Flavour catalysts, compositions and methods thereof

Abstract

This disclosure concerns a method of imparting and / or enhancing an olfactory perception of a meat flavour in a food, comprising a step of adding iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour. The disclosure also concerns an iron chlorophyllin composition.

Description

[0001] Flavour Catalysts, Compositions and Methods Thereof

[0002] Technical Field

[0003] The present invention relates, in general terms, to flavour catalysts, compositions comprising the flavour catalysts and their methods of fabrication and uses thereof.

[0004] Background

[0005] Climate change, geopolitical instabilities and reduced global agricultural production capacities has made animal-based meats an increasingly less affordable source of protein for the common masses. Currently, animal-based meats have undergone price inflation of 10.5%, far outpacing global inflation of 8% in 2021 alone. Alternative proteins (AP), particularly plant-based meats (PBM), are proteins that are not derived from animal livestock. These proteins promise a more sustainable and accessible source of nutrition since they are less carbon and resource intensive to produce. Thus, PBM market size predicted to increase from USD10.11B in 2022 to USD33.99B by 2027. Furthermore, certain market factors favour consumer adoption of PBMs, such as the increasing flexitarian demographic that have positive reception towards PBM products globally and locally.

[0006] However, this has yet to materialize. Instead, PBM's market size represents only 1.5% of the total meat industry (which totals USD1, 289.36B in 2022), owing to low consumer adoption rates of such products. This is because PBM and AP often offer lower value propositions compared to animal meats, due to their higher prices and inferior palatability compared to animal meats. Consequently, consumers have shown a greater willingness to pay more for animal meats over PBM, indicating that animal meats command a price premium over its alternatives. Thus, to increase consumer adoption of PBM, PBMs must simultaneously be much more affordable but be as delectable as animal meats.

[0007] Thus far, two classes of solutions to improve the flavour profile of plant-based meats exist, namely (a) vegan meat flavourings that utilizes Heme-containing proteins, which are flavourings produced by Impossible Foods, Motif foodworks, Paleo and (b) chemicalbased vegan meat flavourings produced by Commercial Flavour houses like Givaudan, Firmenich & Symrise to name a few. For the former, Heme-containing proteins are used as catalysts to increase the abundance of cooking reactions and flavour molecules formed to impart a meat-like flavour to AP products. For the latter, these flavouring mixtures are usually process flavours or chemical reconstitutions of flavours and aromas of animal meats to mimic their flavour profile. These flavouring solutions are inadequate for AP products as they often involve (i) long & expensive flavouring processes, (ii) are difficult to incorporate into existing PBM production pipelines, (iii) may be classified as GMO or novel and therefore subjected to longer food safety approval processes and (iv) fail to produce meat-identical flavourings due to their inability to mimic the complex chemical profile that constitutes the flavour of animal meats.

[0008] Moreover, Heme B or hemoprotein-based flavouring production usually consists of (I) synthesizing it from chemical subunits, (ii) precision fermentation where genetically modified bacteria or yeast cells are configured to biosynthesize heme or its hemecontaining proteins or (iii) extraction from animal sources. These production methods produce high-cost, non-vegan and / or GMO flavouring ingredients as their production methodologies are complex, require significant purification efforts and / or from unacceptable provenance (being derived from GMO or animal sources).

[0009] Hence, these solutions fail to improve the payability or reduce production costs of AP products to a level that is acceptable to the consumers. For the alternative protein sales to improve, AP must first be (i) equivalently palatable to but (ii) be a magnitude more adorable than animal meats. Thus, an affordable, efficacious and simple-to-use vegan meat flavouring would be highly sought after by the USD10.11B PBM and USD8.7B vegan flavours market.

[0010] It would be desirable to overcome or ameliorate at least one of the above-described problems.

[0011] Summary

[0012] The present disclosure provides a method of imparting and / or enhancing an olfactory perception of a meat flavour in a food, comprising a step of adding iron chlorophyllin at 0.002 %w / w to 5 %w / w relative to the food, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour.

[0013] In some embodiments, the iron chlorophyllin is selected from trisodium iron chlorophyllin a, trisodium iron chlorophyllin b, disodium iron chlorophyllin a, disodium iron chlorophyllin b, monosodium iron chlorophyllin a, monosodium iron chlorophyllin b, iron chlorophyllin a, iron chlorophyllin b, iron pheophytin a, iron pheophytin b, or a combination thereof.

[0014] In some embodiments, the iron chlorophyllin comprises iron (II), iron (III), or a combination thereof.

[0015] In some embodiments, the food is an edible composition comprising an alternative protein, plant-based meat, or a combination thereof.

[0016] In some embodiments, the component in the food is selected from a protein, an amino acid, a fat, an oil, a sugar, vitamin, a food additive, or a combination thereof.

[0017] In some embodiments, the method further comprises adding a flavour precursor selected from sugar, amino acid, vitamin, fat, flavour enhancer, or a combination thereof.

[0018] In some embodiments, the sugar is selected from monosaccharide, disaccharide, oligosaccharide, polysaccharide groups and their derivatives thereof.

[0019] In some embodiments, the sugar is selected from glucose, fructose, galactose, mannose, xylose, lactose, maltose, isomaltose, trehalose, sorbitol, mannitol, amylose, amylopectin, pectin, dextrin, cellulose, hemicellulose, their respective DL-isomers or a combination thereof, wherein the sugar is about 2 %w / w to about 20 %w / w relative to the food.

[0020] In some embodiments, the amino acid is selected from D-amino acid, L-amino acid, DL- amino acid or their respective dipeptide, tripeptide, oligopeptide and polypeptide thereof.

[0021] In other embodiments, the amino acid is selected from D-alanine, L-alanine, D-arginine, L-arginine, L-arginine hydrochloride, D-arginine hydrochloride, D-asparagine, L- asparagine, D-aspartate salt, L-aspartate salt, D-aspartic acid, L-aspartic acid, D- cysteine, L-cystine, D-cysteine hydrochloride, L-cysteine hydrochloride, D-glutamate salt, L-glutamate salt, D-glutamic acid, L-glutamic acid, D-glutamine, L-glutamine, glycine, D-histidine, L-histidine, D-histidine hydrochloride, L-histidine hydrochloride, D- isoleucine, L-isoleucine, D-leucine, L-leucine, D-lysine, L-lysine, D-lysine hydrochloride, L-lysine hydrochloride, D-methionine, L-methionine, D-ornithine, L-ornithine, D- phenylalanine, L-phenylalanine, D-proline, L-proline, D-serine, L-serine, taurine, D- threonine, L-threonine, D-tryptophan, L-tryptophan, D-tyrosine, L-tyrosine, D-valine, L-valine, their hydrates, derivatives, or combination thereof, wherein the amino acid is about 5 %w / w to about 50 %w / w relative to the food.

[0022] In some embodiments, the vitamin is selected from thiamine (Vitamin Bl), thiamine hydrochloride, ascorbic acid (Vitamin C), sodium ascorbate (vitamin C), potassium ascorbate (vitamin C), or a combination thereof, wherein the vitamin is about 0.5 %w / w to about 10 %w / w relative to the food.

[0023] In some embodiments, the flavour enhancer is selected from nucleoside, nucleotide, vitamin, protein hydrolysate from animal, plant, fungal, bacterial and / or in vitro origin, lecithin, or a combination thereof, wherein the flavour enhancer is about 0.5 %w / w to about 10 %w / w relative to the food.

[0024] In some embodiments, the fat is selected from animal-based and / or plant-based lipids, wherein the fat is about 30 %w / w to about 90 %w / w relative to the food.

[0025] In some embodiments, the fat is selected from canola oil, soybean oil, safflower oil, flaxseed oil, sunflower oil, olive oil, coconut oil, palm oil, corn oil, linseed oil, algae oil, rice bran oil, pumpkin seed oil, peanut oil, sesame oil, beef tallow, chicken fat, fish oil, pork fat, mutton fat, or a combination thereof.

[0026] In some embodiments, when the meat flavour is a beef flavour, the flavour precursor is selected from beef fat, canola oil, palm oil, corn oil, or a combination thereof; when the meat flavour is a poultry flavour, the flavour precursor is selected from corn oil, sunflower oil, canola oil, palm oil, safflower oil, chicken fat or a combination thereof; when the meat flavour is a seafood flavour, the flavour precursor is selected from fish oil, algal, flaxseed oil or a combination thereof; when the meat flavour is a pork flavour, the flavour precursor is selected from corn oil, sunflower oil, canola oil, palm oil, safflower oil, pork fat or a combination thereof; and when the meat flavour is a mutton flavour, the flavour precursor is selected from mutton fat, canola oil, palm oil and corn oil or a combination thereof.

[0027] In some embodiments, the volatiles are selected from Pentane, 3-Methyl butanal, Pentanal, Hexanal, Nonanal, (E)-2-Octenal, Furfural, (E,E)-2,4-Heptadienal, (E)-2- Nonenal, (E,E)-2,4-Nonadienal, 2-Undecenal, 2,4-Decadienal, trans-3-Nonen-2-one, or a combination thereof.

[0028] In some embodiments, iron chlorophyllin is configured to interact with a protein in the food in order to generate Amadori rearrangement products. Maillard Reaction products, Strecker degradation products, melanoidins, advanced glycation end-products, volatile, non-volatile molecular products or a combination thereof that influence aroma and flavour of a food product.

[0029] The present disclosure also provides a method of forming a food product, comprising a step of adding iron chlorophyllin at about 0.002% w / w to about 5% w / w relative to the food product, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food product in order to generate volatiles which replicate the meat flavour.

[0030] The present disclosure also provides a food product comprising iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food product, wherein the food product is selected from an alternative protein, plant-based meat, or a combination thereof; wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour.

[0031] The present disclosure also provides an iron chlorophyllin composition, comprising : a) iron chlorophyllin at about 0.1 %w / w to about 5 %w / w relative to the composition; and b) a flavor precursor at about 95 %w / w to about 99.9 %w / w relative to the composition.

[0032] In some embodiments, the iron chlorophyllin composition is a powder.

[0033] The present disclosure also provides a method of synthesizing an iron chlorophyllin composition, comprising a step of mixing iron chlorophyllin with a flavour precursor, wherein iron chlorophyllin is about 0.1 %w / w to about 5 %w / w relative to the composition; and wherein the flavour precursor is about 95 %w / w to about 99.9 %w / w relative to the composition.

[0034] In some embodiments, the method further comprises a step of reacting chlorophyll or sodium magnesium chlorophyllin with an iron salt in order to form iron chlorophyllin, wherein the chlorophyll is obtained from a plant, fungi or bacteria.

[0035] In some embodiments, chlorophyll is derived from a mixture of green vegetables.

