Composition comprising polyketone compound pigment

Abstract

The present invention provides a food colouring composition, in particular, the present invention provides a composition or colouring composition comprising at least one polyketone compound pigment (i) and one or more of the following compounds (ii) carotenoid (e.g., lycopene, annatto and / or norannatto), rosmarinic acid, chlorogenic acid, rutin glucoside, and gamma-cyclodextrin and / or tocopherol.

Description

Technical Field

[0001] This invention relates to food coloring compositions, and in particular to compositions or coloring compositions comprising (i) polyketide pigments and (ii) carotenoids (e.g., lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, and methods for preparing said stabilized coloring compositions.

[0002] The present invention also relates to the use of the food coloring compositions as described herein in coloring food and to food comprising the food coloring compositions as described herein. Background of the Invention

[0004] Synthetic red dyes, especially azo dyes such as Allura Red AC (Red Dye 40), are commonly used for food coloring due to their attractive cost, vibrant red color, and excellent stability to light, heat, oxygen, pH, and low microbial contamination. However, these pigments have several health side effects due to their toxicity.

[0005] This major limitation has created increasing pressure to find alternatives to these pigments, with the most widely used red food colorings currently being anthocyanins (E163), red beetroot (E162), and carmine (E120). However, these pigments have a number of drawbacks.

[0006] Anthocyanins are unstable at pH > 3, which limits their use in dairy, baked goods, and meat applications in the pH range of 5.5 to 6.5.

[0007] Beetroot extract exhibits poor stability due to several degradation reactions of β-anthocyanin molecules under thermal stress, such as hydrolysis, decarboxylation, oxidation, and photodegradation (Herbach, KM, Stintzing, FC, and Carle, R. (2006), Betalain Stability and Degradation—Structural and Chromatic Aspects. Journal of Food Science, 71: R41-R50).

[0008] Carmine is a bright red-pink pigment obtained from an aluminum complex derived from carmine acid. This pigment is quite stable to light and heat, making it an attractive product in the food industry. However, this pigment is extracted from an animal source (cochineal insects), which makes it not a vegetarian-friendly product. Furthermore, this pigment is not entirely natural because it is chemically modified (by chelating with aluminum).

[0009] Faced with these limitations, manufacturers have been under pressure to find alternatives to satisfy natural, vegan, halal, and Jewish consumers, making the search for new food dyes based on natural compounds with high stability a very active activity today.

[0010] Red yeast rice pigment, a natural red solution, has been used in East Asia as a natural coloring agent and food additive. This tasteless and odorless pigment is produced by fermentation of various red yeast molds (M. purpureus i), is stable in a pH range of 2–10, and is known to be heat-stable, making it an attractive sustainable product. *Monascus purpureus* is deposited at the China General Microbiological Culture Collection Center (CGMCC) under accession number CGMCC No. 11317.T.

[0011] However, Monascus pigments are poorly stable to light; several papers have reported their sensitivity to sunlight, and more specifically, to UV radiation. It has been reported that under light irradiation, the side chains of Monascus purpureus break, producing superoxide anions, hydroxyl radicals, and other free radicals. These free radicals undergo further reactions with the double bonds in the pigment structure, disrupting the double bond conjugation in Monascus pigments and thus leading to loss of color properties and fading.

[0012] Several attempts were made to improve the stability of red yeast pigments and red yeast-like pigments, for example, during fermentation.

[0013] CN201410118907 reports a fermentation method for preparing highly photostable red yeast rice pigment. Yang Yijin et al. reported stabilization using rutin and quercetin in Frontiers in Microbiology Journal (2021, Vol. 12, DOI = 10.3389 / fmicb.2021.678903); however, these molecules have poor solubility in aqueous conditions, limiting their use in alcoholic beverages. Chinese patent CN102702780A discloses a method for preventing the fading of red yeast rice pigment, which involves dissolving the pigment in a 0.1% solution of tryptophan, histidine, tyrosine, or methionine.

[0014] Chinese patent CN103589189A discloses the application of retrograde starch in reducing the light fading of red yeast rice pigment. It involves adding retrograde starch to an aqueous solution of red yeast rice pigment so that the aqueous solution of red yeast rice pigment is completely adsorbed into the retrograde starch, thereby obtaining a red yeast rice pigment product with anti-light radiation function.

[0015] Chinese patent CN101530190B discloses a food-grade red yeast rice pigment color protectant, which is composed of 5-10% catechin, 10-25% vitamin C, 30-40% glucose, and the balance rutin.

[0016] Despite these extensive experiments, stabilization of polyketide pigments (such as azaphilone) has not been successfully achieved, and there remains a growing need to identify effective solutions to improve their stability. Invention Overview

[0018] In this invention, we introduce a novel stabilization method for enhancing the photostability of polyketide pigments, such as azafiron, using natural water-soluble or water-dispersible components.

[0019] The applicant has surprisingly and unexpectedly discovered that the use of carotenoids (such as lycopene) and / or other water-soluble compounds such as rosmarinic acid, chlorogenic acid, rutin glucoside, and / or tocopherol results in the fading of polyketide pigments such as azafione upon exposure to light. Unbound by any theory, the polyketide pigments such as azafione are protected due to reduced UV light absorption (the primary factor contributing to this photodamage).

[0020] This improvement helps stabilize polyketide pigments, such as azafirone, in beverages and confectionery, resulting in a bright and stable red color. Using the solution described in this application, we can benefit from its clean, non-GMO label, good nutritional value, and neutral taste, without any off-flavors in the final application.

[0021] Therefore, the present invention provides a method for stabilizing the color of a polyketide compound pigment, the method comprising contacting (i) the polyketide compound pigment with (ii) carotenoids (e.g., lycopene), rosmarinic acid, rutin glucoside, cyclodextrin and / or tocopherol, wherein the resulting polyketide compound pigment is light stable.

[0022] In another aspect, the present invention provides stabilized pigments obtained by the stabilization method according to the present invention.

[0023] In another aspect, the present invention provides a coloring composition comprising a stabilized pigment and another suitable carrier or excipient.

[0024] In another aspect, the present invention provides food, medicine, nutraceutical, fragrance or cosmetic that contains, optionally, a stabilized pigment or coloring composition according to the invention that is exposed to light.

[0025] In another aspect, the present invention provides a method for producing food, pharmaceuticals, nutritional supplements, fragrances, or cosmetics, the method comprising the step of incorporating a stabilized pigment or a coloring composition according to the present invention into the food, pharmaceuticals, nutritional supplements, fragrances, or cosmetics.

[0026] In another aspect, the present invention provides a method for producing food, medicine, nutritional supplement, fragrance or cosmetic, the method comprising the steps of incorporating a component (i) and a component (ii) as defined in any of the preceding claims, wherein component (i) is added directly to the product and subsequently product (ii) is also added to the product, or wherein component (ii) is added directly to the product and subsequently product (i) is also added to the product, particularly when the product is a liquid or semi-solid. Brief description of the attached diagram

[0028] Figure 1 Photostability measurements of solutions 1A, 1B, and 1C. Pigment retention.

[0029] Figure 2 Photostability measurements of solutions 1A, 1B, and 1C. dE2000.

[0030] Figure 3 Photostability measurements of solutions 2A, 2B, 2C, 2D, 2E, and 2F. Pigment retention.

[0031] Figure 4 dE2000 measurements of solutions 3A, 3B, 3C and 3D.

[0032] Figure 5 Pigment retention over time. Samples 3A, 3B, 3C, and 3D.

[0033] Figure 6 Pigment retention over time. Samples 4A, 4B, 4C, and 4D.

[0034] Figure 7 dE2000 measurements of samples 4A, 4B, 4C and 4D.

[0035] Figure 8 dE2000 measurements of samples 5A, 5B, 5C, 5D and 5E.

[0036] Figure 9 Pigment retention over time. Samples 5A, 5B, 5C, 5D, and 5E.

[0037] Figure 10 Color changes of sugar pastes of samples 7A, 7B, 7C and 7D after 8 hours of light irradiation.

[0038] Figure 11dE2000 measurements of samples 6A, 6B, 6C and 6D.

[0039] definition

[0040] As used in this article, the term "pigment" refers to any substance that imparts color by absorbing or scattering light of different wavelengths.

[0041] The term "coloring composition" refers to any pigment formulated together with one or more other products, such as a carrier.

[0042] The term "color" refers to color properties such as hue, chroma, purity, saturation, intensity, vividness, value, lightness, brightness, and darkness, as well as the parameters of the color model system used to describe these properties, such as the L*a*b* values ​​of the CIELAB color space.

[0043] The term "hue" refers to the color property that gives a color a name (such as red, blue, and brown).

[0044] Detailed description

[0045] The terms “comprises,” “comprising,” “has,” “having,” “includes,” “including,” “contains,” “containing,” or any other variation thereof are open-ended and intended to cover a non-exclusive inclusion of elements, such that an article, apparatus, compound, composition, combination, method, or process comprising not only those elements but also other elements not expressly listed, enumerated, or written in the specification or claims. An element or feature beginning with the language “comprising…a,” “containing…a,” “having…a,” or “comprising…a” does not, without further constraint, exclude the presence or inclusion of additional elements or features in an article, apparatus, compound, composition, combination, method, or process that comprises, contains, has, or includes that element or feature.

[0046] The terms “a” and “an” are defined as one or more unless otherwise expressly stated or construed in the other language of this document. An element or feature beginning with “a” or “an” can be interpreted as one or more of the elements or features mentioned. For example, CGA can be interpreted as one chlorogenic acid or more than one chlorogenic acid.

[0047] The terms “about,” “approximately,” “essentially,” “substantially,” any other version thereof, or any other similar relative or approximate term are defined as close to, as understood by one of ordinary skill in the art. By way of non-limiting illustrative embodiments, these terms are defined as being within 20% of the value, or within 10% of the value, or within 5% of the value, or within 4% of the value, or within 3% of the value, or within 2% of the value, or within 1% of the value, or within 0.5% of the value, or within 0.25% of the value, or within 0.1% of the value.

[0048] It should be understood that when quantities are described as weight percentages in this disclosure, it is intended that any and every quantity (including endpoints) within that range be considered as explicitly disclosed. For example, the disclosure of "a range from about 1 to about 10" should be interpreted as indicating every possible number along the continuum between about 1 and about 10. It should be understood that the inventors recognize and understand that any and all data points within that range are considered to have been specified, and that the inventors own the entire range and all points within that range.

[0049] To avoid ambiguity, unless the context otherwise requires, preferences, options, particular features, etc. indicated by a feature or parameter for a given aspect of the invention should be considered as disclosed in combination with any and all other preferences, options, particular features, etc. indicated by the same or other aspects, features, and parameters for the invention.

[0050] The following text provides a broad description of many different embodiments of this disclosure. The specification is to be interpreted as exemplary only and does not describe every possible embodiment, as describing every possible embodiment would be impractical, if not impossible. It should be understood that any feature, characteristic, component, composition, ingredient, product, step, or method described herein may be removed in whole or in part, combined with, or substituted for any other feature, characteristic, component, composition, ingredient, product, step, or method described herein. Many alternative embodiments may be implemented using current technology or technology developed after the filing date of this patent, which will still fall within the scope of the claims.

[0051] Preferred and / or optional features of the invention will now be described. Unless the context otherwise requires, any aspect of the invention may be combined with any other aspect of the invention. Unless the context otherwise requires, any preferred or optional feature of any aspect may be combined, alone or in combination, with any aspect of the invention and with any other preferred or optional feature.

