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In 2011, Impossible™ Foods (Impossible) was founded with the aim of providing meat products with the taste and nutritional benefits of meat but without the negative health and environmental impacts.  In 2016, Impossible™ launched its first product, the Impossible™ burger, which is available in restaurants (e.g., Burger King®) and grocery stores.  The four main ingredients in the Impossible™ burger are protein (soy and potato proteins), fat (coconut and sunflower oils), binders (methylcelluloses) and flavor (a heme, specifically, soy leghemoglobin).  As discussed in more detail below, Impossible™ discovered that heme is the key ingredient that provides meat with its aroma and flavor.

Impossible™ discovered that certain characteristics of meaty flavors (e.g., beef, bacon, umami, savory, blood, etc.) produced during the cooking process were the result of a chemical reaction between flavor precursor molecules and iron complexes.  As a result of this discovery, Impossible™ combined flavor precursor molecules and iron complexes to produce consumable food products having a range of savory and meaty aromas and tastes.

The flavor precursor molecules that can be used in these products can be sugars, sugar alcohols, sugar acids, sugar derivatives (e.g., glucose, fructose, ribose, sucrose, etc.), oils (e.g., coconut oil, mango oil, sunflower oil, cottonseed oil, etc.), free fatty acids (e.g., caprylic acid, capric acid, lauric acid, myristic acid, oleic acid, etc.), amino acids and derivatives thereof (e.g., cysteine, cystine, methionine, isoleucine, leucine, lysine, etc.), nucleosides and nucleotides (e.g., inosine, guanosine, adenosine, etc.), vitamins (e.g., vitamin D, vitamin B6, vitamin E), acids (e.g., acetic acid, alpha hydroxy acids, tricarboxylic acids, dicarboxylic acids, etc.), peptides and protein hydrolysates (e.g., glutathione, vegetable protein hydrolysates, etc.), or extracts (e.g., malt extracts, yeast extract, etc.).

The iron complexes that can be used can be a heme moiety or other highly conjugated heterocyclic ring complexed to an iron ion.  Specifically, the heme moiety can be a heme cofactor, such as a heme-containing protein.  Heme-containing proteins include globins, such as soy leghemoglobin, which is currently used in the Impossible™ burger.

It is not surprising that Impossible™ filed for patent protection covering food products containing these iron complexes having the flavor and aroma of meat.  This post examines one patent family owned by Impossible™ covering these food products.  Specifically, this post compares the issued claims granted in Australia, Europe, Japan, Russia, and the United States (U.S.).

Australia

Australia Patent No.  2014205114B2

1.  A ground beef-like food product, comprising:

a) 1% – 5% by weight of a heme-containing protein;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, and galactose, and mixtures of two or more thereof;

c) at least 1.5 mM of a compound selected from cysteine, cystine, thiamine, methionine, and mixtures of two or more thereof; and

d) one or more plant proteins;

wherein the ground beef-like food product contains no animal product;

wherein cooking the ground beef-like food product results in the production of at least two volatile compounds which have a beef-associated aroma.

Australia Patent No. 2018200969B2 (Divisional of Australia Patent No. 2014205114B2)

1. A meat substitute comprising:

a) a porphyrin or a chlorin complexed to an iron ion; and

b) one or more flavor precursor molecules selected from the group consisting of glucose, fructose, ribose, arabinose, glucose-6-phosphate, fructose 6-phosphate, fructose 1,6-diphosphate, maltose, galactose, lactose, xylose, sucrose, maltodextrin, thiamine, cysteine, cystine, a cysteine sulfoxide, allicin, selenocysteine, methionine, isoleucine, leucine, lysine, phenylalanine, threonine, tryptophan, 5-hydroxytryptophan, valine, arginine, histidine, alanine, asparagine, aspartate, glutamate, glutamine, glycine, proline, serine and tyrosine;

wherein cooking imparts a taste and smell of meat to the meat substitute; and

wherein said porphyrin or a chlorin complexed to an iron ion is ferrous chlorin.

Europe

EP Patent No. 2943072B1

1. A meat substitute comprising:

a) a heme-containing protein; and

b) at least two flavor precursor molecules selected from the group consisting of glucose, fructose, ribose, arabinose, glucose-6-phosphate, fructose 6-phosphate, fructose 1,6-diphosphate, maltose, galactose, lactose, xylose, sucrose, maltodextrin, thiamine, cysteine, cystine, a cysteine sulfoxide, allicin, selenocysteine, methionine, isoleucine, leucine, lysine, phenylalanine, threonine, tryptophan, 5-hydroxytryptophan, valine, arginine, histidine, alanine, asparagine, aspartate, glutamate, glutamine, glycine, proline, serine and tyrosine;

wherein a taste and smell of meat is given to the meat substitute during the cooking process.

