when asafoetida is heated include typically one or more selected from the cyclic dipeptides assigned Asafoetida IDs: 1 to 22 listed in the table at the end of the Examples. Furthermore, heating asafoetida increases one or more selected from sulfurol, sulfurol acetate, and organic acids, and in particular increases one or more selected from sulfurol, tartaric acid, malic acid, and citric acid.
  • the method for producing a flavor enhancing composition may use the spices themselves after heating as the flavor enhancing composition, or may further include a step of extracting, concentrating or purifying the cyclic dipeptide from the spices after heating, or may further include a step of processing the spices themselves after heating or the cyclic dipeptide extracted, concentrated or purified from the spices after heating into a form such as powder, granules, paste or liquid.
  • a third embodiment of the present invention comprises: A food product containing the taste enhancing composition according to the first embodiment of the present invention; Regarding.
  • the food according to this embodiment is a food with enhanced taste.
  • the food according to this embodiment is preferably a food that contains one or more taste components as described above in a reduced amount compared to normal (e.g. a reduced-salt food that contains less salt than normal).
  • the food according to this embodiment can preferably contain one or more taste components, and more preferably can contain salt.
  • the amount of the flavor enhancing composition according to the first embodiment of the present invention in the food according to this embodiment is not particularly limited and can be adjusted appropriately depending on the form of the food.
  • the flavor enhancing composition according to the first embodiment of the present invention can be blended so that the cyclic dipeptide is preferably 0.005 g or more, more preferably 0.010 g or more, particularly preferably 0.020 g or more, preferably 0.005 g or more and 50.0 g or less, more preferably 0.010 g or more and 20.0 g or less, particularly preferably 0.020 g or more and 10.0 g or less per 100,000 g of salt equivalent of the food.
  • a fourth embodiment of the present invention comprises: A method for producing a food product comprising blending a taste enhancing composition according to a first embodiment of the present invention into the food product, Methods for enhancing the flavor of foods, Regarding.
  • the method according to this embodiment can enhance the taste of food, and can therefore be suitably used to enhance the taste of food that contains one or more of the above-mentioned flavor components in reduced amounts compared to normal (e.g., reduced-salt foods that contain less salt than normal).
  • the amount of the taste enhancing composition according to the first embodiment of the present invention is not particularly limited and can be adjusted appropriately depending on the form of the food.
  • the taste enhancing composition according to the first embodiment of the present invention can be blended so that the cyclic dipeptide is preferably 0.005 g or more, more preferably 0.010 g or more, particularly preferably 0.020 g or more, preferably 0.020 g or more and 50.0 g or less, more preferably 0.010 g or more and 20.0 g or less, particularly preferably 0.020 g or more and 10.0 g or less, per 100,000 g of salt equivalent of the food.
  • the type of food is not limited, but examples include curry sauce, stew sauce, meat products, prepared foods, confectionery, and the like.
  • the food may be a food that contains one or more of the above-mentioned taste components in a reduced amount compared to normal.
  • the food may be a food that contains one or more taste components, such as salt.
  • One or more further embodiments of the present invention include Use of cyclic dipeptides to enhance the taste of foods; A method for enhancing the taste of food, comprising blending a cyclic dipeptide into the food; Cyclic dipeptides for use in enhancing the taste of food, or Use of a cyclic dipeptide in the manufacture of an additive for enhancing the taste of food. Regarding.
  • the cyclic dipeptide can preferably have the characteristics described for the cyclic dipeptide contained in the taste enhancing composition according to the first embodiment of the present invention.
  • the cyclic dipeptide may be a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, ⁇ -terpinen-7-al, and an organic acid.
  • the cyclic dipeptide can be contained in one or more heat-treated spices selected from the group consisting of coriander, paprika, cumin, and asafoetida.
  • the heat-treated spices can preferably have the characteristics described for the heat-treated spices that can be contained in the flavor enhancing composition according to the first embodiment of the present invention.
  • the food product may preferably have the characteristics described in relation to the third and fourth embodiments of the present invention.
