EP3344068A1 - Aliments contenant des produits d'agrumes et des 4-hydroxyflavanones ajoutées - Google Patents

Aliments contenant des produits d'agrumes et des 4-hydroxyflavanones ajoutées

Info

Publication number
EP3344068A1
EP3344068A1 EP15756929.4A EP15756929A EP3344068A1 EP 3344068 A1 EP3344068 A1 EP 3344068A1 EP 15756929 A EP15756929 A EP 15756929A EP 3344068 A1 EP3344068 A1 EP 3344068A1
Authority
EP
European Patent Office
Prior art keywords
juice
citrus
ppm
formula
ingredients
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.)
Pending
Application number
EP15756929.4A
Other languages
German (de)
English (en)
Inventor
Johannes KIEFL
Susanne Paetz
Jakob Ley
Gerhard Krammer
Thomas Riess
Kathrin Langer
Günter Kindel
Morine VERWOHLT
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP3344068A1 publication Critical patent/EP3344068A1/fr
Pending legal-status Critical Current

Links

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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • 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
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/03—Products from fruits or vegetables; Preparation or treatment thereof consisting of whole pieces or fragments without mashing the original pieces
    • 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
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/03—Products from fruits or vegetables; Preparation or treatment thereof consisting of whole pieces or fragments without mashing the original pieces
    • A23L19/07—Fruit waste products, e.g. from citrus peel or seeds
    • 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
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A23L2/04—Extraction of juices
    • A23L2/06—Extraction of juices from citrus fruits
    • 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
    • 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
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
    • A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits
    • 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
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • 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
    • A23L27/86—Addition of bitterness inhibitors
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/16—Taste affecting agent