[0052] Methods for stabilizing polyketide pigments

[0053] Surprisingly, it was found that by combining polyketide pigments (e.g., azafione), more specifically red yeast rice pigments, with one or more of carotenoids (e.g., lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, and / or tocopherols, stabilized polyketide pigments (e.g., azafione), more specifically red yeast rice pigments, exhibit increased stability to light exposure compared to polyketide pigments (e.g., azafione), more specifically red yeast rice pigments alone.

[0054] Therefore, the present invention provides a method for stabilizing the color of a polyketide pigment (e.g., azafione), the method comprising contacting (i) the polyketide pigment with (ii) a carotenoid (e.g., lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, wherein the resulting polyketide pigment (e.g., azafione) is photostable.

[0055] The present invention also provides a method for preparing a light-stable polyketide compound pigment (e.g., azafiron), the method comprising the steps of: a) contacting (i) the polyketide compound pigment with (ii) a carotenoid (e.g., lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, and optionally b) mixing (i) and (ii).

[0056] Therefore, "stabilized polyketone compound pigments" or "light-stabilized polyketone compound pigments" obtained using the methods of the present invention are also provided. In this specification, the two terms "stabilized polyketone compound pigments" or "light-stabilized polyketone compound pigments" are used interchangeably.

[0057] Without being bound by theory, it is believed that polyketide pigments (such as azafirone) and lycopene form complexes that provide stabilized coloring compositions with colors such as red, orange, or yellow that are stable to light exposure (i.e., the color hue does not fade when exposed to light).

[0058] As used herein, “contact” can refer to the physical interaction between polyketide pigments (e.g., azafirone) and compounds as described herein (ii) carotenoids (e.g., lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, (γ) cyclodextrin and / or tocopherols, which promote the stabilization (photostabilization) of polyketide pigments.

[0059] "Contact with compound (ii)" can correspond to contact with a single compound (e.g., lycopene) or a mixture of compounds (e.g., lycopene and CHA).

[0060] Optionally, the method of the present invention may include additional steps of mixing (i) and (ii) to obtain a homogeneous mixture.

[0061] Polyketone compound pigments

[0062] Polyketone compounds that form part of this invention include, but are not limited to, azafirone, anthraquinone, hydroxyanthraquinone, and naphthoquinone.

[0063] To avoid ambiguity, the term "polyketide pigment" or "the polyketide pigment" in this invention is defined as one or more polyketide pigments, that is, it may refer to only one type of polyketide compound (e.g., purified azafifenone), or it may refer to a combination of several pigments (e.g., a mixture of atrorosin-type azafifenone pigments obtained from *Talaromyces atroroseus* disclosed in EP3622081A1).

[0064] In a preferred embodiment, mycotoxins are excluded. In one preferred embodiment, the polyketide pigment is substantially free of mycotoxins, such as penicillin and its derivatives, spiciferinone, spirosporacin A, Austerdiol and its derivatives.

[0065] The azafirone constituting a part of this invention can be any of those compounds obtainable from fungal genera, including those obtainable from: *Aspergillus* genus, *Chaetomium* genus, *Hypoxylon* genus, *Monascus* genus, *Muycopron* genus, *Penicillium* genus, *Phomopsis* genus, *Pleosporales* genus, *Talaromyces* genus, *Pestalotiopsis* genus, *Phomopsis* genus, *Emericella* genus, *Epicoccum* genus, *Hypoxylon* genus (Jin-Ming) Gao et al., Azaphilones: Chemistry and Biology Chem. Rev. 2013, 113, 7, 4755-4811).

[0066] Specific classes of azafifenone include, but are not limited to, azafifenone nitrified, ostradiol, spiciferinone and its derivatives, deflectins, helotialins, bulgarialactones, spiroazafifenone, O-substituted azafifenone (especially O-containing red yeast rice pigments), lactone azafifenone, hydrogenated azafifenone, chaetoviridins and chaetomugilins, sequoiatones, tricoflectin and safrole azafifenone, penicillic acid-type azafifenone, sclerotiorins, multiformins and cohaerins, chitodisporins, chrysodin-type azafifenone, hydrogenated spiroazafifenone, chlorofusins ​​and styracin.

[0067] More specifically, azaphilone pigments include those deep rosemary azaphilone pigments disclosed in EP3622081A1 and Rasmussen KB et al. (“Talaromyces atroroseus-Genome sequencing, Monascus pigments and azaphilonegene cluster evolution” 2015. Retrieved from the Internet: https: / / orbit.dtu.dk / en / publications / italaromyces-atroroseusi-genome-sequencing-monascus-pigments-and-), which are incorporated herein by reference.

[0068] The deep rose pigments described in EP3622081A1 and by Rasmussen KB et al. are “monascus”-like pigments biosynthesized by *Monascus purpureus*, and are incorporated herein by reference. These *Monascus purpureus*-like pigments possess an azafione skeleton similar to that of orange *Monascus* pigment PP-O, with a carboxylic acid group Cl, but are unique in that they incorporate an amino acid into the isochromene system. The deep rose pigments described in EP3622081A1 and by Rasmussen KB et al. are primarily red pigments, and their production is free of mycotoxins.

[0069] The pigments described in EP3622081A1 and Rasmussen KB et al. are biosynthesized by *Pterocarya stenoptera* using organic (e.g., one or more amino acids, peptides, amino sugars and / or primary amines) and / or inorganic compounds as nitrogen sources.

[0070] Azaphilone pigments also include those listed in Jin-Ming Gao et al. (Azaphilones: Chemistry and Biology Chem. Rev. 2013, 113, 7, 4755-4811), including but not limited to monascusone B (isolated from a yellow mutant of Monascus kaoliang grown on rice), Monascuspiloin and monascusazaphilol (two distinct metabolites from Monascus pilosus strains), Sequoiamonascin C (isolated from the endophytic fungus Aspergillus parasiticus), monarubrin and rubropunctin (identified from monascus pigments and broths of Monascus ruber). monaphilones A and B (isolated from Rhodotorula purpureus NTU 568 fermented with erythromycetes), and biscogniazaphilones A and B (obtained from the endophytic fungus Biscogniauxia formosana BCRC33718).

[0071] Azaphilone pigments include Monascus-type azaphilones, including but not limited to the yellow pigments monascin (C21H26O5) and ankaflavin (C23H30O5), the orange pigments monascorubrin (C23H26O5) and rubropunctatin (C21H22O5), and the red pigments monascorubramine (C23H27NO4) and rubropuntamine (C21H23NO4) (Jin-MingGao et al., Azaphilones: Chemistry and Biology Chem. Rev. 2013, 113, 7, 4755-4811), all their derivatives, and monascorubramine (compound of formula (I)).

[0072]

[0073] In the aforementioned erythroside (C23H27NO4), erythroside (C21H23NO4), and erythroside amino acid, NR is selected from amino acids, peptides, amino sugars, and primary amines.

[0074] Furthermore, the wavy bond represents the unspecified configuration of adjacent double bonds between carbon 2 and 3.

[0075] The double bond adjacent to the carboxyl group of the compound of formula (I) may have an E- or Z- configuration, or the compound may exist as a mixture.

[0076] For example, the amino acid is selected from alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, serine, threonine, tyrosine, valine, and ornithine. (The amino acid can be L or D configuration, or a mixture thereof.)

[0077] For example, amino sugars are selected from glucosamine and galactosamine.

[0078] For example, primary amines are selected from anthranilic acid, aniline, p-phenylenediamine, and ethanolamine.

[0079] In this article, "derivatives" refers to basic structures with different amino acid chains at position 10 (e.g., the basic structure of the aforementioned Monascus purpureus-type azafibrone). For example, it has been reported that culturing Monascus purpureus (M. ruber) and Monascus purpureus A on a chemically defined medium using glutamic acid as the nitrogen source produces two pigments, N-glutamyl erythroside and N-glutamyl erythroside, which are linked to glutamic acid via an amino group. Similarly, the fungus Monascus purpureus (M. ruber) produces two water-soluble red pigments, N-glucosyl erythroside and N-glucosyl erythroside, in submerged cultures.

[0080] N-containing red yeast rice pigments typically consist of an isoquinoline skeleton with n-octanoyl or n-hexanoyl side chains, a 1-propenyl chain, and a γ-lactone ring. Most pigments are various amino acid derivatives of erythropoietin and erythropoietin (erythropoietin amine and erythropoietin amine).

[0081] Depending on the supplementation of the fermentation medium, different Monascus-like pigments can be obtained (e.g., alanine or aspartic acid derivatives of Monascus rubrum and Monascus erythropoietin, threonine derivatives of Monascus rubrum, and arginine derivatives). It has been found that culturing resting Monascus purpureus cells with glycine yields a dark red substance containing non-natural amino acids (e.g., derivatives containing penicillamine (H-Pen), cyclohexylalanine (H-Cha), butylglycine (Lt-Bg), and ortholeucine (H-Nle)).

[0082] In addition, this article includes cavenamine pigments as described in WO202094830.

[0083] The pigments mentioned above can be obtained by extracts from natural sources or otherwise derived from natural sources, such as plants, fungi, bacteria or algae.

[0084] Pigments can be natural, meaning they can be extracted from their natural state without modification, or extracted from their natural state and purified or even chemically modified.

[0085] They can be provided as a mixture, or they can be prepared or separated individually.

[0086] If the compound is prepared alone, it can be extracted and purified from natural sources, or it can be prepared by chemical synthesis or by fermentation.

[0087] Carotenoids

[0088] Carotenoids, or tetraterpenoids, are yellow, orange, and red organic pigments produced by plants and algae, as well as several bacteria and fungi.

[0089] In some embodiments, the carotenoid may be selected from (i) pure hydrocarbons called carotene, including but not limited to compounds such as β-carotene, α-carotene, γ-carotene or lycopene, (ii) molecules called xanthophylls containing various forms of oxygen (hydroxyl, epoxy, etc.), including but not limited to astaxanthin, zeaxanthin, capsanthin, cantaxanthin, lutein, etc., and (iii) molecules called apocarotenoids, such as annatto and nonatto, and any mixture thereof.

[0090] In certain cases, the carotenoid composition of the present invention can be mixed with oil to form an oily solution of the carotenoid composition, such that the final carotenoid content is equal to or greater than 30% w / w. In a preferred embodiment, the final carotenoid content in the oily solution is at least 31%, at least 32%, at least 33%, at least 34%, at least 35%, at least 36%, at least 37%, at least 38%, at least 39%, at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, or at least 75% (w / w).

[0091] The oily solution of the carotenoid can optionally be emulsified into an oil-in-water emulsion containing 1% to 20% oil (preferably olive oil, sunflower oil, oils containing medium-chain triglycerides, or mixtures thereof). In one specific embodiment, the final concentration of carotenoid in the oil-in-water emulsion is 0.1% to 10%, more preferably 0.5% to 8%.

[0092] In a preferred embodiment, the carotenoid is lycopene.

[0093] Lycopene (CAS No. 502-65-8) is a symmetrical tetraterpene, assembled from eight isoprene units. It is a member of the carotenoid family of compounds and, because it is composed entirely of carbon and hydrogen, is also classified as a carotenoid. Lycopene (C40H56) is an intermediate in the biosynthetic pathways of β-carotene and lutein. It has a molecular weight of 536.85 and the following molecular formula:

[0094]

[0095] Although lycopene exists in different forms with varying colors and intensities, the term "lycopene" is used in all cases to refer to the chemical entity. However, it should be noted that crystalline lycopene has a strong red color and differs from soluble, dispersed, or solubilized lycopene, which has a yellow-orange color. Furthermore, lycopene naturally present in fruits exists in chromoplasts in crystalline form and is thus able to retain its red color, as in tomatoes.