[0036] In some embodiments, the iron salt is an iron(II) or iron (III) salt selected from food grade iron(II) chloride, iron(III) chloride, iron(II) bromide, iron(III) bromide, iron(II) iodide, iron(III) iodide, iron(II) sulfate, iron (III) sulfate, iron(II) nitrate, iron(III) nitrate, iron(II) fumurate, iron(III) fumurate, iron(II) gluconate, iron(III) gluconate, iron(II) lactate, iron(III) lactate, iron (II) ascorbate, iron (III) ascorbate, iron (II) aspartate, iron (III) aspartate, iron (II) glycinate, iron (III) glycinate, iron (II) carbonate, iron (III) carbonate, iron (II) citrate, iron (III) citrate, iron (II) malate, iron (III) malate, iron (II) oxalate, iron (III) oxalate, iron (II) phosphate, iron (III) phosphate, iron (II) tartrate, iron (III) tartrate, iron (II) ammonium citrate, iron (III) ammonium citrate, iron (II) glycerophosphate, iron (III) glycerophosphate, iron (II) pyrophosphate, iron (III) pyrophosphate, their hydrates and derivatives thereof.

[0037] Brief description of the drawings

[0038] Embodiments of the present invention will now be described, by way of non-limiting example, with reference to the drawings in which:

[0039] Figure 1A shows structural differences between Heme, Sodium Iron Chlorophyllin (SIC) Figure IB shows other Sodium Iron Chlorophyllin (SIC) and Hydrogen Iron Chlorophyllin acid (HIC)

[0040] Figure 2 shows a mass spectrum indicating the detected molecular masses of SIC and their identified structures

[0041] Figure 3 shows a UV-vis absorption spectra for SIC and HIC in MeOH media

[0042] Figure 4 shows a mass spectrum indicating the detected molecular masses of HIC and their identified structures

[0043] Figure 5 shows amino acid content after acid hydrolysis with different catalysts added (N : no catalysts; H: Heme; S: SIC; F: inorganic iron)

[0044] Figure 6 shows amino acid content after acid hydrolysis with different concentrations of HCI with different catalysts

[0045] Figure 7 shows SPME-GCMS chromatograms of Mixture F + Hemin Flavour Catalyst (black) vs. Mixture F + SIC flavour catalyst (grey). The chromatogram has been base shifted for clarity, but the abundances of the volatiles have remained unchanged. The similar volatile profiles of both samples shows that hemin and SIC have equivalent flavour catalyst activity.

[0046] Figure 8 shows SPME-GCMS chromatograms of equivalent loadings of Mixture F + Beef Fat with SIC (black; top) and without SIC (light grey; bottom). The chromatogram has been base shifted for clarity, but the abundances of the volatiles have remained unchanged. The sample with SIC showed higher concentrations and greater diversity of volatiles detected (labelled by black circles) compared to the sample without SIC, indicating that SIC enhances the production of volatiles during the cooking process.

[0047] Figure 9 shows SPME-GCMS chromatograms of Mixture F + Mutton Fat with SIC (black; bottom) and without SIC (light grey; top). The chromatogram has been base shifted for clarity, but the abundances of the volatiles have remained unchanged. The sample with SIC showed higher concentrations and greater diversity of volatiles detected (indicated by black circles) compared to the sample without SIC, indicating that SIC enhances the production of volatiles during the cooking process.

[0048] Detailed description

[0049] The present disclosure is predicated on the understanding that the flavour profile of animal meats is a consequence of heme-catalysed cooking reactions that results in a greater abundance and diversity of "meaty" flavour molecules being formed. However, no systematic scientific investigation has been performed into elucidating the reaction mechanisms underlying such catalysis.

[0050] The inventors had accrued evidence demonstrating the concentration-dependence catalytic activity of eggshell-derived Heme B and its role as a flavour catalytic, and have identified key reactive oxygen species (ROS) that are indispensable for meaty volatile generation. When added to AP and / or PBM, eggshell-derived Heme B may function as a molecular catalyst to form meat-identical flavours. Such compounds may be termed "flavour catalysts", which are defined as food additives that produce meat-identical volatiles and flavour molecules through the catalyst-mediated upregulation of cooking reactions, such as Maillard reaction, Strecker Degradation reactions, Lipid Autoxidation reactions and thiamine degradation.

[0051] However, eggshell-derived Heme B flavour catalysts retains significant drawbacks, as it is not considered vegan due to its avian origins and has high production costs because of the low abundance of Heme precursor's (i.e. protoporphyrin IX) in the cutaneous layer of the eggshells.

[0052] To overcome the limitations of the Heme B flavour catalyst, the present disclosure concerns an alternative flavour catalyst based on a chlorophyllin backbone, namely sodium iron chlorophyllin (SIC) and hydrogen iron chlorophyllin acid (HIC). SIC and HIC are characteristic as they are (i) vegan, (ii) non-GMO, and (iii) significantly more affordable flavour catalysts that are (iv) equivalently efficacious at generating meatidentical flavours as the eggshell-derived Heme B.

[0053] SIC includes the following forms, namely trisodium iron (III) chlorophyllin a, trisodium iron (III) chlorophyllin b, trisodium iron(II) chlorophyllin a, trisodium iron(II) chlorophyllin b, disodium iron (III) chlorophyllin a, disodium iron (III) chlorophyllin b, disodium iron(II) chlorophyllin a, disodium iron(II) chlorophyllin b, monosodium iron(III) chlorophyllin a, monosodium iron(III) chlorophyllin b, monosodium iron(II) chlorophyllin a, monosodium iron (II) chlorophyllin b. Meanwhile, HIC refers to iron(III) chlorophyllin a acid, iron(III) chlorophyllin b acid, iron(II) chlorophyllin a acid, iron(II) chlorophyllin b acid, iron(III) pheophytin a, iron(III) pheophytin b, iron(II) pheophytin a and iron(II) pheophytin b structures (see Figure 1A and IB).

[0054] HIC and SIC may be manufactured from vegetable-based precursors (i.e. vegetables or vegan-based commercial precursors) using a facile, efficient, high-yield and cost- effective process. The process is also easily scalable using contemporary chemical industrial manufacturing techniques and infrastructure. Moreover, the process may use significantly milder reaction conditions (i.e. lower temperature, pressure, and reaction times), safer chemicals and lesser steps compared to the protoporphyrin IX (PPY9) extraction from eggshells. Resultingly, SIC and HIC manufacturing processes may require substantially less infrastructure for larger scale production, with infrastructural costs being SGD23,220 compared to Heme's infrastructural cost of SGD75,500 for pilot scale production (approximately 100,000 servings per day).

[0055] Additionally, the precursor chemicals for HIC and SIC, namely chlorophyll a & b, are present in more abundant quantities in green leaf sources. For comparison, brown eggshells contain approximately 7.32 ng to 10.15 ng of Heme B precursor per g of eggshell, while concentrations of chlorophyll a and b are approximately 105to 106-fold greater in green leafy vegetables (ranging from 1.43 to 4.07 mg g-1).

[0056] Due to the use of low-cost feedstock (i.e. vegetable sources) and highly efficient SIC and HIC production processes, both SIC and HIC are estimated to be 10-20 times cheaper to manufacture at an industrial scale (approximately USD20M) compared to Precision Fermentation Heme (approximately USD220M). Moreover, HIC's production price is approximately SGD250 per kilogram, 42 times lower compared to eggshell- derived Heme B, which costs SGD10,500 per kilogram to manufacture.

[0057] SIC has traditionally been used a semi-synthetic green food colouring with greater thermal stability compared to its magnesium counterpart. In particular, SIC is a food ingredient (food additive number 267 according to Regulations for Enforcement of the Food Sanitation Act, Appended Table 1) which has been approved by the Japanese Ministry Health, Labour and Welfare since 1996. It has been employed extensively as food colouring for candies, buck wheat noodles and frozen desserts with no maximum limit indicated in the Standards for Use of Food Additives. SIC's safety profile has been determined as having a very high No Observed Adverse Effect Limit (NOAEL) in F344 Rats at 609 mg per kg of body weight per day (mg / kg bw / day) for male rats, and 678 mg / kg bw / day for females.

[0058] Accordingly, the present disclosure provides a method of imparting and / or enhancing an olfactory perception of a meat flavour in a food, comprising a step of adding and / or contacting iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour and / or odour / aroma.

[0059] Olfactory perception is a process that starts in the nose with the stimulation of olfactory sensory neurons and terminates in higher cerebral centers which, when activated, make the user consciously aware of an odor. This perception may be further reinforced by visual and / or auditory cues, such as the sight of a piece of meat or the sound of sizzling when meat contacts a hot grill.

[0060] When heated, iron chlorophyllin may interact with proteins, amino acids, fats, oils, sugars, and other additives such as flavour enhancers in order to generate volatiles. These volatiles when taken in by a user via olfactory means, provide a perception of a "meat flavor" to the user. Thus, by combining the composition with various types of AP or PBM, the perception of cooking and / or eating beef, poultry, seafood, mutton, pork and the likes may be replicated and / or enhanced.

[0061] As used herein, the term "iron chlorophyllin" refers to a metalloporphyrin complex molecule whereby an iron cation (Fe2+or Fe3+) is coordinated to a porphyrin scaffold. The porphyrin scaffold may be chlorophyll. The term includes their derivatives, analogs stereoisomers, and salts thereof. For example, the chlorophyllin molecule may be modified through the attachment of additional ligand molecules to the central metal ion (via the formation of dative bonds) or by covalently linking to the chlorophyllin's organic scaffold. For example, the carboxylic functionalities on the chlorophyllin molecule can undergo an amide coupling reaction to append a histidine or imidazole moiety, which can subsequently then form a dative bond at the axial location of Fe2+ / Fe3+central ion. Alternatively, independent and discrete ligands, such as CO molecules, can readily bind to the Fe2+ / Fe3+central ion through the formation of strong and robust dative bonds. These modifications modulate the electrochemical properties and catalytic activity of chlorophyllin, resulting in the production of different flavour and aromatic compounds during cooking as compared to unmodified chlorophyllin. It should be noted that Heme B is structurally different from SIC and HIC as it contains an iron atom chelated in a tetrapyrrolic macrocylic structure (which has 22-n electrons), while SIC and HIC contain an iron atom chelated in a chlorin macrocyclic structure (which contains 20-n electrons). Soy leghemoglobin is structurally different from SIC and HIC, as it consists of a polypeptide chain and a heme b prosthetic group. Heme and associated complexes such as leghemoglobin are not within the scope of this disclosure.

[0062] In some embodiments, the iron chlorophyllin is selected from sodium iron chlorophyllin (SIC), hydrogen iron chlorophyllin acid (HIC), or a combination thereof. In some embodiments, the iron chlorophyllin is selected from trisodium iron chlorophyllin a, trisodium iron chlorophyllin b, disodium iron chlorophyllin a, disodium iron chlorophyllin b, monosodium iron chlorophyllin a, monosodium iron chlorophyllin b, iron chlorophyllin a, iron chlorophyllin b, iron pheophytin a, iron pheophytin b, or a combination thereof.