Note:  claim 1 as shown above is the claim as granted.  EP Patent No. 2943072B1 is currently subject of an opposition, the claims as granted may change as a result of the opposition procedure.

Japan

Japanese Patent No. 6553516B2

1. A food product which, when cooked, reproduces the taste of meat products, comprising:

a) 1% to 1% (w/v) of a heme-containing protein;

b)  sugars, sugar alcohols, sugar acids or sugar derivatives selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphoric acid, maltose, galactose, and mixtures of two or more of these;

c)  a compound selected from cysteine, cystine, selenocysteine, thiamine, and mixtures of 2 or more of these; and

d)  one or more plant proteins.

Russia

Russian Patent No. 2701852C2

1. A meat analog containing:

a) a highly conjugated heterocyclic ring complexed with an iron ion; and

b) one or more taste precursor molecules selected from the group consisting of: glucose, fructose, ribose, arabinose, glucose-6-phosphate, fructose-6-phosphate, fructose-1,6-diphosphate, inositol, maltose, sucrose, maltodextrin, glycogen, nucleotide bound sugars, molasses, lecithin, inosine, inosine monophosphate (IMP), guanosine monophosphate (HMP), pyrazine, adenosine monophosphate (AMP), lactic acid, succinic acid, glycolic acid, thiamine , creatine, pyrophosphate, algae oil, safflower oil, linseed oil, rice oil, cottonseed oil, coconut oil, mango oil, cysteine, methionine, isoleucine, leucine, lysine, phenylalanine, threonine, tryptophan, valine, arginine, histidine, alanine, asparagine, aspartate, glutamate, glutamine, glycine, proline, serine, tyrosine, glutathione, an amino acid derivative, protein hydrolysate, malt extract, yeast extract, and peptone.

United States

U.S. Patent No. 9,700,067B2

1. A ground beef-like food product comprising:

a) 1%-5% by weight of a heme-containing protein comprising an amino acid sequence having at least 80% sequence identity to the polypeptide set forth in SEQ ID NO:4;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, and galactose, and mixtures of two or more thereof;

c) at least 10 mM of a compound selected from cysteine, cystine, selenocysteine, thiamine, methionine, and mixtures of two or more thereof; and

d) 10% or more by weight of one or more plant proteins;

wherein the ground beef-like food product contains no animal products; and

wherein cooking the ground beef-like food product results in the production of at least two volatile compounds which have a beef-associated aroma.

U.S. Patent No. 9,808,029B2 (Continuation of U.S. Patent No. 9,943,096B2)

1. A ground beef-like food product, comprising:

a) 01%-5% by weight of a heme-containing protein;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, and galactose, and mixtures of two or more thereof;

c)  at least 1.5 mM of a compound selected from cysteine, cystine, thiamine, methionine, and mixtures of two or more thereof, and

d) one or more plant proteins;

wherein the ground beef-like food product contains no animal product; and

wherein cooking the ground beef-like food product results in the production of at least two volatile compounds which have a beef-associated aroma.

U.S. Patent No. 9,826,772B2 (Continuation of U.S. Patent No. 9,943,096B2)

1. A ground beef-like food product, comprising:

a) 1%-5% by weight of a heme-containing protein;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, and galactose, and mixtures of two or more thereof;

c) at least 10 mM of a compound selected from cysteine, cystine, thiamine, methionine, and mixtures of two or more thereof; and

d) one or more plant proteins;

wherein the ground beef-like food product contains no animal product; and

wherein cooking the ground beef-like food product results in the production of at least two volatile compounds which have a beef-associated aroma.

U.S. Patent No. 9,943,096B2 (continuation of U.S. Patent No. 9,700,067B2)

1. A food flavor additive composition comprising:

a) an isolated heme-containing protein;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, maltodextrin, and galactose, and mixtures of two or more thereof; and

c) a compound selected from cysteine, cystine, thiamine, methionine, and mixtures of two or more thereof;

wherein the flavor additive composition contains no animal products; and

wherein cooking the food flavor additive composition results in the production of at least two volatile compounds which have a meat-associated aroma.