  • the cyclic dipeptide is preferably blended with the food in an amount of preferably 0.005 g or more, more preferably 0.010 g or more, particularly preferably 0.020 g or more, preferably 0.005 g or more and 50.0 g or less, more preferably 0.010 g or more and 20.0 g or less, particularly preferably 0.020 g or more and 10.0 g or less per 100,000 g of salt equivalent of the food, and can be used to enhance the taste of the food.
  • Experiment 1 Flavor enhancement effect of heat-treated coriander and cyclic dipeptides contained therein 1.1.
  • Preparation of heat-treated coriander Coriander was prepared by heat-treating coriander under the conditions shown in the table below.
  • the heating value is the value obtained by integrating the CV value according to the above formula ("reference temperature” is 110°C, "Z value” is 30 (°C)) by the heating time (minutes).
  • the temperature and time listed in the heating conditions column are the maximum temperature reached and the holding time, while the calculation of the heating value also took into account the change in temperature over time, including the temperature and time when the temperature was rising and falling.
  • the control was coriander that had not been heat-treated, including heat sterilization.
  • coriander The heat treatment of coriander was carried out by placing 100 g of whole coriander seeds in an open container (oven) under the heating conditions and heating values shown in Table 1.
  • the water activity (Aw) of unheated (control) and heated coriander was measured under the temperature conditions shown in the table above.
  • the test tube was stirred at room temperature and 1,800 rpm for 30 minutes using a high-speed shaker (CM-1000, Tokyo Rikakikai), and after centrifugation, 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filtration Device 3K, Nippon Pall).
  • the ultrafiltration filter was centrifuged at room temperature at 15,000 rpm for 20 minutes, after which 0.5 mL of ultrapure water was added to the filtrate below the filter and vortexed for 10 seconds.
  • Coriander ID is a number identifying the 60 cyclic dipeptides that were found to be increased in heat-treated coriander compared to unheated coriander.
  • A1 and A2 represent the two amino acids that constitute each cyclic dipeptide identified by “Compound ID” and "Coriander ID.”
  • the peak area ratios of the cyclic peptides detected in the LC-MS/MS samples prepared from each sample relative to the internal standard are shown in Figures 1 and 2 and in the table below.
  • the peak area ratios of sulfurol, sulfurol acetate, and organic acids (tartaric acid, malic acid, and trans-aconitic acid) detected in the LC-MS/MS samples prepared from each sample relative to the internal standard are shown in Figure 3. It was confirmed that heating coriander significantly increased the contents of the 60 cyclic dipeptides shown in the table above, as well as sulfurol, sulfurol acetate, and organic acids (tartaric acid, malic acid, and trans-aconitic acid).
  • the salt equivalent per 100g of this curry roux was 10.6g.
  • the salt equivalent per 100g of this reduced-salt curry roux was 7.7g.
  • powdered heated coriander or unheated coriander prepared in 1.1 above, or the aqueous cyclic dipeptide solution prepared in (3) (corresponding to heated coriander) was added to a final concentration of 0.2% (w/w), and a sensory evaluation was performed.
  • the "enhancement of flavor” was scored as follows: 1, 2, 3, 4, and 5 points. Three evaluators evaluated the flavor of each sample in increments of 0.1 points, and the average score was calculated. 1 point: Taste is about the same as reduced-salt curry roux 2 points: Taste is slightly stronger than reduced-salt curry roux 3 points: Taste is stronger than reduced-salt curry roux 4 points: Taste is much stronger than reduced-salt curry roux 5 points: Taste is about the same as regular curry roux
  • An average score of 1.0 or less was designated an "F”
  • 1.1 to 1.9 was designated a “C”
  • 2.0 to 2.5 was designated a “B”
  • 2.6 to 2.9 was designated an "A”
  • 3.0 or more was designated an “AA.”
  • the evaluation results are shown in the table below.