[0096] As mentioned above, the intense red color of lycopene is due to its crystalline form and is influenced by its particle size distribution. When the crystals dissolve, lycopene loses its ability to stain within the red range, which readily occurs in various organic solvents (such as oils). When lycopene oleoresins are solubilized in aqueous solutions, it exhibits a pale yellow to orange color, depending on the concentration.

[0097] In some embodiments, the lycopene used in this invention is in its crystalline form.

[0098] In some embodiments, the lycopene used in this invention may be obtained or available from natural sources, or may have a synthetic source. In some embodiments, lycopene may be obtained or available from plants, photosynthetic bacteria, fungi, and / or algae.

[0099] As will be understood by those skilled in the art, the term "available from" as used herein means that lycopene can be obtained directly from plants / algae / animals / prokaryotes, or can be isolated from plants, photosynthetic bacteria, fungi and / or algae, or can be obtained from alternative sources, such as through chemical synthesis or enzymatic production. The term "obtained" as used herein means that the extract is directly derived from plant, photosynthetic bacteria, fungi and / or algae sources.

[0100] In some implementations, lycopene may be obtained from or may be obtained from plant products such as: tomatoes, carrots, peppers, vegetable oils, autumn olives, gac, watermelons, pink grapefruits, pink guavas, papayas, sea buckthorn, goji berries (a berry relative of tomatoes), rose hips, and any mixture thereof.

[0101] The lycopene used in this invention can be produced from plant products using any kind of method, such as the method described in patent WO97 / 48287, which describes a method for preparing lycopene-rich oleoresin from tomatoes by pressing tomatoes until pulp is obtained, extracting lycopene from the pulp with an organic solvent, and then removing the solvent by evaporation to obtain an oleoresin with a lycopene content in the range of 2-10%. Similar methods for obtaining oleoresins, typically rich in carotenoids and particularly lycopene, from plants and oils are described in various patents, such as precipitation with calcium salts in USPat. No. 5,245,095 and EP580745, transesterification with oil followed by distillation in USPat. No. 5,019,668, fractionating tomatoes into various fractions comprising carotenoid-rich oleoresins in WO95 / 16363, and extraction of lycopene using supercritical fluids in PCT WO90 / 08584, although the resulting extract is a mixture of various carotenoids, the extraction yield is very low due to their low solubility. All these methods are incorporated herein by reference.

[0102] In some implementations, lycopene is in the form of natural oleoresins, such as capsicum oleoresin, tomato oleoresin, etc.

[0103] Biologically derived lycopene preparations can also be obtained by fermenting *Mucor* fungi of the genera *Phycomyces*, *Blakeslea*, and *Choanephora* [GB 1008469, US Pat. No. 3,097,146,3,369,974, JP73016189, JP73016190, RU2102416, WO00 / 77234], which are incorporated herein by reference. Lycopene can also be obtained from the fungus *B. trispora*, as described in WO03 / 056028A1, which is incorporated herein by reference.

[0104] Certain Dunaliella-type microalgae rich in carotenoids are another important source of lycopene. As reflected in US Pat. Nos. 5,378,369,4,713,398 and 4,680,314, various methods exist for extracting carotenoids, particularly lycopene, from these organisms by means of organic solvents (chlorinated hydrocarbons, hydrocarbons, etc.) or edible oils (DE4342798). Different methods are described in PCT WO98 / 08584, in which lycopene extracts are obtained using supercritical CO2, although the resulting extracts have a lower purity relative to lycopene. All these methods are incorporated herein by reference.

[0105] Oleoresins containing lycopene of varying purities can be used in this invention. In some embodiments, the oleoresin may contain at least 2% lycopene, such as at least 5%, such as at least 10%, at least 50%, or at least 99% lycopene.

[0106] In some embodiments, lycopene is a tomato oleoresin containing about 40%-100% free-flowing powdered lycopene.

[0107] In some implementations, lycopene is trans-lycopene, cis-lycopene, or a mixture thereof.

[0108] In some embodiments, lycopene is in crystalline form, characterized by a crystal purity of more than 10%, for example, more than 20%, for example, more than 50%, for example, more than 95%. In some embodiments, the crystals have a cis-lycopene content of less than 3% and a content of less than 3% of other carotenoids.

[0109] In some implementations, lycopene crystals may be mixed with other carotenoids as described herein.

[0110] In some embodiments, lycopene is prepared according to patent application number US5965183A, which is incorporated herein by reference. That patent application describes a method for preparing a stable lycopene concentrate comprising reduced-size lycopene crystals in a food-compatible liquid medium in which lycopene is substantially insoluble. The patent application also describes a method for preparing a crystalline lycopene composition, the method comprising treating a lycopene-containing oleoresin with a solvent or solvent mixture (such as an acetone / ethyl acetate solvent mixture) to remove most of the oleoresin lipids, said solvent or solvent mixture dissolving the lipid phase of the oleoresin and substantially insoluble in the lycopene.

[0111] In some embodiments, lycopene crystals are preferably ground to an average particle size of less than about 5 μm, for example, about 1-3 μm.

[0112] In some embodiments, lycopene is dissolved in a food-compatible liquid selected from glycerol, propylene glycol, and ethanol, or mixtures thereof, or mixtures thereof with other food-compatible liquids. In some embodiments, the lycopene solution further comprises lecithin and / or sucrose esters.

[0113] In some embodiments, lycopene is extracted from tomatoes using ethyl acetate and ethanol, and after purification and concentration, the final product is formulated in glycerol, lecithin, sucrose esters, and water.

[0114] In another preferred embodiment, the carotenoid is annatto and / or nonatto.

[0115] In some implementations, annatto or annattoin can be obtained or may be obtained from plant products, such as the seeds of the annatto tree (Bixa Orellana). The oil from the seeds of the annatto tree is commonly referred to as annatto or annatto colorant. In the European Union, annatto is identified by E160b.

[0116] In some embodiments, the present invention uses annatto colorant obtained or available from the seeds of annatto trees containing annatto and / or noannattoin.

[0117] In other embodiments, annatto or noannatto is derived from a synthetic source.

[0118] In other embodiments, the carotenoid is a mixture of lycopene, annatto, and / or nonatto.

[0119] Rosmarinic acid can be of natural or synthetic origin. In some embodiments, rosmarinic acid is a natural product, for example, in the form of a Lamiaceae extract.

[0120] As used herein, the term "Lamiaceae extract" can refer to extracts from plants of the Lamiaceae family, including but not limited to rosemary, sage, oregano, thyme, mint, and the following genera: Melissa officinalis (or lemon balm), Sage (e.g., Salvia apiana and Salvia officinalis), Rosemary (e.g., Rosmarinus officinalis), Lepechinia, Oregano, Thymus, Hyssopus, and any mixture thereof.

[0121] The Lamiaceae material used for extracting Lamiaceae extracts rich in rosmarinic acid can be any part of the plant, such as leaves, roots, flowers, stems, etc. In a preferred embodiment, the plant part is the leaf and / or stem.

[0122] Lamiaceae materials can be processed before extraction, such as by washing, drying, grinding, or pulverizing.

[0123] Lamiaceae extracts (e.g., rosemary and / or lemon balm extracts) can be obtained or are available by solvent extraction of the aerial parts of the Lamiaceae extracts (e.g., rosemary and / or lemon balm extracts) followed by optional purification based on the desired concentration of rosmarinic acid in the final extract.

[0124] Specific solvents that can be used in the extraction process include water, alcohols (e.g., methanol, ethanol), acetone, ethyl acetate, hexane, dichloromethane, and any mixtures thereof, such as alcohol / water mixtures (e.g., mixtures of methanol and water). For example, the extraction solvent can be water, a water-alcohol mixture (alcohol in water at about 1% to about 99%, such as alcohol in water at about 30% to about 75%, or alcohol in water at about 30% to about 50%, such as alcohol in water at about 35% or about 40%), or any alcohol. Specific alcohols that may be mentioned include ethanol (EtOH) and methanol (MeOH).

[0125] In some embodiments, the Lamiaceae extract (e.g., rosemary and / or lemon balm extract) contains at least 1% w / w, such as at least 3% rosmarinic acid. In some embodiments, the Lamiaceae extract (e.g., rosemary and / or lemon balm extract) contains 1% to 99% rosmarinic acid.

[0126] Chlorogenic acid (CGAs)

[0127] In the following text, the term “CGA” or “chlorogenic acid” refers to one or more chlorogenic acids and their derivatives, including but not limited to: neo-CGA (5-O-caffeoylquinic acid or 5-CQA), crypto-to-CGA (4-O-caffeoylquinic acid or 4-CQA), n-CGA (3-O-caffeoylquinic acid or 3-CQA), isochlorogenic acid A (iso-CGA A; 3,5-dicaffeoylquinic acid), isochlorogenic acid B (iso-CGA B; 3,4-dicaffeoylquinic acid), isochlorogenic acid C (iso-CGAC; 4,5-dicaffeoylquinic acid), other chlorogenic acids and isochlorogenic acids and combinations thereof known in the art.

[0128] CGA can be of natural or synthetic origin.

[0129] CGA can be extracted from a variety of natural sources. Therefore, in a preferred embodiment, chlorogenic acid is extracted from biological materials containing chlorogenic acid, such as plants, animals, or prokaryotes.

[0130] Biomaterials containing CGA are preferably plant biomaterials. Plant biomaterials can be obtained from or can be obtained from plant roots and / or above-ground parts of plants, such as leaves, flowers, stems, bark, fruits and / or seeds, their tissues (e.g., the outer skin of fruits), or mixtures thereof. For example, plant biomaterials can be plant leaves.

[0131] As will be understood by those skilled in the art, the term "available from" as used herein means that plant and / or animal and / or prokaryotic material can be obtained directly from plants / algae / animals / prokaryotes, or can be isolated from plants / algae / animals / prokaryotes, or can be obtained from alternative sources, such as through chemical synthesis or enzymatic production. The term "obtained" as used herein means that the extract is directly derived from plant / algae / animal / prokaryotic sources.

[0132] Non-limiting examples of plant biomaterials containing one or more CGAs are green coffee beans from any species of the genus *Coffea*, such as Arabica, Robusta, Liberica, etc.; leaves of *Ilex paraguayanus*; pome fruits (e.g., apples and pears); stone fruits (e.g., cherries and plums); berry fruits; citrus fruits; brassica vegetables (e.g., kale, cabbage, and Brussels sprouts); nightshade family (e.g., potato tubers, tomatoes, and eggplants); aster family (e.g., chicory and artichokes); and various other mixed vegetables. It can also be found in grains (e.g., oats, barley, rye, rice, corn, and wheat). The amount and different types of chlorogenic acid present vary depending on the source. Chlorogenic acid can be extracted from one or more plant sources and / or can be synthesized.

[0133] In a preferred embodiment, CGA is obtained from or may be obtained from Arabica, Robusta, and / or Liberica green coffee beans, and is defined herein as "green coffee extract".

[0134] Naturally derived CGA may be present in the compositions of the present invention as purified CGA or as a natural extract obtained or available from the aforementioned Arabica, Robusta, and / or Liberica green coffee beans.

[0135] CGA can be obtained using various extraction methods known in the art. For example, solvents that can be used for extraction include, but are not limited to, water, alcohols (such as ethanol), acetone, and any mixtures thereof.

