WO2019185891A1 - Nouvelle utilisation de chroman-6-ols substitués - Google Patents

Nouvelle utilisation de chroman-6-ols substitués Download PDF

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Publication number
WO2019185891A1
WO2019185891A1 PCT/EP2019/058055 EP2019058055W WO2019185891A1 WO 2019185891 A1 WO2019185891 A1 WO 2019185891A1 EP 2019058055 W EP2019058055 W EP 2019058055W WO 2019185891 A1 WO2019185891 A1 WO 2019185891A1
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oil
alkyl
compound
formula
independently
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PCT/EP2019/058055
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English (en)
Inventor
Laure CLASADONTE
André DUESTERLOH
Weerasinghe INDRASENA
Thomas Netscher
René Tobias STEMMLER
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Dsm Ip Assets B.V.
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Publication of WO2019185891A1 publication Critical patent/WO2019185891A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides

Definitions

  • the present invention is directed to the use of a compound of formula (I) as antioxidant in oil,
  • R 1 and R 2 are independently from each other H or C M 1 -alkyl or (CH 2 ) n — OH with n being an integer from 1 to 4, or R 1 and R 2 represent together a keto group,
  • R 3 , R 4 and R 6 are independently from each other H or Ci- 4 -alkyl, and wherein R 5 is H or OH or Ci- 4 -alkyl or Ci- 4 -alkoxy;
  • oil contains polyunsaturated fatty acids and/or their esters, and wherein the oil is for human consumption.
  • Oils containing polyunsaturated fatty acids and/or their esters are gaining more and more attention, because of their beneficial health effects in humans. Since these oils are only of limited stability, because they are oxidized very easily, there is a need to provide efficient antioxidants for their stabilization.
  • R 3 , R 4 and R 6 are independently from each other H or Ci- 4 -alkyl, and wherein R 5 is H or OH or Ci- 4 -alkyl or Ci- 4 -alkoxy;
  • oil contains polyunsaturated fatty acids and/or their esters, and wherein the oil is for human consumption.
  • alkyl and“alkoxy” in the context of the present invention encompass linear alkyl and branched alkyl, and linear alkoxy and branched alkoxy, respectively.
  • R 1 and R 2 are identical to each other.
  • R 1 and R 2 are independently from each other H or C I -alkyl or (CH 2 ) n — OH with n being an integer from 1 to 4,
  • A is CHR 3
  • R 3 , R 4 and R 6 are independently from each other H or Ci- 4 -alkyl and R 5 is H or Ci- 4 -alkyl or Ci- 4 -alkoxy in the compound of formula (I) with the proviso that at least one of the
  • R 1 and R 2 are C5-11 -alkyl or if one of R 1 and R 2 is a (CH 2 ) n — OH group with 4 C-atoms, the other substituent is preferably H.
  • R 1 and R 2 are independently from each other H or Ci- 4 -alkyl or (CH 2 ) n — OH with n being 1 or 2
  • R 3 , R 4 and R 6 are independently from each other H or Ci- 2 -alkyl
  • R 5 is H or Ci- 2 -alkyl or Ci- 2 -alkoxy.
  • R 1 and R 2 are independently from each other H or C1-4- alkyl or (CH 2 ) n — OH with n being 1 or 2
  • R 3 , R 4 and R 6 are independently from each other H or Ci- 2 -alkyl
  • R 5 is H or Ci- 2 -alkyl or Ci- 2 -alkoxy with the proviso that at least one of the substituents R 4 , R 5 and R 6 is not methyl.
  • R 1 and R 2 are independently from each other H or Ci- 2 -alkyl or (CH 2 ) n — OH with n being 1 or 2
  • R 3 , R 4 and R 6 are independently from each other H or Ci- 2 -alkyl
  • R 5 is H or Ci- 2 -alkyl or Ci- 2 -alkoxy, preferably with the proviso that at least one of the substituents R 4 , R 5 and R 6 is not methyl.
  • R 1 and R 2 are independently from each other H or methyl or (CH 2 )— OH
  • R 3 , R 4 and R 6 are independently from each other H or methyl
  • R 5 is H or methyl or methoxy, preferably with the proviso that at least one of the substituents R 4 , R 5 and R 6 is not methyl.
  • R 3 is H, preferably with the proviso that at least one of the substituents R 4 , R 5 and R 6 is not methyl, more preferably with the proviso that R 5 and R 6 are not methyl.
