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WO2017202893A1 - Améliorations apportées ou associées à des composés organiques - Google Patents

Améliorations apportées ou associées à des composés organiques Download PDF

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Publication number
WO2017202893A1
WO2017202893A1 PCT/EP2017/062508 EP2017062508W WO2017202893A1 WO 2017202893 A1 WO2017202893 A1 WO 2017202893A1 EP 2017062508 W EP2017062508 W EP 2017062508W WO 2017202893 A1 WO2017202893 A1 WO 2017202893A1
Authority
WO
WIPO (PCT)
Prior art keywords
aminoacetophenone
beef
flavour
beef flavour
products
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.)
Ceased
Application number
PCT/EP2017/062508
Other languages
English (en)
Inventor
Harry Renes
Yixiao GONG
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.)
Givaudan SA
Original Assignee
Givaudan SA
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 Givaudan SA filed Critical Givaudan SA
Publication of WO2017202893A1 publication Critical patent/WO2017202893A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A23L27/26—Meat flavours
    • 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
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40—Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42—Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/428—Addition of flavours, spices, colours, amino acids or their salts, peptides, vitamins, yeast extract or autolysate, nucleic acid or derivatives, organic acidifying agents or their salts or acidogens, sweeteners, e.g. sugars or sugar alcohols; Addition of alcohol-containing products
    • 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
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/60—Comminuted or emulsified meat products, e.g. sausages; Reformed meat from comminuted meat product
    • A23L13/65—Sausages