[0063] In some embodiments, the iron chlorophyllin comprises iron (II), iron (III), or a combination thereof. In some embodiments, the iron chlorophyllin comprises iron (II).

[0064] In some embodiments, the iron chlorophyllin is about 0.002 %w / w to about 5 %w / w relative to the food. In other embodiments, the concentration is about 0.005 %w / w to about 5 %w / w, about 0.01 %w / w to about 5 %w / w, about 0.05 %w / w to about 5 %w / w, about 0.1 %w / w to about 5 %w / w, about 0.3 %w / w to about 5 %w / w, about 0.5 %w / w to about 5 %w / w, about 0.8 %w / w to about 5 %w / w, about 1 %w / w to about 5 %w / w, about 1.5 %w / w to about 5 %w / w, about 2 %w / w to about 5 %w / w, about 2.5 %w / w to about 5 %w / w, about 3 %w / w to about 5 %w / w, about 3.5 %w / w to about 5 %w / w, or about 4 %w / w to about 5 %w / w. In other embodiments, the concentration is about 0.002 %w / w to about 4.5 %w / w, about 0.002 %w / w to about 4 %w / w, about 0.002 %w / w to about 3.5 %w / w, about 0.002 %w / w to about 3 %w / w, about 0.002 %w / w to about 2.5 %w / w, about 0.002 %w / w to about 2 %w / w, about 0.002 %w / w to about 1.5 %w / w, about 0.002 %w / w to about 1 %w / w, about 0.002 %w / w to about 0.5 %w / w, or about 0.002 %w / w to about 0.1 %w / w.

[0065] In some embodiments, the iron chlorophyllin is trisodium iron (III) chlorophyllin a, trisodium iron (III) chlorophyllin b, trisodium iron(II) chlorophyllin a, trisodium iron(II) chlorophyllin b, disodium iron (III) chlorophyllin a, disodium iron (III) chlorophyllin b, disodium iron(II) chlorophyllin a, disodium iron(II) chlorophyllin b, monosodium iron(III) chlorophyllin a, monosodium iron(III) chlorophyllin b, monosodium iron(II) chlorophyllin a, monosodium iron(II) chlorophyllin b, iron(III) chlorophyllin a acid, iron(III) chlorophyllin b acid, iron(II) chlorophyllin a acid, iron(II) chlorophyllin b acid, iron(III) pheophytin a, iron(III) pheophytin b, iron(II) pheophytin a, iron(II) pheophytin , and their respective carboxylate salts. The cation associated with the carboxylate salts may be a food safe cation, such as sodium, potassium, magnesium, calcium, ammonium or a combination thereof.

[0066] As used herein, "food" refers to a food product in its final form for consumption by a consumer. The iron chlorophyllin is added as a flavouring agent or as a component of a flavouring composition.

[0067] The iron chlorophyllin may be added to a surface of the food, or may be incorporated into the food. For example, the food may be minced and the iron chlorophyllin mixed into the minced food.

[0068] The food may be a meat, such as beef, poultry, seafood, mutton, and pork. In this regard, the addition and heating of iron chlorophyllin with the meat enhances the olfactory perception of a meat flavour. In some embodiments, the food is an edible composition. The edible composition may comprise an alternative protein, plant-based meat, or a combination thereof. In this regard, the addition and heating of iron chlorophyllin with the meat imparts and / or enhances the olfactory perception of a meat flavour.

[0069] In some embodiments, the alternative protein is derived from a source selected from plant, insect, fungus, bacteria, in vitro cultured animal cells, or a combination thereof.

[0070] In some embodiments, the alternative protein is derived from a plant source selected from soy, pea, wheat, lentil, lupin, vetch, chickpea, cowpea, pigeon pea, adzuki bean, bambara bean, black bean, fava bean, kidney bean, lima bean, long bean, mung bean, navy bean, tepary bean, velvet bean, yam bean, oat, rice, quinoa, buckwheat, amaranth, camelina seed, hemp seed, pumpkin seed, rapeseed, sunflower seed, peanut, cashew nut, potato, jackfruit, duckweed, sweet potato, tapioca or a combination thereof. In some embodiments, the alternative protein is derived from a fungus source selected from Aspergillus spp., Agrocybe spp. (Poplar mushrooms), Fusarium spp. (Microfungus), Monascus spp., Mucor spp., Neurospora spp., Komagataella spp., Rhizopus spp., Saccharomyces spp., Zygosaccharomyces spp., Agaricus bisporus (button mushroom), Flammulina filiformis (enokitake), Grifola frondosa (maitake), Lentinula edodes (shiitake), Lyophyllum shimeji (hon-shimeji), Morchella spp. (morels), Pleurotus spp. (oyster mushrooms), Volvariella volvacea (straw mushroom), or a combination thereof.

[0071] In some embodiments, the alternative protein is derived from an insect source selected from the Insecta Class.

[0072] Plant-based meat refers to meat-like products that are made entirely from plant-based ingredients, rather than animal-derived ingredients, such as soy, pea, wheat, or mushroom, nut, mycoprotein-based ingredients, or a combination thereof.

[0073] In some embodiments, the component in the food is selected from a protein, an amino acid, a fat, an oil, a sugar, vitamin, a food additive, or a combination thereof.

[0074] If the food is lacking in the component, it may be added to the food as a flavour precursor. In some embodiments, the method further comprises adding a flavour precursor to the food. The flavour precursor may be a sugar, amino acid, vitamin, fat, flavour enhancer, or a combination thereof. The flavour precursor interacts with the iron chlorophyllin when heated in order to generate volatiles replicating a "meat flavour" when the food is lacking of it, or to further enhance a meat flavour of the food. The replicated "meat flavour" thus depends on the type and / or combinations of flavour precursor used. For example, as shown in Table 2, a pork flavour may be replicated when the flavour precursor is a combination of linoleic acid and oleic acid. A fish flavour may be replicated when the flavour precursor is docosahexaenoic acid. A beef flavour may be replicated when the flavour precursor is a combination of beef fat, palm oil and / or coconut oil. It was found that the interaction of iron chlorophyllin with beef fat, palm oil and / or coconut oil increases the perception of beef-like flavours compared to just beef fat alone.

[0075] In some embodiments, the sugar is selected from monosaccharide, disaccharide, oligosaccharide, polysaccharide and their derivatives thereof. In other embodiments. the sugar is selected from glucose, fructose, galactose, mannose, xylose, lactose, maltose, isomaltose, trehalose, sorbitol, mannitol, amylose, amylopectin, pectin, dextrin, cellulose, hemicellulose, their respective DL-isomers or a combination thereof. In other embodiments, the sugar is selected from glucose, fructose, galactose, mannose, xylose, lactose, maltose, isomaltose, trehalose, sorbitol, mannitol, amylose, amylopectin, pectin, their respective DL-isomers or a combination thereof.

[0076] In some embodiments, the sugar is about 2 %w / w to about 20 %w / w relative to the food. In some embodiments, the sugar is about 2 %w / w to about 18 %w / w, about 2 %w / w to about 16 %w / w, about 2 %w / w to about 15 %w / w, about 2 %w / w to about 14 %w / w, about 2 %w / w to about 12 %w / w, or about 2 %w / w to about 10 %w / w. In some embodiments, the sugar is about 5 %w / w to about 10 %w / w relative to the food. In some embodiments, the sugar is at least about 2 %w / w relative to the food, about 4 %w / w, about 5 %w / w, about 8 %w / w, about 10 %w / w, about 15 %w / w, or about 20 %w / w.

[0077] The common natural forms of amino acids have the structure -NH3+(-NH2+- in the case of proline) and -CO2- functional groups attached to the same C atom, and are thus a-amino acids. With the exception of achiral glycine, natural amino acids have the L configuration. The L and D convention for amino acid configuration refers to the optical activity of the isomer of glyceraldehyde from which that amino acid can be synthesized (D-glyceraldehyde is dextrorotatory; L-glyceraldehyde is levorotatory). Alternatively, (S) and (R) designators can be used to specify the absolute configuration. Almost all of the amino acids in proteins are (S) at the a carbon, with cysteine being (R) and glycine non-chiral.

[0078] In some embodiments, the amino acid is selected from D-amino acid, L-amino acid, DL- amino acid or their respective dipeptide, tripeptide, oligopeptide and polypeptide thereof. In some embodiments, the amino acid is glutamate. In some embodiments, the amino acid is selected from D-alanine, L-alanine, D-arginine, L-arginine, L-arginine hydrochloride, D-arginine hydrochloride, D-asparagine, L-asparagine, D-aspartate salt, L-aspartate salt, D-aspartic acid, L-aspartic acid, D-cysteine, L-cystine, D-cysteine hydrochloride, L-cysteine hydrochloride, D-glutamate salt, L-glutamate salt, D-glutamic acid, L-glutamic acid, D-glutamine, L-glutamine, glycine, D-histidine, L-histidine, D- histidine hydrochloride, L-histidine hydrochloride, D-isoleucine, L-isoleucine, D-leucine, L-leucine, D-lysine, L-lysine, D-lysine hydrochloride, L-lysine hydrochloride, D- methionine, L-methionine, D-ornithine, L-ornithine, D-phenylalanine, L-phenylalanine, D-proline, L-proline, D-serine, L-serine, taurine, D-threonine, L-threonine, D- tryptophan, L-tryptophan, D-tyrosine, L-tyrosine, D-valine, L-valine, their hydrates, derivatives or a combination thereof. The derivative may be a sodium, potassium, magnesium and / or calcium derivative.

[0079] In some embodiments, the amino acid is about 5 %w / w to about 50 %w / w relative to the food. In some embodiments, the amino acid is about 5 %w / w to about 45 %w / w, about 5 %w / w to about 40 %w / w, about 5 %w / w to about 35 %w / w, about 5 %w / w to about 30 %w / w, about 5 %w / w to about 25 %w / w, or about 5 %w / w to about 20 %w / w. In some embodiments, the amino acid is about 10 %w / w to about 30 %w / w relative to the food. In some embodiments, the amino acid is at least about 5 %w / w relative to the food, about 10 %w / w, about 15 %w / w, about 20 %w / w, about 25 %w / w, or about 30 %w / w.

[0080] In some embodiments, the vitamin is selected from thiamine (Vitamin Bl), thiamine hydrochloride, ascorbic acid (Vitamin C), sodium ascorbate (vitamin C), potassium ascorbate (vitamin C), or a combination thereof. In other embodiments, the vitamin is selected from vitamin B2, B3, B5, B6, B12 and D.