U.S. Patent No. 10,314,325B2 (Continuation of U.S. Patent No. 9,943,096B2)

1. A food product, comprising:

a) a heme, wherein the heme is present in an amount equivalent to the amount of heme present in the food product when the food product contains a heme-containing protein in an amount of 0.01% to 5% by weight;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, and galactose, and mixtures of two or more thereof;

c) at least 1.5 mM of a compound selected from cysteine, cystine, thiamine, methionine, and mixtures of two or more thereof; and

d) one or more plant proteins;

wherein the food product contains no animal product; and

wherein cooking the food product results in the production of at least two volatile compounds selected from the group consisting of (1-ethyl-1-propenyl)-benzene, (E)-2-decenal, (E)-2-heptenal, (E)-2-hexenal, (E)-2-nonenal, (E)-2-octen-1-ol, (E)-2-octenal, (E)-2-tridecen-1-ol, (E)-3-penten-2-one, (E)-4-octene, (E)-5-decene, (E,E)-3,5-octadien-2-one, (Z)-2-decenal, (Z)-2-heptenal, (Z)-3-decen-1-ol, acetate, [(methyl sulfonyl)methyl]-benzene, 1-(ethylthio)-2-(methylthio)-buta-1,3-diene, 1-(methylthio)-propane, 1,1′-(1,2-cyclobutanediyl)bis-cis-benzene, 1,10-undecadiene, 1,3,5-cycloheptatriene, 1,3-bis(1,1-dimethylethyl)-benzene, 1,3-diisopropoxy-1,3-dimethyl-1,3-disilacyclobutane, 1,3-dimethyl-benzene, 1-decen-3-one, 1-heptanol, 1-heptyl-1,2,3,4-tetrahydro-4-methyl-naphthalene, 1-hexanol, 1-hydroxy-2-propanone, 1-nonanol, 1-octanol, 1-octen-3-ol, 1-octen-3-one, 1-octene, 1-pentanol, 1-penten-3-one, 1-undecanol, 2,2,4,6,6-pentamethyl-heptane, 2,3,4-trimethyl-pentane, 2,3-butanedione, 2,3-dihydro-5-methyl-furan, 2,3-dimethyl-pyrazine, 2,4-decadienal, 2,4-dimethyl-1-heptene, 2,5-dimethyl-pyrazine, 2-acetatyl-1-propene, 2-acetyl-propen-2-ol, 2-acetylthiazole, 2-butanone, 2-butenal, 2-butyl-1-decene, 2-decanone, 2-decenal, 2-ethyl-5-methyl-pyrazine, 2-ethylacrolein, 2-ethyl-furan, 2-heptanone, 2-heptenal, 2-hexyl furan, 2-methyl-1(H)-pyrrole, 2-methyl-1-heptene, 2-methyl-1-penten-1-one, 2-methyl-3-(methylthio) furan, 2-methyl-3-furanthiol, 2-methyl-5-(methylthio)-furan, 2-methyl-butanal, 2-methyl-cyclopentanone, 2-methyl-furan, 2-methyl-heptane, 2-methyl-pentanal, 2-methyl-propanal, 2-methyl-thiazole, 2-n-octylfuran, 2-nonanone, 2-nonen-4-one, 2-octanone, 2-octenal, 2-pentanone, 2-pentyl-furan, 2-pentyl-thiophene, 2-phenylpropenal, 2-propenal, 2-propenoic acid, methyl ester, 2-thiophenecarboxaldehyde, 2-tridecen-1-ol, 2-undecanone, 2-undecenal, 3-(methylthio)-propanenitrile, 3-(phenylmethyl)-2,5-piperazinedione, 3,3′-dithiobis-2-methyl-furan, 3,5-bis(1,1-dimethylethyl)-phenol, 3,5-di-tert-butylbenzoic acid, 3-decen-2-one, 3-ethylcyclopentanone, 3-ethyl-pentane, 3-methyl-2-butenal, 3-methyl-2-thiophenecarboxaldehyde, 3-methyl-3-buten-2-one, 3-methyl-butanal, 3-methyl-furan, 3-methylheptyl acetate, 3-methyl-pentanal, 3-pentyl-furan, 3-phenyl-furan, 3-thiophenecarboxaldehyde, 3-thiophenemethanol, 4,7-dimethyl-undecane, 4-chloro-2,6-bis(1,1-dimethylethyl)-phenol, 4-ethoxy-benzoic acid, ethyl ester, 4-ethyl-2-methyl-pyrrole, 4-ethyl-benzaldehyde, 4-methyl-2-heptanone, 4-methyl-5-thiazoleethanol, 4-methylthiazole, 4-nitrophenyl 2-thiophenecarboxylic acid ester, 4-penten-2-one, 4-quinolinecarboxaldehyde, 5-(2-chloroethyl)-4-methylthiazole, 5-ethenyl-4-methyl-thiazole, 5-ethyldihydro-2(3H)-furanone, 5-formyl-4-methylthiazole, 5-methyl-1-undecene, 6-methyl-2-heptanone, 7-methyl-(E)-5-undecene, 9-octadecenal, acetaldehyde, acetic acid, acetone, acetonitrile, acetophenone, acetyl valeryl, aminophenylacetylene, benzaldehyde, benzene, benzoic acid, benzyl alcohol, bis(2-methyl-4,5-dihydro-3-furyl) disulfide, butanal, butanone, butyrolactone, carbon disulfide, decanal, dihydro-3-(2H)-thiophenone, dihydro-5-pentyl-2(3H)-furanone, dimethyl selenone, dimethyl sulfide, dimethyl trisulfide, dodecanal, ethanol, ethyl acetate, formic acid, heptyl ester, furan, furfural, heptanal, hexanoic acid, isopropyl alcohol, isothiazole, isothiocyanato-methane, m-aminophenylacetylene, methacrolein, methanethiol, methional, methyl (methylthio)methyl disulfide, methyl isopropyl disulphide, methyl thiolacetate, methyl vinyl ketone, methyl-pyrazine, methyl-thiirane, nonanal, octanal, octane, oxalic acid, diallyl ester, oxalic acid, isobutyl pentyl ester, p-Cresol, p-dithiane-2,5-diol, pentanal, pentanoic acid, 2,2,4-trimethyl-3-hydroxy-, isobutyl ester, phenol, phenylacetaldehyde, propanal, propyl-cyclopropane, p-xylene, pyrazine, pyrrole, styrene, thiazole, thiocyanic acid, methyl ester, thiophene, toluene, trans-2-(2-pentenyl)furan, trichloromethane, and tridecane.

