WO2017202893A1 - Improvement in or relating to organic compounds - Google Patents
Improvement in or relating to organic compounds Download PDFInfo
- 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
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- 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
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Classifications
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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
- A23L27/20—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
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- 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
Use of 2'-aminoacetophenone in a flavour formulation, particularly a beef flavour formulation.
Description
Improvement in or Relating to Organic Compounds
Field of the Invention
This disclosure relates to the use of 2'-aminoacetophenone as a flavour ingredient in beef flavour formulations.
Background of the Invention
It has been said that people eat with their eyes. However, if a food-stuff does not taste good, consumers will not respond favourably to it.
As consumers become ever more educated, curious and adventurous about their food, the desire for the familiar nevertheless remains high. And although the drive for novel and creative flavours remains, the flavours must remain authentic.
There is a constant need for new flavour ingredients. In the search for new flavour ingredients, it is conventional to prepare extracts of natural food products and subject them to aroma analysis. In this way, it is possible to identify key aroma compounds that can form the basis for new flavour creations.
Summary of the Invention
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.
Addressing this problem, applicant surprisingly found that authenticity can be brought to beef flavour formulations using 2'-aminoacetophenone as a flavour ingredient
Accordingly, 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.
In another aspect, the invention provides a beef flavour formulation comprising 2'- aminoacetophenone. In yet another aspect, the invention provides a comestible product comprising a beef flavour formulation containing 2'-aminoacetophenone.
Detailed Description of the Invention
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. 5, 1971) describes the continuous extraction of a beef broth and the analysis of this extract by gas-liquid chromatography. The odour of a fraction of this extract was determined to have an odour reminiscent of 2'- aminoacetophenone; however, that molecule was not identified in the extract.
Likewise, applicant could not identify 2'-aminoacetophenone in beef fat. And it was indeed surprising that this molecule was found to add authenticity to beef flavours.
2'-aminoacetophenone can be used in all manner of beef flavour formulations to deliver authenticity thereto, and particularly an authentic beef fatty profile. In particular, 2'- aminoacetophenone provides a flavour generally associated with aged beef.
In an embodiment of the invention, 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.
In an embodiment of the invention, 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.
A particularly desirable authentic beef flavour can be achieved when a beef flavour formulation contains 2'-aminoacetophenone at very low concentrations. Thus, according to a preferred embodiment, 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. According to a particularly preferred embodiment, 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. They may be added to a comestible by simple mixing with other ingredients in the final blending of a comestible, such as a convenience food. Alternatively, they may be added to the outside of a comestible, for exa mple, by the process of dusting or spray coating a snack food. Still further, 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. For instance, such 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. 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
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. When a free flowing agent or anticaking agent is employed in the flavour composition, it may be used in amounts from 0 to about
15 10%, by weight of the flavour composition. 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.
There now follows a series of examples that serve to further illustrate the invention.
Example 1: Target Aroma Profile
25 Outer fat from an aged T-bone steak was extracted after poaching at 52 °C for 45 minutes.
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.
Based on the analysis of said extract, an aroma recombinant (i.e. a flavour formulation) was created, 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.
Both the extract and the aroma recombinant were tasted by a trained panel. Panellists indicated that the extract captured the essential fatty beefy, animalic, buttery, roasted, sweet pop-corn-like aspects. However, they perceived the aroma recombinant as artificial and lacking in authenticity.
Example 2: Evaluation against Methyl Anthranilate
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.
However, panellists indicated that methyl anthranilate was too harsh and artificial; it led flavours to the sweet fruit direction instead of sweet meaty fatty direction.
Example 3: Flavour Creation with 2'-Aminoacetophenone
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.
Example 4: Technical Tasting by Expert Panel
The technical tasting was done at a lab, by bench evaluation.
Four different flavours - beef, pork, chicken and corn - were applied on a basic evaluation base for savoury, 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.
2'-AAP on Beef Flavour:
General profile of this flavour: beef meaty, sulphury, metallic, red meat, slightly roasted
Depending on the amount of 2'-AAP added, panelists described the flavours as: - @ 1-2 ppt: made a difference, added fattier character, less meaty, it gave more beef collagen character than lean meat.
@ 5, 10, 20, 50 ppt: profile changed a lot, the flavour got more rare meat character. In general, the pannelists felt that 2'-AAP added an aged beef character and authenticity. 2'-AAP on Pork Flavour: General profile of this flavour: porky, fatty, after taste: meaty & cooked pork character @ 5 ppt 2'-AAP: no difference can be noticed. 2'-AAP on Chicken Flavour:
General profile of this flavour: fatty, roasted, chicken meaty, crispy skin, grilled
@ 5 ppt 2'-AAP: grilled dripping fat character enhanced. It gave an effect, but the panellists did not feel that this added authenticity to the chicken flavour.
2'-AAP on Corn Flavour:
General profile of this flavour: Corn, pyrazine, roasted, toasted @ 5 ppt 2'-AAP: no difference can be noticed.
