WO2001039610A2 - Compositions de flaveurs et d'aromes d'agrumes - Google Patents

Compositions de flaveurs et d'aromes d'agrumes Download PDF

Info

Publication number
WO2001039610A2
WO2001039610A2 PCT/US2000/042145 US0042145W WO0139610A2 WO 2001039610 A2 WO2001039610 A2 WO 2001039610A2 US 0042145 W US0042145 W US 0042145W WO 0139610 A2 WO0139610 A2 WO 0139610A2
Authority
WO
WIPO (PCT)
Prior art keywords
cysteine
flavor
citrus
composition according
oil
Prior art date
Application number
PCT/US2000/042145
Other languages
English (en)
Other versions
WO2001039610A3 (fr
Inventor
Lawrence L. Buckholz, Jr.
Bryan Byrne
Original Assignee
J.Manheimer, Inc.
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 J.Manheimer, Inc. filed Critical J.Manheimer, Inc.
Priority to AU47075/01A priority Critical patent/AU4707501A/en
Publication of WO2001039610A2 publication Critical patent/WO2001039610A2/fr
Publication of WO2001039610A3 publication Critical patent/WO2001039610A3/fr

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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering 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
    • 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
    • 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
    • A23L27/29—Fruit flavours

Definitions

  • This invention relates to citrus flavor and aroma compositions suitable for use in foodstuffs, tobacco products, cosmetics, fragrances and pharmaceuticals. This invention also relates to a process for preparing the inventive compositions.
  • orange juice can be flavored with either peel or essence oil to get the main orange taste.
  • trace materials such as acetaldehyde, 1- penten-3-one and ethyl butyrate are widely added in order to obtain the fresh squeezed juicy flavor.
  • These materials are derived from orange aroma, the aqueous part of the essence, recovered from orange juice concentration in TASTE (Thermally Accelerated Short Time Evaporators) units.
  • TASTE Thermally Accelerated Short Time Evaporators
  • a recent patent assigned to Proctor & Gamble indicates that a fresh squeezed taste is obtained when the right balance of acetaldehyde, ethyl butyrate, trans-2-hexanal and ethyl 3- hydroxyhexanoate, recovered from orange aroma, is added to the concentrate. It is well known in the art that the bulk of the research into improving flavors has been either to add very volatile flavor ingredients back or to minimize (or eliminate) the thermal stress places on the juice. This is evidenced by the growing market for "not from concentrate" orange juice.
  • Cysteine is an amino acid used extensively in beef and chicken flavors, particularly for reaction flavors and Maillard products. Cysteine and its salts are well known in the art and is described, for example, in "The Merck Index", 10th ed., M. Wildholz, ed., Merck & Co., Inc., Rahway, NJ (1983), herein incorporated by reference. Processes for its syntheses are described, for example, in U.S. Patent 2,376,186; 2,406,362; and 2,449,303, also herein incorporated by reference. Thus, there is an interest in the citrus and flavor industry in making citrus flavor and juices that have a more fresh squeezed taste.
  • compositions with improved organoleptic properties.
  • inventive compositions comprise a treated citrus oil, flavor or aroma, which is obtained by reacting said citrus oil, flavor, or aroma with cysteine or a salt or ester thereof, a cysteine precursor, or a cysteine derivative, optionally in the presence of a solvent.
  • This invention further provides for foodstuffs cosmetics, fragrances, sweeteners, and pharmaceuticals comprising the inventive compositions as well as a process for preparing these compositions.
  • the cysteine flavor or aroma compositions of the present invention comprise a treated citrus oil, flavor or aroma obtained by mixing said citrus oil flavor or aroma with cysteine, a salt or ester thereof, a cysteine precursor or a cysteine derivative, optionally in the presence of a solvent.
  • the process by which the treated citrus flavors or aromas are obtained vary in time, temperature, solvent and source of cysteine. How this is achieved is limited to the resourcefulness of those skilled in the art and not meant to be the limiting factor of this invention.
  • the temperature for the mixing process may range from low temperatures to high temperatures and the process may be conducted under atmospheric conditions or pressure. In a preferred embodiment, the temperature for the process may range from room temperature (about 20°C) to about 110°C. Depending upon the source of cysteine and contact time needed to complete the process, temperatures above 110°C to about 250°C, with commensurably shorter contact times, may be used.