  • the compound of formula (I) is preferably selected from the group of the compounds of formulae (II) and (III), more preferably from the group of the compounds of formula (IV):
  • R 5a is H or methoxy, preferably whereby R 5a is H;
  • R 1b and R 2b are independently from each other CH 2 OH or linear C 1-3 - alkyl or branched C 4- n-alkyl, preferably whereby one of R 1b and R 2b is methyl and the other one of R 1b and R 2b is CH 2 OH or linear Ci- 3 -alkyl or branched C 4- 11 -alkyl, more preferably whereby one of R 1b and R 2b is methyl and the other one of R 1b and R 2b is methyl, CH 2 OH or [CH 2 -CH 2 -CH 2 -CH(CH 3 )] m CI-l 3 with m being 1 or 2;
  • R 1c and R 2c are independently from each other H or linear Ci- 3 -alkyl or branched C 4- n-alkyl, preferably whereby R 1c and R 2c are independently from each other H, methyl or [CH 2 -CH 2 -CH 2 -CH(CH 3 )] m CI-l 3 with m being 1 or 2.
  • Preferred examples of the compound of formula (II) are the compounds of formulae (1 ), (2), (3), (4), (7), (8), (10) and (1 1 ).
  • Preferred examples of the compound of formula (III) are the compounds of formulae (5), (6) and (9).
  • Preferred examples of the compound of formula (IV) are the compounds of formulae (1 ), (2), (3), (7) and (8).
  • the compound of formula (8) (chemical name: 2-(4,8-dimethylnonyl)-2- methyl-chroman-6-ol) is a novel compound. Thus, this compound is also an object of the present invention.
  • the compounds of the present invention are efficient as antioxidants in PUFA-containing oils for human consumption.
  • PUFA(s) means polyunsaturated fatty acid(s) such as docosahexaenoic acid (“DHA”) and/or eicosapentaenoic acid (“EPA”) and/or docosapentaenoic acid (“DPA”) and/or oleic acid and/or stearidonic acid and/or linoleic acid and/or alpha-linolenic acid (“ALA”) and/or gamma-linolenic acid and/or arachidonic acid (“ARA”) and/or the esters of all of them, whereby the term“esters” encompasses monoglycerides, diglycerides and triglycerides as well as Ci- 6 - alkyl esters such as especially the methyl esters and the ethyl esters, whereby the triglycerides are often dominant. DHA, EPA, ALA and stearidonic acid are omega-3 fatty acids, whereas linoleic acid,
  • DPA encompasses two isomers, the omega-3 fatty acid clupanodonic acid (7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid) and the omega-6 fatty acid osbond acid (4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid).
  • the polyunsaturated fatty acid is preferably DHA and/or EPA and/or DPA and/or any ester thereof, more preferably the polyunsaturated fatty acid (PUFA) is preferably DHA and/or EPA and/or any ester thereof.
  • - marine oil such as preferably fish oil
  • microbial oil containing polyunsaturated fatty acids and/or their esters
  • DHA docosahexaenoic acid
  • EPA eicosapentaenoic acid
  • DPA docosapentaenoic acid
  • DHA docosahexaenoic acid
  • EPA eicosapentaenoic acid
  • DPA docosapentaenoic acid
  • PUFA-containing plant oil such as e.g. canola seed oil, linseed/flaxseed oil, hempseed oil, pumpkin seed oil, evening primrose oil, borage seed oil, blackcurrent seed oil, sallow thorn/sea buckthorn oil, chia seed oil, argan oil and walnut oil.
  • Marine oils, microbial oils and algal oils are especially preferred.
  • the compounds of formula (I) can be used in combination with one or more other antioxidants as described below.
  • the PUFA-containing oils of the present invention comprising a compound of formula (I) additionally comprise ascorbyl palmitate.
  • esters of ascorbic acid such as the esters of ascorbic acid with linear C 12-20 alkanols, preferably the esters of ascorbic acid with linear Ci 4-18 alkanols, may also be used, so that further embodiments of the present invention are directed to PUFA-containing oils of the present invention comprising a compound of formula (I) that additionally comprise esters of ascorbic acid with linear C 12-20 alkanols, preferably esters of ascorbic acid with linear Ci 4-18 alkanols, more preferably ascorbyl palmitate.