Comparison of 2' -Aminoacetophenone and Methyl Anthranilate on Beef Flavour
Methyl anthranilate was evaluated vs 2'-AAP on beef flavour
@ 5 ppt (i.e. at the same concentration)
- @ 65 ppt, 100 ppt, 200 ppt, and 500 ppt
- @ 1 ppb, 2 ppb, and even 5 ppb (i.e. at lOOOx higher concentration)
No effect from methyl anthranilate could be observed at any of these concentrations.
Example 5: Comparison of Odour Activity Values (OAV)
The aroma impactfor 2'-aminoacetophenone and methyl anthranilate was evaluated at two different levels: iso-concentration (5 ppt) and iso-OAV (0.023 and 0.0044/0.0046).
Concentration Concentration Threshold in water OAV
Compound used [ppt] used [ppm] [ppm] [conc/threshold]
2'-aminoaceto- 2.5 0.0000025 0.00108 0.0023 phenone 5 0.000005 0.0046
5 0.000005 0.0281 0.0002 methyl 65 0.000065 0.0023 anthranilate 125 0.000125 0.0044
5000 0.005 0.1779
Claims
1. The use of 2'-aminoacetophenone in a beef flavour formulation.
2. Use according to claim 1, wherein the beef flavour comprises 2'- aminoacetophenone and one or more ingredients selected from the group consisting of unsaturated aldehydes, e.g. 2,4-decadienal, 2,4-nonadienal; sulphur components such as 2-methyl-3-furanthiol and 2-acetylthiazole; and Maillard- derived ingredients, such as furaneol, pyrazines, and 2-methyl-3-furanthiol.
3. Use according to claim 1 or claim 2, wherein 2'-aminoacetophenone is present in the beef flavour formulation in amounts of 1 to 100 parts per trillion.
4. A beef flavour formulation comprising 2'-aminoacetophenone.
5. A beef flavour formulation according to claim 4 that comprises 2'- aminoacetophenone and one or more ingredients selected from the group consisting of unsaturated aldehydes, e.g. 2,4-decadienal, 2,4-nonadienal; sulphur components such as 2-methyl-3-furanthiol and 2-acetylthiazole; and Maillard- derived ingredients, such as furaneol, pyrazines, and 2-methyl-3-furanthiol.
6. A beef flavour formulation according to claim 4 or 5, wherein 2'- aminoacetophenone is present in an amount of 1 to 100 parts per trillion.
7. A comestible comprising the beef flavour composition as defined in any of the claims 4 through 6.
8. A cosmestible according to claim 7 that is selected from the group consisting of 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.
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 (en) | 2017-11-30 |
Family
ID=56410673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2017/062508 Ceased WO2017202893A1 (en) | 2016-05-27 | 2017-05-24 | Improvement in or relating to organic compounds |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB201609394D0 (en) |
| WO (1) | WO2017202893A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019221221A1 (en) * | 2018-05-17 | 2019-11-21 | 高砂香料工業株式会社 | Chicken flavor improving agent |
Citations (7)
| 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 (en) * | 2008-10-30 | 2009-03-25 | 中国农业科学院北京畜牧兽医研究所 | A method for identifying the authenticity of fermented beef ham |
| JP2012075349A (en) * | 2010-09-30 | 2012-04-19 | Ogawa & Co Ltd | Flavor improving agent of soy milk or food and drink containing soy milk |
| JP5174231B1 (en) * | 2011-12-15 | 2013-04-03 | 小川香料株式会社 | Flavor improver for foods and drinks with peanut flavor |
-
2016
- 2016-05-27 GB GBGB1609394.0A patent/GB201609394D0/en not_active Ceased
-
2017
- 2017-05-24 WO PCT/EP2017/062508 patent/WO2017202893A1/en not_active Ceased
Patent Citations (7)
| 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 (en) * | 2008-10-30 | 2009-03-25 | 中国农业科学院北京畜牧兽医研究所 | A method for identifying the authenticity of fermented beef ham |
| JP2012075349A (en) * | 2010-09-30 | 2012-04-19 | Ogawa & Co Ltd | Flavor improving agent of soy milk or food and drink containing soy milk |
| JP5174231B1 (en) * | 2011-12-15 | 2013-04-03 | 小川香料株式会社 | Flavor improver for foods and drinks with peanut flavor |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019221221A1 (en) * | 2018-05-17 | 2019-11-21 | 高砂香料工業株式会社 | Chicken flavor improving agent |
| CN112118746A (en) * | 2018-05-17 | 2020-12-22 | 高砂香料工业株式会社 | Chicken flavor improving agent |
| JPWO2019221221A1 (en) * | 2018-05-17 | 2021-06-17 | 高砂香料工業株式会社 | Chicken flavor improver |
Also Published As
| Publication number | Publication date |
|---|---|
| GB201609394D0 (en) | 2016-07-13 |
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