[0081] In some embodiments, the vitamin is about 0.5 %w / w to about 10 %w / w relative to the food. In some embodiments, the vitamin is about 0.5 %w / w to about 9 %w / w, about 0.5 %w / w to about 8 %w / w, about 0.5 %w / w to about 7 %w / w, about 0.5 %w / w to about 6 %w / w, or about 0.5 %w / w to about 5 %w / w. In some embodiments, the vitamin is about 1 %w / w to about 5 %w / w relative to the food. In some embodiments, the vitamin is at least about 0.5 %w / w relative to the food, about 1 %w / w, about 1.5 %w / w, about 2 %w / w, about 2.5 %w / w, about 3 %w / w, about 3.5 %w / w, about 4 %w / w, about 4.5 %w / w, or about 5 %w / w.

[0082] Flavour enhancers are compounds that are added to a food in order to supplement or enhance its own natural flavour. In some embodiments, the flavour enhancer is selected from animal-based and plant-based lipids such as short (5 carbon atoms or less), medium (6 to 12 carbon atoms), long (13 to 21 carbon atoms) and very long-chained (22 carbon atoms or more) saturated and / or unsaturated fatty acids either in their free fatty acid forms and / or contained within a triglyceride or phospholipid molecule, nucleoside, nucleotide, vitamin, protein hydrolysate from animal, plant, fungal, bacterial and / or in vitro origin, lecithin, or a combination thereof.

[0083] In some embodiments, the flavour enhancer is selected from nucleoside, nucleotide, vitamin, protein hydrolysate from animal, plant, fungal, bacterial and / or in vitro origin, lecithin, or a combination thereof. In some embodiments, the flavour enhancer is selected from glutamic acid (E620), ribonucleotides including disodium inosinate (E631), disodium guanylate (E627), thiamine hydrochloride (FEMA1030), yeast extract, hydrolysed vegetable protein or a combination thereof.

[0084] In some embodiments, the flavour enhancer is about 0.5 %w / w to about 10 %w / w relative to the food. In some embodiments, the flavour enhancer is about 0.5 %w / w to about 9 %w / w, about 0.5 %w / w to about 8 %w / w, about 0.5 %w / w to about 7 %w / w, about 0.5 %w / w to about 6 %w / w, or about 0.5 %w / w to about 5 %w / w. In some embodiments, the flavour enhancer is at least about 0.5 %w / w relative to the food, about 1 %w / w, about 1.5 %w / w, about 2 %w / w, about 2.5 %w / w, about 3 %w / w, about 3.5 %w / w, about 4 %w / w, about 4.5 %w / w, or about 5 %w / w.

[0085] In some embodiments, the fat or lipid is a fatty acid. In some embodiments, the fat is a short chain fatty acid (less than C5), medium chain fatty acid (C6-C12), long chain fatty acid (C13-C21) or very long chain fatty acid (more than C22). In some embodiments, the fat is a saturated fatty acid or an unsaturated fatty acid. The fat may either be in their free fatty acid forms and / or contained within a triglyceride, diglyceride, monoglyceride or phospholipid molecule or a combination thereof. In some embodiments, the fat is selected from linoleic acid, oleic acid, docosahexaenoic acid, or a combination thereof.

[0086] In some embodiments, the fat is selected from canola oil, soybean oil, safflower oil, flaxseed oil, sunflower oil, olive oil, coconut oil, palm oil, corn oil, linseed oil, algae oil, rice bran oil, pumpkin seed oil, peanut oil, sesame oil, beef tallow, chicken fat, fish oil, pork fat and mutton fat.

[0087] In some embodiments, the fat is about 30 %w / w to about 90 %w / w relative to the food.

[0088] In some embodiments, the fat is about 30 %w / w to about 85 %w / w, about 30 %w / w to about 80 %w / w, about 30 %w / w to about 75 %w / w, or about 30 %w / w to about 70 %w / w. In some embodiments, the fat is about 50 %w / w to about 70 %w / w relative to the food. In some embodiments, the fat is at least about 30 %w / w relative to the food, about 35 %w / w, about 40 %w / w, about 45 %w / w, about 50 %w / w, about 55 %w / w, about 60 %w / w, about 65 %w / w, or about 70 %w / w.

[0089] It was found that as fats are the main substrate for lipid oxidation reactions, the most volatiles are generated which impart the food product with animal-specific flavours. The fats also function as a solvent and crucially controls the rate of release of other flavour molecules, greatly influencing the perception of flavour and aroma.

[0090] In some embodiments, when the meat flavour is a beef flavour, the flavour precursor is selected from beef fat, canola oil, palm oil, corn oil, or a combination thereof. In other embodiments, when beef fat and a vegetable oil is present, a weight ratio of beef fat to vegetable oil is about 2: 1 to about 5: 1, or preferably 3: 1.

[0091] In some embodiments, when the meat flavour is a poultry flavour, the flavour precursor is selected from corn oil, sunflower oil, canola oil, palm oil, safflower oil, chicken fat or a combination thereof. In other embodiments, when chicken fat and a vegetable oil is present, a weight ratio of chicken fat to vegetable oil is about 2: 1 to about 5: 1, or preferably 3: 1.

[0092] In some embodiments, when the meat flavour is a seafood flavour, the flavour precursor is selected from fish oil, algal, flaxseed oil or a combination thereof. In other embodiments, when fish oil and a vegetable oil is present, a weight ratio of fish oil to vegetable oil is about 2: 1 to about 5: 1, or preferably 3: 1.

[0093] In some embodiments, when the meat flavour is a pork flavour, the flavour precursor is selected from corn oil, sunflower oil, canola oil, palm oil, safflower oil, pork fat or a combination thereof. In other embodiments, when beef fat and a vegetable oil is present, a weight ratio of beef fat to vegetable oil is about 2: 1 to about 5: 1, or preferably 3: 1.

[0094] In some embodiments, when the meat flavour is a mutton flavour, the flavour precursor is selected from mutton fat, canola oil, palm oil and corn oil. In other embodiments. when mutton fat and a vegetable oil is present, a weight ratio of mutton fat to vegetable oil is about 2: 1 to about 5: 1, or preferably 3: 1.

[0095] The food may be heated to about 90 °C to about 700 °C in order to generate the volatiles. In some embodiments, the food is heated to about 100 °C to about 650 °C, about 100 °C to about 600 °C, about 100 °C to about 550 °C, about 100 °C to about 500 °C, about 100 °C to about 450 °C, about 100 °C to about 400 °C, about 100 °C to about 350 °C, about 100 °C to about 300 °C, or about 100 °C to about 250 °C.

[0096] In some embodiments, the volatiles generated are as listed in Table 3. In some embodiments, the volatiles are compounds selected from alkane, alkene, aldehyde, alcohol, ketone, furan, carboxylic acid, organosulfur, or a combination thereof. In some embodiments, the volatiles are selected from Pentane, Heptane, 2,3-Dimethyl-pentanal, Octane, Butanal, 2-Methyl butanal, 3-Methyl butanal, 2-Nonanol, 2-Ethyl furan, Pentanal, l-Penten-3-one, 1-Decene, 2-Butenal, 2,3-Pentanedione, Hexanal, (E)-2- Pentenal, l-Penten-3-ol, Heptanal, 2-Pentyl furan, 2,4-Nonadienal, 1-Pentanol, Octanal, 2-Methyl-3-furanthiol, 2,3-Octanedione, (Z)-2-Heptenal, Nonanal, l-Octen-3- ol, (E)-2-Octenal, Furfural, 2-Tetradecanol, (E,E)-2,4-Heptadienal, (E)-2-Nonenal, 3,5- Octadien-2-one, (E,Z)-2,6-Nonadienal, Hexadecanol, (E)-2-Decenal, (E)-2-Tridecenal, (E,E)-2,4-Nonadienal, 2-Undecenal, 4-Methyl-5-thiazoleethanol, 2,4-Decadienal, (Z)-7- Tetradecenal, Heptanoic acid, Tetradecanoic acid, 4-Heptenal, 2-Pentadecanone, Octanoic Acid, trans-3-Nonen-2-one, Nonanoic acid, 2-Octenoic acid, or a combination thereof. In some embodiments, the volatiles are selected from Pentane, 3-Methyl butanal, Pentanal, Hexanal, Nonanal, (E)-2-Octenal, Furfural, (E,E)-2,4-Heptadienal, (E)-2-Nonenal, (E,E)-2,4-Nonadienal, 2-Undecenal, 2,4-Decadienal, trans-3-Nonen-2- one, or a combination thereof. In some embodiments, the volatiles are hexanal, 2,4- decadienal, furfural, 4-methyi-5-thiazoleethanol, and a combination thereof. It is believed that the combination of volatiles creates a chemically complexed environment, which is the basis for producing a meat-identical flavour.

[0097] In some embodiments, the volatiles replicating a pork flavour is selected from Pentane, Heptane, Octane, 3-Methyl butanal, 2-Ethyl furan, Pentanal, Hexanal, l-Penten-3-ol, Heptanal, 2-Pentyl furan, 2,4-Nonadienal, 1-Pentanol, Octanal, 2-Methyl-3-furanthiol, 2,3-Octanedione, (Z)-2-Heptenal, Nonanal, (E)-2-Octenal, Furfural, (E,E)-2,4- Heptadienal, (E)-2-Nonenal, Hexadecanol, (E)-2-Decenal, (E,E)-2,4-Nonadienal, 2- Undecenal, 2,4-Decadienal, (Z)-7-Tetradecenal, Heptanoic acid, Tetradecanoic acid, Octanoic Acid, trans-3-Nonen-2-one, Nonanoic acid, 2-Octenoic acid, or a combination thereof.

[0098] In some embodiments, the volatiles replicating a fish flavour is selected from Pentane, 2,3-Dimethyl-pentanal, 3-Methyl butanal, 2-Ethyl furan, Pentanal, 2,3-Pentanedione, Hexanal, l-Penten-3-ol, Nonanal, l-Octen-3-ol, (E)-2-Octenal, Furfural, (E,E)-2,4- Heptadienal, (E)-2-Nonenal, (E)-2-Tridecenal, (E,E)-2,4-Nonadienal, 2-Undecenal, 2,4- Decadienal, 4-Heptenal, trans-3-Nonen-2-one, or a combination thereof.

[0099] In some embodiments, the volatiles replicating a beef flavour is selected from Pentane, HeptaneOctane, 2-Methyl butanal, 3-Methyl butanal, Pentanal, Hexanal, Nonanal, (E)- 2-Octenal, Furfural, (E,E)-2,4-Heptadienal, (E)-2-Nonenal, (E)-2-Decenal, (E,E)-2,4- Nonadienal, 2-Undecenal, 4-Methyl-5-thiazoleethanol, 2,4-Decadienal, Tetradecanoic acid, 4-Heptenal, Octanoic Acid, trans-3-Nonen-2-one, Nonanoic acid, or a combination thereof.