[0136] Rutin glycosides

[0137] Polysaccharidated rutin, which forms part of this invention, has the following formula:

[0138]

[0139] Among them, glycosylated rutin with a molar concentration of more than 50% has an n greater than 2.

[0140] Glycosylation of rutin (a polyphenolic flavonoid) is well known in the art, for example, from the Journal of Microbiology and Biotechnology, Volume 26, Issue 11, pp. 1845-1854 (2016) and US Patent 5145781. Glycosylated rutin is known to be more water-soluble than rutin, thus making rutin more readily available.

[0141] The glycosylation of rutin occurs on the fourth carbon of the glucose unit. This process always results in an expansion of the value of n, ranging from 1 upwards. In this disclosure, glycosylated rutin with n>2 constitutes the majority of glycosylated rutin, exceeding 50%, and more particularly exceeding 60% molar concentration. In specific embodiments, the average value of n is 2-11, particularly at least 3, and more particularly 3-4.

[0142] Tocopherol

[0143] In this disclosure, tocopherols (or vitamin E) may include four tocopherols and four tocotrienols. In some embodiments, the tocopherols are selected from α, β, γ, and δ tocopherols or mixtures thereof. As food additives, tocopherols are designated with the number E: E306 (tocopherol), E307 (α-tocopherol), E308 (γ-tocopherol), and E309 (δ-tocopherol).

[0144] In some embodiments, the tocopherol used in this invention may be obtained from or be available from a natural source. In some embodiments, it may have a synthetic source. In some embodiments, the tocopherol may be obtained from or be available from plants, photosynthetic bacteria, fungi, and / or algae.

[0145] In some embodiments, tocopherols may be obtained from or can be obtained from crude vegetable oils, such as soybean oil, sunflower oil, rapeseed oil, cottonseed oil, safflower oil, corn oil, palm oil, palm kernel oil, and rice bran oil.

[0146] Water-soluble vitamin E (α-tocopherol, αT), such as its esters with acetate (αTA), succinic acid (αTS), or phosphate (αTP), has increased solubility in water and stability against free radical reactions.

[0147] In some implementations, the tocopherol is a water-dispersible tocopherol.

[0148] γ-cyclodextrin:

[0149] Cyclodextrins are a family of cyclic oligosaccharides composed of macrocycles of glucose subunits linked by α-1,4 glycosidic bonds. Cyclodextrins are produced from starch through enzymatic conversion. In this invention, α, β, and / or γ cyclodextrins may be used.

[0150] In a preferred embodiment, γ-cyclodextrin is used. γ-cyclodextrin has CAS number 17465-86-0. γ-cyclodextrin is a cyclic amylose composed of eight α-(1→4) linked D-glucopyranose units. Its molecular weight is 1297.1.

[0151] In the method of the present invention, a polyketide pigment (e.g., azafirone mentioned herein) is mixed with a second product (ii) selected from carotenoids (e.g., lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol.

[0152] In a preferred embodiment, azafiron is a deep rose-type azafiron pigment disclosed in EP3622081A1 or Rasmussen KB et al.

[0153] In another preferred embodiment, azafironone is the pigment described by Jin-Ming Gao et al.

[0154] In another preferred embodiment, azafione is a red pigment, such as one or more of monaxanthin (C21H26O5), monaxanthin xanthophyll (C23H30O5), monaxanthin erythroside (C23H26O5), erythroside, monaxanthin erythramine (C23H27NO4), and / or erythroside erythramine (C21H23NO4).

[0155] In another preferred embodiment, the azafione is obtained from or may be obtained from the genera *Aspergillus*, *Chaetomium*, *Hypoxylon*, *Monascus*, *Muycopron*, *Penicillium*, *Phomopsis*, *Pleosporales*, *Talaromyces* (e.g., *Talaromyces rubrotinctum*), *Pestalotiopsis*, *Phomopsis*, *Emericella*, *Epicoccum*, and *Hypoxylon*.

[0156] Polyketide pigments (such as azafibrone mentioned herein) can be present in solid form (e.g., powder) or in liquid solutions. Therefore, in some embodiments, the polyketide pigment (e.g., azafibrone) is an aqueous solution. In some embodiments, the aqueous solution may contain at least 50% water, such as at least 70% water, or at least 90% water.

[0157] Product (ii) may be present in solid form (e.g., powder) or as a liquid solution. "Liquid solution" as used herein includes, but is not limited to, any solution, emulsion, or dispersion of the components of the mixture in a liquid solvent. The liquid solvent may be water, glycerol, or any mixture of other liquids or solvents suitable for dissolving or dispersing the components of the mixture (polyketide pigments (e.g., azafibrone mentioned herein) and component (ii)). In some embodiments, the aqueous solution may contain at least 50%, such as at least 70%, or even at least 90%, of water.

[0158] In some embodiments, the polyketide pigment (e.g., azafiron) is present in an aqueous solution.

[0159] In some embodiments, the two products, the polyketide pigment and product (ii), may be in powder form or mixed in powder form. Optionally, the resulting mixed powder is then added to a suitable solvent (such as water) and optionally mixed until a homogeneous solution is obtained.

[0160] In other embodiments, the polyketide pigment is in powder form and is added to the second component (ii) in liquid form.

[0161] In other embodiments, the polyketide pigment is in liquid form, and component (ii) is in powder form added to the liquid polyketide pigment.

[0162] Optionally, the polyketide pigment and component (ii) may be further mixed until a homogeneous mixture is obtained. The mixing of the two components may be carried out for at least 5 minutes, for example, at least 10 minutes, for example, at least 30 minutes, for example, at least 1 hour. Any method of mixing components known in the art can be used in this invention.

[0163] In a preferred embodiment, lycopene is used. As previously described, lycopene forms crystals, which are typically provided in the form of an emulsion in which lycopene is insoluble (e.g., glycerol, water, and mixtures thereof). Therefore, in some embodiments, a suspension of lycopene crystals is used in the method of the present invention.

[0164] In some implementations, lycopene is in the form of an emulsion.

[0165] In some implementations, the carotenoids are selected from lycopene, annatto, and / or noannatto.

[0166] In some embodiments, the method of the present invention further includes a step of further filtration to remove insoluble fractions.

[0167] In some embodiments, the method of the present invention further includes the step of concentrating the stabilized polyketide pigment obtained using the method described herein.

[0168] In some embodiments, the method of the present invention further includes a drying step, such as a spray drying step.

[0169] The stabilized polyketide pigment (e.g., azafione) obtained using the methods described herein comprises a polyketide pigment (e.g., azafione) as already mentioned and one or more compounds selected from carotenoids (e.g., lycopene, annatto and / or noannatto), rosmarinic acid, chlorogenic acid, rutin glucoside or tocopherol, and has improved light exposure stability.

[0170] As those skilled in the art will recognize, carotenoids such as lycopene, annatto, and / or nonatto can be used alone to stabilize polyketide pigments (e.g., azafione), or they can be used in combination with one or more of rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin, or tocopherol. If more than one component is used to stabilize a polyketide pigment (e.g., azafione), they can be used together or can be added sequentially to the polyketide pigment.

[0171] As previously mentioned, rosmarinic acid, rutin glucoside, cyclodextrin, and / or tocopherol can be provided in solid or liquid form. Therefore, in some embodiments, they are provided in solid form, for example, as powders that can be added directly to a solution of a polyketide pigment (e.g., azafifenone). When they are provided as a solution, the two solutions (the polyketide pigment (e.g., azafifenone) and rosmarinic acid, etc.) can be brought into contact and optionally mixed (step b).

[0172] The ratio between the polyketide dye (e.g., azafibrone) and compound (ii) can be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0173] The ratio between the polyketide dye (e.g., azafibrone) and compound (ii) can be equal to or less than 99:1 or about 99:1. In some embodiments, this ratio is equal to or less than 95:5 or about 95:5. In some embodiments, this ratio is equal to or less than 90:10 or about 90:10. In some embodiments, this ratio is equal to or less than 85:15 or about 85:15. In some embodiments, this ratio is equal to or less than 80:20 or about 80:20. In some embodiments, this ratio is equal to or less than 70:30 or about 70:30. In some embodiments, this ratio is equal to or less than 60:40 or about 60:40. In some embodiments, this ratio is equal to or less than 50:50 or about 50:50. In some embodiments, this ratio is equal to or less than 40:60 or about 40:60. In some embodiments, this ratio is equal to or less than 30:70 or about 30:70. In some implementations, the ratio is equal to or less than 20:80 or about 20:80. In some implementations, the ratio is equal to or less than 10:90 or about 10:90.

[0174] In some embodiments, the ratio between the polyketide dye (e.g., azafifenone) and compound (ii) may be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0175] In some embodiments, a polyketide pigment (e.g., azafione) is contacted with carotenoids (e.g., lycopene, annatto, and / or norannatto) at a weight ratio of 99:1 to 75:25.

[0176] In some embodiments, the ratio between the polyketide pigment (e.g., azafione) and the carotenoid (e.g., lycopene, annatto, and / or norannatto) may be equal to or less than 99:1 or about 99:1. In some embodiments, the ratio is equal to or less than 95:5 or about 95:5. In some embodiments, the ratio is equal to or less than 90:10 or about 90:10. In some embodiments, the ratio is equal to or less than 85:15 or about 85:15. In some embodiments, the ratio is equal to or less than 80:20 or about 80:20. In some embodiments, the ratio is equal to or less than 70:30 or about 70:30. In some embodiments, the ratio is equal to or less than 60:40 or about 60:40. In some embodiments, the ratio is equal to or less than 50:50 or about 50:50. In some embodiments, the ratio is equal to or less than 40:60 or about 40:60. In some implementations, the ratio is equal to or less than 30:70 or about 30:70. In some implementations, the ratio is equal to or less than 20:80 or about 20:80. In some implementations, the ratio is equal to or less than 10:90 or about 10:90.

[0177] In some embodiments, the ratio between the polyketide pigment (e.g., azafione) and the carotenoid (e.g., lycopene, annatto, and / or norannatto) can be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0178] In some embodiments, the ratio between the polyketide pigment (e.g., azafione) and the carotenoid (e.g., lycopene, annatto, and / or norannatto) may be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some implementations, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0179] In some embodiments, a polyketide pigment (e.g., azafione) is contacted with rosmarinic acid at a weight ratio of 75:25. In a preferred embodiment, rosmarinic acid is obtained or available from or from the Lamiaceae family, such as rosemary or lemon balm. In a preferred embodiment, a Lamiaceae extract is used, such as rosemary and / or lemon balm extracts containing rosmarinic acid. As those skilled in the art will recognize, natural extracts can have variable concentrations of rosmarinic acid, and the Lamiaceae extract will be used at a concentration that provides the ratio of polyketide pigment (e.g., azafione) and rosmarinic acid as defined herein.

[0180] In some embodiments, the ratio between the polyketide pigment (e.g., azafibrone) and rosmarinic acid may be equal to or less than 99:1 or about 99:1. In some embodiments, the ratio is equal to or less than 95:5 or about 95:5. In some embodiments, the ratio is equal to or less than 90:10 or about 90:10. In some embodiments, the ratio is equal to or less than 85:15 or about 85:15. In some embodiments, the ratio is equal to or less than 80:20 or about 80:20. In some embodiments, the ratio is equal to or less than 70:30 or about 70:30. In some embodiments, the ratio is equal to or less than 60:40 or about 60:40. In some embodiments, the ratio is equal to or less than 50:50 or about 50:50. In some embodiments, the ratio is equal to or less than 40:60 or about 40:60. In some embodiments, the ratio is equal to or less than 30:70 or about 30:70. In some embodiments, the ratio is equal to or less than 20:80 or about 20:80. In some embodiments, the ratio is equal to or less than 10:90 or about 10:90. In a preferred embodiment, the polyketide pigment (e.g., azafione) is contacted with rosmarinic acid at a weight ratio of 75:25.