  • the PUFA-containing oils of the present invention comprising a compound of formula (I) may also comprise additionally alpha-tocopherol and/or gamma- tocopherol, whereby either an ester of ascorbic acid with a linear C 12-20 alkanol with the preferences as given above may additionally be present.
  • PUFAs polyunsaturated fatty acids
  • DHA docosahexaenoic acid
  • EPA eicosapentaenoic acid
  • DPA docosapentaenoic acid
  • microbial oil - oil containing high amounts of PUFAs, especially containing high amounts of DHA and/or EPA and/or DPA and/or their esters extracted from microbial biomass as e.g., fungi (“fungal oil”) or algae (“algal oil”);
  • PUFA- containing plant oil such as e.g. canola seed oil, linseed/flaxseed oil, hempseed oil, pumpkin seed oil, evening primrose oil, borage seed oil, blackcurrent seed oil, sallow thorn/sea buckthorn oil, chia seed oil, argan oil and walnut oil.
  • DHA does not only encompass the acid but also derivatives thereof such as monoglycerides, diglycerides and triglycerides as well as Ci- 6 -alkyl esters such as the methyl and ethyl esters.
  • EPA monoglycerides
  • DPA dihydroxyacetyl acetate
  • Fish oil and algal oil are commonly used by humans. Instead of fish oil and algal oil also other PUFA-containing oils may be used for human consumption, i.e.:
  • biomass such as especially fungal oil
  • the above-mentioned PUFA-containing oils may not only be used as alternative of fish oil and algal oil, but also in addition.
  • suitable marine oils include, but are not limited to, Atlantic fish oil, Pacific fish oil, or Mediterranean fish oil, or any mixture or combination thereof.
  • a suitable fish oil can be, but is not limited to, pollack oil, bonito oil, pilchard oil, tilapia oil, tuna oil, sea bass oil, halibut oil, spearfish oil, barracuda oil, cod oil, menhaden oil, sardine oil, anchovy oil, capelin oil, herring oil, mackerel oil, salmonid oil, tuna oil, and shark oil, including any mixture or combination thereof.
  • marine oils suitable for use herein include, but are not limited to, squid oil, cuttle fish oil, octopus oil, krill oil, seal oil, whale oil, and the like, including any mixture or combination thereof.
  • the other PUFA- containing oils such as microbial oil, algal oil, fungal oil and PUFA-containing plant oil.
  • a commercially available example of marine oil is the fish oil “MEG-3” (Bleached 30S TG Fish oil) from DSM Nutritional Products, LLC (US) whose specification and composition is shown in Tables 1 and 2 below:
  • the peroxide value is defined as the amount of peroxide oxygen per 1 kilogram of oil. Traditionally this is expressed in units of milliequivalents or meq/kg. Winterization is part of the processing of fish oil, and it is performed to remove solid fat in the oil. The“cold test” is performed to check if any solid fat is present and precipitated in the oil when cooled to 0°C within a specific period of time. In this fish oil (Product Code: FG30TG), any such precipitation is checked for 3 hours at 0°C.
  • Algal oil is an oil containing high amounts of DHA and/or EPA and/or DPA and/or their esters extracted from algae as microbial source /biomass.
  • algal oil is the commercially available“Algal oil containing EPA+DPA” from DSM Nutritional Products, LLC (US) whose composition is shown in the Table 3 below: Table 3
  • a further example of a crude oil containing high amounts of DHA and/or EPA extracted from microbial sources as e.g., algae, is the oil extracted from Algae Schizochytrium Biomass, whose specification is given in the following
  • Microbial biomass containing polyunsaturated fatty acids especially docosahexaenoic acid and/or eicosapentaenoic acid and/or docosapentaenoic acid (“DPA”) and/or their esters
  • the biomass preferably comprises cells which produce PUFAs hetero- trophically.
  • the cells are preferably selected from algae, fungi, particularly yeasts, bacteria, or protists.
  • the cells are more preferably microbial algae or fungi.
  • Suitable cells of oil-producing yeasts are, in particular, strains of Yarrowia, Candida, Rhodotorula, Rhodosporidium, Cryptococcus, Trichosporon and Lipomyces.
  • Oil produced by a microorganism or obtained from a microbial cell is referred to as“microbial oil”.
  • Oil produced by algae and/or fungi is referred to as an algal and/or a fungal oil, respectively.