[0100] In some embodiments, the volatiles replicating a mutton flavour is selected from Pentane, Heptane, Octane, Butanal, 3-Methyl butanal, 2-Nonanol, 2-Ethyl furan, Pentanal, l-Penten-3-one, 1-Decene, 2-Butenal, 2,3-Pentanedione, Hexanal, (E)-2- Pentenal, l-Penten-3-ol, Heptanal, 2-Pentyl furan, Octanal, (Z)-2-Heptenal, Nonanal, (E)-2-Octenal, Furfural, 2-Tetradecanol, (E,E)-2,4-Heptadienal, (E)-2-Nonenal, 3,5- Octadien-2-one, (E,Z)-2,6-Nonadienal, Hexadecanol, (E)-2-Decenal, (E,E)-2,4- Nonadienal, 2-Undecenal, 2,4-Decadienal, 4-Heptenal, 2-Pentadecanone, Octanoic Acid, trans-3-Nonen-2-one, Nonanoic acid, or a combination thereof.

[0101] In some embodiments, iron chlorophyllin is further configured to interact with a protein in the food in order to generate an amino acid. The iron chlorophyllin may interact with protein in the presence of an acid, such as lemon juice and / or vinegar. The protein may be hydrolyzed by iron chlorophyllin. The amino acid may be hydrolysed to a volatile, thus providing the meat flavour. The protein may be an oligopeptide or a polypeptide.

[0102] For example, as shown herein, SIC and HIC are able to catalyse amide bond hydrolysis, thereby finding utility in food manufacturing processes that hydrolyse proteins into smaller subunits for flavour production, such as in the soy sauce and process flavours industry.

[0103] In some embodiments, iron chlorophyllin is configured to interact with a protein in order to generate Amadori rearrangement products, Maillard Reaction products, Strecker degradation products, melanoidins, advanced glycation end-products, volatile, nonvolatile molecular products or a combination thereof that influence aroma and flavour of a food product. The macromolecules are thus broken down in order to generate the volatiles.

[0104] Further advantageously, SIC and HIC are potent photodynamic inactivators in the presence of light, being able to exert bacteriocidal and bacteriostatic effects on grampositive and gram-negative bacteria. This may help in extending a shelf life of a food.

[0105] In some embodiments, an antioxidant or radical scavenger is added. Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals and chain reactions that may damage the cells of organisms. Antioxidants such as thiols, ascorbic acid (vitamin C), vitamin A and E may act to inhibit these reactions. In some embodiments, the antioxidant is selected from DL-a-tocopherol, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), propyl gallate, trihydroxybutyrophenone (THBP), nordihydroguaiaretic acid, t-butylhydroquinone (TBHQ), dilauryl thiodiopropionate, ascorbic acid, sodium ascorbate, potassium ascorbate, erythorbic acid, ascorbyl palmitate, ascorbyl acetal, or a combination thereof.

[0106] In some embodiments, the antioxidant concentration is about 0.25 %w / w to about 4.5 %w / w, about 0.25 %w / w to about 4 %w / w, about 0.25 %w / w to about 3.5 %w / w, about 0.25 %w / w to about 3 %w / w, about 0.25 %w / w to about 2.5 %w / w, about 0.25 %w / w to about 2 %w / w, about 0.25 %w / w to about 1.5 %w / w, about 0.25 %w / w to about 1 %w / w, about 0.25 %w / w to about 0.9 %w / w, about 0.25 %w / w to about 0.8 %w / w, about 0.25 %w / w to about 0.7 %w / w, about 0.25 %w / w to about 0.6 %w / w, about 0.25 %w / w to about 0.5 %w / w, about 0.25 %w / w to about 0.4 %w / w, or about 0.25 %w / w to about 0.3 %w / w.

[0107] In some embodiments, a stabiliser is added. The stabiliser may be about 1 %w / w to about 4 %w / w relative to the food. In other embodiments, the concentration is about 2 %w / w to about 4 %w / w, or about 3 %w / w to about 4 %w / w. The stabiliser may be a hydrocolloid such as alginate, agar, carrageen, cellulose and cellulose derivatives, gelatin, guar gum, gum Arabic, locust bean gum, pectin, starch, and xanthan gum.

[0108] In some embodiments, a food colouring is added. For example, red colouration may be added using food grade colouring. These food colourings include Carmines (E120), Azorubine / Carmoisine (E122), Amaranth (E123), Ponceau 4R / Cochineal red A (E124), Erythrosine (E127), allura red AC (E129), beetroot extract, betanin, or a combination thereof. The food colouring may be about 0.025 %w / w to about 6 %w / w relative to the food. In other embodiments, the concentration is about 0.025 %w / w to about 5.5 %w / w, about 0.025 %w / w to about 5 %w / w, about 0.025 %w / w to about 4.5 %w / w, about 0.025 %w / w to about 4 %w / w, about 0.025 %w / w to about 3.5 %w / w, about 0.025 %w / w to about 3 %w / w, about 0.025 %w / w to about 2.5 %w / w, about 0.025 %w / w to about 2 %w / w, about 0.025 %w / w to about 1.5 %w / w, about 0.025 %w / w to about 1 %w / w, about 0.1 %w / w to about 0.5 %w / w, about 0.15 %w / w to about 0.5 %w / w, about 0.2 %w / w to about 0.5 %w / w, about 0.25 %w / w to about 0.5 %w / w, about 0.3 %w / w to about 0.5 %w / w, about 0.35 %w / w to about 0.5 %w / w, or about 0.4 %w / w to about 0.5 %w / w.

[0109] In some embodiments, when heated, the food comprising iron chlorophyllin is characterised by at least a one time increase in amino acid concentration relative to a food without iron chlorophyllin. In other embodiments, the increase is at least 1.1 times, 1.2 times, 1.5 times, or 2 times.

[0110] The present disclosure provides a method of forming a food product, comprising a step of adding iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food product, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food product in order to generate volatiles which replicate the meat flavour.

[0111] The present disclosure also provides a food product comprising iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food product, wherein the food product is selected from an alternative protein, plant-based meat, or a combination thereof; wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour. In some embodiments, the food product further comprises a flavour precursor, wherein the flavour precursor is selected from sugar, amino acid, vitamin, fat, flavour enhancer, or a combination thereof.

[0112] The iron chlorophyllin may be provided as a composition, for adding to a food. The present disclosure provides an iron chlorophyllin composition, comprising: a) iron chlorophyllin at about 0.1 %w / w to about 5 %w / w relative to the composition; and b) a flavour precursor at about 95 %w / w to about 99.9 %w / w relative to the composition.

[0113] The iron chlorophyllin composition may be a flavouring product, for use as a flavour catalyst. The iron chlorophyllin composition may be added to food such that when heated, a meat flavour is provided to the food or an initial meat flavour of the food is enhanced.

[0114] In some embodiments, the iron chlorophyllin is about 0.1 %w / w to about 5 %w / w relative to the composition. In other embodiments, the concentration is about 0.2 %w / w to about 5 %w / w, about 0.4 %w / w to about 5 %w / w, about 0.5 %w / w to about 5 %w / w, about 0.8 %w / w to about 5 %w / w, about 1 %w / w to about 5 %w / w, about 1.5 %w / w to about 5 %w / w, about 2 %w / w to about 5 %w / w, about 2.5 %w / w to about 5 %w / w, about 3 %w / w to about 5 %w / w, about 3.5 %w / w to about 5 %w / w, or about 4 %w / w to about 5 %w / w.

[0115] When SIC and HIC is applied as a flavour catalyst into various vegan meat flavouring products, the flavour catalyst may interact with flavour precursors, such as lipids, reducing sugars, vitamins and L-amino acids. The interaction form a diverse matrix of flavour and aroma molecules that accurately replicate the organoleptic experience of cooking and consuming meats in alternative proteins, to recreate vegan versions of beef, pork, and fish flavours.

[0116] SIC and HIC as functional ingredients may thus improve a flavour profiles of AP and BPM through the production of meat-identical flavours and aromas, thereby keeping alternative protein production costs down due to SIC and HIC's high affordability. SIC and HIC also provides highly bioavailable iron nutrition (that is usually deficient in most vegan foods).

[0117] The iron chlorophyllin composition may comprise a flavour precursor as disclosed herein. For example, the flavour precursor may be selected from a protein, an amino acid, a fat, an oil, a sugar, vitamin, a flavour enhancer, food additive, or a combination thereof. In some embodiments, the flavour precursor (or a combination thereof) is about 95 %w / w to about 99.9 %w / w relative to the composition, about 95 %w / w to about 99 %w / w, about 95 %w / w to about 98 %w / w, about 95 %w / w to about 97 %w / w, or about 95 %w / w to about 96 %w / w.

[0118] The iron chlorophyllin composition may be in a powder form, or may be dissolved or dispersed in an aqueous medium.

[0119] The term 'aqueous medium' used herein refers to a water based solvent or solvent system, and which comprises of mainly water. Such solvents can be either polar or nonpolar, and / or either protic or aprotic. Solvent systems refer to combinations of solvents which resulting in a final single phase. Both 'solvents' and 'solvent systems' can include, and is not limited to, pentane, cyclopentane, hexane, cyclohexane, benzene, toluene, dioxane, chloroform, diethylether, dichloromethane, tetrahydrofuran, ethyl acetate, acetone, dimethylformamide, acetonitrile, dimethyl sulfoxide, nitromethane, propylene carbonate, formic acid, butanol, isopropanol, propanol, ethanol, methanol, acetic acid, ethylene glycol, diethylene glycol or water. Water based solvent or solvent systems can also include dissolved ions, salts and molecules such as amino acids, proteins, sugars and phospholipids. Such salts may be, but not limited to, sodium chloride, potassium chloride, ammonium acetate, magnesium acetate, magnesium chloride, magnesium sulfate, potassium acetate, potassium chloride, sodium acetate, sodium citrate, zinc chloride, HEPES sodium, calcium chloride, ferric nitrate, sodium bicarbonate, potassium phosphate and sodium phosphate. As such, biological fluids, physiological solutions and culture medium also falls within this definition.

[0120] The present disclosure provides a method of synthesising iron chlorophyllin, comprising the step of reacting chlorophyll or sodium magnesium chlorophyllin with an iron salt, wherein the chlorophyll is obtained from a plant, fungi or bacteria. The fungi may be a plankton.

[0121] In some cases, precursors of HIC and SIC may be obtained as commercially available chlorophyll and chlorophyllin and metalation. In other cases, said precursors may be sourced directly from any green vegetable. The green vegetable may be a single-type green vegetable leaves or a mixture of green vegetables, such as excess vegetables collected from wholesale or supermarkets. This diverse source of vegetable precursors ensures a sustained low-cost feedstock for production of HIC and SIC.

[0122] The method of synthesis of HIC and SIC is rapid, specific and in high yield under in situ conditions using internationally approved food additives. This methodology entails dissolving specific precursors in a particular sequence in a food-grade solvent, allows for SIC and HIC molecules to spontaneously form at ambient conditions (i.e. temperature and pressure). These precursors used in SIC and HIC's formation are internationally approved food ingredients with long known and accepted safety profiles.