Definitions

  • the invention is in the field of foodstuffs and relates to foods containing citrus and in particular orange products with added 4-hydroxyflavanones with the aim of reducing the unpleasant, in particular the sour and bitter taste of these foods.
  • Foodstuffs in particular beverages, which are mainly produced from fruits of various citric species, play a very prominent role in the international food market.
  • orange juice (Citrus x sinensis L. or Citrus x aurantium) in the form of juice or reconstituted juice from concentrate and foods based on orange juice such as nectars or fruit juice drinks should be mentioned.
  • a balanced sweetness in combination with an acidic taste impression and also a certain bitterness are decisive for the sensory quality of these drinks.
  • the object of the present invention to find flavors or flavoring mixtures, which are able, even at low concentrations, the unpleasant, especially the sour and bitter taste of sour and bitter-tasting foods, and thereby citrus products in general and of orange products in particular to reduce or extinguish, and preferably also to enhance the sweet taste.
  • the additives should be naturally occurring and preferably obtained from ingredients of the genus Citrus.
  • a first aspect of the invention relates to foods containing
  • Ri is hydrogen or a hydroxy or a methoxy group and the carbon atom is present at the position (C2) marked with * in a (2S) or a (2R) configuration or in any mixture of the two configurations, and optionally
  • component (b) is present in an amount sufficient to improve the acidic and / or bitter taste of component (a).
  • the 4-hydroxyflavanones naringenin and eriodictyol are normally only present as glycosides bound in citrus products; e.g. as Narirutin (naringen-rutinoside) in the range of 1 to 50 ppm in orange juice (Gil-lzquierdo, A .; Gil, M.I., Ferreres, F., Tomas-Barberan, FA, "In Vitro Availability of Flavonoids and Other Phenolics in Orange Juice J.
  • naringin naringenin neohesperidoside
  • grapefruit naringenin neohesperidoside
  • eriodictoyl has only been described in traces Homoeriodictyol has hitherto not been described in citrus fruits, especially in oranges.
  • Naringenin, hesperetin and eriodictyol in free form do not occur in a sufficient for the inventive effect sufficiently high concentration (> 5 ppm) in orange juices. So in Yanez, YES; Remsberg, C.M .; Miranda, N. D .; Vega Villa, KR; Andrews, PK; Davies, N. M., "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and erythrocytes.
  • the foods of the present invention are preferably beverages or desserts.
  • citrus-containing beverages include the group formed by freshly squeezed, direct juices, reconstituted juices from juice concentrate, nectars, juice spritzers, juice-containing soft drinks, juice-containing dairy products, juice-containing carbonated beverages and juice-containing ice tea.
  • citrus-containing desserts are in the group formed by yogurts, frozen ice-creams, sherbets, ice cream, creams, puddings, fillings for chocolates or biscuit products, jams and dried juice or fruit preparations.
  • citrus products for the purposes of the present invention, the juice, the marrow, the meat, the shells and all other ingredients of citrus fruits to understand; it is subsequently used as a synonym for group (a).
  • Citrus fruits whose bitter and / or sour taste is to be improved include oranges, grapefruit, lemons, limes, mandarins and their mixtures.
  • group (a) comprises acidic and bitter orange products: orange varieties derived from fruits of the genus Citrus (Citrus x sinensis L. or Citrus x aurantium, Var. Hamlin, Valencia), especially by a proportion of early or emergency maturing Oranges derived from HLB-infected trees such as juices, juice concentrates, juice fractions with or without albedo, with or without pulp.
  • group (a) comprises acidic and bitter orange products: orange varieties derived from fruits of the genus Citrus (Citrus x sinensis L. or Citrus x aurantium, Var. Hamlin, Valencia), especially by a proportion of early or emergency maturing Oranges derived from HLB-infected trees such as juices, juice concentrates, juice fractions with or without albedo, with or without pulp.
  • the citrus products minimum concentrations of special bitter substances and maximum concentrations of natural 4-hydroxyflavanones, namely
  • the citrus products which form group (a) should have a pH in the range of 3 to 6.
  • component (b) contain:
  • the teaching of the present invention comprises the fact that the 4-hydroxyflavanols are present in any desired form of the respective stereoisomers.
  • the foods contain 4-hydroxyflavanones of the formula (I) in which the (2S) and (2R) enantiomers in the weight ratio of 99: 1 to 1:99, and more preferably from about 90:10 to about 45:55.
  • the 4-Hydroxyflavanols of the formula (I) based on the component (a) in amounts of about 5 to about 1000 ppm, and especially about 30 to about 250th ppm, and more preferably about 50 to about 100 ppm are present, added or selectively produced.
  • the food may contain as component (c) further flavoring or flavoring preparations.
  • these may be selected from substances for altering or masking an unpleasant taste impression and / or for enhancing a pleasant taste impression or flavoring agents are preferably selected from the following group: hesperetin as described in EP 2,368,442-Bl or EP 1,909,599-B1, hydroxybenzoic acid amides, such as for example 2,4-dihydroxybenzoic acid vanillylamide (in particular those as described in WO 2006/024587), 4-hydroxydihydrochalcones (preferably as described in US 2008/0227867 Al and WO 2007/107596), in particular phloretin and davidigenin, hesperetin as in WO 2007/014879, or extracts of Rubus suavissimus as described in US Provisional Application 61 / 333,435 (Symrise) and the patent applications based thereon, 3,7'-dihydroxy-4'-methoxyflavan
  • flavoring or flavoring preparations may be selected from the list of volatile flavoring agents, e.g. Acetaldehyde, acetophenone, alpha-cadinol, alpha-copen, alpha-cubeben, alpha-humulene, alpha-pinene, alpha-terpinene, alpha-terpineol, anisaldehyde, benzaldehyde, benzophenone, beta-copaen, beta-cubeben, beta-cyclocitral, beta-elemen, beta-lonone, beta-myrcene, beta-ocimene, beta-pinene, butanol, butylacetate, camphene, caryophyllene, cis-4-decenal, cis-4-heptenal, cis-3-hexenal, cis 3-hexenol, cis-8-tetradecenal, citric, citronellol, citronellal, citr
  • the proportion of 4-hydroxyflavanones in general and naringenin, homoeriodictyol and / or eriodictyol in particular to these preparations can be from 0.1 to 99.9% by weight, preferably from about 0.5 to about 25% by weight. % and in particular about 1 to about 10 wt .-% amount.
  • Further flavoring substances are the abovementioned substances.