  • the hot water reduced-salt curry roux to which the cyclic dipeptides of Examples 1 to 14 were added gave a stronger impression of "enhanced flavor" compared to reduced-salt curry roux to which no cyclic dipeptides were added, and in particular the hot water reduced-salt curry roux to which the cyclic dipeptides of Examples 2, 3, 7, 11, 13 and 14 were added gave a taste similar to that of regular hot water curry roux. Furthermore, the hot water reduced-salt curry roux to which heated coriander was added gave a stronger impression of "enhanced flavor" compared to reduced-salt curry roux to which unheated coriander (control) was added.
  • Flavor enhancement by heat-treated paprika 2.1. Preparation of heat-treated paprika Paprika was prepared by heat-treating paprika powder under the conditions shown in the table below. As described above, the heating value is the value obtained by integrating the CV value according to the above formula ("reference temperature” is 110°C, "Z value” is 30 (°C)) over the heating time (minutes). The temperature and time listed in the heating conditions column are the maximum temperature reached and the time it was maintained, while the heating value was calculated based on the change in temperature over time, including the temperature and time when the temperature was rising and falling.
  • Comparative example 201 is paprika powder that has not been heat-treated, including heat sterilization.
  • Comparative Example 202 was prepared by aging the paprika powder of Comparative Example 201 at 40°C for 8 days using the same method as in Examples 207 to 210 below.
  • Heating of paprika powder at a specified temperature and time without adding water was carried out as follows. 100 g of paprika powder was filled into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was performed under a gauge pressure of 0.2 MPa.
  • Heating of paprika powder to a specified temperature and time with water was carried out as follows. 100 g of paprika powder and 10 g of water were filled into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was performed under a gauge pressure of 0.2 MPa.
  • the paprika powders of Examples 207 to 210 were heated under specified conditions, filled into an aluminum foil pouch, and sealed to trap air. The sealed pouch was stored at 40°C for 8 days to mature.
  • the paprika powders of Examples 211 to 216 were heated in oil according to the following procedure. 100 g of palm oil (melting point 45°C) was heated, and when it reached 80°C, 100 g of paprika powder was mixed in, and the resulting mixture was heated to the specified temperature shown in the above table while stirring, and was held at that temperature for a specified time, and then the mixture was cooled. Cooling was performed while stirring until the mixture reached about 60°C so that the paprika powder did not separate in the mixture, and thereafter the mixture was kept in a refrigerator until it solidified. Note that "reaching temperature" in Examples 211 to 213 means that heating was stopped and cooling was started immediately when the mixture reached the specified temperature.
  • the water activity (Aw) of the paprika powders of Comparative Example 201 and Examples 201 to 210 was measured under the temperature conditions shown in the above table.
  • Flavor enhancing effect Regular curry roux and reduced-salt curry roux were prepared according to the procedures described in 1.3. (1) and (2) above. Two samples were prepared by dissolving 44 g of the reduced-salt curry roux described in 1.3.(2) above in 300 g of boiling water.
  • paprika powder from the comparative example or example was added to give a final concentration of 0.0464% by mass.
  • the taste was scored as 1, 2, 3, 4, or 5 points as follows, and three evaluators evaluated the taste of each sample in increments of 0.1 points to calculate the average score.
  • L-lysine- 13 C 6 monohydrochloride was added at 47 ⁇ g/g and ribitol was added at 99 ⁇ g/g.
  • the test tube was stirred at room temperature and 1,800 rpm for 30 minutes using a high-speed shaker (CM-1000, Tokyo Rikakikai), and after centrifugation, 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filter Device 3K, Nippon Pole).
  • the ultrafiltration filter was centrifuged at room temperature and 15,000 rpm for 20 minutes, after which 0.5 mL of ultrapure water was added to the filtrate under the filter and vortexed for 10 seconds.
  • the above-mentioned 200 mg paprika sample refers to the mass converted into a paprika sample excluding fats and oils, and refers to 200 mg as the mass of the heat-treated paprika samples of Examples 201 to 210 in which only paprika or a mixture of paprika and water was heat-treated, and refers to 400 mg as the mass of the heat-treated paprika samples of Examples 211 to 216 in which a mixture of paprika and fats and oils was heat-treated.