  • This source of cysteine in the present invention includes cysteine itself, as well as its salts and ester forms. Preferred are the inorganic and organic salts of cysteine, with cysteine hydrochloride being especially preferred. Also preferred are the carboxylic acid alkyl esters of cysteine, with the methyl, ethyl, propyl, isopropyl, butyl and isobutyl ester being most preferred. These sources of cysteine are well known in the art and are obtained either commercially or by processes known in the art.
  • the source of cysteine may also be precursors of cysteine, such as its amino acid esters. Again, these precursors are well known in the art and are obtained either commercially or by processes known in the art. Derivatives of cysteine include the cysteine adducts obtainable by the reaction of cysteine or an ester or salt thereof
  • the citrus flavor and aroma compounds for the invention can be derived from any of a variety of citrus fruits such as, for example, from oranges, grapefruits, lemons, tangerines, limes, kumquats, or mixtures thereof.
  • These flavor and aroma compounds can be crude citrus oils (single fold oils), refined citrus oils, fractionated or folded oils or compounded natural or artificial flavors.
  • the citrus oils, flavors or aromas used are obtained commercially or may be obtained by known techniques.
  • the ratio of substrate oil or flavor to cysteine can be varied to achieve a particular economic goal, but is not limited to large excesses of one ingredient or the other. It is the preferred embodiment that cysteine be used in parts per million to a one to one weight ratio to the citrus oil. When treating distilled whole citrus oils it is economically advantageous to treat about 99.9 parts of citrus oil with about 0.1 parts cysteine with the product being used directly "as is". In the case of highly purified fractions, nearly one to one ratios of cysteine to the fraction are most effective, with the product being further diluted in other flavors or oils to impart enhanced sweetness, flavor strength, freshness, juiciness and flavor stability. A wide range of solvents may be used in the inventive process.
  • the solvent includes those which are commonly used in foodstuffs, cosmetics and pharmaceutical preparations. It is also possible to use non-edible solvents, provided that they are removed by a removal step. In a preferred embodiment, ethanol, water or mixtures thereof are used as solvents. Also preferred is the use of no solvent.
  • the pH can be varied depending upon the solvent used, if any, and the cysteine source. Other considerations are conditions necessary to generate cysteine from a precursor or derivative. The preferred embodiment is a pH of about 1 to about 10, although, this is not intended to limit the scope of the invention.
  • the citrus flavor and aroma compositions may be used in a wide range of products and fragrances such as of foodstuffs, tobacco products, pharmaceuticals, oral care products, sweeteners and cosmetics.
  • Especially preferred food products include beverages, such as orange juice or lemonade, confectioneries, such as chewing gums.
  • Especially preferred oral care products include mouthwashes or toothpastes.
  • the contents are cooled to room temperature and the phases separated.
  • the treated Valencia Orange is used as is.
  • a solution of treated orange oil from Example #1 is made by using 0.1 g
  • Citric Acid 502 (wt./vol.) Solution 7.0 ml Flavor (Treated and Control) 9.0 ml Water 180.5 ml
  • the treated flavor has more flavor retained with greater sweetness and fidelity of flavor.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne des compositions de flaveurs et d'arômes d'agrumes adaptés à être employés dans des produits alimentaires, des produits cosmétiques, des parfums, des produits édulcorants et pharmaceutiques. Elle concerne aussi un procédé de préparation de ces compositions.
PCT/US2000/042145 1999-11-12 2000-11-13 Compositions de flaveurs et d'aromes d'agrumes WO2001039610A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47075/01A AU4707501A (en) 1999-11-12 2000-11-13 Citrus flavor and aroma compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43824399A 1999-11-12 1999-11-12
US09/438,243 1999-11-12

Publications (2)

Publication Number Publication Date
WO2001039610A2 true WO2001039610A2 (fr) 2001-06-07
WO2001039610A3 WO2001039610A3 (fr) 2001-10-25

Family

ID=23739847

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/042145 WO2001039610A2 (fr) 1999-11-12 2000-11-13 Compositions de flaveurs et d'aromes d'agrumes

Country Status (2)

Country Link
AU (1) AU4707501A (fr)
WO (1) WO2001039610A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022101424A1 (fr) 2020-11-16 2022-05-19 Firmenich Sa Extrait d'huile d'agrumes

