Patent Summary: Methods and Compositions for Affecting the Flavor and Aroma of Consumables (beef flavor)

The basics for patent US9826772B2:

METHODS AND COMPOSITIONS FOR AFFECTING THE FLAVOR AND AROMA PROFILE OF CONSUMABLES

Based on the patent document (US9826772B2), here is a summary.

1) What the patent is all about

This patent, titled "Methods and Compositions for Affecting the Flavor and Aroma Profile of Consumables," is fundamentally about creating or enhancing meaty flavors and aromas in food products, especially plant-based meat substitutes. The core invention is the use of a specific chemical combination to achieve this.

The key components are:

• An iron complex, which is a highly conjugated heterocyclic ring (like a heme moiety) bound to an iron ion. This can be in the form of a heme-containing protein, such as leghemoglobin from plants.
• One or more flavor precursor molecules (e.g., sugars, amino acids, fats).

The patent explains that during cooking, the iron complex catalyzes chemical reactions (like the Maillard reaction) between the flavor precursors, generating the volatile compounds responsible for the characteristic taste and smell of cooked meat (e.g., beef, pork). This technology allows for the creation of food products that are free of animal products but still deliver a convincing meaty sensory experience.

2) The idea behind this patent to achieve the target

The central idea is to catalytically generate meaty flavors in situ during cooking, rather than adding pre-formed artificial flavors. The mechanism is based on the following principles:

• Catalysis by Iron Complex: The iron complex (e.g., heme) acts as a catalyst. It facilitates reactions between flavor precursors that would otherwise occur slowly or not at all, producing a complex mixture of aroma compounds associated with cooked meat.
• Mimicking Meat Chemistry: In animal meat, heme-proteins like myoglobin and hemoglobin are naturally present and contribute to flavor generation upon cooking. This invention replicates that chemistry by introducing a similar iron complex (which can be from a non-animal source) into a food product.
• Controllable Flavor Profile: The patent posits that the final flavor and aroma can be modulated by carefully selecting and adjusting:
  • The type and concentration of the iron complex.
  • The specific combination of flavor precursor molecules (see Table 1).
  • Cooking conditions like temperature, pH, and time.

The target is to create a consumable, particularly a plant-based meat analog, that when cooked, develops the complex, savory, and "meaty" flavors that are typically absent in existing vegetarian products.

3) Examples or embodiments

The patent provides numerous examples and embodiments. Here are some key ones, including precursors, conditions, and results.

Example 1: Beef-Flavored Patties

• Precursors: A "Magic Mix" containing cysteine and ribose (both are flavor precursors, see Table 1) was combined with a source of heme (soybean leghemoglobin, isolated from soybean root nodules).
• Reaction Conditions: The mixture was formed into patties and cooked.
• Result/Quality Improvement: As shown in Figure 2 of the patent, patties containing the heme protein and the "Magic Mix" received a significantly higher "Beefiness Rating" from a sensory panel compared to patties with no added flavor precursors. This demonstrates the synergistic effect of the iron complex and precursors in generating beef-like flavor.

Example 2: Desired Flavor and Aroma Compounds
The patent extensively lists the types of flavors and aromas targeted (Table 2, 7, 11) and the specific chemical compounds generated (Table 3, 8, 9, 12, 14, 16, 17).

• Target Flavors/Aromas: Beefy, bacony, umami, savory, bloody, brothy, gravy-like, metallic, bouillon-like.
• Generated Compounds: Key meaty aroma compounds generated include 2-methyl-3-furanthiol, 2-furfurylthiol, 3-mercapto-2-pentanone, and various sulfur-containing heterocyclic compounds. These are well-known in flavor chemistry for contributing to meaty, roasted notes.

Example 3: Sources of Precursors and Iron Complex

• Iron Complex (Heme Source): The patent lists numerous protein sequences (SEQ ID NOs: 1-27 in Figure 1) that can be used. These include leghemoglobin from various plants (soy, cowpea, mung bean), myoglobin from animals (cow, pig, horse), and hemoglobins from bacteria and fungi. This shows the invention is not limited to one source.
• Flavor Precursor Sources: Precursors don't have to be purified. They can be derived from ingredients like yeast extract, vegetable oils (corn, soybean, canola, olive), and other protein-rich or fat-rich fractions.

4) What are the claims

The patent concludes with 19 specific claims that define the legal scope of the invention. Here is a summary of the key independent and dependent claims:

• Claim 1: A food product (that is free of animal products) comprising:
  • (a) An iron complex (specifically a heme cofactor comprising a highly conjugated heterocyclic ring complexed to an iron ion).
  • (b) One or more flavor precursor molecules selected from the group consisting of a carbohydrate, a protein, a peptide, an amino acid, a fat, a fatty acid, a nucleic acid, a vitamin, an organic acid, and any combination thereof.
• Claim 2: The food product of claim 1, where the heme cofactor is part of a heme-containing protein (e.g., a globin, cytochrome, peroxidase).
• Claim 7: The food product of claim 2, where the heme-containing protein is plant-based, specifically a leghemoglobin (e.g., from soybean, cowpea, mung bean).
• Claim 9: The food product of claim 1, where the one or more flavor precursors are selected to generate, upon cooking, a specific flavor profile, such as beef, pork, lamb, chicken, or turkey.
• Claim 12: The food product of claim 1, where the one or more flavor precursors are provided by an ingredient selected from yeast extract, textured vegetable protein, or an oil (e.g., vegetable oil, corn oil, soybean oil).
• Claim 15: A method for making a food product with a modulated flavor profile, the method comprising:
  • (a) Providing an iron complex (heme cofactor).
  • (b) Providing one or more flavor precursor molecules.
  • (c) Combining them to form the food product, which is then cooked to generate a specific flavor (e.g., beef, pork).
• Claim 19: The method of claim 15, where the food product is a plant-based meat analog.