  • cyclic Gly-His
  • cyclic Gly-Ser
  • cyclic hyPro-Pro
  • cyclic Gly-Val
  • cyclic Tyr-Asp
  • cyclic Al-Asp
  • Foods such as curry shown in the "Food" column of the table below were prepared using a commercially available instant food kit. To facilitate evaluation of flavor enhancement, each food was prepared using approximately 1.2 times the amount of water specified in the kit. Each of the prepared foods was mixed with heated paprika powder of Example 203 to a final concentration in the range of 0.03 to 0.07% (w/w) to prepare a sample. Each of the above foods without added paprika powder served as a negative control sample. Additionally, each food was prepared as a positive control sample using the amount of water specified in the kit.
  • the scores were determined as follows: 1, 2, 3, 4, and 5. The taste intensity of each sample was evaluated by three evaluators in increments of 0.5 points, and the average score was calculated. 1 point: Taste similar to the negative control sample 2 points: Taste slightly stronger than the negative control sample 3 points: Taste slightly stronger than the negative control sample 4 points: Taste slightly stronger than the negative control sample 5 points: Taste similar to the positive control sample
  • Example 203 The evaluation results are shown in the table below. It was confirmed that the heat-treated paprika powder of Example 203 has a high effect of enhancing the flavor of various food ingredients.
  • Experiment 3 Flavor enhancement effect of heat-treated cumin 3.1. Preparation of heat-treated cumin Whole cumin seeds (cumin seeds) were heat-treated under the conditions shown in the table below.
  • the heating value is the value obtained by integrating the CV value according to the above formula ("reference temperature” is 110°C, "Z value” is 30 (°C)) by the heating time (minutes).
  • the temperature and time listed in the heating condition column are the maximum temperature reached and the time it was maintained, while the calculation of the heating value also took into account the change in temperature over time, including the temperature and time when the temperature was rising and falling.
  • Comparative example 301 is cumin seeds that have not been heat-treated, including heat sterilization.
  • Cumin seeds were heated to a specified temperature and time without adding water as follows: 100 g of cumin seeds were packed into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was carried out under a gauge pressure of 0.2 MPa.
  • Cumin seeds were heated with water to a specified temperature and time as follows: 100 g of cumin seeds and 10 g of water were packed in an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was carried out under a gauge pressure of 0.2 MPa.
  • the cumin seeds of Examples 307, 308, 313, and 314 were heated and then crushed and aged according to the following procedure.
  • the heated cumin seeds were ground into powder using a stamp mill for 3 minutes per 20 g.
  • the powder was then filled into an aluminum foil pouch and sealed to contain air.
  • the sealed pouch was stored at 40° C. for 8 days to mature.
  • the cumin in the comparative examples and examples other than Examples 307, 308, 313, and 314 was also ground and powdered under the same conditions and used as samples for the following water activity measurements, confirmation of flavor enhancement effects, and component analysis.
  • the cumin in Examples 307, 308, 313, and 314 was used as it was as a sample after aging.
  • Unheated cumin seeds were ground into powder using a stamp mill for 5 minutes per 75g.
  • the taste (“salt angle at the top” and “fullness in the middle”) was scored as 1, 2, 3, 4, or 5 points as follows, and three evaluators evaluated the taste of each sample in increments of 0.1 points to calculate the average score.
  • the ultrafiltration filter was centrifuged at room temperature and 15,000 rpm for 20 minutes, and then 0.5 mL of ultrapure water was added to the filtrate under the filter and vortexed for 10 seconds.
  • the above 200 mg of cumin sample means the mass converted into a cumin sample excluding fats and oils, and means 200 mg of the mass of the heat-treated cumin samples of Examples 301 to 314 in which only cumin or a mixture of cumin and water was heat-treated, and means 400 mg of the mass of the heat-treated cumin samples of Examples 315 to 319 in which a mixture of cumin and fats and oils was heat-treated.
  • CM-1000 Tokyo Rikakikai Co., Ltd.