[0181] In some embodiments, the ratio between the polyketide pigment (e.g., azafione) and rosmarinic acid can be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0182] In some embodiments, the ratio between the polyketide pigment (e.g., azafibrone) and rosmarinic acid may be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0183] In some embodiments, a polyketide pigment (e.g., azafione) is contacted with CGA at a weight ratio of 95:5 to 80:20. In a preferred embodiment, the CGA is provided by a green coffee extract obtained or available from green coffee beans from one or more species of the Coffea genus, such as Arabica, Robusta, and Liberica. In a preferred embodiment, the CGA is provided by a natural extract containing CGA. As those skilled in the art will recognize, natural extracts containing CGA (e.g., green coffee extract) can have variable concentrations of CGA, and therefore, natural extracts containing CGA (e.g., green coffee extract) will be used in this invention at concentrations that provide the ratio of polyketide pigment (e.g., azafione) and CGA as defined herein.

[0184] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and CGA may be equal to or less than 99:1 or about 99:1. In some embodiments, the ratio is equal to or less than 95:5 or about 95:5. In some embodiments, the ratio is equal to or less than 90:10 or about 90:10. In some embodiments, the ratio is equal to or less than 85:15 or about 85:15. In some embodiments, the ratio is equal to or less than 80:20 or about 80:20. In some embodiments, the ratio is equal to or less than 70:30 or about 70:30. In some embodiments, the ratio is equal to or less than 60:40 or about 60:40. In some embodiments, the ratio is equal to or less than 50:50 or about 50:50. In some embodiments, the ratio is equal to or less than 40:60 or about 40:60. In some embodiments, the ratio is equal to or less than 30:70 or about 30:70. In some implementations, the ratio is equal to or less than 20:80 or about 20:80. In some implementations, the ratio is equal to or less than 10:90 or about 10:90.

[0185] In some embodiments, the ratio between the polyketide compound pigment (e.g., azafifenone) and CGA can be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0186] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and CGA may be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0187] In some embodiments, a polyketide pigment (e.g., azafione) is contacted with rutin glucoside at a weight ratio of 80:20 to 50:50, for example, 75:25.

[0188] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and rutin glucoside may be equal to or less than 99:1 or about 99:1. In some embodiments, the ratio is equal to or less than 95:5 or about 95:5. In some embodiments, the ratio is equal to or less than 90:10 or about 90:10. In some embodiments, the ratio is equal to or less than 85:15 or about 85:15. In some embodiments, the ratio is equal to or less than 80:20 or about 80:20. In some embodiments, the ratio is equal to or less than 70:30 or about 70:30. In some embodiments, the ratio is equal to or less than 60:40 or about 60:40. In some embodiments, the ratio is equal to or less than 50:50 or about 50:50. In some embodiments, the ratio is equal to or less than 40:60 or about 40:60. In some embodiments, the ratio is equal to or less than 30:70 or about 30:70. In some implementations, the ratio is equal to or less than 20:80 or about 20:80. In some implementations, the ratio is equal to or less than 10:90 or about 10:90.

[0189] In some embodiments, the ratio between the polyketide pigment (e.g., azafifenone) and rutin glucoside may be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0190] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and rutin glucoside may be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0191] In some embodiments, a polyketide pigment (e.g., azafiron) is contacted with cyclodextrin, particularly γ-cyclodextrin, at a weight ratio of 80:20 to 50:50.

[0192] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and cyclodextrin (particularly gamma-cyclodextrin) may be equal to or less than 99:1 or about 99:1. In some embodiments, the ratio is equal to or less than 95:5 or about 95:5. In some embodiments, the ratio is equal to or less than 90:10 or about 90:10. In some embodiments, the ratio is equal to or less than 85:15 or about 85:15. In some embodiments, the ratio is equal to or less than 80:20 or about 80:20. In some embodiments, the ratio is equal to or less than 70:30 or about 70:30. In some embodiments, the ratio is equal to or less than 60:40 or about 60:40. In some embodiments, the ratio is equal to or less than 50:50 or about 50:50. In some embodiments, the ratio is equal to or less than 40:60 or about 40:60. In some embodiments, the ratio is equal to or less than 30:70 or about 30:70. In some implementations, the ratio is equal to or less than 20:80 or about 20:80. In some implementations, the ratio is equal to or less than 10:90 or about 10:90.

[0193] In some embodiments, the ratio between the polyketide pigment (e.g., azafiron) and cyclodextrin (particularly γ-cyclodextrin) can be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0194] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and cyclodextrin (particularly γ-cyclodextrin) may be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0195] In some embodiments, a polyketide pigment (e.g., azafiron) is contacted with tocopherol, particularly soluble or dispersible tocopherol, at a weight ratio of 99:1 to 90:10.

[0196] In some embodiments, the ratio between the polyketide pigment (e.g., azafibrone) and tocopherol (particularly soluble tocopherol) may be equal to or less than 99:1 or about 99:1. In some embodiments, the ratio is equal to or less than 95:5 or about 95:5. In some embodiments, the ratio is equal to or less than 90:10 or about 90:10. In some embodiments, the ratio is equal to or less than 85:15 or about 85:15. In some embodiments, the ratio is equal to or less than 80:20 or about 80:20. In some embodiments, the ratio is equal to or less than 70:30 or about 70:30. In some embodiments, the ratio is equal to or less than 60:40 or about 60:40. In some embodiments, the ratio is equal to or less than 50:50 or about 50:50. In some embodiments, the ratio is equal to or less than 40:60 or about 40:60. In some embodiments, the ratio is equal to or less than 30:70 or about 30:70. In some implementations, the ratio is equal to or less than 20:80 or about 20:80. In some implementations, the ratio is equal to or less than 10:90 or about 10:90.

[0197] In some embodiments, the ratio between the polyketide pigment (e.g., azafione) and tocopherol (particularly soluble tocopherol) can be 10:90 to 99:1, or about 10:90 to about 99:1, 10:90 to 90:1, or about 10:90 to about 90:1, 20:80 to 80:20, or about 20:80 to about 80:20, 50:50 to 80:20, or about 50:50 to about 80:20, or 60:40 to 80:20, or about 60:40 to about 80:20.

[0198] In some embodiments, the ratio between the polyketide dye (e.g., azafibrone) and the soluble or dispersible tocopherol may be equal to or greater than 10:90 or about 10:90. In some embodiments, the ratio is equal to or greater than 20:80 or about 20:80. In some embodiments, the ratio is equal to or greater than 30:70 or about 30:70. In some embodiments, the ratio is equal to or greater than 40:60 or about 40:60. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some implementations, the ratio is equal to or greater than 95:5 or about 95:5. In some implementations, the ratio is equal to or greater than 99:1 or about 99:1.

[0199] In some embodiments, the polyketide pigment (e.g., azafibrone) is contacted with two or more products (ii).

[0200] The inventors of this invention have demonstrated the synergistic effect of tocopherol and rosmarinic acid (e.g., lemon balm extract) in protecting and stabilizing polyketide pigments (e.g., azafione) exposed to light.

[0201] Therefore, the present invention provides a method for stabilizing the color of a polyketide pigment (e.g., azafione), the method comprising contacting (i) the polyketide pigment with (ii) rosmarinic acid and / or tocopherol, wherein the resulting polyketide pigment (e.g., azafione) is photostable.

[0202] The present invention also provides a method for preparing a light-stable polyketide compound pigment (e.g., azafiron), the method comprising the steps of: contacting (i) the polyketide compound pigment with (ii) rosmarinic acid and / or tocopherol, and optionally b) mixing (i) and (ii).

[0203] The resulting coloring composition comprises a polyketide pigment and rosmarinic acid and / or tocopherol. In a preferred embodiment, the tocopherol is water-dispersible.

[0204] The ratio between rosmarinic acid and tocopherol can be equal to or greater than 15:1 or about 15:1.

[0205] In some embodiments, the ratio is equal to or greater than 10:1 or about 10:1. In some embodiments, the ratio is equal to or greater than 20:1 or about 20:1. In some embodiments, the ratio is equal to or greater than 30:1 or about 30:1. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some embodiments, the ratio is equal to or greater than 95:5 or about 95:5. In some embodiments, the ratio is equal to or greater than 99:1 or about 99:1.

[0206] Synergistic effect of γ-cyclodextrin and lemon balm

[0207] The inventors of this invention have demonstrated the synergistic effect of gamma cyclodextrin and rosmarinic acid (e.g., lemon balm extract) in protecting and stabilizing polyketide pigments (e.g., azafiron) exposed to light.

[0208] Therefore, the present invention provides a method for stabilizing the color of a polyketide pigment (e.g., azafirone), the method comprising contacting (i) the polyketide pigment with (ii) rosmarinic acid and / or cyclodextrin, particularly γ-cyclodextrin, wherein the resulting polyketide pigment (e.g., azafirone) is photostable.

[0209] The present invention also provides a method for preparing a light-stable polyketide compound pigment (e.g., azafiron), the method comprising the steps of: contacting (i) the polyketide compound pigment with (ii) rosmarinic acid and / or cyclodextrin, particularly γ-cyclodextrin, and optionally b) mixing (i) and (ii).

[0210] The resulting coloring composition comprises a polyketide pigment and rosmarinic acid and / or cyclodextrin, particularly γ-cyclodextrin. In a preferred embodiment, tocopherol is water-soluble.

[0211] The ratio between rosmarinic acid and cyclodextrin (especially γ-cyclodextrin) can be equal to or greater than 15:1 or about 15:1.

[0212] In some embodiments, the ratio is equal to or greater than 10:1 or about 10:1. In some embodiments, the ratio is equal to or greater than 20:1 or about 20:1. In some embodiments, the ratio is equal to or greater than 30:1 or about 30:1. In some embodiments, the ratio is equal to or greater than 50:50 or about 50:50. In some embodiments, the ratio is equal to or greater than 60:40 or about 60:40. In some embodiments, the ratio is equal to or greater than 70:30 or about 70:30. In some embodiments, the ratio is equal to or greater than 80:20 or about 80:20. In some embodiments, the ratio is equal to or greater than 85:15 or about 85:15. In some embodiments, the ratio is equal to or greater than 90:10 or about 90:10. In some embodiments, the ratio is equal to or greater than 95:5 or about 95:5. In some embodiments, the ratio is equal to or greater than 99:1 or about 99:1.

[0213] In another aspect, the present invention relates to a coloring composition comprising a stabilized polyketide compound pigment (e.g., azafirone) obtained using the method of the present invention.

[0214] The coloring composition of the present invention may also include a carrier.

[0215] Suitable carriers include inert solid diluents or fillers, sterile aqueous solutions, and various organic solvents. Examples of solid carriers are lactose, gypsum powder, sucrose, cyclodextrin, maltodextrin, dextrin, talc, gelatin, agar, pectin, gum arabic, magnesium stearate, magnesium hydroxide; stearic acid, gum arabic, modified starch, and lower alkyl ethers of cellulose, sucrose, and silica. Examples of liquid carriers are syrups, vegetable oils, phospholipids, fatty acids, fatty acid amines, polyoxyethylene, and water. Furthermore, carriers or diluents may comprise any sustained-release material known in the art, such as glyceryl monostearate or glyceryl distearate, alone or in mixture with waxes.