Definitions

  • This disclosure relates to the use of 2'-aminoacetophenone as a flavour ingredient in beef flavour formulations.
  • flavours must remain authentic.
  • the applicant carried out extraction and aroma analysis on beef, and in particular beef fat. Key aroma compounds were identified, but flavour formulations containing these key aroma compounds, whilst identifiable as being beef flavours, were nevertheless deemed to be somewhat artificial and non-authentic.
  • the invention provides in a first aspect the use of 2'-aminoacetophenone as a flavour ingredient.
  • 2'-aminoacetophenone is typically abbreviated as "2'-AAP”. It corresponds to CAS Number 551-93-9.
  • the invention provides a beef flavour formulation comprising 2'- aminoacetophenone.
  • the invention provides a comestible product comprising a beef flavour formulation containing 2'-aminoacetophenone.
  • 2'-aminoacetophenone is a known compound. It is known to occur naturally in wine, grapes, rice, corn-flower tortilla and dairy powders. As regards its presence in meat products, it has been reported in Food Research International 62, (2014) 35-42 that it is present in the back fat of pigs, and may contribute to the undesirable off-note in pork products known as "boar taint".
  • the use of 2'-aminoacetophenone in flavour formulations has been described in, e.g., JP 5,174,231 Bl and JP 2005/013138 A. Tonbeek et al. (J. Agr. Food Chem. vol. 19, No.
  • 2'-aminoacetophenone can be used in all manner of beef flavour formulations to deliver authenticity thereto, and particularly an authentic beef fatty profile.
  • 2'- aminoacetophenone provides a flavour generally associated with aged beef.
  • beef flavour formulations may contain aminoacetophenone in combination with one or more fat-derived ingredients, such unsaturated aldehydes, e.g. 2,4-decadienal, 2,4-nonadienal, and sulphury components, such as 2-methyl-3-furanthiol and 2-acetylthiazole.
  • unsaturated aldehydes e.g. 2,4-decadienal, 2,4-nonadienal
  • sulphury components such as 2-methyl-3-furanthiol and 2-acetylthiazole.
  • beef flavour formulations may contain 2'- aminoacetophenone in combination with one or more Maillard-derived ingredients, such as furaneol, pyrazines, and 2-methyl-3-furanthiol.
  • Maillard-derived ingredients such as furaneol, pyrazines, and 2-methyl-3-furanthiol.
  • a particularly desirable authentic beef flavour can be achieved when a beef flavour formulation contains 2'-aminoacetophenone at very low concentrations.
  • the concentration of 2'-aminoacetophenone is from about 1 to about 100 parts per trillion (ppt), preferably from about 1 to about 50 ppt, and more preferably from about 1 to about 20 ppt.
  • the concentration of 2'-aminoacetophenone is from about 1 to about 12 ppt.
  • Beef flavour formulations referred to herein may be employed in all manner of comestible products.
  • Particular comestibles include foods and beverages, such as meat products, e.g. ham, fresh or raw sausage preparations, and seasoned or marinated fresh or salt meat products; baked products; snack foods preferably selected from the group consisting of baked or fried potato chips or potato dough products, bread dough products and corn or peanut-based extrudates; spice blends; condiments; fermented products; ready-to-heat foods; ready-to-eat meals; seasoning preparations; sauces; soups; bouillon; and noodles.
  • Beef flavour formulations of the present invention can make a general improvement to the flavour of comestibles.
  • a comestible may be added to a comestible by simple mixing with other ingredients in the final blending of a comestible, such as a convenience food.
  • they may be added to the outside of a comestible, for exa mple, by the process of dusting or spray coating a snack food.
  • the beef flavour formulation may be added to a comestible during its formation, in a process which is sometimes referred to as internal flavouring.
  • Beef flavour formulations of the present invention are typically spray-dried, encapsulated and/or applied in another delivery system.
  • the formulations may optionally comprise additional ingredients, in particular those outlined in the IOFI (International Organization of the Flavor Industry) LISTS OF FLAVOURINGS AND NON-FLAVOURING FLAVOUR INGREDIENTS.
  • additional ingredients include, but are not limited to, fillers, flowing agents, carriers, 5 delivery systems, weighting agents, emulsifiers and stabilizers.
  • Suitable fillers include, but are not limited to, flour, rice, maltodextrins, modified starches, gums, cellulose, medium chain triglyceride, alginates, silicon dioxide, why powder and pectines.
  • a filler When a filler is employed in the flavour composition, it may be used in amounts from 0 to about 99%, by weight of the flavour composition.
  • Suitable free flowing agents or anticaking agents include, but are not limited to, flour, rice, maltodextr
  • flavour composition 10 include, but are not limited to, aluminum silicate, calcium aluminum silicate, calcium carbonate, calcium silicate, magnesium carbonate, magnesium silicate, mono-, di- and tri- calcium orthophosphate, potassium aluminum silicate, silicon dioxide (amorphous), sodium aluminum silicate and stearic acid salts.
  • a free flowing agent or anticaking agent is employed in the flavour composition, it may be used in amounts from 0 to about
  • Suitable carriers include, but are not limited to, maltodextrins, starches, gelatine, and gums.
  • the beef flavour formulations of the present invention may be mixed or blended with other components or the full base (e.g. the dough) of a consumer product or they may also be coated on the consumer product. In particular, they may be added as powder 20 blended flavours to culinary products or snacks. For instance, the beef flavour formulations of the present invention may be added to the dough of an extruded product.
  • the fat was removed, frozen in liquid nitrogen and extracted with Pentane/Dichloromethane (2/1).
  • the extract contained key beef fat flavour components comprising a mixture of aldehydes, acids, phenols and ketones including 2,4-decadienal, 2,4-nonadienal, hexanoic acid, p-cresol and octadien-2-one.
  • an aroma recombinant i.e.
  • flavour formulation containing 2,4-decadienal, 2,4-nonadienal, hexanoic acid, p-cresol, octadien- 2-one, 6-methyl-heptanal, 4-cis-heptenal, 2 pentyl pyridine, 2-propionly thiazole, 2-acetyl- 2-thiazoline, 5,6,7,8-tetrahydroquinoxaline, benzothiazole, and 4-methyl octanoic acid as the major components.
  • Methyl anthranilate was chosen for comparison, as this ingredient is typically used in grape flavours to provide a similar note.
  • Methyl anthranilate was added at 125 ppt to a standard beef entrecote base to determine if this could add the missing authenticity.
  • the standard beef entrecote base comprises taste and aroma active flavour compounds such as yeast powders, sodium chloride and other minerals, lactic acids, furaneol, 2,4- decadienal and 2,4-nonadienal.
  • 2'-aminoacetophenone was added to the standard beef entrecote base (see example 2) at 2.5 ppt level. Panellists indicated that this demonstrated a significant positive effect: The usage of 2'- aminoacetophenone in combination with above mentioned known beefy fatty ingredients was deemed to reach the objective, creating an authentic aged beef fat flavour.
  • flavoured savoury bases which contains NaCI (0.3%), MSG (0.02%) and 5'-IMP/5'-GMP (50/50) (0.007%). 2'-aminoacetophenone was added to these flavoured savoury bases at different concentrations for comparison.
  • flavours - @ 1-2 ppt: made a difference, added fattier character, less meaty, it gave more beef collagen character than lean meat.
  • Methyl anthranilate was evaluated vs 2'-AAP on beef flavour