  • the flavorings may be encapsulated and / or adsorbed and / or emulsified, or incorporated into the formulation.
  • Both the 4-Hydroxyflavanols that form the group (b), as well as flavoring preparations containing these substances can be encapsulated and then added as capsules to food.
  • Capsules are spherical aggregates to understand containing at least one solid or liquid core enclosed by at least one continuous shell.
  • the fragrances may be encapsulated by coating materials and present as macrocapsules having diameters of from about 0.1 to about 5 mm or of microcapsules having diameters from about 0.0001 to about 0.1 mm.
  • Suitable coating materials are, for example, starches, including their degradation products and chemically or physically generated derivatives (especially dextrins and maltodextrins), gelatin, gum arabic, agar-agar, ghatti gum, gellan gum, modified and unmodified celluloses, pullulan, Curdlan, carrageenans, alginic acid, alginates, pectin, inulin, xanthan gum and mixtures of two or more of these substances.
  • the solid encapsulating material is preferably a gelatin (especially pork, beef, poultry and / or fish gelatin), which preferably has a threshold factor of greater than or equal to 20, preferably greater than or equal to 24.
  • gelatin especially pork, beef, poultry and / or fish gelatin
  • gelatin is particularly preferred because it is well available and can be obtained with different threshold factors.
  • maltodextrins especially based on cereals, especially corn, wheat, tapioca or potatoes
  • DE values in the range of 10 to 20.
  • celluloses e.g., cellulose ethers
  • alginates e.g., sodium alginate
  • carrageenan e.g., beta-, jota, lambda, and / or kappa-carrageenan
  • gum arabic curdlan, and / or agar agar.
  • alginate capsules as described in detail in the following documents: EP 0389700 AI, US 4,251,195, US 6,214,376, WO 2003 055587 or WO 2004 050069 AI.
  • the shell of the capsules consists of melamine-formaldehyde resins or coacervation products of cationic monomers or biopolymers (such as chitosan) and anionic monomers such as (meth) acrylates or alginates.
  • the capsules are generally finely dispersed liquid or solid phases coated with film-forming polymers, in the preparation of which the polymers precipitate on the material to be coated after emulsification and coacervation or interfacial polymerization.
  • molten waxes are taken up in a matrix ("microsponge") which, as microparticles, can additionally be coated with film-forming polymers
  • microsponge a matrix
  • particles are coated alternately with polyelectrolytes of different charge (“layer-by-layer” process) ).
  • the microscopic capsules can be dried like powder.
  • multinuclear aggregates also called microspheres, are known which contain two or more cores distributed in the continuous shell material.
  • Mono- or polynuclear microcapsules can also be enclosed by an additional second, third, etc., sheath.
  • the shell may be made of natural, semisynthetic or synthetic consist of materials.
  • casing materials are, for example, gum arabic, agar agarose, agarose, maltodextrins, alginic acid or its salts, for example sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysaccharides, such as starch or dextran, polypeptides, protein hydrolysates, sucrose and waxes.
  • Semi-synthetic shell materials include chemically modified celluloses, in particular cellulose esters and ethers, for example cellulose acetate, ethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose and carboxymethylcellulose, and also starch derivatives, in particular starch ethers and esters.
  • Synthetic envelope materials are, for example, polymers such as polyacrylates, polyamides, polyvinyl alcohol or polyvinylpyrrolidone.
  • microcapsules of the prior art are the following commercial products (in parentheses is the shell material): Hallcrest Microcapsules (gelatin, gum arabic), Coletica Thalaspheres (marine collagen), Lipotec Millicapseln (alginic acid, agar-agar), Indutem unispheres (lactose, microcrystalline cellulose, hydroxypropylmethylcellulose); Unicerin C30 (lactose, microcrystalline cellulose, hydroxypropylmethylcellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar-agar) and Kuhs Probiol Nanospheres (phospholipids) as well as Primaspheres and Primasponges (chitosan, alginates) and Primasys (phospholipids) ,
  • Microcapsules with average diameters in the range of 0.0001 to 5, preferably 0.001 to 0.5 and in particular 0.005 to 0.1 mm, consisting of an enveloping membrane and a matrix containing the active ingredients can be obtained, for example, by
  • steps (a) and (c) are interchangeable insofar as one uses instead of the cationic polymers in step (a) anionic polymers and vice versa.
  • Another object of the invention relates to a method for reducing the acidic and / or bitter taste of citrus fruit products, comprising the following steps:
  • 4-hydroxyflavanols of the formula (I) or flavoring compositions containing them for improving the acidic and / or bitter taste of citrus fruit products, wherein here too the additional amount or the amount that is generated selectively, again preferably about 5 to about 1000 ppm, especially about 30 to about 250 ppm based on the citrus component.
  • naringenin at the inherently low concentration of 20 ppm, leads to a marked reduction of the bitter taste, reduction of the acid impression and at the same time an increase in the sweetness impression and improvement of the overall flavor profile of the tested orange juice.
  • Table 2 the results are reproduced with the addition of eriodictyol.
  • Pectin filling (all quantities are by weight) To prepare the formulation B, the dry substances are dissolved in water and boiled together with the pectin and sodium citrate for about 3-5 minutes at 106 ° C to a Brix value of 77-78 °. Thereafter, the orange juice concentrate and the flavors are stirred. After gentle cooling, the mass is rapidly filled into molds and cooled.
  • emulsifier and stabilizer are mixed with sugar and dissolved in water; Glucose syrup is added and dissolved. The mixture is then pasteurized and cooled. Into the mixture are added the flavor ingredients and the fruit juice concentrate, the pH is adjusted to 3.8-4.2 with 50% citric acid solution, and the preparation is frozen in an ice cream machine with 40-80% overrun.
  • Preparation Dissolve the sugar with water. Continue to add ingredients and dissolve. Pasteurize and cool.
  • Preparation Dissolve beer base with sugar and water. Add more ingredients and dissolve. Pasteurize and cool.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Grain Derivatives (AREA)
  • Alcoholic Beverages (AREA)
  • Confectionery (AREA)
  • Tea And Coffee (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Dairy Products (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