[0216] In another aspect, the present invention relates to a stabilized coloring composition comprising a polyketide pigment (e.g., azafifenone) and a mixture of at least one product (ii) selected from carotenoids (e.g., lycopene, annatto, and / or norannatto), rosmarinic acid, chlorogenic acid, rutin glucoside, (γ)cyclodextrin, and / or tocopherol. The stabilized pigment of the present invention can be obtained using the methods of the present invention. As previously stated, the polyketide pigment (e.g., azafifenone) and at least one product (ii) selected from carotenoids (e.g., lycopene, annatto, and / or norannatto), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin, and / or tocopherol can be in solid form, then mixed, and then dissolved in a suitable solvent. Furthermore, as previously stated, the two components in the stabilized coloring composition of the present invention can be provided in liquid form and thus directly mixed in liquid form. The two components in the stabilized composition of the present invention can be mixed using any method known in the art.

[0217] In some embodiments, the stabilized polyketide pigments (e.g., azafiron) of the present invention have a color with a maximum absorption band at 480 nm ± 5 nm.

[0218] In some embodiments, the stabilized polyketide compound pigment (e.g., azafiron) of the present invention has a color (yellow pigment) with a maximum absorption band of 300+ / -5nm to 450nm+ / -5nm.

[0219] In some embodiments, the stabilized polyketide compound pigments (e.g., azafiron) of the present invention have a color (orange pigment) with a maximum absorption band of 350+ / -5nm to 500nm+ / -5nm.

[0220] In some embodiments, the stabilized polyketide compound pigments (e.g., azafiron) of the present invention have a color (red pigment) with a maximum absorption band of 450+ / -5nm to 600nm+ / -5nm.

[0221] All embodiments relating to the polyketide pigments of the previously defined methods of the present invention are also applicable to the stabilized polyketide pigments (e.g., azafifenone) and stabilized coloring compositions of the present invention. Furthermore, all embodiments relating to the product (ii) previously defined for the methods of the present invention are also applicable to the stabilized polyketide pigments (e.g., azafifenone) and stabilized coloring compositions of the present invention.

[0222] In a preferred embodiment, the stabilized polyketide pigment (e.g., azafione) and stabilized coloring composition of the present invention comprise one or more of the following: azafione pigment, monaxanthin, monaxanthin, erythropoietin, monaxanthin amine, erythropoietin, duracin, and their derivatives.

[0223] In some embodiments, the stabilized coloring composition of the present invention has a color with a maximum absorption band of 380 nm ± 5 nm.

[0224] In some embodiments, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 450 nm + / - 5 nm.

[0225] In some embodiments, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 500 nm + / - 5 nm.

[0226] In some embodiments, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 520 nm + / - 5 nm.

[0227] The stabilized coloring composition of the present invention may further contain other pigments, such as

[0228] Food, nutritional supplements, nutritional health products, flavorings or cosmetic compositions and methods of their production.

[0229] The stabilized coloring compositions of the present invention can be used to provide colors for any consumer product requiring stable red, orange, or yellow.

[0230] Therefore, in another aspect, the present invention relates to a method for stabilizing the color of food, pharmaceuticals, nutritional supplements, fragrances, or cosmetics, said method comprising the step of incorporating the stabilized pigment or stabilized coloring composition of the present invention into the food, pharmaceuticals, nutritional supplements, fragrances, or cosmetics. In a preferred embodiment, the color is stable to light exposure.

[0231] Components (i) and (ii) can be formulated together and can be incorporated into the product at any stage of the product manufacturing process.

[0232] The inventors have observed that premixed components (i) and (ii) are necessary for delivering a more stable colorant. Without being bound by any theory, it is believed that polyketide pigments (e.g., red yeast rice pigments or red yeast rice-like pigments) are stabilized by the second component (ii), and that a premix of the components is required before the stable colorant is mixed with the product (food, cosmetics, etc.) to achieve this stability. As can be seen from Example 7, the polyketide pigment (e.g., red yeast rice pigments or red yeast rice-like pigments) is unstable if the two components are added separately to the product matrix (without a premix in which stabilization occurs). However, some liquid matrices allow components (i) and (ii) to mix and complex “in situ” (i.e., directly in the matrix) without the prior step of mixing and formulating the two components together.

[0233] Therefore, in some implementations, when the product is in liquid or semi-solid form (such as beverages, dairy products such as milk, yogurt, cream, etc.), components (i) and (ii) can be added separately, i.e., one after the other, without forming a blend or premix.

[0234] Therefore, in another aspect, the present invention relates to a method for producing food, pharmaceuticals, nutritional supplements, fragrances or cosmetics, the method comprising the steps of incorporating a component (i) and a component (ii) as defined in any of the preceding claims, wherein the component (i) is added directly to the product and subsequently the product (ii) is also added to the product, or wherein the component (ii) is added directly to the product and subsequently the product (i) is also added to the product, particularly when the product is a liquid or semi-solid.

[0235] All embodiments of the pigments or coloring compositions of the present invention already mentioned are also applicable to the methods of the present invention.

[0236] In another aspect, the present invention relates to food, pharmaceutical, nutritional supplement, nutritional health product, fragrance, or cosmetic products comprising a stabilized pigment or stabilized coloring composition as defined herein, said stabilized pigment or stabilized coloring composition comprising a mixture of a polyketide pigment (e.g., azafione) and at least one product selected from carotenoids (e.g., lycopene, annatto and / or norannatto), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin, and / or tocopherol, and optionally a carrier sufficient to formulate the composition into said food, pharmaceutical, nutritional supplement, nutritional health product, fragrance, or cosmetic product.

[0237] Therefore, this invention relates to foods, pharmaceuticals, nutritional supplements, health products, flavorings, or cosmetics comprising stabilized pigments or stabilized coloring compositions as defined herein, wherein the color of the food, pharmaceutical, nutritional supplement, health product, flavoring, or cosmetic is stable to light exposure. In a preferred embodiment, the pigments or coloring compositions of the invention are obtained using the methods of the invention. In some embodiments, the foods, pharmaceuticals, health products, flavorings, or cosmetics obtained using the methods of the invention are characterized by having a light-stable red, orange, or yellow color.

[0238] In this invention, the term "photostable" or "stable against light exposure" means that the color hue provided by the stabilized pigments or stabilized coloring compositions of this invention does not change or has a change of less than 30% relative to the color hue measured under dark conditions. Therefore, in some embodiments, the color provided by the coloring compositions of this invention is stable after light exposure for more than 5 minutes, e.g., more than 30 minutes, e.g., more than 1 hour, e.g., more than 2 hours, 5 hours, 10 hours, 12 hours, 24 hours, 2 days, 10 days, e.g., more than 30 days, or e.g., more than 60 days or more than 6 months.

[0239] Foods or food products include the following general food categories as defined by the Food and Drug Administration (FDA): Baked goods and baking mixtures, including all ready-to-eat and ready-to-bake products, flour and mixtures that require preparation before consumption; alcoholic beverages, including malt beverages and cocktail mixtures; non-alcoholic beverages and beverage bases, including only specialty or spiced teas, soft drinks, coffee substitutes, and fruit and vegetable flavored gelatin beverages; cheeses, including curd and whey cheeses, cream, natural, grated, processed, spread, marinated, and blended cheeses; chewing gum, including all forms; coffee and tea, including regular, decaffeinated, and instant types; condiments and flavorings, including common condiments, sauces and spreads, olives, pickles, and flavorings, but excluding aromatics. Vanilla or herb; sugars and icings, including confectionery and flavored icings, marshmallows, baked chocolates and brown sugar, rock sugar, rock sugar, maple syrup, powdered sugar and raw sugar; toppings and other non-dairy products; egg products, including liquid, frozen or dried eggs, and egg dishes made from them, i.e., egg rolls, egg custards, egg salads and frozen multicourse egg powders, but not fresh eggs; fats and oils, including margarine, salad dressings, butter, salad oil, shortening and cooking oils; fish products, including all prepared main courses, salads, appetizers, frozen multicourse egg powders and spreads containing fish, shellfish and other aquatic animals but not fresh fish; fresh eggs, including hard-boiled eggs and egg dishes made only from fresh, shell-on eggs; fresh fish, including only fresh and frozen fish, shellfish and other aquatic animals; fresh meat This includes only fresh or home-frozen beef or veal, pork, lamb or mutton, and home-prepared fresh meat dishes, salads, appetizers or sandwich spreads made from them; fresh poultry, including only fresh or home-frozen poultry and game birds, and home-prepared fresh poultry dishes, salads, appetizers or sandwich spreads made from them; pasta, including macaroni and pasta products, rice dishes and frozen multicourses that do not contain meat or vegetables; gravy and sauces, including all meat sauces and gravy, as well as tomato, milk, butter and specialty sauces; herbs, seeds, spices, seasonings, blends, extracts and flavorings, including all natural and artificial spices, blends and flavorings; meat products, including all meats and meat-containing products. Dishes, salads, appetizers, frozen multi-course meat powder and sandwich ingredients prepared using commercially processed or commercially processed meat in home preparation; whole milk and skim milk, including only whole milk, low-fat milk and skim milk; dairy products, including flavored milk and milk beverages, dry milk, toppings, snack dips, spreads, weight-controlled milk beverages and other dairy-derived products; plant protein products, including the National Academy of Sciences / National Research Council "Reconstructed Plant Protein" category, as well as meat, poultry and fish substitutes, analogues and extender products made from plant proteins; poultry products, including all poultry and dishes, salads, appetizers, frozen multi-course poultry powder and sandwich ingredients prepared using commercially processed or commercially processed poultry in home preparation;All commercially processed vegetables, vegetable dishes, frozen multi-course meal powders and vegetable juices and blends; snack foods, including potato chips, pretzels and other novelty snacks; homemade soups, including meat, fish, poultry, vegetable and combination home-prepared soups; soups and soup mixtures, including commercially prepared meat, fish, poultry and vegetable soups, and combination soups and soup mixtures.

[0240] As used herein, "nutritional supplement" refers to compounds that beneficially affect one or more bodily functions to provide better health and well-being. Therefore, such nutritional supplements may be intended for the prevention and / or treatment of diseases or pathogenic factors. Consequently, the term "nutritional composition" of this invention can be used as a synonym for functional foods or foods or medical foods for specific nutritional purposes. Nutritional compositions are similar to the nutritional compositions of regular foods and are consumed as part of a normal diet. In a preferred embodiment, a nutritional supplement is a nutritional supplement.

[0241] As used herein, the term "nutritional supplement or nutritional product" refers to a product intended for human or animal use that contains one or more natural products with therapeutic effects, providing health benefits or being associated with disease prevention or reduction. This includes dietary supplements contained in a non-food matrix (e.g., capsules, powders, etc.) of a concentrated natural bioactive product that is commonly found (or not found) in food and, when taken at doses higher than those found in food, has a more beneficial effect on health than normal food might have. Therefore, the term "nutritional product" includes isolated or purified foods as well as additives or food supplements that are typically available in dosage forms for oral use, such as capsules, tablets, sachets, and drinkable vials; such products provide physiological benefits or protection against disease (typically chronic).

[0242] As used herein, “pharmaceutical product” refers to physiologically tolerable compositions and molecular entities. Preferably, the term “pharmaceutical acceptable” means that it has been approved by a state or federal regulatory agency, or is included in the United States Pharmacopeia or other recognized pharmacopoeias for use in animals, and more particularly in humans.

[0243] As used herein, "cosmetics" refers to compositions suitable for personal hygiene in humans or animals, or for enhancing natural beauty or altering the appearance of the body without affecting the structure or function of the human or animal body, comprising one or more products that provide such effects. Where desired, in addition to the compositions of this invention, the cosmetic compositions provided by this invention may contain one or more cosmetics or cosmetic products, i.e., substances or mixtures intended for contact with external parts of the human or animal body (e.g., epidermis, hair system, nails, lips, etc.) or with teeth and buccal mucosa, for the sole or primary purpose of cleansing them, scenting them, altering their appearance, protecting them, keeping them in good condition, or correcting body odor. Illustrative examples of acceptable carriers for cosmetics include products listed in the INCI (International Nomenclature of Cosmetic Ingredients) list. The compositions of the present invention can be added to a wide variety of cosmetic applications, including cosmetics, creams (e.g., day and night creams, makeup remover creams, foundation creams, and sunscreens) for cleansing, protecting, treating, or caring for the skin, particularly the face, hands, and feet; liquid foundations; makeup remover lotions; protective or skin-care body lotions; sunscreen lotions; skin-care lotions; gels or foams, such as cleansing, sun protection, and artificial tanning lotions; bath preparations; deodorant compositions; aftershave gels or lotions; hair removal creams; and compositions for insect bites and pain relief. The compositions of the present invention can take any of a variety of forms and include, for example, dressings, lotions, solutions, sprays, creams, gels, or ointments.

[0244] The stabilized pigment or coloring composition of the present invention can be added in an amount that effectively increases, enhances, and / or alters the color characteristics of a product (e.g., food) or a portion thereof. In some embodiments, the stabilized pigment or coloring composition of the present invention can be added in an amount that effectively achieves the desired effect, such as imparting a specific red, orange, or yellow color that is stable to light exposure.

[0245] For example, the food coloring compositions described above can be used to impart a red color to foods (e.g., dairy products, confectionery, beverages, sauces / gravy, etc.), similar to the color obtained when using carmine or artificial pigments.

[0246] Dairy products can refer to yogurt, custard, milk smoothies, milkshakes, and dairy ice cream.

[0247] Confectionery products can refer to sweets or confectionery foods, such as chewing gum or hard and soft candy products. Non-limiting examples of confectionery products include cakes, cookies, pies, chocolates, chewing gum, gelatin, ice cream, puddings, jams, jellies, soft candies, hard candies, chewing candies, cereals and other breakfast foods, canned fruit and fruit jams.

[0248] Beverage products can refer to beverages, beverage mixtures, and concentrates, including but not limited to alcoholic and non-alcoholic ready-to-drink and powdered beverages. Non-limiting examples of beverages may include carbonated and non-carbonated beverages, such as soda water, fruit juice, or vegetable juice.

[0249] Sauce products can refer to semi-solid compositions of sweet or savory flavor added to dishes to enhance flavor, moisture, and / or visual appeal. Non-limiting examples of sauces include gravy and barbecue sauces.

[0250] Meat-like products can refer to foods made from plant-based ingredients that approximate certain aesthetic qualities (such as texture, flavor, and appearance) or chemical properties of a particular type of meat. Non-limiting examples of meat-like products include veggie burgers.

[0251] Those skilled in the art will recognize that the optimal amount of a food coloring composition present in a given food is determined by factors such as the overall desired color, solubility, and regulatory approvals. Those skilled in the art can readily determine the optimal color amount for a given product based on these factors.

[0252] In some implementations, the product (food, medicine, nutritional supplement, nutritional health product, fragrance, or cosmetic) is packaged in transparent or semi-transparent packaging.

[0253] Reagent test kit

[0254] The present invention also relates to a kit comprising the different elements of the coloring compositions of the present invention, and optionally instructions on how to mix, prepare, and / or use the ingredients. In some embodiments, the kit comprises elements that have already been mixed and prepared (e.g., as a blend) and optionally instructions on how to use the ingredients. In some embodiments, the kit comprises other pigments, such as yellow or red pigments.

[0255] Color rating

[0256] A spectrophotometer can be used to analyze coloring compositions and products containing coloring compositions of this disclosure, and CIELAB L*a*b* values ​​can be calculated from spectral data, as described in more detail below. L*a*b* values ​​provide a means of representing color characteristics and assessing the magnitude of the difference between two colors. L*a*b* values ​​also provide a means of representing color characteristics and assessing the magnitude of the difference between two colors not only in solutions but also in products. Measurements of coloring compositions and products in solid form are performed using reflectance measurements from the product surface.

[0257] For example, the L*a*b* value consists of a set of coordinate values ​​defined in a three-dimensional Cartesian coordinate system. L* is the lightness coordinate and provides a lightness scale from black (0 L* units) to white (100 L* units) on the vertical axis. a* and b* are coordinates related to both hue and chroma. a* provides a scale from green (-a* units) to red (+a* units) on the horizontal axis, with neutral at the center point (0 a* units); b* provides a scale from blue (-b* units) to yellow (+b* units) on a second horizontal axis perpendicular to the first horizontal axis, with neutral at the center point (0 b* units). The three axes intersect at a value of 50 for L* and at zero for both a* and b*.

[0258] ΔE is a measure of the total color difference between two colors in the CIELAB L*a*b* color space. It has been reported that when ΔE is approximately 2.3 or less, experienced color observers cannot distinguish any difference between the two colors. Using Equation 1, calculate the ΔE for two different colors with L*a*b* values, L*1a*1b*1 and L*2a*2b*2:

[0259]

[0260] The invention is further illustrated by the following non-limiting embodiments. Example

[0261] Materials and methods

[0262] Materials and methods:

[0263] - Red yeast rice extract: The pigment was purchased from CNJ Nature. According to the supplier, the red pigment was obtained from fermented rice and extracted with ethanol, purified, then formulated with maltodextrin, and finally spray-dried, with a pigment content of approximately 71%.

[0264] - Water-soluble rutin: The sophora japonica extract is enzymatically glycosylated, a reaction that adds sugar to the rutin backbone, making it water-soluble. Figure 2 The final product was prepared using a water-glycerol carrier and contained 4.5% rutin glucoside.

[0265] Rutin polyglucoside

[0266]

[0267] Rutin polyglucoside structure

[0268] - Lemon balm (4-7%): Lemon balm flowers were extracted twice with ethanol (70%) and purified with charcoal. The concentrated product was mixed with propylene glycol to obtain 4-7% rosmarinic acid.

[0269] - Water-dispersible tocopherol: Tocopherol is formulated using water and gum arabic, then spray-dried to form a dry emulsion. The final concentration of tocopherol is 15%.

[0270] - Lycopene suspension: Lycopene was purchased from Lycored. Lycopene was extracted from tomatoes using ethyl acetate and ethanol, purified and concentrated, and then formulated with glycerol, lecithin, sucrose ester and water to prepare the final product, with a final pigment content of 2%.

[0271] - Green coffee beans: Chlorogenic acid was extracted using a mixture of water and ethanol, purified, and then formulated with maltodextrin to achieve a final concentration of 4.5% chlorogenic acid.

[0272] - Gamma-cyclodextrin: The product was purchased from Sigma-Aldrich and has a purity >98%.

[0273] CAS No. 17465-86-0

[0274] Example 1: Using lycopene to improve the photostability of Monascus purpureus

[0275] Solution 1A: Mix 0.03g of red yeast rice extract powder (71% pigment) with 0.015g of lycopene suspension (2% lycopene), and introduce the blend into 99.95g of DI water (Solution 1A).

[0276] The (1A) solution was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L, a, b parameters and set as a reference. Initial absorbance at 490 nm was also recorded for pigment retention calculations.

[0277] The samples were then subjected to light stress using SUNTEST cps+ (350 w / m2, 26 h at 4 °C), and degradation kinetics were measured by displaying pigment retention R and dE2000.

[0278] As a control, solutions of Monascus purpureus (1B) and lycopene (1C) alone were simultaneously irradiated along with solution (1A).

[0279] Composition 1B: 0.03% red yeast rice extract, 99.97% water

[0280] 1C Composition: 0.015% lycopene suspension, 99.98% water

[0281] As previously mentioned, the kinetics of Monascus purpureus degradation are illustrated by the evolution of pigment retention at DE2000 and 490 nm, where:

[0282]

[0283] Result. For example. Figure 1and 2 As shown, the photostability of solution 1A (a mixture of Monascus purpureus and lycopene) increased.

[0284] Figure 1 The study showed a rapid degradation of Monascus purpureus molecules induced by light irradiation. Surprisingly, mixing with lycopene introduced a protective effect against Monascus purpureus, reflected by an increase in color retention in the mixture from 6% (control) to 55%, while the mixture produced a smaller color change (dE2000). Figure 2 Unbound by any theory, we hypothesize that lycopene exhibits a protective effect against Monascus purpureus (sacrificing chromophores).

[0285] Example 2: Screening of polyphenols for photostabilization

[0286] In this example, 0.03 g of red yeast rice extract powder (71% pigment) was mixed with 0.15 g to 1 g of water-soluble polyphenols. The blend was introduced into dissolved water (DI) to achieve a final concentration of red yeast rice extract of 0.03%. The solution was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L, a, b parameters and set as a reference. For pigment retention calculations, the initial Abs were also recorded at the maximum wavelength (490 nm).

[0287] The samples were then subjected to light stress for 20 hours using SUNTEST cps+ (350 w / m², T4 °C), and degradation kinetics were measured by displaying pigment retention R and DE2000 during irradiation. This 20-hour period corresponds to approximately 20 days under normal light storage conditions in a supermarket.

[0288] ●2A Composition: 0.03% Red Yeast Rice Extract + 99.97% Water

[0289] ●2B Composition: 0.03% Monascus purpureus + 0.15% Lemon balm extract (extracted with ethanol) + 1% water-soluble rutin (4% rutin glucoside) + 98.82% water.

[0290] ●2C composition: 0.03% Monascus purpureus + 0.15% Lemon balm extract (extracted with ethanol) + 99.82% water.

[0291] ●2D composition: 0.03% Monascus purpureus + 0.15% raw coffee bean extract + 99.82% water.

[0292] ●2E composition: 0.03% Monascus purpureus + 0.15% raw coffee bean extract + 1% water-soluble rutin (4% rutin glucoside) + 98.82% water.

[0293] ●2F composition: 0.03% Monascus purpureus + 1% water-soluble rutin (4% rutin glucoside) + 98.97% water.

[0294] Results: As found in Example 1, Figure 3 The light irradiation induced a rapid degradation of Monascus molecules. Surprisingly, mixing with rutin glucoside introduced a protective effect against Monascus, which was reflected by an increase in color retention in the mixture from 10% (control) to 57%.

[0295] A stabilizing effect was also observed when using lemon balm extract (ethanol extract), where Monascus purpureus retention increased to 56%, resulting in a smaller color change (dE2000). Figure 4 ).

[0296] Example 3: Screening different proportions of lemon balm

[0297] 0.03 g of red yeast rice extract powder (71% pigment) was mixed with 0.1 to 0.4 g of lemon balm extract, and the blend was introduced into dissolved water to achieve a final concentration of 0.03% red yeast rice extract. The solution was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L, a, b parameters and set as a reference. Initial Abs were also recorded at the maximum wavelength (490 nm) for pigment retention calculations.

[0298] The samples were then subjected to light stress using SUNTEST cps+(350w / m2)T4℃, and degradation kinetics were measured by displaying pigment retention R and DE00 during irradiation (25h).

[0299] ●3A Composition: 0.03% red yeast rice extract + 99.97% water.

[0300] ●3B Composition: 0.03% Monascus purpureus + 0.1% Lemon Balm Extract (7-15% Rosmarinic Acid) + 99.87% Water.

[0301] ●3C composition: 0.03% Monascus purpureus + 0.2% Lemon balm extract (7-15% rosmarinic acid) + 99.77% water.

[0302] ●3D composition: 0.03% Monascus purpureus + 0.4% Lemon balm extract (7-15% rosmarinic acid) + 99.57% water.

[0303] Result: From Figure 6 As can be seen, at 0.4% lemon balm, increasing the dosage of lemon balm extract improved pigment retention to 70%, which produced a smaller color change (dE2000). Figure 5 .

[0304] Example 4: Screening of water-dispersible tocopherols with different ratios

[0305] 0.03 g of red yeast rice extract powder (71% pigment) was mixed with 0.01 g to 0.1 g of tocopherol powder (15% tocopherol), and the blend was introduced into dissolved water to achieve a final concentration of 0.03% red yeast rice extract. The solution was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L, a, b parameters and set as a reference. Initial Abs were also recorded at the maximum wavelength (490 nm) for pigment retention calculations.

[0306] The samples were then subjected to light stress using SUNTEST cps+ (350w / m^2, T4℃), and degradation kinetics were measured by displaying pigment retention R and DE00 during irradiation.

[0307] ●4A Composition: 0.03% red yeast rice extract + 99.97% water.

[0308] ●4B composition: 0.03% Monascus purpureus + 0.01% water-dispersible tocopherol (15% tocopherol content) + 99.96% water.

[0309] ●4C composition: 0.03% Monascus purpureus + 0.05% water-dispersible tocopherol (15%) + 99.92% water.

[0310] ●4D composition: 0.03% Monascus purpureus + 0.1% water-dispersible tocopherol (15%) + 99.87% water.

[0311] Result: From Figure 7 As can be seen, at 0.1% tocopherol, increasing the tocopherol dose increased pigment retention to 60%, which produced a small color change (dE2000). Figure 8 .

[0312] Example 5: Synergistic effect of tocopherol and lemon balm

[0313] 0.03 g of red yeast rice extract powder (71% pigment) was mixed with 0.25 g of lemon balm extract and different proportions of water-dispersible tocopherols. The blend was then introduced into dissolved water (DI) to achieve a final concentration of 0.03% red yeast rice extract. The solution was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L, a, b parameters and set as a reference. The sample was then subjected to light stress using SUNTEST cps+ (350 w / m², T4℃), and DE2000 was measured after 20 h of light irradiation.

[0314] ●5A Composition: 0.03% Red Yeast Rice Extract + 99.97% Water

[0315] ●5B Composition: 0.03% Monascus purpureus + 0.25% Lemon balm (7-14% rosmarinic acid) + 99.96% water.

[0316] ●5C composition: 0.03% Monascus purpureus + 0.25% Lemon balm (7-14% rosmarinic acid) + 0.02% water-dispersible tocopherol (15%) + 99.70% water.

[0317] ●5D composition: 0.03% Monascus purpureus + 0.25% Lemon balm (7-14% rosmarinic acid) + 0.05% water-dispersible tocopherol (15%) + 99.70% water.

[0318] Result: From Figure 10 As can be seen, at 0.025% and 0.05% tocopherol and 0.25% lemon balm, mixing tocopherol with lemon balm increased pigment retention to 84%, which produced a smaller color change (dE2000). Figure 9 This result indicates a synergistic effect of light-protection between lemon balm and tocopherol.

[0319] Example 6: Synergistic effect of γ-cyclodextrin and lemon balm

[0320] 0.03 g of red yeast rice extract powder (71% pigment) was mixed with 0.2 g of lemon balm extract (ethanol extract (4-7% rosmarinic acid)) or 0.2 g of γ-cyclodextrin (purchased from Sigma, 98% purity). Mixtures of lemon balm extract and γ-cyclodextrin (the above composition) were also tested. The mixture was introduced into DI water to achieve a final concentration of 0.03% red yeast rice extract. The solution was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L, a, b parameters and set them as references. The sample was then subjected to light stress using SUNTEST cps+ (350 w / m², T4C), and DE2000 was measured after 15 h of light irradiation.

[0321] ●6A Composition: 0.03% red yeast rice extract + 99.97% water.

[0322] ●6B composition: 0.03% Monascus purpureus + 0.2% Lemon balm (4-7% rosmarinic acid) + 99.95% water.

[0323] ●6C composition: 0.03% Monascus purpureus + 0.20% γ-cyclodextrin + 99.95% water.

[0324] ●5D composition: 0.03% Monascus purpureus + 0.2% Lemon balm (4-7% rosmarinic acid) + 0.2% γ-cyclodextrin + 99.57% water.

[0325] Result: From Figure 11 The results show that cyclodextrin can improve pigment stability. Surprisingly, pigment stability was improved when lemon balm was mixed with γ-cyclodextrin, resulting in a smaller color change (dE2000). This result suggests a possible synergistic effect of light protection between lemon balm and cyclodextrin.

[0326] Unbound by any theory, we believe that lemon balm protects against photodegradation during oxygen scavenging and UV light filtration, while γ-cyclodextrin provides protection by partially accommodating the carbon chains of Monascus purpureus within its hydrophobic cavity.

[0327] Example 7: Stabilization of Lycopene in a Sugar Paste Matrix

[0328] Example 7 was conducted to investigate the importance of the mixed components for stabilizing Monascus purpureus.

[0329] Sample 7A: 0.03g of red yeast rice extract powder (71% pigment) was mixed with 0.015g of lycopene suspension (2% lycopene), mixed with 300ul of DI water, and the blend was introduced into 99.95g of sugar paste water (Sample 7A).

[0330] The sample was measured on a spectrophotometer (Konica Minolta) to evaluate the initial L,a,b parameters and set them as a reference.

[0331] The samples were then subjected to light stress using SUNTEST cps+ (350 w / m2, 8 h at 4 °C), and degradation kinetics were measured by displaying pigment retention R and dE2000.

[0332] As a control, a sample of Monascus purpureus alone (7B) and lycopene alone (7C) and an unmixed sample of Monascus purpureus and lycopene (7D) were simultaneously irradiated with solution (7A).

[0333] Composition 7B: 0.03% red yeast rice extract, 99.97% saccharin syrup

[0334] 7C composition: 0.015% lycopene suspension, 99.98% slurry

[0335] 7D composition: First, 0.03% red yeast rice extract is incorporated into the syrup, and then 0.015% lycopene is added to 99.98% of the syrup, instead of pre-mixing as in 7A.

[0336] As we are Figure 11 As can be seen, the premixing of lycopene and Monascus provides better retention against light stress.

Claims

1. A method of stabilizing the color of a polyketide pigment, comprising contacting (i) a polyketide pigment with (ii) a carotenoid, rosmarinic acid, rutin glucoside, cyclodextrin and / or tocopherol, wherein the resulting polyketide pigment is photostable.

2. The method according to claim 1, wherein the polyketide is selected from azaphilaquinone, anthraquinone, hydroxyanthraquinone and / or naphthoquinone.

3. The method according to claim 1 or 2, wherein the azafylon is selected from one or more of the following: nitrided azafylon, osterdiol, spiciferinone and derivatives, deflectins, helotialins, bulgarialactones, spiro azafylon, O-substituted azafylon (especially O-containing monascus pigments), lactone azafylon, hydrogenated azafylon, chaetoviridins and chaetomugilins, sequoiatones, tricoflectin and safrole azafylon, penicillic acid-type azafylon, sclerotiorins, multiformins and cohaerins, ascosporin, chrysodin-type azafylon, hydrogenated spiro azafylon, chlorofusins, deep rosein, N-containing monascus pigments, deep rosein-type azafylon.

4. The method according to claim 3, wherein the azaphilone is selected from the group consisting of monascin, monascus yellow, monascus red, erythrophore, monascus amine, erythrophore amine and / or monascus amine (compounds of formula (I)) and any derivatives thereof, wherein in the monascus amine (C23H27NO4), erythrosine (C21H23NO4) and monascus amine, NR is selected from amino acids, peptides, amino sugars and primary amines, and where the wavy bond represents an unassigned configuration of the adjacent double bond between carbons 2 and 3.

5. The method according to any one of the preceding claims, wherein the polyketide is obtained or obtainable from one or more of the following fungal genera: Aspergillus genus, Chaetomium genus, Hypoxylon genus, Monascus genus, Muycopron genus, Penicillium genus, Phomopsis genus, Pleosporales genus, Talaromyces genus, Pestalotipsis genus, Phomopsis genus, Emericella genus, Epicoccum genus and / or Hypoxylon genus.

6. The method according to claim 5, wherein the Talaromyces is Talaromyces atroroseus.

7. A method according to any one of the preceding claims, wherein the pigment is extracted from its natural state without modification, or is removed from its natural state and purified or chemically modified.

8. A method according to any one of the preceding claims, wherein the pigment is a mixture or a single compound.

9. The method according to any one of the preceding claims, wherein the carotenoid is selected from lycopene, annatto, norbixin or mixtures thereof.

10. The method of claim 9, wherein the lycopene is in crystalline form.

11. The method according to claim 9 or 10, wherein in addition to lycopene, annatto and / or norbixin, one or more of rosmarinic acid, rutin glucoside, cyclodextrin and / or tocopherol are used.

12. The method according to any one of claims 1 to 8, wherein (ii) is tocopherol and rosmarinic acid.

13. The method according to any one of claims 1 to 8, wherein (ii) is cyclodextrin and rosmarinic acid.

14. A method according to any one of the preceding claims, wherein rosmarinic acid is obtained or obtainable from the Lamiaceae family, in particular rosemary and / or lemon balm.

15. The method according to any one of the preceding claims, wherein chlorogenic acid is additionally used, and wherein the chlorogenic acid is obtained or obtainable from green coffee beans from any species of the genus Coffea, such as Coffea Arabica, Coffea Canephora, Coffea Liberia.

16. Stabilized pigment obtained by the method according to any one of claims 1 to 15.

17. A stabilized polyketide pigment comprising (i) a polyketide pigment according to any one of claims 1 to 8 and (ii) one or more of a carotenoid (e.g., annatto, norbixin or a mixture thereof), rosmarinic acid, chlorogenic acid, rutin glucoside, (γ) cyclodextrin and / or tocopherol.

18. The stabilized pigment according to claim 16 or 17, characterized in that Has a color that is stable to light exposure.

19. A colouring composition comprising the stabilised pigment according to any one of claims 16 to 18.

20. Food, drug, nutraceutical, fragrance or cosmetic comprising a stabilized pigment according to any one of claims 16 to 18 or a coloring composition according to claim 20, optionally exposed to light.

21. A method for producing a food, a drug, a nutraceutical, a flavor or a cosmetic, comprising the step of incorporating the stabilized pigment according to any one of claims 16 to 18 or the coloring composition according to claim 19 into the food, the drug, the nutraceutical, the flavor or the cosmetic.

22. A method for producing a food, a drug, a nutraceutical, a fragrance or a cosmetic comprising the steps of incorporating component (i) and component (ii) as defined in any one of the preceding claims, wherein component (i) is added directly to the product and subsequently product (ii) is also added to the product, or wherein component (ii) is added directly to the product and subsequently product (i) is also added to the product, in particular when the product is a liquid or semi-solid.

23. A food, medicine, nutritional supplement, fragrance or cosmetic obtained by the method of claim 21 or 22, characterized in that Has a light-stable red, orange or yellow color.

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