  • microorganism refers to organisms such as algae, bacteria, fungi, protist, yeast, and combinations thereof, e.g., unicellular organisms.
  • a microorganism includes but is not limited to, golden algae (e.g., microorganisms of the kingdom Stramenopiles); green algae; diatoms; dinoflagellates (e.g., microorganisms of the order Dinophyceae including members of the genus Crypthecodinium such as, for example,
  • Thraustochytriales yeast ( Ascomycetes or Basidiomycetes ); and fungi of the genera Mucor, Mortierella, including but not limited to Mortierella alpina and Mortierella sect, schmuckeri, and Pythium, including but not limited to Pythium insidiosum.
  • microorganisms of the kingdom Stramenopiles may in particular be selected from the following groups of microorganisms:
  • the microorganisms are from the genus Mortierella, genus Crypthecodinium, genus Thraustochytrium, and mixtures thereof. In a further embodiment, the microorganisms are from Crypthecodinium Cohnii. In a further embodiment, the microorganisms are from Mortierella alpina. In a still further embodiment, the microorganisms are from
  • the microorganisms are selected from Crypthecodinium Cohnii, Mortierella alpina,
  • the microorganisms include, but are not limited to, microorganisms belonging to the genus Mortierella, genus Conidiobolus, genus Pythium, genus Phytophthora, genus Penicillium, genus Clodosporium, genus Mucor, genus Fusarium, genus Aspergillus, genus Rhodotorula, genus Entomophthora, genus Echinosporongium, and genus Saprolegnia.
  • the microorganisms are from microalgae of the order Thraustochytriales, which includes, but is not limited to, the genera Thraustochytrium (species include arudimentale, aureum, benthicola, globosum, kinnei, motivum, multirudimentale, pachydermum, proliferum, roseum, striatum); the genera Schizochytrium (species include aggregatum, limnaceum, mangrovei, minutum, octosporum ); the genera Ulkenia (species include amoeboidea, kerguelensis, minuta, profunda, radiate, sailens, sarkariana, schizochytrops, visurgensis, yorkensis); the genera Aurantiacochytrium; the genera Oblongichytrium; the genera Sicyoidochytium; the genera Parientichytrium; the genera Botryochytrium; and combinations thereof.
  • the microorganisms are from the order Thraustochytriales. In yet another embodiment, the microorganisms are from Thraustochytrium.
  • the microorganisms are from Schizochytrium sp.
  • the oil can comprise a marine oil.
  • suitable marine oils are the ones as given above.
  • the biomass according to the invention preferably comprises cells, and preferably consists essentially of such cells, of the taxon
  • Labyrinthulomycetes Labyrinthulea , net slime fungi, slime nets), in particular, those from the family of Thraustochytriaceae .
  • the family of the Thraustochytriaceae includes the genera Althomia, Aplanochytrium, Aurantiochytrium, Botryochytrium, Elnia, Japonochytrium, Oblongichytrium, Parietichytrium, Schizochytrium, Sicyoidochytrium, Thraustochytrium, and Ulkenia.
  • the biomass particularly preferably comprises cells from the genera Aurantiochytrium, Oblongichytrium, Schizochytrium, or Thraustochytrium, more preferably from the genus Schizochytrium.
  • the polyunsaturated fatty acid is preferably DHA and/or EPA and/or their esters as defined above.
  • the cells present in the biomass are preferably distinguished by the fact that they contain at least 20 weight-%, preferably at least 30 weight-%, in particular at least 35 weight-%, of PUFAs, in each case based on cell dry matter.
  • cells in particular a Schizochytrium strain, is employed which produces a significant amount of EPA and DHA, simultaneously, wherein DHA is preferably produced in an amount of at least 20 weight-%, preferably in an amount of at least 30 weight-%, in particular in an amount of 30 to 50 weight-%, and EPA is produced in an amount of at least 5 weight-%, preferably in an amount of at least 10 weight-%, in particular in an amount of 10 to 20 weight-% (in relation to the total amount of lipid as contained in the cells, respectively).
  • PTA-10208 PTA-10209, PTA-10210, or PTA-10211 , PTA-10212, PTA-10213, PTA-10214, PTA-10215.
  • DHA and EPA producing Schizochytrium strains can be obtained by consecutive mutagenesis followed by suitable selection of mutant strains which demonstrate superior EPA and DHA production and a specific EPA:DHA ratio.