  • the above 15 mg of cumin sample means the mass converted into the cumin sample excluding fats and oils, and means 15 mg as the mass of the heat-treated cumin samples of Examples 301 to 314 in which only cumin or a mixture of cumin and water was heat-treated, and means 30 mg as the mass of the heat-treated cumin samples of Examples 315 to 319 in which a mixture of cumin and fats and oils was heat-treated.
  • cyclic (Phe-Tyr), cyclic (Phe-Ala), cyclic (Tyr-Ser), cyclic (Leu/Ile-Ser), cyclic (Ala-Tyr), cyclic (Gly-Tyr), cyclic (Ala-Pro), cyclic (Gly-Val), cyclic (hyPro-Pro) and cyclic (Glu-Glu) are components specific to heat-treated cumin that are not contained in unheated cumin (below the detection limit).
  • Example 305 The evaluation results are shown in the table below. It was confirmed that the heat-treated cumin of Example 305 has a high effect of enhancing the flavor of various food ingredients.
  • Experiment 4 Flavor enhancement effect of heat-treated asafoetida 4.1. Preparation of heat-treated asafoetida The asafoetida powder used in the following experiments contained 12% by mass of asafoetida (resin), 60% by mass of gum arabic, and 28% by mass of rice flour. The asafoetida powder was prepared by dissolving asafoetida, mixing it with gum arabic and rice flour, drying, and then powdering. The Asafoetida powder was heat-treated under the conditions shown in the table below.
  • the heating value is the value obtained by integrating the CV value according to the above formula ("reference temperature” is 110°C, and “Z value” is 30 (°C)) with respect to the heating time (minutes).
  • the temperature and time listed in the heating condition column are the maximum temperature reached and the holding time thereat, while the calculation of the heating value also takes into account the change in temperature over time, including the temperature and time during temperature rise and fall.
  • Comparative example 401 is asafoetida powder that has not been heat-treated, including heat sterilization.
  • Heating of Asafoetida powder in Example 401 was carried out according to the following procedure. 100 g of Asafoetida powder was filled into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was carried out under a gauge pressure of 0.2 MPa.
  • Heating of Asafoetida powder in oil in Examples 402, 403 and 404 was carried out according to the following procedure.
  • Asafoetida powder containing 12% by mass of asafoetida
  • palm oil melting point 45°C
  • Asafoetida powder and palm oil were mixed in a mass ratio of 50:50, heated with stirring at a specified temperature for a specified time, and then cooled to obtain asafoetida heated in oil that was in the form of a solid curry roux at room temperature.
  • the water activity (Aw) of the Asafoetida powder of Comparative Example 401 was measured under the temperature conditions shown in the table above.
  • the asafoetida of the comparative example or the example was added so that the final concentration was 0.00077% by mass.
  • the amount of asafoetida heated in oil added in Example 402, 403, or 404 is the amount added including the oil and fat.
  • the "enhancement of flavor” was scored as follows: 1, 2, 3, 4, and 5 points. Three evaluators evaluated the flavor of each sample in increments of 0.1 points, and the average score was calculated. 1 point: Taste is about the same as reduced-salt curry roux 2 points: Taste is slightly stronger than reduced-salt curry roux 3 points: Taste is stronger than reduced-salt curry roux 4 points: Taste is much stronger than reduced-salt curry roux 5 points: Taste is about the same as regular curry roux
  • the test tube was stirred at room temperature, 1,800 rpm, for 30 minutes using a high-speed shaker (CM-1000, Tokyo Rikakikai), and 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filtration Device 3K, Nippon Pole) after centrifugation.
  • the ultrafiltration filter was centrifuged at room temperature, 15,000 rpm x 20 minutes, and 0.3 mL of the filtrate under the filter was loaded onto a solid-phase extraction column InertSep C18 (100 mg/1 mL, GL Science), and the eluate was collected.
  • cyclic (Val-Ser), cyclic (Pro-Pro) and cyclic (Pro-Glu) are components specific to heat-treated asafoetida that are not present in unheated asafoetida (below the detection limit).
  • Example 403 The evaluation results are shown in the table below. It was confirmed that the heat-treated asafoetida of Example 403 has a high effect of enhancing the flavor of various food ingredients.