[0123] In some embodiments, chlorophyll is obtained from a mixture of plants. The plants may be from Kingdom Plantae. In some embodiments, chlorophyll is obtained from a mixture of plants selected from xiao bai cai (Brassica rapa), kang kong (Ipomoea aquatica), spinach (Spinacia oleracea L.), spring onion (Allium fistulosum), kai Ian (Brassica oleracea Alboglabra Group), chye sim (Brassica rapa Caisin Group), and cabbage. In some embodiments, chlorophyll is obtained from green algae and chlorophyll-containing bacteria under the Kingdom Protista and Monera.

[0124] In some embodiments, chlorophyll is obtained by extraction using an organic solvent.

[0125] In some embodiments, the organic solvent in the extraction solvent is a polar solvent. In some embodiments, the organic solvent is selected from acetone, methanol, ethanol, isopropanol, ethyl acetate, propyl acetate, butyl acetate, alkyl ester, or a combination thereof. In some embodiments, the alkyl ester is derived from a Cl-5 alcohol and Cl-5 carboxylic acid. In some embodiments, the Cl-5 carboxylic acid is selected from formic acid, acetic acid, acetoacetic acid, 2-hydroxypropionic acid, 2-oxopropionic acid, malonic acid, maleic acid, malic acid, fumaric acid, or a combination thereof. In some embodiments, the Cl-5 alcohol is selected from methanol, ethanol, propanol, butanol, pentanol, or a combination thereof.

[0126] In some embodiments, chlorophyll or sodium magnesium chlorophyllin is saponified. The saponification step may be performed with an alkali. A pheophorbic acid may be formed.

[0127] In some embodiments, the iron salt is an iron (III) salt. The iron (III) salt may be food grade iron(III) chloride, iron(III) bromide, iron(III) iodide, iron (III) sulfate, iron(III) nitrate, iron(III) fumurate, iron(III) gluconate, iron(III) lactate, iron (III) ascorbate, iron (III) aspartate, iron (III) glycinate, iron (III) carbonate, iron (III) citrate, iron (III) malate, iron (III) oxalate, iron (III) phosphate, iron (III) tartrate, iron (III) ammonium citrate, iron (III) glycerophosphate, iron (III) pyrophosphate and their respective hydrates and derivative complexes, or a combination thereof. In some embodiments, the iron salt is iron(II) sulphate heptahydrate.

[0128] In some embodiments, the iron salt is an iron (II) salt. The iron (II) salt may be food grade iron(II) chloride, iron(II) bromide, iron(II) iodide, iron(II) sulfate, iron(II) nitrate, iron(II) fumurate, iron(II) gluconate, iron(II) lactate, iron (II) ascorbate. Iron (II) aspartate, Iron (II) glycinate, Iron (II) carbonate, Iron (II) citrate, Iron (II) malate, Iron (II) oxalate, Iron (Il)phosphate, Iron (II) tartrate, Iron (II) ammonium citrate, Iron (II) glycerophosphate, Iron (II) pyrophosphate and their respective hydrates and derivative complexes.

[0129] In some embodiments, a mole ratio of iron salt to chlorophyll is about 1 : 1 to about 10: 1. In other embodiments, the mole ratio is about 1 : 1 to about 9: 1, about 1 : 1 to about 8: 1, about 1 : 1 to about 7: 1, about 1 : 1 to about 6: 1, about 1: 1 to about 5: 1, about 1 : 1 to about 4: 1, about 1 : 1 to about 3: 1, or about 1 : 1 to about 2: 1.

[0130] In some embodiments, the reaction is performed at an alkaline pH. The pH may be above 7, to about 12.

[0131] In some embodiments, the reaction with an iron salt is performed for about 1 h to about 6 h. In some embodiments, the reaction with an iron salt is performed for about 1 h to about 4 h. In some embodiments, the reaction with an iron salt is performed at about 20°C to about 150°C. In some embodiments, the reaction with an iron salt is performed at about 20°C to about 120°C.

[0132] In some embodiments, the iron chlorophyllin is purified by filtration and drying.

[0133] In some embodiments, the method further comprises a step of cation exchanging the iron chlorophyllin in the presence of an alkali. The alkali may be selected from sodium hydroxide, potassium hydroxide, calcium hydroxide ammonium hydroxide, and a combination thereof.

[0134] Thus, in some embodiments, the iron chlorophyllin is derived from a vegetable or vegan product.

[0135] The present disclosure also provides a method of synthesizing an iron chlorophyllin composition, comprising a step of mixing iron chlorophyllin with a flavour precursor, wherein iron chlorophyllin is about 0.1 %w / w to about 5 %w / w relative to the composition; and wherein the flavour precursor is about 95 %w / w to about 99.9 %w / w relative to the composition.

[0136] In some embodiments, the method further comprises a step of reacting chlorophyll or sodium magnesium chlorophyllin with an iron salt in order to obtain iron chlorophyllin, wherein the chlorophyll is obtained from a plant, fungi or bacteria.

[0137] Examples

[0138] Food Grade SIC and HIC

[0139] Sustainable extraction of chlorophyll from uncontaminated vegetable side stream and its processing to food-grade SIC and HIC

[0140] Extraction of chlorophyll from leaves are usually done on specific single sources of plants but not from heterogenous vegetable side streams. Heterogeneous vegetable side streams include any source of chlorophyll such as organisms under the Kingdom Plantae. Examples include but are not limited to xiao bai cal (Brassica rapa), kang kong (Ipomoea aquatica), spinach (Spinacia oleracea L.), spring onion (Allium fistulosum). kai Ian (Brassica oleracea Alboglabra Group), chye sim (Brassica rapa Caisin Group), and various types of cabbages. Other possible sources comprise of green algae and chlorophyll-containing bacteria under the Kingdom Protista and Monera. The vegetables are sorted, wherein the green parts, such as leaves, are collected and dried in fan oven at 60-160°C for 3-12h to dryness, while preserving the green colouration. The said dried vegetable matter is then crushed by a mill or grinder to form fine green powder.

[0141] This present invention describes an extraction method for chlorophyll from dried green heterogenous vegetable powder, using an organic extraction solvent (A), wherein the solvent is later removed in vacuo to obtain crude chlorophyll. Organic solvent A comprises of food-grade, analytical-grade and technical grade solvents like acetone, isopropanol, ethyl acetate, propyl acetate, butyl acetate or any other lower alkyl esters formed from alcohol and carboxylic acid components which are 1 to 5 carbon atoms long, such as esters formed between carboxylic acids such as formic acid, acetic acid, acetoacetic acid, 2-hydroxypropionic acid, 2-oxopropionic acid, malonic acid, maleic acid, malic acid and fumaric acid, alcohols such as methanol, ethanol, propanol, butanol and pentanol, halogenated organic compounds like chloroform, dichloromethane and dichloroethane, tetra hydrofuran, acetonitrile, diethyl ether, petroleum ether, dimethylformamide, dimethyl sulfoxide and saturated and unsaturated hydrocarbons which are 4 to 10 carbon atoms long, including but not limited to alkanes, alkenes and alkynes and all their isomeric forms.

[0142] Food safe synthesis of pheophorbic acid and sodium pheophorbide

[0143] This present invention describes the chemical conversion of chlorophyll to pheophorbic acid by saponifying the chlorophyll solution (wherein chlorophyll is dissolved in organic solvent A) by heating with aqueous alkali (B) solution, where B comprises 70-95% of aqueous solution volume-by-volume (v / v),at 60-100°C for 0.5-2 hours followed by acidification with inorganic acid (C). Pheophorbic acid will be precipitated as a black solid and collected using suction filtration and subsequently oven dried at 60-160°C for 0.5- 2h to remove all moisture.

[0144] Alkali B includes sodium hydroxide, potassium hydroxide, calcium hydroxide and ammonium hydroxide, and acid C includes inorganic acids like hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and organic acids like citric acid, tartaric acid, malic acid, phosphoric acid, folic acid, acetic acid, fumaric acid, and lactic acid. Food safe synthesis of SIC and HIC

[0145] This present invention describes the solubilisation of pheophorbide in organic solvent (D) for reaction with a food-safe iron(II) salt (E) to synthesise SIC and HIC. SIC herein refers to Sodium iron chlorophyllin and HIC herein refers to its acidified form: hydrogen iron chlorophyllin acid. The mixture is stirred for 1-4 hours at 20-120°C, before hydration with 50-200% by volume of water to precipitate HIC as a black solid. The mixture is suction-filtered, and the residue is subsequently oven dried at 60-160°C for 0.5-2h to remove all moisture to obtain solid HIC. SIC is synthesised by dropwise addition of alkali B until all solids dissolves to form a deep green solution. Solid SIC is collected through lyophilisation.

[0146] Organic solvent D includes formic acid, acetic acid, acetoacetic acid, 2-hydroxypropionic acid, 2-oxopropionic acid, malonic acid, maleic acid, malic acid, fumaric acid, acetone, ethanol, dimethyl sulfoxide and N,N-dimethylformamide. Food safe iron(II) salt E includes food grade iron(II) chloride, iron(III) chloride, iron(II) bromide, iron(III) bromide, iron(II) iodide, iron(III) iodide, iron(II) sulfate, iron (III) sulfate, iron(II) nitrate, iron(III) nitrate, iron(II) fumurate, iron(III) fumurate, iron(II) gluconate, iron(III) gluconate, iron(II) lactate, iron(III) lactate, iron (II) ascorbate, iron (III) ascorbate, iron (II) aspartate, iron (III) aspartate, iron (II) glycinate, iron (III) glycinate, iron (II) carbonate, iron (III) carbonate, iron (II) citrate, iron (III) citrate, iron (II) malate, iron (III) malate, iron (II) oxalate, iron (III) oxalate, iron (II) phosphate, iron (III) phosphate, iron (II) tartrate, iron (III) tartrate, iron (II) ammonium citrate, iron (III) ammonium citrate, iron (II) glycerophosphate, iron (III) glycerophosphate, iron (II) pyrophosphate, iron (III) pyrophosphate and their respective hydrates and derivative complexes.

[0147] Food safe synthesis of SIC and HIC from SMC

[0148] In some embodiments, SIC and HIC can be synthesised from Sodium Magnesium Chlorophyllin (SMC). Such SMC may be obtained from commercial sources of nonanimal origins. This present invention describes the solubilisation of SMC in organic solvent (D) for reaction with a food-safe iron(II) salt (E) to synthesise HIC. The mixture is stirred for 1-4 hours at 20-120°C, before hydration with 50-200% by volume of water to precipitate HIC as a black solid. The mixture is suction-filtered, and the residue is subsequently oven dried at 60-160°C for 0.5-2h to remove all moisture to obtain solid HIC. SIC is synthesised by dropwise addition of alkali B until all solids dissolves to form a deep green solution. Solid SIC is collected through lyophilisation.