  • Any chemical or nonchemical (e.g. ultraviolet (UV) radiation) agent capable of inducing genetic change to the yeast cell can be used as the mutagen.
  • UV radiation ultraviolet
  • These agents can be used alone or in combination with one another, and the chemical agents can be used neat or with a solvent.
  • Methods for producing the biomass in particular, a biomass which comprises cells containing lipids, in particular PUFAs, particularly of the order
  • Thraustochytriales are described in detail in the prior art (see e.g. WO 91 /07498, WO 94/08467, WO 97/37032, WO 97/36996, WO 01 /54510).
  • the production takes place by cells being cultured in a fermenter in the presence of a carbon source and a nitrogen source, along with a number of additional substances like minerals that allow growth of the
  • biomass densities of more than 100 grams per litre and production rates of more than 0.5 gram of lipid per litre per hour may be attained.
  • the process is preferably carried out in what is known as a fed-batch process, i.e. the carbon and nitrogen sources are fed in incrementally during the
  • production may be induced by various measures, for example by limiting the nitrogen source, the carbon source or the oxygen content or combinations of these.
  • the cells are grown until they reach a biomass density of at least 80 or 100 g/l, more preferably at least 120 or 140 g/l, in particular at least 160 or 180 g/l (calculated as dry-matter content).
  • a biomass density of at least 80 or 100 g/l, more preferably at least 120 or 140 g/l, in particular at least 160 or 180 g/l (calculated as dry-matter content).
  • the cells are fermented in a medium with low salinity, in particular, so as to avoid corrosion.
  • This can be achieved by using chlorine- free sodium salts as the sodium source instead of sodium chloride, such as, for example, sodium sulphate, sodium carbonate, sodium hydrogen carbonate or soda ash.
  • chloride is used in the fermentation in amounts of less than 3 g/l, in particular, less than 500 mg/l, especially preferably less than 100 mg/l.
  • PUFA-containing plant oils Plant oils with relatively high amounts of PUFAs, especially with high amounts of DHA and/or EPA such as e.g. , canola seed oil
  • the plant cells may, in particular, be selected from cells of the families Brassicaceae, Elaeagnaceae and Fabaceae.
  • Brassicaceae may be selected from the genus Brassica, in particular, from oilseed rape, turnip rape and Indian mustard; the cells of the family
  • Elaeagnaceae may be selected from the genus Elaeagnus, in particular, from the species Oleae europaea ; the cells of the family Fabaceae may be selected from the genus Glycine, in particular, from the species Glycine max.
  • - Canola seed oil with a content of EPA of at least 9% by weight, of at least 12% by weight, of at least 15% by weight, or of at least 20% by weight, based on the total weight of the canola seed oil.
  • PUFA-containing plant oils containing high amounts of other PUFAs than EPA and/or DHA and/or DPA and/or their esters are linseed/flaxseed oil, hempseed oil, pumpkin seed oil, evening primrose oil, borage seed oil, blackcurrent seed oil, sallow thorn/sea buckthorn oil, chia seed oil, argan oil and walnut oil.
  • the compounds of formulae (4), (6), (8) and (9), preferably the compounds of formulae (4), (8) and (9), more preferably the compounds of formulae (4) and (8), are especially suitable for stabilizing marine oil, microbial oil and algal oil.
  • Gaudino D. Carnaroglio, A. Barge, S. Tagliapietra, G. Cravotto, RSC Adv. 2016, 6, 63515-63518.
  • Compound of formula (12) is an intermediate in the synthesis of compound of formula (4) as described in example 4.
  • Example 1 Antioxidant activities of compounds of formulae (4). (6). (8) and (9) in fish oil
  • the compounds of formulae (4), (6), (8) and (9) have been tested.
  • the blank oil i.e. oil without any antioxidant, and oil containing“MNT” have been used as benchmark. Any compound better in antioxidant activity than the blank oil indicates that it has antioxidant activity.
  • the comparison with MNT gives an indication about the amount of the antioxidant effect, relative to the activity of MNT.
  • MNT are mixed natural tocopherols commercially available as e.g., “Tocomix 70 IP” from AOM (wholesome Aires, Argentina).
  • Tocomix 70 IP comprises d-alpha-tocopherol, d-beta-tocopherol, d-gamma-tocopherol and d-delta-tocopherol, whereby the total amount of tocopherols is at least 70.0 weight-% and the amount of non-alpha tocopherols is at least 56.0 weight-%.