  • the following table shows 64 cyclic dipeptides that were confirmed to be increased in heat-treated coriander, paprika, cumin, and asafoetida compared to unheated ones.
  • each cyclic dipeptide was assigned a "compound ID”
  • cyclic dipeptides confirmed to be increased in heat-treated coriander were assigned a "coriander ID.”
  • cyclic dipeptides confirmed to be increased in heat-treated paprika were assigned a "paprika ID”
  • cyclic dipeptides confirmed to be increased in heat-treated cumin were assigned a "cumin ID”
  • cyclic dipeptides confirmed to be increased in heat-treated asafoetida were assigned a "asafoetida ID.”
  • A1 and A2 indicate the two amino acids that make up each cyclic dipeptide identified by the "compound ID.”
  • Cyclic dipeptides prepared by the applicant were used in this experiment.
  • Leu/Ile-containing cyclic dipeptide an equal mixture of a Leu-containing cyclic dipeptide and an Ile-containing cyclic dipeptide was used.
  • An average score of 1.0 or less was designated an "F”
  • 1.1 to 1.9 was designated a "C”
  • 2.0 to 2.5 was designated a “B”
  • 2.6 to 2.9 was designated an "A”
  • 3.0 or more was designated an "AA”.
  • ID refers to the compound ID.
  • Core 0.5% and “Coriander 1.0%” refer to the addition of the aqueous solution of cyclic dipeptide equivalent to heat-treated coriander to final concentrations of 0.5% (w/w) and 1.0% (w/w), respectively.
  • Paperrika 0.5% and “Paprika 1.0%” refer to the addition of the aqueous solution of cyclic dipeptide equivalent to heat-treated paprika to final concentrations of 0.5% (w/w) and 1.0% (w/w), respectively.

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  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)
PCT/JP2024/003191 2023-01-31 2024-01-31 呈味増強用組成物、その製造方法、食品、及び、食品の呈味を増強する方法 Ceased WO2024162422A1 (ja)

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JPS5058271A (https=) * 1973-09-28 1975-05-21
JPH04330262A (ja) * 1991-05-01 1992-11-18 House Food Ind Co Ltd スパイス風味油の製造方法
JP2000236844A (ja) * 1999-02-19 2000-09-05 Lion Corp 焙煎風味香辛料
JP2002325553A (ja) * 2001-04-27 2002-11-12 House Foods Corp 焙煎玉ねぎの製造方法
JP2020103257A (ja) * 2018-12-28 2020-07-09 ハウス食品株式会社 混合香辛料及び混合香辛料の製造方法
JP2023001775A (ja) * 2021-06-21 2023-01-06 日清オイリオグループ株式会社 油脂組成物、及び食品の塩味増強方法
WO2023285674A1 (en) * 2021-07-16 2023-01-19 Givaudan Sa Flavor enhancer for providing roasted chicken flavor

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JP5872187B2 (ja) 2011-05-17 2016-03-01 小川香料株式会社 塩味増強剤
JP2018102142A (ja) 2016-12-22 2018-07-05 株式会社カネカサンスパイス 塩味増強用スパイスミックス及び食品
JP7397827B2 (ja) 2021-07-16 2023-12-13 株式会社バンダイ 演出出力玩具

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JPS5058271A (https=) * 1973-09-28 1975-05-21
JPH04330262A (ja) * 1991-05-01 1992-11-18 House Food Ind Co Ltd スパイス風味油の製造方法
JP2000236844A (ja) * 1999-02-19 2000-09-05 Lion Corp 焙煎風味香辛料
JP2002325553A (ja) * 2001-04-27 2002-11-12 House Foods Corp 焙煎玉ねぎの製造方法
JP2020103257A (ja) * 2018-12-28 2020-07-09 ハウス食品株式会社 混合香辛料及び混合香辛料の製造方法
JP2023001775A (ja) * 2021-06-21 2023-01-06 日清オイリオグループ株式会社 油脂組成物、及び食品の塩味増強方法
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