U.S. Patent No. 10,327,464B2 (Continuation of U.S. Patent No. 9,943,096B2)

1. A food product, comprising:

a) 01%-5% by weight of a heme-containing protein;

b) a compound selected from glucose, ribose, fructose, lactose, xylose, arabinose, glucose-6-phosphate, maltose, and galactose, and mixtures of two or more thereof;

c) at least 1.5 mM of a compound selected from cysteine, cystine, thiamine, methionine, and mixtures of two or more thereof; and

d) one or more plant proteins;

wherein the food product contains no animal products that contain heme; and

wherein cooking the food product results in the production of at least two volatile compounds selected from the group consisting of (1-ethyl-1-propenyl)-benzene, (E)-2-decenal, (E)-2-heptenal, (E)-2-hexenal, (E)-2-nonenal, (E)-2-octen-1-ol, (E)-2-octenal, (E)-2-tridecen-1-ol, (E)-3-penten-2-one, (E)-4-octene, (E)-5-decene, (E,E)-3,5-octadien-2-one, (Z)-2-decenal, (Z)-2-heptenal, (Z)-3-decen-1-ol, acetate, [(methylsulfonyl)methyl]-benzene, 1-(ethylthio)-2-(methylthio)-buta-1,3-diene, 1-(methylthio)-propane, 1,1′-(1,2-cyclobutanediyl)bis-cis-benzene, 1,10-undecadiene, 1,3,5-cycloheptatriene, 1,3-bis(1,1-dimethylethyl)-benzene, 1,3-diisopropoxy-1,3-dimethyl-1,3-disilacyclobutane, 1,3-dimethyl-benzene, 1-decen-3-one, 1-heptanol, 1-heptyl-1,2,3,4-tetrahydro-4-methyl-naphthalene, 1-hexanol, 1-hydroxy-2-propanone, 1-nonanol, 1-octanol, 1-octen-3-ol, 1-octen-3-one, 1-octene, 1-pentanol, 1-penten-3-one, 1-undecanol, 2,2,4,6,6-pentamethyl-heptane, 2,3,4-trimethyl-pentane, 2,3-butanedione, 2,3-dihydro-5-methyl-furan, 2,3-dimethyl-pyrazine, 2,4-decadienal, 2,4-dimethyl-1-heptene, 2,5-dimethyl-pyrazine, 2-acetatyl-1-propene, 2-acetyl-propen-2-ol, 2-acetylthiazole, 2-butanone, 2-butenal, 2-butyl-1-decene, 2-decanone, 2-decenal, 2-ethyl-5-methyl-pyrazine, 2-ethylacrolein, 2-ethyl-furan, 2-heptanone, 2-heptenal, 2-hexyl furan, 2-methyl-1(H)-pyrrole, 2-methyl-1-heptene, 2-methyl-1-penten-1-one, 2-methyl-3-(methylthio) furan, 2-methyl-3-furanthiol, 2-methyl-5-(methylthio)-furan, 2-methyl-butanal, 2-methyl-cyclopentanone, 2-methyl-furan, 2-methyl-heptane, 2-methyl-pentanal, 2-methyl-propanal, 2-methyl-thiazole, 2-n-octylfuran, 2-nonanone, 2-nonen-4-one, 2-octanone, 2-octenal, 2-pentanone, 2-pentyl-furan, 2-pentyl-thiophene, 2-phenylpropenal, 2-propenal, 