[0149] Applications of SIC and HIC

[0150] Applications of SIC and HIC comprises of the following. Firstly, SIC and HIC can be applied to alternative protein products as a flavour and odour catalyst. SIC and HIC improves the appearance, aroma and taste of the alternative protein product as a dynamic flavourant, rather than a traditional static one. Secondly, SIC and HIC can also contribute to the iron content of the alternative protein as a highly bioavailable nutritional source of iron. Thirdly, SIC and HIC can act as a general catalyst for hydrolysis reactions in process flavour manufacturing.

[0151] Alternative protein products are defined as food products for human consumption, intended to mimic or replicate animal meat protein products organoleptically and nutritionally without addition of animal meats or products. Alternative protein products may be made with but not limited to proteins derived from plants, insects, fungal, bacterial and in vitro origins.

[0152] The first application of SIC and HIC refers to its use as a flavour catalyst, where it participates in key chemical reactions that contribute to meaty flavour, taste and colour being produced in the alternative protein products during cooking. The reactions comprise of but are not limited to the Maillard reaction, Strecker degradation, lipid oxidation and thiamine degradation that occurs during the cooking of animal meats. In some embodiments, the SIC and HIC flavour catalyst speeds up these key reactions among the flavour precursors during cooking (or heating) and allow them to occur at higher rates and frequencies to form more flavour, aroma and colour compounds for a meat-identical organoleptic, cooking and dining experience in alternative proteins.

[0153] The SIC and HIC catalysts are most effective when used together with food safe flavour precursors to produce the meat-identical flavours. In some embodiments, these precursors include but are not limited to monosaccharides, disaccharides, oligosaccharides, polysaccharides and their derivatives, D / L-amino acids and their respective dipeptides, tripeptides, oligopeptides and polypeptides, nucleosides, nucleotides, vitamins, protein hydrosylates from animal, plant, fungal, bacterial and in vitro origin, lecithin and other food-safe and edible organic molecules. Other flavour precursors include lipids from non-meat sources such as short (5 carbon atoms or less), medium (6 to 12 carbon atoms), long (13 to 21 carbon atoms) and very long-chained (22 carbon atoms or more) saturated and / or unsaturated fatty acids either in their free fatty acid forms and / or contained within a triglyceride or phospholipid molecule. A nonlimiting example of the list of flavour and / or odourant precursors with SIC or HIC (herein called "Mixture F") are shown in Table 1. The composition of Mixture F maybe adjusted slightly to tune the flavours to different species of meat, including but not limited to, pork, beef, mutton, poultry and fish.

[0154] Table 1. Example of composition of Mixture F with SIC, HIC or Heme flavour catalyst ingredient

[0155] The second application of SIC and HIC refers to its contribution as a highly bioavailable iron source in alternative proteins. Alternative protein products do not only have to replicate the macronutrients of animal meats but the micronutrients as well. Iron is a crucial mineral that is often lacking in alternative protein products, either entirely absent or present in the form of inorganic iron that has low gastrointestinal stability and bioavailability. SIC has been shown to be stable and provide bioavailable iron in in vitro studies, displaying cellular uptake levels similar to heme iron as the porphyrin ring is recognised by the heme carrier protein 1 (HCP1) in the intestines for absorption.

[0156] Alternative protein meat analogue

[0157] In some embodiments, SIC and HIC may be supplied in a powder-form flavouring (consisting of but not limited to ingredients shown in Table 1), which can then be reconstituted with hot or room temperature water to form a solution mixture flavouring containing flavour catalyst for more homogenous and effective application. In this form, the said flavouring solution can be added to a dried meat analogue such as texturised vegetable proteins, post extrusion, as a flavourant, colourant and source of bioavailable iron. In some embodiments, SIC and HIC may be supplied in the said powder-form flavouring containing flavour catalyst that can be added to the feedstock, such as preextrudate mixtures, to produce alternative protein products comprising of high moisture meat analogues and low moisture meat analogues that are pre-flavoured and ready-to- cook. Herein, SIC and HIC is also a flavourant, colourant and source of bioavailable iron.

[0158] SIC and HIC as general catalysts for process flavours

[0159] Beside functioning as catalysts for flavour generation in alternative protein flavourings, SIC and HIC also functions as a catalyst for protein hydrolysis in the manufacturing of, but not limited to, hydrolysed vegetable protein (HVP) and soy sauce. Typical manufacturing process of such hydrolysate products involves high temperature and pressure, as well as extreme pH conditions. The invention here claims the superior efficacy of SIC and HIC in improving the protein hydrolysis efficiency as compared to contemporary methods (i.e. acid and enzyme catalysed protein hydrolysis). In acid- catalysed hydrolysis of vegetable proteins to produce HVP (where the acidic environment is contributed by a strong inorganic acid), the addition of SIC and / or HIC at concentration ranges between 0.001% to 0.5% w / v results in 1-3 times higher product yield. Similarly, the usage of said catalysts in the abovementioned range reduces the acid concentration needed to obtain the same product yield by 8 to 15-fold. This significant reduction in inorganic acid concentrations results in milder conditions used to manufacture HVP, thereby in turn preventing denaturation and reducing risk of carcinogen formation. This preservation of amino acids also facilitates glycation during the further flavour processing such as the Maillard reaction, and enhances the development of protein functionality. Use of less acid during hydrolysis also reduces the sodium content of the hydrolysate product, which resolves a running concern of the nutritional properties of hydrolysed proteins in the food industry of high sodium content.

[0160] Example 1: Food safe synthesis of HIC from uncontaminated vegetable sidestream From a mixture of uncontaminated vegetable sidestream, the green parts are dried in a fan oven at 110°C for 3 hours, the ground to a fine powder using a mill. 10 times the weight of ethanol was added to the powder, which was then removed in vacuo to obtain the crude chlorophyll. The crude chlorophyll was saponified with 5% sodium hydroxide at 100°C for 0.5 hours, followed by acidification with hydrochloric acid to below pH 3 to obtain pheophorbic acid as a precipitate. The solids were separated using suction filtration and dried in the oven at 60°C for 0.5h to obtain dry solids. The dry solids were then dissolved in acetic acid and saturated iron (II) sulfate solution was added and the mixture was stirred for 1 hour at room temperature. 200% by volume of water was added to the mixture and acidified HIC was precipitated and separated using suction filtration and dried in the oven at 60°C for 0.5h to obtain dry HIC. Characterisation for SIC: ESI (MS) m / z = 694.1 [M-Na + H]+, ,672.2 [M-2Na + 2H]+,650.2 [M-3Na + 3H]+(see Figure 2). UV-absorption spectra in MeOH, Xabs,max = 398 nm (B band), 498 nm, 603 nm, 661 nm (see Figure 2). Characterisation for HIC: ESI (MS) m / z = 620.2 [M-CO2H]+, 606.4 [M- CO2H]+, 578.3 [M-CO2H-CH3-CHCH2]+, 563.5 [M-CO2H-CH3-CHCH2]+(see Figure 4). UV-absorption spectra in MeOH, \abs,max - 395 nm (B band), 599 nm (see Figure 3).

[0161] Example 2: Food safe synthesis of HIC from SMC

[0162] The powdered SMC was dissolved in acetic acid and saturated iron (II) sulfate solution was added. The mixture was stirred for 1 hour at room temperature. 200% by volume of water was added to the mixture and acidified HIC was precipitated and separated using suction filtration and dried in the oven at 60°C for 0.5h to obtain dry HIC.

[0163] Example 3: Synthesis of SIC from HIC

[0164] SIC can also be synthesised from the wet HIC solids. SIC was synthesised by dropwise addition of sodium hydroxide until all solids dissolved to form a deep green solution of SIC. Solid sodium iron chlorophyllin was obtained by lyophilisation.

[0165] Example 4: Formulation examples of SIC and HIC flavour catalyst for producing alternative protein flavourings

[0166] SIC and HIC can be added to different combinations of the flavour precursors in Table 1 (above) for a diversity of flavours. Said flavours comprise of but are not limited to species-specific replicas of beef, pork, mutton, poultry and various seafoods. Following the formulation in Table 2, the following species-specific flavours can be obtained.

[0167] Table 2. Example of species-specific replicas of different meat flavours. Flavours and ingredients are from non-animal origins unless otherwise stated. Units are in g / mL of the final hydrated solution.

[0168]

[0169] Chemical data shows that the addition of iron chlorophyllin to animal fats resulted in a significant increase in the diversity and abundance of flavour products, which is then perceived by sensory panellists as being more beef-like or mutton-like flavours when compared against samples with the animal fats but without the iron chlorophyllin catalyst. This is further demonstrated via chromatographic data in Figures 8 (beef) and Figure 9 (mutton).

[0170] Each mixture was hydrated separately with water to form a water-and-oil mixture which was heated separately in a crucible at 110°C for 7 minutes for flavour generation reactions to take place. The cooked mixtures were transferred to a lOmL headspace glass vial and the headspace composition was analysed using Solid-Phase Microextraction (SPME) with gas-chromatography mass-spectrometry (GCMS). The profile of volatile odorous compounds is shown in Table 3, while there were some common volatiles, there were some unique volatiles to each formulation that may account for differences in the aroma. The volatiles mainly comprise of Maillard reaction products like 2 and 3-methyl butanal as well as lipid oxidation products like hexanal and 2,4-decadienal, which are also present in analysis of cooked animal meats. Compounds like 2-methyl-3-furanthiol contribute to a cooked meat smell and 4-methyl-5- thiazoleethanol contributes to a beefy flavour. Others like hexanal and (E,E)-2,4- decadienal contributes to a fatty flavour in meat.

[0171] Table 3. List of volatiles present in the heated samples

[0172] Similar to the GCMS results, the different formulations resulted differing sensory experience. Simple flavour descriptions were provided for each sample, presented in Table 4.

[0173] Table 4. Description of the flavours of heated example formulations

[0174] Example 5: Application of said flavourings in alternative protein vehicle

[0175] The SIC and HIC flavour catalysts provided in the above formulations in Table 2 may be separately reconstituted with hot water in the ratio of 1 :4 and stirred thoroughly to form a mixture. This said mixture can then be added to low moisture meat analogues in the form of dry extruded soy protein, as a flavourant, colourant and source of bioavailable iron. In some embodiments, SIC and HIC may be supplied in the said powder-form flavouring containing flavour catalyst that can be added to the feedstock, such as preextrudate mixtures, to produce alternative protein products comprising of high moisture meat analogues and low moisture meat analogues that are pre-flavoured and ready-to- cook. Herein, SIC and HIC is also a flavourant, colourant and source of bioavailable iron.