In essence, the claims protect the specific combination of a heme-iron complex and flavor precursors in a food product, the methods of making such products, and their use to replicate the flavor of various meats, with a strong emphasis on plant-based applications.

Detailed Examples

Based on the patent document (US9826772B2), here are the specific details for the three examples, focusing on the reaction process and parameters.

Example 1: Beef-Flavored Patties (Figure 2)

This is the core working example demonstrating the synergistic effect of the heme protein and flavor precursors.

• Precursors: The example uses a "Magic Mix" containing cysteine and ribose. These are classic Maillard reaction precursors for generating meaty flavors. The heme source is soybean leghemoglobin isolated from soybean root nodules .
• Reaction Process: The process involves mixing the isolated soybean leghemoglobin with the cysteine/ribose "Magic Mix" and forming the mixture into patties.
• Reaction Conditions (pH, Temperature, Time, Reactor):
  • pH: Not specified in the example text.
  • Temperature & Time: Not specified in the example text, but the reaction is explicitly triggered by cooking. The temperature would be that of a standard cooking process (e.g., grilling or frying a patty, typically reaching internal temperatures >70°C (160°F) and surface temperatures exceeding 150°C (300°F)).
  • Reactor: The "reactor" is the food product itself—the patty being cooked in a pan, on a grill, etc.
• Main Flavor Compounds Generated: The example does not list the specific chemical compounds generated. Instead, it measures the sensory outcome: a significant increase in "Beefiness Rating" as judged by a sensory panel. Based on the patent's broader teaching and the precursors used (cysteine and ribose), the key compounds generated would likely include 2-methyl-3-furanthiol, 2-furfurylthiol, and various other sulfur-containing heterocyclic compounds known for their meaty, roasted notes.

Example 2: Desired Flavor and Aroma Compounds

This example is not a single experiment but rather a comprehensive listing throughout the patent of the target flavors and the specific chemical compounds that the invention aims to generate. It links the precursors to the final flavor profile.

• Precursors: The patent lists an extensive array of potential precursors (see Table 1 within the patent). Key examples include:
  • Sulfur-containing amino acids: Cysteine, methionine.
  • Reducing sugars: Ribose, glucose, fructose.
  • Vitamins: Thiamine.
  • Nucleotides: Inosine monophosphate (IMP), guanosine monophosphate (GMP).
  • Lipids/Fatty Acids: Oleic acid, linoleic acid, and various oils (canola, coconut, sunflower).
• Reaction Process: The process is the thermal reaction (cooking) of these precursors in the presence of an iron complex (heme protein).
• Reaction Conditions (pH, Temperature, Time, Reactor):
  • pH: Not specified as a controlled variable in a reactor for this example, as it pertains to the final food product.
  • Temperature & Time: Not specified in a tabular format, but the reaction is always initiated by heating/cooking.
  • Reactor: The food product itself during cooking.
• Main Flavor Compounds Generated: The patent lists numerous target compounds that contribute to specific meat flavors. Here are some highlights from tables within the patent:
  • For Beef Flavor: Compounds include 2-methyl-3-furanthiol, bis(2-methyl-3-furyl) disulfide, 2-furfurylthiol, 3-mercapto-2-pentanone, methional, and various aldehydes like (E,E)-2,4-decadienal .
  • For Pork Flavor: Compounds include many of the same thiols and furans as beef, but also specific lactones and aldehydes derived from lipid degradation, such as γ-dodecalactone and various unsaturated aldehydes.
  • For Chicken Flavor: The patent identifies compounds like 2-methyl-3-furanthiol, 2-furfurylthiol, (E,E)-2,4-decadienal, and various pyrazines and thiazoles .

Example 3: Sources of Precursors and Iron Complex

This example highlights the flexibility of the invention by demonstrating that the key components can be derived from various natural sources, not just purified chemicals.