  • the compounds of formulae (4), (6), (8) and (9) were evaluated primarily for their oxidative stability by the Oil Stability Index (OSI) measurements. Two different levels of these antioxidants (0.5 and 2 mg/g) were used in 5 g of natural fish oil (Product code: FG30TG) and used in the Oxidative
  • Oil Stability Index for these compounds at 500 and 2000 ppm levels, in comparison with the same amounts of MNT, are shown in Tables 6-8.
  • the Protection Factors (PF) for each compound in oil were calculated in percentage as: 100% x (OSI of the sample with compound - OSI of the sample without compound)
  • Table 14 Improvement of the Protection Factors of compounds of formulae (6) and (9) with AP in FG30TG fish oil
  • Tables 17, 18 and 19 show the PV (peroxide value), p- AV (p-anisidine value) and CD (Conjugated dienoic acid %) of the fish oil samples stabilized with compounds of formulae (6), (8) and (9), respectively.
  • a combination of complex, polymeric compounds generated at the end of the oxidation cascade of unsaturated fatty acids indicate the levels of overall oxidation of the matrix.
  • the generation of such polymers in fish oil containing these novel antioxidant compounds could be reduced
  • Example 12 Antioxidant activities of compounds of formulae (3) and (7) in fish oil
  • antioxidant activity than the blank oil indicates that it has antioxidant
  • each compound, as percentage, in oil were calculated as, 100% x (OSI of the sample with compound - OSI of the sample without compound)
  • Compound of formula (3) showed slightly higher Oil Stability Indices than those of MNT indicating that compound of formula (3) possesses relatively higher antioxidant properties than MNT at the specified concentration levels. Compound of formula (10) showed comparable antioxidant activity to MNT.
  • Peroxide values of fish oil samples at low (0.5 mg/g) and high levels (2 mg/g) are shown in Tables 21 and 22, respectively, whereas the p-AV of the same samples at low (0.5 mg/g) and high levels (2 mg/g) are shown in Tables 23 and 24, respectively.
  • Table 21 Peroxide values (PV, meq/kg) of compounds of formulae (3) and (7) during storage at 25°C (0.5 mg/g level)
  • Table 23 p-Anisidine value (p-AV) of compounds of formulae (3) and (7) during storage at 25°C (0.5 mg/g level)
  • Table 24 p-Anisidine value (p-AV) of compounds of formulae (3) and (7) during storage at 25°C (2 mg/g level)
  • the compounds of formulae (3) and (7) improved the oxidative stability of crude algal oil when compared with an oil sample which did not contain any of these compounds (Table 25) showing the antioxidant effect of these compounds in algal oil as well.
  • Tables 26 and 27 show the Protection Factors of the compounds of formulae (3) and (7) in fish oil and crude algal oil, respectively.
  • Table 26 Protection Factors of compounds of formulae (3) and (7) in fish oil (80°C)
  • the compounds of formulae (3) and (7) have antioxidant properties that are comparable in activity with MNT in fish oil.
  • Compound of formula (3) has slightly higher Oil Stability Indices compared to MNT.

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Abstract

La présente invention concerne l'utilisation de chroman-6-ols substitués de formule (I) dans laquelle R1 et R2 représentent indépendamment l'un de l'autre H ou un groupe alkyle en C1-11 or (CH2)n-OH, n étant un nombre entier de 1 à 4, ou R1 et R2 représentent ensemble un groupe céto, A représente CHR3 ou C(=O), et dans laquelle R3, R4 et R6 représentent indépendamment les uns des autres H ou un groupe alkyle en C1-4, et dans laquelle R5 représente H ou OH ou un groupe alkyle en C1-4 ou alcoxy en C1-4, comme antioxydants dans des huiles contenant des AGPI telles qu'une huile marine, un huile microbienne, une huile fongique, une huile algale et une huile végétale contenant des AGPI pour la consommation humaine. La présente invention concerne en outre ces huiles contenant des AGPI comprenant de tels chroman-6-ols substitués de formule (I).
PCT/EP2019/058055 2018-03-29 2019-03-29 Nouvelle utilisation de chroman-6-ols substitués WO2019185891A1 (fr)

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Citations (8)

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US3329689A (en) * 1964-06-05 1967-07-04 Merck & Co Inc Preparation of chromanols
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