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957745A (en) * 1974-07-25 1976-05-18 Universal Oil Products Company Flavoring and fragrance compositions
US3961093A (en) * 1974-06-11 1976-06-01 International Flavors & Fragrances Inc. Novel flavoring compositions and products containing 2-methyl-3-thio-(2-methylbutyryl)-furan
US3989856A (en) * 1975-05-29 1976-11-02 International Flavors & Fragrances Inc. 3-Furyl beta-oxoalkyl sulfides and methods for using same for altering, modifying or enhancing the organoleptic properties of foodstuffs
US4612942A (en) * 1984-03-08 1986-09-23 Stevia Company, Inc. Flavor enhancing and modifying materials
US4913923A (en) * 1984-09-12 1990-04-03 Firmenich Sa Process for improving or modifying the taste and aroma of citrus fruit compositions
US6074683A (en) * 1996-01-17 2000-06-13 Lipton, Inc. Process for the preparation of a savory flavor

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3961093A (en) * 1974-06-11 1976-06-01 International Flavors & Fragrances Inc. Novel flavoring compositions and products containing 2-methyl-3-thio-(2-methylbutyryl)-furan
US3957745A (en) * 1974-07-25 1976-05-18 Universal Oil Products Company Flavoring and fragrance compositions
US3989856A (en) * 1975-05-29 1976-11-02 International Flavors & Fragrances Inc. 3-Furyl beta-oxoalkyl sulfides and methods for using same for altering, modifying or enhancing the organoleptic properties of foodstuffs
US4612942A (en) * 1984-03-08 1986-09-23 Stevia Company, Inc. Flavor enhancing and modifying materials
US4913923A (en) * 1984-09-12 1990-04-03 Firmenich Sa Process for improving or modifying the taste and aroma of citrus fruit compositions
US6074683A (en) * 1996-01-17 2000-06-13 Lipton, Inc. Process for the preparation of a savory flavor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022101424A1 (fr) 2020-11-16 2022-05-19 Firmenich Sa Extrait d'huile d'agrumes

Also Published As

Publication number Publication date
AU4707501A (en) 2001-06-12
WO2001039610A3 (fr) 2001-10-25

Similar Documents

Publication Publication Date Title
EP1541039B1 (fr) Utilisation de cubebol comme agent aromatisant
CN106714581B (zh) 溶解度提高的莱鲍迪甙a和甜菊糖甙
KR101411035B1 (ko) 풍미 개선제 및 그것을 함유하는 음식품
US7329767B2 (en) Conjugated dienamides, methods of production thereof, compositions containing same and uses thereof
US8445051B2 (en) Thiol-containing fragrance and flavor materials
EP3811786A1 (fr) Édulcorant à base de stevia hautement soluble et son procédé de préparation
EP1919303B1 (fr) Compositions aromatisantes ameliorees
JPH09221667A (ja) 酸化防止剤組成物
US5523105A (en) Improved mint composition and method for producing the same
JPWO2020022179A1 (ja) 炭酸刺激飲食品用の炭酸感増強剤
WO2001035768A1 (fr) Exhausteurs de fraicheur de flaveur
JP2003299459A (ja) 呈味改善剤
KR101771811B1 (ko) 초피나무 추출물에 의한 고감미도 감미료의 정미 개선제
JP4234349B2 (ja) 柑橘系香味の劣化抑制剤、柑橘系香料、食品およびシトラールの環化抑制剤
WO2001039610A2 (fr) Compositions de flaveurs et d'aromes d'agrumes
EP0605261A2 (fr) Agent modifiant le goût et procédé pour modifier le goût
CN106659204B (zh) 甜味剂组合物
WO2001035918A1 (fr) Compositions de flaveur et d'arome de menthe
WO2021100678A1 (fr) Extrait végétal contenant une 2-acétyl-1-pyrroline
CN111526728A (zh) 香草组合物
JP2616270B2 (ja) 整味料の製造方法
US20130236629A1 (en) Sweetening compositions including rebaudiosides and methods of preparation
JP4286400B2 (ja) 柑橘果実由来のフレーバー劣化防止剤
CN107105722B (zh) 前体调味料递送粉末
JP5393367B2 (ja) 呈味付与剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase