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WO2016146802A1 - Compositions d'astaxanthine (ii) - Google Patents

Compositions d'astaxanthine (ii) Download PDF

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Publication number
WO2016146802A1
WO2016146802A1 PCT/EP2016/055920 EP2016055920W WO2016146802A1 WO 2016146802 A1 WO2016146802 A1 WO 2016146802A1 EP 2016055920 W EP2016055920 W EP 2016055920W WO 2016146802 A1 WO2016146802 A1 WO 2016146802A1
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WO
WIPO (PCT)
Prior art keywords
astaxanthin
monoester
acid
composition
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/EP2016/055920
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German (de)
English (en)
Inventor
Jesper Feldthusen Jensen
Tamara Alexandra RAUSCH
Claudia Scholten
Bernd Schaefer
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
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Publication of WO2016146802A1 publication Critical patent/WO2016146802A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate

Definitions

  • the present invention relates to astaxanthin compositions for use in
  • Astaxanthin (3,3'-dihydroxy-ß, ß-carotene-4,4'dione) is a red carothinoid dye from the group of xanthophylls, which is described by the following formula (shown is the all-trans isomer).
  • Astaxanthin hereinafter also AXT, has an asymmetric center in the 3 'and 3' position and can therefore be used as a mixture of diastereomers of (3R, 3'R) -, (3S, 3'S) - and (3S, 3'R) - Isomers, as a racemate of (3R, 3'R) and (3S, 3'S) are present in the form of pure isomers or.
  • Synthetic AXT is often a mixture of diastereomers (3S, 3'S), (3R, 3'S) and
  • Astaxanthin is produced predominantly synthetically - see G. Britton, S. Liaanen- Jensen, H. Pfander (Editor), Carotenoids, Vol. 2, Birkhäuser Verlag, Basel, 1996, in particular S. 1 1, pp. 267 et seq Pp. 281 ff. And references cited therein; B. Shufer, natural products of the chemical industry, Academic Publishing House, Heidelberg, 2007, p. 427 et seq. And references cited therein; EP 1 197483, EP 1285912.
  • astaxanthin can also be obtained on an industrial scale from the blood rain algae (Haematococcus pluvialis) (EA Johnson, GH An, Crit Rev.
  • Astaxanthin is approved as a feed additive and is primarily referred to as
  • AXT has a vitamin-like effect has a positive effect on the fertility and the immune defense of fish in breeding facilities and leads to an attractive pigmentation of the meat. Astaxanthin is also used as an additive for dietary supplements, used as a cosmetic additive with antioxidant properties or as a food colorant. AXT can protect the skin from the stress caused by UV radiation and in this function has a much stronger effect than vitamin E. AXT complements the protective effect of sunscreen and is not washable.
  • AXT is basically suitable for the treatment of a number of different disorders - see, for example, B.J.H. Weisburger, Am. J. Clin. Nutr. 1991, 53: 226S-237S; M. Guerin, Trends in Biotechnology, 2003, 21: 210-216; Ghazi Hussein et al., J. Nat. Prod., 2006, 69: 443-449, Astaxanthin and Human Health - Literature Survey: http: //www.astapure- algatech.com/Data/Sub2_1/Files/algatechnologies.pdf, each with additional evidence.
  • AXT increases blood flow and vascular tone - see, eg, B. Yanai et. al. (2008) Integrated Blood Pressure Control 1: 1-3.
  • carotenoids such as astaxanthin have beneficial effects on heart disease - D.A. Cooper et al., Nutr. Rev. 1999, 57: 210-214, J. Krappi et. al., Int. J. Nutr. Res. 2006, 77 (1): 3-1 1. Due to its antioxidant activity, in particular its effect to inhibit the oxidation of low-density lipoproteins, carotenoids such as astaxanthin are proposed for the prevention of arteriosclerosis - see T. Iwamoto et al. , J. Atheroscler. Thromb. 2000, 7: 216-222.
  • Astaxanthin also plays a role in modulating the immune system - see H.
  • astaxanthin is proposed for the treatment of joint diseases, in particular for improving the symptoms of inflammatory joint diseases - see Y. Nir, G. Spiller C. Multz C. Effect of an astaxanthin-containing product on carpal tunnel syndrome. American College of Nutrition Annual Meeting, San Antonio, Texas, October 2002, Y. Nir, G. Spiller. Los Altos, California: Health Research and Studies Center 2002. Y. Nir, G. Spiller. J Am Coli Nutr, 2002, 21.
  • AXT favorably influences the course of bacterial infections, in particular inflammation of the gastrointestinal tract, caused by Helicobacter pylori infections - see M.
  • astaxanthin is proposed for the prevention of ocular diseases such as damage to the lens and retina by UV radiation, macular degeneration, cataract and glaucoma to improve male fertility, memory and attention and physical performance - K. Sawaki et al. Journal of Clinical Therapeutics & Medicines, 2002, 18: 73-88.
  • Astaxanthin can significantly help to delay skin aging and reduce the appearance of wrinkles, age spots and freckles - Suganuma K et al., Jichi Medical University Journal. 2012, 35: 25-33; K. Tominaga K et al., Acta Biochim Pol.
  • astaxanthin is therefore of interest for the production of medicines as well as for feed, food and nutritional supplements, especially those for human nutrition.
  • astaxanthin is poorly absorbed by the human or animal organism when administered orally, and that the serum levels achieved in the blood or lymph serum are only slight.
  • Astaxanthin can be improved by special fat-based formulations, wherein the emulsifiers used here have a strong influence on the bioavailability.
  • the improvement of oral bioavailability by formulations limits and limits the potential applications of astaxanthin.
  • Astaxanthin has improved oral bioavailability. However, the commercial availability of natural astaxanthin is very limited. Due to the complexity of such a mixture, it is not very attractive for pharmaceutical applications.
  • Difatty acid esters of astaxanthin by esterification of astaxanthin with fatty acid chloride in the presence of a tertiary amine base. If, instead of the acid chloride, the free acid is used, predominantly the monofatty acid ester is formed, which can be obtained from the reaction mixture by removal of unreacted astaxanthin. In addition, it is possible to obtain the monofatty acid esters by using substoichiometric amounts of acid chloride in admixture with unreacted astaxanthin and difatty acid esters. The monoester can be isolated from the mixture, for example by chromatography.
  • astaxanthin compositions containing at least 80 wt .-%, in particular at least 90 wt .-%, especially at least 95 wt .-%, based on the total weight of astaxanthin and astaxanthin derivatives in the
  • composition a monoester of astaxanthin with an aliphatic, unbranched Ci8-C22 monocarboxylic acid, have a particularly good bioavailability.
  • the invention therefore relates to the use of astaxanthin compositions in foods, dietary supplements or animal feed, wherein the
  • Astaxanthin compositions at least 80 wt .-%, in particular at least 90% by weight, especially at least 95 wt .-%, based on the total weight of astaxanthin and astaxanthin derivatives in the composition, a monoester of astaxanthin with an aliphatic, unbranched Ci8-C22 monocarboxylic acid contain.
  • the invention also relates to those described here and below
  • Astaxanthin composition and at least one suitable for pharmaceutical purposes adjuvant.
  • the present invention also relates to additives for foods comprising the astaxanthin composition of the invention and at least one food additive, d. H. at least one food grade adjuvant.
  • the present invention further relates to additives for feed comprising the astaxanthin composition of the invention and at least one additive suitable for feed, d. H. at least one feed suitable for feed.
  • the present invention also relates to dietary supplements comprising the astaxanthin composition of the invention and at least one supplement suitable for dietary supplements, i. H. at least one adjuvant suitable for dietary supplements.
  • Nutritional supplement and pharmaceutical composition contain the astaxanthin according to the invention as the sole, astaxanthin-containing ingredient and in particular that they contain no further, unesterified astaxanthin or other derivatives of astaxanthin.
  • the invention has a number of advantages. For one thing, the
  • compositions according to the invention have a better oral bioavailability than unesterified astaxanthin or corresponding diesters and the serum levels of astaxanthin in the blood plasma are several times higher. Surprisingly, the oral bioavailability of the astaxanthin compositions according to the invention is even better than that of the "natural astaxanthin.” In addition, the compositions are synthetically readily available, not least because of their better oral bioavailability Compositions of the invention are also particularly attractive for pharmaceutical applications.
  • compositions according to the invention are for the
  • joint diseases in particular inflammatory joint diseases such as rheumatoid arthritis, osteoarthritis and the carpal tunnel syndrome, prevention and treatment of eye diseases such as damage to the lens or retina, z. B. for the prevention of macular degenerata, the cataract or the
  • Glaucoma and the protection of the lens and the retina from UV rays are Glaucoma and the protection of the lens and the retina from UV rays
  • Concomitant diseases for example prevention and treatment of the metabolic syndrome, for lowering the blood sugar level in insulin-resistant individuals or for the treatment and prevention of diabetic nephropathy,
  • Cervical carcinoma, bladder cancer, breast and lung carcinoma prevention and treatment of diseases of the blood vessels such as arteriosclerosis, - treatment of bacterial infections, in particular to improve the course of diseases of the gastrointestinal tract, which are caused by infection with Helicobacter pylori,
  • a treatment according to the invention includes not only the treatment of acute or chronic signs, symptoms and / or dysfunctions but also a preventive treatment (prophylaxis), in particular as a recurrence or phase prophylaxis.
  • the treatment may be symptomatic, for example as symptom suppression. she can be carried out on a short-term, medium-term basis, or it may also be a long-term treatment, for example in the context of maintenance treatment.
  • a feed additive is accordingly understood to mean a formulation, eg. B. in powder or liquid form, which can be incorporated in the manufacture of a feed in the feed.
  • a food a nutrient-containing agent for human nutrition, which serves primarily to absorb nutrients such as fats, proteins and carbohydrates.
  • a food additive is understood to mean a formulation, e.g. In powder or liquid form, which can be incorporated in the preparation of a foodstuff in the food.
  • a nutritional supplement is a formulation suitable for oral administration, which is taken in addition to the conventional diet of humans with the primary aim of administering active ingredients, here of astaxanthin or a derivative, in order to improve the
  • Dietary supplements are located at the interface between food and medicines and are governed by EU Directive 2002/46 / EC.
  • C n -C m used herein for generic terms such as monocarboxylic acid or fatty acid indicates a range of the number of carbon atoms that a member of the group designated by the generic term may have.
  • the astaxanthin compositions according to the invention contain predominantly, i. H. at least 80% by weight, in particular at least 90% by weight, especially at least 95% by weight, based on the total weight of astaxanthin and astaxanthin derivatives in the
  • composition a monoester of astaxanthin with an aliphatic, unbranched Ci8-C22 monocarboxylic acid.
  • inventive composition a monoester of astaxanthin with an aliphatic, unbranched Ci8-C22 monocarboxylic acid.
  • Astaxanthinzusammen schen also contain unesterified astaxanthin and / or one or more diesters of astaxanthin, wherein the proportion thereof according to the invention 20 wt .-%, in particular 10 wt .-%, especially 5 wt .-%, based on the total weight of astaxanthin and astaxanthin derivatives in the Composition, does not exceed.
  • the proportion thereof according to the invention 20 wt .-%, in particular 10 wt .-%, especially 5 wt .-%, based on the total weight of astaxanthin and astaxanthin derivatives in the Composition, does not exceed.
  • astaxanthin composition can also exclusively or almost exclusively, ie more than 95 wt .-% consist of the monoester of astaxanthin with an aliphatic, unbranched Ci8-C22 monocarboxylic acid.
  • the monoester is uniform, ie it is essentially, ie at least 80 wt .-%, in particular at least 90 wt .-% of the monoester exactly one aliphatic, unbranched Ci8-C22 monocarboxylic acid.
  • the term "exactly one" means in this
  • the aliphatic, unbranched C 18 -C 22 monocarboxylic acids may be saturated or unsaturated.
  • Unsaturated, aliphatic, unbranched Ci8-C22 monocarboxylic acids may contain one or more, for. B. 1, 2, 3, 4, 5 or 6 ethylenic double bonds. These may have an ice or trans configuration with respect to the particular double bond.
  • Ci8-C22 monocarboxylic acids are typically non-functionalized, i. H. in addition to the two oxygen atoms of the carboxyl group, they have no further heteroatoms.
  • saturated aliphatic, unbranched C 18 -C 22 -monocarboxylic acids are, in particular, even-numbered acids, such as stearic acid, arachic acid and behenic acid.
  • unsaturated aliphatic, unbranched C 18 -C 22 monocarboxylic acids are, in particular, monounsaturated C 18 -C 22 -monocarboxylic acids, such as oleic acid and the like
  • Double bond isomers of petroselinic acid, elaidic acid and vaccenic acid (C18-1 acids), C20-1 acids such as losenoic acid and gadoleic acid, C22-1 acids such as cetoleic acid and erucic acid.
  • Ci8-C22 monocarboxylic acids such as linoleic acid (C18-2 acid)
  • Preferred C 18 -C 22 -monocarboxylic acids are selected from mono- or polyunsaturated aliphatic, unbranched C 18 -C 22 monocarboxylic acids.
  • the at least monounsaturated C 18 -C 22 monocarboxylic acid is selected from C18-1, C18-2, C18-3 and C18-4 fatty acids. Specifically, it is a C18-1 fatty acid.
  • the astaxanthin compositions according to the invention are those in which at least 90% by weight of the monoester of astaxanthin is a monoester of astaxanthin with one, in particular exactly one aliphatic, unbranched cis-monocarboxylic acid, this cis-monocarboxylic acid especially under C18-0-, C18 C1-, C18-2, C18-3 and C18-4 fatty acids, including monoesters of cis / trans mixtures
  • astaxanthin compositions according to the invention those are particularly preferred in which at least 90% by weight of the monoester of astaxanthin is a monoester of astaxanthin having one, in particular exactly one aliphatic, unbranched C 18 -C 22 -monocarboxylic acid, which is monosubstituted or polysubstituted, eg. B.
  • compositions according to the invention preference is given in particular to those in which at least 90% by weight of the monoester of astaxanthin is a monoester of astaxanthin having one, in particular exactly one aliphatic, unbranched C 18 -C 22
  • Monocarboxylic acid is selected from C18-1, C18-2, C18-3 and C18-4 fatty acids. It has proven to be particularly advantageous if in the monoester not more than 60%, in particular not more than 40% and especially not more than 30% of the C18-1, C18-2, C-18-3 and C- 18-4 fatty acids are present as trans fatty acids, d. H. not more than 60%, in particular not more than 40% and especially not more than 30% of all double bonds in the fatty acid radical of the monoester are present in the transform.
  • the astaxanthin compositions according to the invention particular preference is given to those in which at least 90% by weight of the monoester of astaxanthin is a monoester of astaxanthin with C18-1-fatty acid, in particular of oleic acid or cis / trans isomeric mixture of oleic acid.
  • the monoesters of C18-1 fatty acid preferably not more than 60%, in particular not more than 40% and especially not more than 30% of the double bonds in the C18-1 fatty acid radical are present in the transform.
  • the astaxanthin compositions according to the invention particular preference is also given to those in which at least 90% by weight of the monoester of astaxanthin is present
  • Monoester of astaxanthin with an unbranched C18-0 fatty acid are at least 40 wt .-%, in particular at least 60 wt .-% or at least 80 wt .-% of the monoester, in particular the monoester of unsaturated aliphatic, unbranched Ci8-C22 monocarboxylic acid, particularly preferably the monoester of C18 -0-, C18-1, C18-2, C18-3 and C18-4 fatty acid and especially the monoester of oleic acid as the monoester of all-E-astaxanthin.
  • 20 to 90% by weight, in particular 30 to 80% by weight or 40 to 70% by weight, of the monoester, in particular of the monoester of unsaturated aliphatic, unbranched C 18 -C 22 -monocarboxylic acid are particularly preferred the monoester of C18-0, C18-1, C18-2, C18-3 and C18-4 fatty acids and especially the monoester of oleic acid as monoester of all-E-astaxanthin and 10 to 80% by weight, in particular 20 to 70 wt.% or 30 to 60 wt.% as one or more Z isomers, e.g.
  • Example as a 9-Z, 13-Z or 15-Z isomer or as a mixture of two or three of these Z-isomers.
  • at least 80% by weight, in particular at least 90% by weight, of the monoester in particular of the monoester of unsaturated aliphatic, unbranched C 18 -C 22 -monocarboxylic acid, more preferably of the monoester of C 18-0, C 18- 1, C18-2, C18-3 and C18-4 fatty acid and especially the monoester of oleic acid as monoester of the 3S, 3'S enantiomer of astaxanthin.
  • At least 80% by weight, in particular at least 90% by weight, of the monoester in particular of the monoester of unsaturated aliphatic, unbranched C 18 -C 22 -monocarboxylic acid, more preferably of the monoester of C 18-0, C 18- 1, C18-2, C18-3 and C18-4 fatty acids and especially the monoester of oleic acid as the monoester of the 3R, 3'R enantiomer of astaxanthin.
  • the monoester in particular the monoester of the unsaturated aliphatic, unbranched C 18-22 monocarboxylic acid, particularly preferably the monoester of C 18-0, C 18-1, C 18-2, C 18-3 and C18-4 fatty acid and especially the monoester of oleic acid to the monoester of a
  • Food additives or feed additives used. This food or
  • Feed additive contains the astaxanthin composition according to the invention and at least one excipient or auxiliaries suitable for foods or feedstuffs.
  • a suitable for food or feed excipient is understood in the context of the invention, a substance approved for animal and / or human nutrition.
  • Suitable auxiliaries are, in particular, those which comprise incorporation of the additive into
  • Foods in which they make the astaxanthin composition to a better dilute manageable concentration in the additive include, in particular, support materials, in particular liquid support materials such as vegetable oils and organic solvents, but also solid support materials such as fats, fatty acids, waxes, fatty alcohols and fatty acid esters of fatty alcohols, carbohydrates, sugar alcohols, and inorganic fillers, which are used for the production of food or feed allowed are.
  • support materials in particular liquid support materials such as vegetable oils and organic solvents, but also solid support materials such as fats, fatty acids, waxes, fatty alcohols and fatty acid esters of fatty alcohols, carbohydrates, sugar alcohols, and inorganic fillers, which are used for the production of food or feed allowed are.
  • solvents examples are:
  • C 1 -C 6 -alkanols such as, for example, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 3-methyl-1-butanol, 1-pentanol and mixtures thereof;
  • C 1 -C 4 -alkyl esters of aliphatic C 1 -C 4 -carboxylic acids such as, for example, the methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl esters of formic acid, of acetic acid , propionic acid or butyric acid such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, ethyl formate and mixtures thereof; such as
  • ketones having 3 to 6 C atoms, such as acetone
  • Suitable carbohydrates include mono-, di-, oligo- and polysaccharides.
  • Monosaccharides and disaccharides are mainly glucose, fructose, galactose, mannose, maltose, sucrose and lactose.
  • Suitable polysaccharides are starch and oligomeric starch degradation products (dextrins) as well as cellulose powder.
  • Suitable sugar alcohols are especially sorbitan and glycerol.
  • Suitable fats and oils may be of synthetic, mineral, vegetable or animal origin.
  • oils are vegetable oils such as soybean oil, sunflower oil, corn oil,
  • Eicosapentaenoic acid EPA
  • docosahexaenoic acid DHA
  • ⁇ -linolenic acid furthermore semisynthetic triglycerides, e.g. Caprylic acid / capric acid triglycerides such as the miglyol types, paraffin oil, liquid hydrogenated polyisobutenes, squalane, squalene, furthermore animal oils and fats such as fish oils including mackerel, sprat, tuna, halibut, cod and salmon oil.
  • vegetable oils and oils of animal origin which are liquid at 40 ° C., in particular vegetable oils such as soybean oil, sunflower oil, thistle oil,
  • oils Corn oil, olive oil, linseed oil, rapeseed oil, rice oil, coconut oil, peanut oil, palm oil, palm kernel oil, PUFA oils, MCT oils, and fish oils, and mixtures of these oils.
  • fats usually have a melting point above 30 ° C. Examples of fats are:
  • saturated fatty acids having 12 to 30 carbon atoms saturated C 12 -C 30 -fatty acids
  • saturated C 4 -C 28 -fatty acids saturated fatty acids having 14 to 28 carbon atoms (saturated C 4 -C 28 -fatty acids) and especially 16 to 24
  • C atoms saturated C 16-24 fatty acids
  • myristic acid palmitic acid
  • Triglycerides of the aforementioned fatty acids and mixtures thereof (hereinafter referred to as fatty acid glycerides), in particular the aforementioned saturated fatty acids and especially those saturated fatty acids having 14 to 28 carbon atoms and especially 16 to 28
  • esters of the aforementioned saturated fatty acids having preferably 14 to 28 carbon atoms and especially 16 to 28 carbon atoms, with Cio-C3o-fatty alcohols, in particular with Ci4-C28 fatty alcohols.
  • the abovementioned esters of saturated fatty acids may contain up to 10% by weight, based on the fatty acid content in the ester, of one or more polyunsaturated fatty acids in esterified form. In particular, the proportion of unsaturated fatty acid constituents in these esters is less than 5% by weight, based on the total fatty acid constituents in the ester;
  • oils and fats can be raffinate oils or crude oils or crude fats, which still contain origin-specific impurities such as proteins, phosphate, (alkaline earth) metal salts and the like in conventional amounts.
  • Suitable fatty alcohols are in particular saturated aliphatic alcohols having 8 to 30 C atoms (hereinafter also referred to as Cs-Cso fatty alcohols), for example cetyl alcohol, stearyl alcohol, nonadecanol, arachidyl alcohol, behenyl alcohol, lignoceryl alcohol,
  • Ceryl alcohol, myricyl alcohol and melissyl alcohol Ceryl alcohol, myricyl alcohol and melissyl alcohol.
  • Waxes are, in particular, natural waxes of plant or animal origin, such as beeswax, candelilla wax, shellac wax, sheathing fat and carnauba wax.
  • Hydrocarbon waxes such as paraffin waxes, ceresin, sasol waxes, ozokerite and
  • inert, food-grade inorganic fillers are inorganic materials in powder form (inorganic fillers), e.g., oxides such as alumina,
  • excipients which are suitable for foodstuffs and animal feeds furthermore include dispersants, including lipophilic dispersants for dispersing the astaxanthin compositions in lipophilic carriers and protective colloids for dispersing the novel tablets
  • Astaxanthin compositions in hydrophilic carriers such as water, further antioxidants (oxidation stabilizers) and food approved dyes.
  • antioxidants examples include tocopherols such as ⁇ -tocopherol, ⁇ -tocopherol palmitate, ⁇ -tocopherol acetate, tert.-butylhydroxytoluene, tert-butylhydroxyanisole, ascorbic acid, their salts and esters such as. Sodium ascorbate, calcium ascorbate, ascorbyl phosphate ester and ascorbyl palmitate and ethoxyquin.
  • the antioxidants are, if desired, in the
  • Additives according to the invention typically in amounts of from 0.01 to 10 wt .-%, based on the total weight of the additive.
  • preservatives examples include benzoic acid and its salts, especially its sodium, potassium and calcium salts, 4-hydroxybenzoic acid (PHB) and its salts,
  • the salts of PHB alkyl esters such as the sodium salt of PHB methyl ester, the sodium salt of PHB ethyl ester and the sodium salt of PHB propyl ester, sorbic acid and its salts, in particular its sodium, potassium and calcium salts, salts of propionic acid, in particular its sodium, potassium and
  • Calcium salts, boric acid and lactic acid and their salts are typically included in the additives in amounts of from 0.001 to 2% by weight, based on the total weight of the additives.
  • Typical lipophilic dispersants are ascorbyl palmitate, polyglycerol fatty acid esters such as polyglycerol-3-polyrizinoleate (PGPR90), sorbitan fatty acid esters, in particular sorbitan-Cio-C28-fatty acid esters such.
  • PGPR90 polyglycerol-3-polyrizinoleate
  • sorbitan fatty acid esters in particular sorbitan-Cio-C28-fatty acid esters such.
  • B. mono- and di-Cio-C28-fatty acid esters of sorbitan such as
  • Lipophilic dispersants are typically included in the additives in amounts of from 0.01% to 10% by weight, based on the total weight of the additives.
  • Protective colloids are polymeric substances suitable for dispersing water-insoluble solids in aqueous compositions. Suitable protective colloids approved for food and feed include, for example
  • oligo- and polysaccharides including modified polysaccharides such as dextrins, cellulose and cellulose derivatives such as methylcellulose, carboxymethylcellulose and their salts, hydroxyethylcellulose, hydroxypropylcellulose and
  • polyvinyl alcohol including partially saponified polyvinyl alcohol, 5) polyvinylpyrrolidone and
  • the proteinaceous protective colloids of group 1) is a water-soluble or swellable polymeric substance which is composed of amino acids and
  • the proteinaceous protective colloid is usually of plant or animal origin.
  • proteinaceous protective colloids of group 1) are caseins and caseinates, including as, ots2, ⁇ and ⁇ casein and mixtures thereof, prolamins, d.
  • Gelatin A100 and A200 alkaline degraded gelatin such as gelatin B100 and B200 and enzymatically degraded gelatin types such as those available under the trade names Gelita® Collagel A, Gelita® Sol DA, Gelita® Sol PA and Gelita® Sol LDA (DGF Stoess), and soy protein and partially hydrolyzed soy protein and lupine protein.
  • Lupine protein is understood to be plant proteins derived from lupine. According to one
  • the powdered composition contains at least one proteinic protective colloid of group 1), optionally in combination with an oligo- or polysaccharide of group 3).
  • Protective colloid is typically in the range of 10,000 to 250,000 daltons, more preferably in the range of 15,000 to 200,000 daltons and especially in the range of 20,000 to 180,000 daltons.
  • Preferred protective colloids are casein, caseinates z.
  • the food or feed additives is a solution or suspension of the
  • Astaxanthin composition according to the invention in an oil or fat suitable for food or feed.
  • concentration of astaxanthin in such additive formulations is generally in the range of 0.01 to 30 wt .-%, in particular in the range of 0.1 to 10 wt .-%, based on the total weight of the additive. In the case of a solution lies the
  • Concentration preferably in the range of 0.01 to 3 wt .-%, in particular in the range of 0.1 to 2 wt .-%.
  • concentration of astaxanthin is in the range of 1 to 30 wt .-%, in particular in the range of 2 to 20 wt .-%.
  • the concentration of astaxanthin indicated the total concentration of astaxanthin in the form of the monoester, the optional diester and the unesterified astaxanthin.
  • the solution may contain the aforementioned additives such as lipophilic dispersants and / or antioxidants and / or dyes, preferably in the aforementioned amounts.
  • suspensions of the invention are examples of the concentration of astaxanthin.
  • astaxanthin compositions have at least 80% by weight, in particular at least 90% by weight, of the particles of the astaxanthin composition
  • the particles of the astaxanthin composition in the suspension have a volume-average particle diameter (D4.3 value) in the range from 0.2 to 50 ⁇ m, in particular in the range from 0.3 to 30 ⁇ m and especially in the range from 0.5 to 20 ⁇ m on.
  • the volume-average particle diameter is understood to mean the volume-average particle diameter determined by means of Fraunhofer diffraction on a dilute 0.01 to 0.1% strength by weight, especially 0.05% strength by weight suspension.
  • the additives for food and feed according to the invention may also be powders. These powders generally have in addition to the invention
  • Astaxanthinzusammen also other powder ingredients on. Which includes
  • a flow aid which is also referred to as an anti-agglomeration agent, is understood to mean a solid, powdery substance which reduces sticking of the powder particles to one another or to container walls.
  • the anti-caking agents are typically inert, food-grade solid inorganic materials in powder form, e.g. For example, oxides such as alumina, silica, in particular in the form of finely divided silica such as fumed silica or silica gel (E 551), or titanium dioxide (E 171), phosphates such
  • Tricalcium phosphate hydroxides such as aluminum hydroxide, carbonates and bicarbonates such as sodium carbonate (E 500), sodium bicarbonate, potassium carbonate (E 501),
  • crystalline mono-, di- and higher polysaccharides such as lactose, sugar
  • the particles of the flow aid have volume-average particle diameters in the range of 1/100 to 1/2 of the volume-average particle diameter of the powder particles of the astaxanthin derivative.
  • the proportion of flow aids will generally not exceed 10% by weight and, if present, is typically 0.1 to 10% by weight, preferably 0.2 to 5% by weight, in particular 0.3 to 3% by weight. -%, based on the total weight of the powdery additive.
  • the powdery additive compositions contain, in addition to
  • Astaxanthin composition one or more other powder ingredients.
  • these include, in particular, other organic and inorganic substances which are suitable for foods and which are preferably a solid at 50 ° C., in particular at 80 ° C.
  • these include in particular the aforementioned fillers, protective colloids, antioxidants and preservatives.
  • powdery compositions generally have at least 90 wt .-% of
  • Powder particles have a particle diameter below 500 ⁇ , in particular a maximum of 200 ⁇ .
  • the powder particles generally have an average particle size (particle diameter, volume average, D4.3 value) in the range from 0.5 to 300 ⁇ m, in particular in the range from 0.5 to
  • the powdery formulation comprises at least one protective colloid.
  • compositions are dispersible in water.
  • weight ratio of ⁇ ⁇
  • Protective colloid to the astaxanthin constituents of the astaxanthin composition is typically in the range of 50: 1 to 1: 5, more preferably in the range of 20: 1 to 1: 2, and especially in the range of 10: 1 to 1: 1.
  • the powdered formulation comprises at least one proteinaceous protective colloid.
  • the proteinaceous protective colloid is in particular a soy protein or a
  • soy protein and another proteinic protective colloid eg.
  • a mixture of soy protein and a prolamine e.g., a mixture of soy protein and a lupine protein, a mixture of soy protein and a casein and / or caseinate, a mixture of
  • Soy protein and soy protein hydrolyzate hydrolyzate.
  • the soy protein forms the
  • Main component of the proteinaceous protective colloid is at least 50 wt .-%, in particular at least 80 wt .-% or at least 90 wt .-%.
  • the proteinaceous protective colloid is especially one
  • partially hydrolyzed soy protein or a mixture of partially hydrolyzed soy protein and another proteinaceous protective colloid e.g. Example, a mixture of partially hydrolyzed soy protein and a prolamine, a mixture of partially hydrolyzed soy protein and a lupine protein, a mixture of partially hydrolyzed soy protein and a casein and / or caseinate.
  • the partially hydrolyzed soy protein forms the main constituent of the proteinaceous protective colloid, the proportion of the protective colloid is at least 50% by weight, in particular at least 80% by weight or at least 90% by weight.
  • partially hydrolyzed soy protein is meant a soy protein which has undergone partial enzymatic degradation with a protease.
  • the degree of degradation DH of such a partially hydrolyzed soy protein is generally at least 1%, in particular at least 5%, z. In the range of 1 to 20% and especially in the range of 5 to 16%.
  • the degree of degradation DH is meant the
  • soya protein isolates and concentrates with protein contents of generally 70 to 90% by weight are usually used as soya proteins for the preparation of the formulations according to the invention, but also for the preparation of the partially hydrolyzed soya proteins remaining 10 to 30 wt .-% represent more or less undefined other plant constituents.
  • the pulverulent formulation comprises at least one protective colloid from the group of
  • Lignosulfonates especially Na-lignosulfonate, optionally in combination with other protective colloids, in particular those from group 3).
  • other protective colloids in particular those from group 3).
  • the main component of the protective colloid, the proportion of the protective colloid is at least 50 wt .-%, in particular at least 80 wt .-% or at least 90 wt .-%.
  • the invention also relates to foods which are an inventive
  • Astaxanthin composition containing the concentration of
  • Astaxanthin composition corresponds to the food-approved content of astaxanthin in the food.
  • concentration of the composition according to the invention, calculated as astaxanthin is in the range from 1 to 500 mg / kg of the respective foodstuff.
  • Compounds include fatty foods such as sausage, cheese,
  • the invention also relates to feedstuffs comprising an inventive
  • Astaxanthin composition containing the concentration of
  • Astaxanthin composition corresponds to the approved for the respective feed content of astaxanthin in the feed.
  • concentration of the composition of the invention, calculated as astaxanthin is in the range of 1 to 500 mg / kg of the respective feed.
  • Typical constituents in feedstuffs are carbohydrate sources, in particular cereal flours such as wheat or maize flour, soybean meal, but also sugars and sugar alcohols, furthermore proteinaceous constituents such as soy concentrate, fish meal, glutens such as maize or corn
  • oils and fats e.g. As the aforementioned edible oils, but also other edible fats of plant or animal origin, continue nutraceuticals such as free
  • Amino acids their salts, vitamins and trace elements, and optionally
  • Processing aids eg. As lubricants, antiblocking agents, inert fillers and the like, and optionally preservatives.
  • Typical fish food compositions contain e.g. As cereal flour in an amount of, for example, 3 to 20 wt .-%, gluten, z. In an amount of from 1 to 30% by weight, one or more protein sources, e.g. B. soya concentrate and / or Fishmeal, z. In a total amount of 10 to 50 wt .-%, fats and / or oils in an amount of for example 10 to 50 wt .-%, optionally one or more vitamins in a total amount, for example, 0.1 to 2 wt. % and optionally amino acids in an amount of, for example, 0.1 to 5 wt .-%, each based on the total amount of feed ingredients.
  • Food with a food or feed additive of the invention in the desired amount can be added during the preparation of the food or feed or by adding to the food or feed ingredients in the production of the food or feed.
  • a specific embodiment of this feed relates to feed pellets, especially
  • Feed pellets for fish feed which can be obtained with the solution according to the invention of the
  • Astaxanthin derivative are loaded. Such pellets contain the inventive
  • Astaxanthin composition typically in an amount of 10 to 200 ppm, based on the total weight of the feed and calculated as astaxanthin.
  • the preparation of such pellets is generally carried out by spraying conventional pellets with a solution of the astaxanthin composition according to the invention, preferably under reduced pressure, wherein the spraying can be carried out continuously or preferably discontinuously.
  • Astaxanthin composition in a food-grade oil in the manner described above spray In this way one obtains pellets which contain in the core the oil and the astaxanthin composition according to the invention.
  • the invention also relates to dietary supplements. These dietary supplements contain the astaxanthin composition of the invention in formulated form, i. H. In addition to the astaxanthin composition according to the invention, they comprise at least one excipient approved for food supplements. These include above all in the
  • excipients such as carriers
  • Dispersants, antioxidants, preservatives and dyes and other, necessary for the preparation of the desired dosage form excipients are Dispersants, antioxidants, preservatives and dyes and other, necessary for the preparation of the desired dosage form excipients.
  • Typical dosage forms for food supplements are powders, powders, granules, tablets, in particular film-coated tablets, lozenges, sachets, cachets, dragees, capsules such as hard and soft gelatine capsules, effervescent tablets and effervescent powder.
  • the amount of astaxanthin composition in the dietary supplement is typically in the range of 0.5 to 100 mg, especially 1 to 50 mg per dose unit, calculated as astaxanthin.
  • compositions according to the invention can be used are the above-mentioned indications.
  • the use according to the invention of the compounds described includes a process as part of the treatment.
  • the subject to be treated preferably a mammal, in particular a human, animal or pet, an effective amount of astaxanthin according to the invention, usually formulated according to the pharmaceutical and veterinary practice, administered.
  • an effective amount of astaxanthin according to the invention usually formulated according to the pharmaceutical and veterinary practice, administered.
  • Whether such treatment is appropriate and what form it takes depends on the individual case and is subject to a medical judgment (diagnosis) of the signs, symptoms and / or dysfunctions present, risks, certain signs, symptoms and / or dysfunctions , and other factors.
  • the treatment is usually carried out by single or repeated daily administration, optionally together or in alternation with other active ingredients or active substance-containing preparations, so that an individual to be treated has a daily dose of preferably about 0.1 to 50 mg / kg body weight, in particular 0.5 to 10 mg / kg body weight, or 1 to 1000 mg, especially 2 to 200 mg, each calculated as astaxanthin, preferably by oral administration is supplied.
  • the invention also relates to the preparation of medicinal preparations, hereinafter also referred to as pharmaceutical agents, for the treatment of an individual, preferably a mammal, in particular a human, animal or pet. So will the
  • Astaxanthin compositions according to the invention are usually administered in the form of medicinal preparations containing a pharmaceutically acceptable excipient, i. H. an excipient, the astaxanthin composition of the invention and optionally one or more other active ingredients. These preparations are preferably administered by oral route.
  • suitable medical preparations include solid dosage forms, such as powders, powders, granules, tablets, in particular film-coated tablets, lozenges, sachets, cachets, dragées, capsules, such as hard and soft gelatine capsules, effervescent tablets, effervescent powder, semisolid
  • compositions such as ointments, creams, hydrogels, pastes or patches, as well as liquid
  • compositions such as solutions, emulsions, in particular oil-in-water emulsions, Suspensions, for example lotions, eye and ear drops.
  • emulsions in particular oil-in-water emulsions
  • Suspensions for example lotions, eye and ear drops.
  • liposomes or microcapsules may also be used.
  • Astaxanthin compositions are usually mixed or diluted with an excipient.
  • Excipients may be solid, semi-solid or liquid materials which serve as a vehicle, carrier or medium for the active ingredient.
  • the compositions of the invention typically contain the astaxanthin composition in an amount equal to the daily dose or a fraction of the daily dose, e.g. B. half, a third or a quarter of
  • Preparation is typically in the range of 0.5 to 200 mg, in particular 1 to 100 mg per dose unit, calculated as astaxanthin.
  • Suitable excipients are listed in the relevant pharmacographies. Further, the formulations may include pharmaceutically acceptable carriers or conventional adjuvants, such as lubricants;
  • wetting agents emulsifying and suspending agents; conserving agents; antioxidants;
  • Antiirritatives ; chelating agents; coating aids; Emulsion stabilizers; film formers; gelling agents;
  • Odor masking agents masking flavors; resins; Hydrocolloids; Solvents;
  • Solubilizing agents Neutralizing agents; permeation; pigments; quaternary ammonium compounds; Refatting and superfatting agents; Ointment, cream or oil bases; Silicone derivatives; spreading aids; stabilizers; Sterilanzien;
  • Tablet excipients such as binders, fillers, lubricants,
  • Disintegrants or coatings Propellant; Desiccant; Opacifiers; Thickener;
  • a related embodiment is based on expert knowledge, such as in Fiedler, H.P., Lexicon of excipients for
  • FI .-% stands for the surface percentages determined by HPLC:
  • Astaxanthin monooleate with the following properties:
  • Enantiomeric purity > 95% ee 3S, 3'S enantiomer
  • Astaxanthin dioleate having the following properties:
  • Enantiomeric purity > 95% ee 3S, 3'S enantiomer; Proportion of trans fatty acid esters 60% by weight.
  • Astaxanthin C18 4-monoester
  • Astaxanthin monopalmitate had been implemented. Astaxanthine dipalmitate was detected only in very small amounts.
  • bioavailability study was carried out by determining the blood plasma level of astaxanthin in Göttingen minipigs. As a measure of the bioavailability, the integral plasma concentration in the blood serum was determined over 96 h (AUC). All astaxanthin derivatives were administered as solutions in olive oil:
  • Formulation 1 astaxanthin monooleate, 4.2% by weight (calculated as free astaxanthin) in
  • Formulation 2 Astaxanthin dioleate, 3.1% by weight (calculated as free astaxanthin) in
  • Formulation 3 Astaxanthin natural product, 2.4% by weight (calculated as free astaxanthin) in
  • the catheters were rinsed daily with saline.
  • the minipigs were fed a commercial diet for mini-pigs (SDS, Essex, UK). The diet was fed on weekday mornings and afternoons, and weekends early in the morning and just before noon.
  • the diet was supplemented with a high-fat diet enriched with 20% corn oil.
  • a high-fat diet enriched with 20% corn oil.
  • 224 g of the commercial mini-pig diet were mixed with 54 g of corn oil.
  • Pig 1 received 140 g of the high-fat diet immediately before the 1st and 2nd
  • Pigs 2 and 3 received 170 g each of the high-fat diet immediately before the 1st and 2nd treatment and 1 10 g immediately after the 1st. and 2 nd treatment and 170 g 2 h before the third treatment and 1 10 g 1 h after the third
  • Pig 3 Formulation 2 Formulation 1 Formulation 3 For treatment, the formulation was administered to each pig by means of a nasogastric tube as a single dose.
  • the single dose was 50 mg / kg astaxanthin.
  • 2 h, 6 h, 7 h, 8 h, 9 h, 10 h, 1 h, 12 h, 1 h, 24 h, 32 h, 48 h, 56 h, 72 h and 96 h after administration about 2 ml of blood was taken from the pigs via the femoral vein.
  • the samples were stored on ice and within 30 min. after removal 10 min. centrifuged at 1500 g and 4-8 ° C. The plasma was placed in sterile, closable
  • tmax time interval of the maximum serum level
  • Ciast concentration before falling below the detection limit
  • AUCiast concentration integral up to the time before the detection limit is undershot
  • AUCoo extrapolated concentration integral

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Abstract

La présente invention concerne des compositions d'astaxanthine destinées à être utilisées dans des produits alimentaires, des compléments alimentaires ou des aliments pour animaux ou encore en tant que médicament. Ces compositions d'astaxanthine, qui contiennent, en proportion d'au moins 80 % en poids, en particulier d'au moins 90 % en poids, plus spécialement d'au moins 95 % en poids, rapportée au poids total de l'astaxanthine et de dérivés de l'astaxanthine dans la composition, un monoester de l'astaxanthine avec un acide monocarboxylique aliphatique linéaire en C18-C22, présentent une biodisponibilité particulièrement bonne. Ainsi, lesdites compositions sont particulièrement appropriées pour être utilisées dans des produits alimentaires, des compléments alimentaires ou des aliments pour animaux ainsi que pour une utilisation thérapeutique en tant que médicament et en tant qu'ingrédient pour des préparations médicales et des produits pharmaceutiques.
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US10836718B2 (en) 2016-11-25 2020-11-17 Basf Se Process for preparing astacene

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