[0176] In some embodiments, the pork-replica flavouring containing SIC was reconstituted with hot water in the ratio of 1 :4 and added to 30% mass of dry soy protein extrudate, to obtain a minced pork-like meat alternative that had a pork like flavour and was used to replace minced pork in typical pork dishes like dumplings and pies.

[0177] Example 6: Application of SIC and HIC as catalysts for amide hydrolysis reactions in protein isolate substrates

[0178] At a concentration of 0.05% w / v, SIC and HIC doubled the amino acid yield under the same acidic reaction conditions when soy protein isolate were subjected to hydrolysis at 90°C (see Figure 5). Similarly, SIC and HIC-catalysed soy protein hydrolysis can achieve the same or more amino acid yield when 0.75M HCI was used as compared to 6M HCI with no catalyst added (see Figure 6).

[0179] Example 7: Heating mixtures containing SIC / HIC-based flavour catalysts and Mixture F produces similar volatile fingerprint profile as flavour mixtures containing Heme-based flavour catalyst and Mixture F

[0180] The flavour mixtures were formed by adding the following ingredients to form mixture F shown in Table 1; namely, L-amino acids, nucleotides, sugars, fatty acids, triglycerides, sodium chloride. Equal quantities of HIC, SIC or heme B (specifically chloridoprotoporphyrinato (IX) iron(iii) complex) were added to mixture F.

[0181] Each sample was heated in a crucible at 300°C on an electric hotplate for 7 to 8 minutes with constant stirring, until the flavour mixtures have turned brown. The reaction solution was then transferred to a lOmL headspace glass vial and the headspace composition was analysed using Solid-Phase Microextraction (SPME). The GCMS spectra are compared in Figure 7 below, where the important flavour volatile peaks are marked out. Equivalent volumes of internal standard of ethyl acetate were added to all samples for standardisation.

[0182] Table 5. Key volatiles observed in GCMS spectra, as noted in Figure 7. The GCMS spectrum of the two samples were very similar, with similar peaks and peak areas. Some of the important volatiles marked out on the spectra were shown in Table 5. These peaks are mostly Maillard reaction products and lipid oxidation products, and the standardised peak areas of the volatiles and their ratios maintained relatively constant and equivalent between the two types of flavour catalysts. This showed that SIC has similar capacity to catalyse cooking reactions to the same degree as the Heme B molecule.

[0183] It will be appreciated that many further modifications and permutations of various aspects of the described embodiments are possible. Accordingly, the described aspects are intended to embrace all such alterations, modifications, and variations that fall within the spirit and scope of the appended claims.

[0184] Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.

[0185] Throughout this specification and the claims which follow, unless the context requires otherwise, the phrase "consisting essentially of", and variations such as "consists essentially of" will be understood to indicate that the recited element(s) is / are essential i.e. necessary elements of the invention. The phrase allows for the presence of other non-recited elements which do not materially affect the characteristics of the invention but excludes additional unspecified elements which would affect the basic and novel characteristics of the method defined.

[0186] The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims

Claims1. A method of imparting and / or enhancing an olfactory perception of a meat flavour in a food, comprising a step of adding iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour.

2. The method according to claim 1, wherein the iron chlorophyllin is selected from trisodium iron chlorophyllin a, trisodium iron chlorophyllin b, disodium iron chlorophyllin a, disodium iron chlorophyllin b, monosodium iron chlorophyllin a, monosodium iron chlorophyllin b, iron chlorophyllin a, iron chlorophyllin b, iron pheophytin a, iron pheophytin b, or a combination thereof.

3. The method according to claim 1 or 2, wherein the iron chlorophyllin comprises iron (II), iron (III), or a combination thereof.

4. The method according to any one of claims 1 to 3, wherein the food is an edible composition comprising an alternative protein, plant-based meat, or a combination thereof.

5. The method according to any one of claims 1 to 4, wherein the component in the food is selected from a protein, an amino acid, a fat, an oil, a sugar, vitamin, a food additive, or a combination thereof.

6. The method according to any one of claims 1 to 5, wherein the method further comprises adding a flavour precursor selected from sugar, amino acid, vitamin, fat, flavour enhancer, or a combination thereof.

7. The method according to claim 6, wherein the sugar is selected from glucose, fructose, galactose, mannose, xylose, lactose, maltose, isomaltose, trehalose, sorbitol, mannitol, amylose, amylopectin, pectin, dextrin, cellulose, hemicellulose, their respective DL-isomers or a combination thereof, wherein the sugar is about 2 %w / w to about 20 %w / w relative to the food.

8. The method according to claim 6 or 7, wherein the amino acid is selected from D-alanine, L-alanine, D-arginine, L-arginine, L-arginine hydrochloride, D-arginine hydrochloride, D-asparagine, L-asparagine, D-aspartate salt, L-aspartate salt, D- aspartic acid, L-aspartic acid, D-cysteine, L-cystine, D-cysteine hydrochloride, L- cysteine hydrochloride, D-glutamate salt, L-glutamate salt, D-glutamic acid, L-glutamic acid, D-glutamine, L-glutamine, glycine, D-histidine, L-histidine, D-histidine hydrochloride, L-histidine hydrochloride, D-isoleucine, L-isoleucine, D-leucine, L- leucine, D-lysine, L-lysine, D-lysine hydrochloride, L-lysine hydrochloride, D- methionine, L-methionine, D-ornithine, L-ornithine, D-phenylalanine, L-phenylalanine, D-proline, L-proline, D-serine, L-serine, taurine, D-threonine, L-threonine, D- tryptophan, L-tryptophan, D-tyrosine, L-tyrosine, D-valine, L-valine, their hydrates, derivatives, or combination thereof, wherein the amino acid is about 5 %w / w to about 50 %w / w relative to the food.

9. The method according to any one of claims 6 to 8, wherein the amino acid is selected from thiamine (Vitamin Bl), thiamine hydrochloride, ascorbic acid (Vitamin C), sodium ascorbate (vitamin C), potassium ascorbate (vitamin C), or a combination thereof, wherein the vitamin is about 0.5 %w / w to about 10 %w / w relative to the food.

10. The method according to any one of claims 6 to 9, wherein the flavour enhancer is selected from nucleoside, nucleotide, vitamin, protein hydrolysate from animal, plant, fungal, bacterial and / or in vitro origin, lecithin, or a combination thereof, the flavour enhancer is about 0.5 %w / w to about 10 %w / w relative to the food.

11. The method according to any one of claims 6 to 10, wherein the fat is selected from canola oil, soybean oil, safflower oil, flaxseed oil, sunflower oil, olive oil, coconut oil, palm oil, corn oil, linseed oil, algae oil, rice bran oil, pumpkin seed oil, peanut oil, sesame oil, beef tallow, chicken fat, fish oil, pork fat, mutton fat, or a combination thereof, the fat is about 30 %w / w to about 90 %w / w relative to the food.

12. The method according to any one of claims 6 to 11, wherein when the meat flavour is a beef flavour, the flavour precursor is selected from beef fat, canola oil, palm oil, corn oil or a combination thereof;wherein when the meat flavour is a poultry flavour, the flavour precursor is selected from corn oil, sunflower oil, canola oil, palm oil, safflower oil, chicken fat or a combination thereof; wherein when the meat flavour is a seafood flavour, the flavour precursor is selected from fish oil, algal, flaxseed oil or a combination thereof; wherein when the meat flavour is a pork flavour, the flavour precursor is selected from corn oil, sunflower oil, canola oil, palm oil, safflower oil, pork fat or a combination thereof; wherein when the meat flavour is a mutton flavour, the flavour precursor is selected from mutton fat, canola oil, palm oil and corn oil or a combination thereof.

13. The method according to any one of claims 1 to 12, wherein the volatiles are selected from Pentane, 3-Methyl butanal, Pentanal, Hexanal, Nonanal, (E)-2-Octenal, Furfural, (E,E)-2,4-Heptadienal, (E)-2-Nonenal, (E,E)-2,4-Nonadienal, 2-Undecenal, 2,4-Decadienal, trans-3-Nonen-2-one, or a combination thereof.

14. The method according to any one of claims 1 to 13, wherein iron chlorophyllin is configured to interact with a protein in the food in order to generate Amadori rearrangement products. Maillard Reaction products, Strecker degradation products, melanoidins, advanced glycation end-products, volatile, non-volatile molecular products or a combination thereof that influence aroma and flavour of a food product.

15. A method of forming a food product, comprising a step of adding iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food, wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour.

16. A food product comprising iron chlorophyllin at about 0.002 %w / w to about 5 %w / w relative to the food product, wherein the food product is selected from an alternative protein, plant-based meat, or a combination thereof; wherein when heated, the iron chlorophyllin is configured to interact with a component in the food in order to generate volatiles which replicate the meat flavour.

17. An iron chlorophyllin composition, comprising:a) iron chlorophyllin at about 0.1 %w / w to about 5 %w / w relative to the composition; and b) a flavor precursor at about 95 %w / w to about 99.9 %w / w relative to the composition.

18. The iron chlorophyllin composition according to claim 17, wherein the iron chlorophyllin composition is a powder.

19. A method of synthesizing an iron chlorophyllin composition, comprising a step of mixing iron chlorophyllin with a flavour precursor, wherein iron chlorophyllin is about 0.1 %w / w to about 5 %w / w relative to the composition; and wherein the flavour precursor is about 95 %w / w to about 99.9 %w / w relative to the composition.

20. The method according to claim 19, further comprising a step of reacting chlorophyll or sodium magnesium chlorophyllin with an iron salt in order to form iron chlorophyllin, wherein the chlorophyll is obtained from a plant, fungi or bacteria.

21. The method according to claim 20, wherein chlorophyll is derived from a mixture of green vegetables.

22. The method according to claim 20 or 21, wherein the iron salt is an iron(II) or iron (III) salt selected from food grade iron(II) chloride, iron(III) chloride, iron(II) bromide, iron(III) bromide, iron(II) iodide, iron(III) iodide, iron(II) sulfate, iron (III) sulfate, iron(II) nitrate, iron(III) nitrate, iron(II) fumurate, iron(III) fumurate, iron(II) gluconate, iron(III) gluconate, iron(II) lactate, iron(III) lactate, iron (II) ascorbate, iron (III) ascorbate, iron (II) aspartate, iron (III) aspartate, iron (II) glycinate, iron (III) glycinate, iron (II) carbonate, iron (III) carbonate, iron (II) citrate, iron (III) citrate, iron (II) malate, iron (III) malate, iron (II) oxalate, iron (III) oxalate, iron (II) phosphate, iron (III) phosphate, iron (II) tartrate, iron (III) tartrate, iron (II) ammonium citrate, iron (III) ammonium citrate, iron (II) glycerophosphate, iron (III) glycerophosphate, iron (II) pyrophosphate, iron (III) pyrophosphate, their hydrates and derivatives thereof.

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