L'invention concerne un aliment contenant : a) du jus, de la purée, de la pulpe, des pelures ou d'autres parties d'au moins un agrume, b) au moins une 4-hydroxyflavanone de formule (I), dans laquelle R1 représente un atome d'hydrogène ou un groupe hydroxy ou méthoxy et l'atome de carbone à la position (C2) repérée par * est présent dans une configuration (2S) ou (2R) ou dans un mélange quelconque des deux configurations, ainsi qu'éventuellement c) d'autres arômes ou préparations aromatiques, à condition que le composant (b) soit présent dans une quantité suffisante pour réduire l'acidité et/ou l'amertume du composant (a).
EP15756929.4A 2015-09-01 2015-09-01 Aliments contenant des produits d'agrumes et des 4-hydroxyflavanones ajoutées Pending EP3344068A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2015/069971 WO2017036518A1 (fr) 2015-09-01 2015-09-01 Aliments contenant des produits d'agrumes et des 4-hydroxyflavanones ajoutées

Publications (1)

Publication Number Publication Date
EP3344068A1 true EP3344068A1 (fr) 2018-07-11

Family

ID=54014831

Family Applications (1)

Application Number Title Priority Date Filing Date
EP15756929.4A Pending EP3344068A1 (fr) 2015-09-01 2015-09-01 Aliments contenant des produits d'agrumes et des 4-hydroxyflavanones ajoutées

Country Status (9)

Country Link
US (1) US10765134B2 (fr)
EP (1) EP3344068A1 (fr)
JP (1) JP6786594B2 (fr)
KR (2) KR20230053003A (fr)
CN (1) CN107920569A (fr)
BR (1) BR112018003221B1 (fr)
MX (1) MX2018002465A (fr)
PH (1) PH12018500418A1 (fr)
WO (1) WO2017036518A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3704954A1 (fr) 2019-03-05 2020-09-09 Symrise AG Mélange comprenant d-allulose et composés de modification du goût
WO2022135661A1 (fr) 2020-12-21 2022-06-30 Symrise Ag Utilisation de la naringénine pour améliorer la qualité gustative de la phlorétine
CN115047127B (zh) * 2022-04-25 2024-03-08 中国检验检疫科学研究院 一种利用挥发性代谢组学技术鉴别nfc和fc橙汁的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA633148A (en) * 1961-12-19 W. Thomas Dudley Conversion of flavonoid glycosides
DE10122898A1 (de) * 2001-05-11 2002-11-14 Haarmann & Reimer Gmbh Verwendung von Hydroxyflavanonen zur Maskierung des bitteren Geschmacks
BRPI0613854B1 (pt) * 2005-07-27 2015-08-11 Symrise Ag Uso de hesperetina para reforçar o sabor doce, preparação e processo para reforçar sabor doce
EP2220945B1 (fr) * 2008-12-11 2013-03-27 Symrise AG Composition aromatiques pour réduire ou supprimer les sensations indésirables de goût amer et astringent des édulcorants
US20110293538A1 (en) 2010-05-11 2011-12-01 Symrise Ag Use of rubusoside for reducing or suppressing certain unpleasant taste impressions
CN103796532B (zh) * 2011-07-14 2016-08-31 高砂香料工业株式会社 风味改善方法
BR112014017552A8 (pt) * 2012-01-21 2017-07-04 Bayer Ip Gmbh utilização de indutores de defesa em hospedeiros para controlar organismos basterianos prejudiciais em plantas úteis

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JAIME A. YÁÑEZ ET AL: "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices", BIOPHARMACEUTICS AND DRUG DISPOSITION., vol. 29, no. 2, 1 January 2008 (2008-01-01), US, pages 63 - 82, XP055754094, ISSN: 0142-2782, DOI: 10.1002/bdd.588 *

Also Published As

Publication number Publication date
PH12018500418A1 (en) 2018-08-29
US20190021378A1 (en) 2019-01-24
KR20230053003A (ko) 2023-04-20
JP2018529330A (ja) 2018-10-11
US10765134B2 (en) 2020-09-08
BR112018003221A2 (pt) 2018-09-25
KR20180039731A (ko) 2018-04-18
JP6786594B2 (ja) 2020-11-18
CN107920569A (zh) 2018-04-17
MX2018002465A (es) 2018-08-24
WO2017036518A1 (fr) 2017-03-09
BR112018003221B1 (pt) 2022-01-18

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