• Precursors (and their sources):
  • Iron Complex (Heme Source): The patent lists numerous protein sequences (SEQ ID NOs: 1-27 in Figure 1) that can be used. This includes leghemoglobin from various plants (soybean, cowpea, mung bean), myoglobin from animals (cow, pig, horse), and hemoglobins from bacteria and fungi. The example demonstrates that the source can be highly varied.
  • Flavor Precursor Sources: The patent specifies that precursors can be provided by whole ingredients rather than purified compounds. Key examples include:
    • Yeast extract: A rich source of amino acids, peptides, nucleotides (like IMP and GMP), and vitamins (like thiamine).
    • Vegetable oils: Oils such as corn, soybean, canola, olive, coconut, and sunflower oil provide fatty acids (e.g., oleic acid, linoleic acid) that break down during cooking to form lipid-derived aroma compounds .
• Reaction Process: The process involves combining these ingredient sources (e.g., a yeast extract and a vegetable oil) with a source of heme protein into a food product and then cooking it.
• Reaction Conditions (pH, Temperature, Time, Reactor):
  • pH: Not specified as a controlled variable for this example.
  • Temperature & Time: Not specified in a discrete example, but inherent to the cooking process.
  • Reactor: The food product during cooking.
• Main Flavor Compounds Generated: The compounds generated would be a complex mixture derived from all the precursor classes present. For example, combining a heme protein with yeast extract (providing cysteine, ribose, thiamine) and soybean oil (providing linoleic acid) could generate a broad spectrum of both water-derived (e.g., 2-methyl-3-furanthiol) and lipid-derived (e.g., 2,4-decadienal) meaty flavor compounds .

Flavor Compounds Related to Beef Flavor

Here are the flavor compounds specifically associated with beef flavor as listed in the patent document (US9826772B2). They are organized by the tables they appear in, along with their chemical names and, where provided, their associated flavor/aroma descriptions.

Flavor Compounds Associated with Beef from Table 3

Additional Beef-Related Volatiles from Table 8

This table lists volatile compounds detected in cooked beef that can be generated using the patent's methods:

• Acetic acid
• 2,3-butanedione
• 3-hydroxy-2-butanone
• Hexanal
• 2-pentylfuran
• Dimethyl disulfide
• Dimethyl trisulfide
• 2-methyl-3-furanthiol
• 2-furfurylthiol
• 2-acetyl-2-thiazoline
• Methional
• 2-acetylthiazole
• Benzothiazole
• Thiazole
• 2-methylthiazole
• 4-methylthiazole
• 2,4-dimethylthiazole
• 2,4,5-trimethylthiazole
• 2-ethyl-4-methylthiazole
• 2-isopropyl-4-methylthiazole
• 2,4-dimethyl-5-ethylthiazole
• Thiophene
• 2-methylthiophene
• 3-methylthiophene
• 2-ethylthiophene
• 2-pentylthiophene
• Thieno[3,2-b]thiophene
• Thieno[2,3-b]thiophene
• Dithienylthiophene isomers
• 2-methyl-3-(methyldithio)furan
• Bis(2-methyl-3-furyl) disulfide
• 2-furylmethanethiol
• 5-methyl-2-furanmethanethiol
• 2-methyl-3-(methylthio)furan
• 2-methyltetrahydrothiophen-3-one
• 2-methyl-3-thiophenethiol
• 2,3-dimethylthiophene
• 2,4-dimethylthiophene
• 3,4-dimethylthiophene
• 2,3,4-trimethylthiophene
• 2,3,5-trimethylthiophene
• 3-methyl-2-thiophenethiol
• 5-methyl-2-thiophenethiol
• Thiazole
• 4-methylthiazole
• 5-methylthiazole
• 2,4-dimethylthiazole
• 2,5-dimethylthiazole
• 4,5-dimethylthiazole
• 2,4,5-trimethylthiazole
• 2-ethyl-4-methylthiazole
• 2-isopropyl-4-methylthiazole
• 2,4-dimethyl-5-ethylthiazole
• Benzothiazole

Thiols, Sulfides, and Disulfides from Table 9

This table lists specific sulfur-containing compounds important for beef flavor:

These compounds collectively contribute to the characteristic beefy, savory, roasted, and fatty notes associated with cooked beef. The most critical ones identified in the patent for beef flavor are 2-methyl-3-furanthiol, bis(2-methyl-3-furyl) disulfide, and 2-furfurylthiol, which are consistently highlighted as key meaty aroma compounds.

Flavor Compounds Grouped, according to their Flavor Notes

Here are all the flavor compounds from the patent (US9826772B2) grouped according to their flavor/aroma notes as described in the document. Note that many compounds have multiple flavor characteristics and appear in multiple categories.

MEATY / BEEFY / BROTHY

ROASTY / TOASTY / POPCORN-LIKE

FATTY / OILY / TALLOWY

SULFURIOUS / SULFUR / ONION/GARLIC-LIKE

SMOKY / PHENOLIC / MEDICINAL

SWEET / CARAMEL-LIKE / FRUITY

CREAMY / BUTTERY

GREEN / GRASSY / VEGETABLE-LIKE

EARTHY / MUSTY

NUTTY

COCOA / CHOCOLATE-LIKE

COFFEE-LIKE

CITRUS-LIKE / SOAPY

SPICY / CLOVE-LIKE / CURRY-LIKE

ACIDIC / SOUR / CHEESY

ANIMAL-LIKE / FECAL / BARN-YARD

FLORAL

WOODY

VANILLA-LIKE

This comprehensive grouping illustrates the complex flavor profile that can be achieved through the patent's technology, with many compounds contributing to multiple sensory dimensions of cooked meat. d

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