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Meat, Egg Or Seafood Products (AREA)

Abstract

Utilisation de 2'-aminoacétophénone dans une formulation d'arôme, en particulier une formulation d'arôme de boeuf.
PCT/EP2017/062508 2016-05-27 2017-05-24 Améliorations apportées ou associées à des composés organiques Ceased WO2017202893A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB1609394.0A GB201609394D0 (en) 2016-05-27 2016-05-27 Improvement in or relating to organic compounds
GB1609394.0 2016-05-27

Publications (1)

Publication Number Publication Date
WO2017202893A1 true WO2017202893A1 (fr) 2017-11-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2017/062508 Ceased WO2017202893A1 (fr) 2016-05-27 2017-05-24 Améliorations apportées ou associées à des composés organiques

Country Status (2)

Country Link
GB (1) GB201609394D0 (fr)
WO (1) WO2017202893A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019221221A1 (fr) * 2018-05-17 2019-11-21 高砂香料工業株式会社 Agent d'amélioration de saveur de poulet

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3615600A (en) * 1967-01-20 1971-10-26 Lever Brothers Ltd Meat flavor composition containing succinic acid
US3709697A (en) * 1969-03-25 1973-01-09 Lever Brothers Ltd Furanone meat flavor compositions
US4096284A (en) * 1977-06-13 1978-06-20 The Quaker Oats Company Flavoring with α-mercaptoacetophenone and derivatives
US4324809A (en) * 1978-07-06 1982-04-13 Firmenich Sa Flavoring with α, β-unsaturated aldehydes
CN101393178A (zh) * 2008-10-30 2009-03-25 中国农业科学院北京畜牧兽医研究所 一种发酵牛肉火腿真假鉴别方法
JP2012075349A (ja) * 2010-09-30 2012-04-19 Ogawa & Co Ltd 豆乳又は豆乳含有飲食品の香味改善剤
JP5174231B1 (ja) * 2011-12-15 2013-04-03 小川香料株式会社 ピーナッツ風味を有する飲食品の香味改善剤

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3615600A (en) * 1967-01-20 1971-10-26 Lever Brothers Ltd Meat flavor composition containing succinic acid
US3709697A (en) * 1969-03-25 1973-01-09 Lever Brothers Ltd Furanone meat flavor compositions
US4096284A (en) * 1977-06-13 1978-06-20 The Quaker Oats Company Flavoring with α-mercaptoacetophenone and derivatives
US4324809A (en) * 1978-07-06 1982-04-13 Firmenich Sa Flavoring with α, β-unsaturated aldehydes
CN101393178A (zh) * 2008-10-30 2009-03-25 中国农业科学院北京畜牧兽医研究所 一种发酵牛肉火腿真假鉴别方法
JP2012075349A (ja) * 2010-09-30 2012-04-19 Ogawa & Co Ltd 豆乳又は豆乳含有飲食品の香味改善剤
JP5174231B1 (ja) * 2011-12-15 2013-04-03 小川香料株式会社 ピーナッツ風味を有する飲食品の香味改善剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019221221A1 (fr) * 2018-05-17 2019-11-21 高砂香料工業株式会社 Agent d'amélioration de saveur de poulet
CN112118746A (zh) * 2018-05-17 2020-12-22 高砂香料工业株式会社 鸡肉风味改善剂
JPWO2019221221A1 (ja) * 2018-05-17 2021-06-17 高砂香料工業株式会社 チキン風味改善剤

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Publication number Publication date
GB201609394D0 (en) 2016-07-13

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