2-propenoic acid, methyl ester, 2-thiophenecarboxaldehyde, 2-tridecen-1-ol, 2-undecanone, 2-undecenal, 3-(methylthio)-propanenitrile, 3-(phenylmethyl)-2,5-piperazinedione, 3,3′-dithiobis-2-methyl-furan, 3,5-bis(1,1-dimethylethyl)-phenol, 3,5-di-tert-butylbenzoic acid, 3-decen-2-one, 3-ethylcyclopentanone, 3-ethyl-pentane, 3-methyl-2-butenal, 3-methyl-2-thiophenecarboxaldehyde, 3-methyl-3-buten-2-one, 3-methyl-butanal, 3-methyl-furan, 3-methylheptyl acetate, 3-methyl-pentanal, 3-pentyl-furan, 3-phenyl-furan, 3-thiophenecarboxaldehyde, 3-thiophenemethanol, 4,7-dimethyl-undecane, 4-chloro-2,6-bis(1,1-dimethylethyl)-phenol, 4-ethoxy-benzoic acid, ethyl ester, 4-ethyl-2-methyl-pyrrole, 4-ethyl-benzaldehyde, 4-methyl-2-heptanone, 4-methyl-5-thiazoleethanol, 4-methylthiazole, 4-nitrophenyl 2-thiophenecarboxylic acid ester, 4-penten-2-one, 4-quinolinecarboxaldehyde, 5-(2-chloroethyl)-4-methylthiazole, 5-ethenyl-4-methyl-thiazole, 5-ethyldihydro-2(3H)-furanone, 5-formyl-4-methylthiazole, 5-methyl-1-undecene, 6-methyl-2-heptanone, 7-methyl-(E)-5-undecene, 9-octadecenal, acetaldehyde, acetic acid, acetone, acetonitrile, acetophenone, acetyl valeryl, aminophenylacetylene, benzaldehyde, benzene, benzoic acid, benzyl alcohol, bis(2-methyl-4,5-dihydro-3-furyl) disulfide, butanal, butanone, butyrolactone, carbon disulfide, decanal, dihydro-3-(2H)-thiophenone, dihydro-5-pentyl-2(3H)-furanone, dimethyl selenone, dimethyl sulfide, dimethyl trisulfide, dodecanal, ethanol, ethyl acetate, formic acid, heptyl ester, furan, furfural, heptanal, hexanoic acid, isopropyl alcohol, isothiazole, isothiocyanato-methane, m-aminophenylacetylene, methacrolein, methanethiol, methional, methyl (methylthio)methyl disulfide, methyl isopropyl disulphide, methyl thiolacetate, methyl vinyl ketone, methyl-pyrazine, methyl-thiirane, nonanal, octanal, octane, oxalic acid, diallyl ester, oxalic acid, isobutyl pentyl ester, p-Cresol, p-dithiane-2,5-diol, pentanal, pentanoic acid, 2,2,4-trimethyl-3-hydroxy-, isobutyl ester, phenol, phenylacetaldehyde, propanal, propyl-cyclopropane, p-xylene, pyrazine, pyrrole, styrene, thiazole, thiocyanic acid, methyl ester, thiophene, toluene, trans-2-(2-pentenyl)furan, trichloromethane, and tridecane.

This post was written by Lisa Mueller.

 

 

 

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