EP1147167A1 - Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters - Google Patents
Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses estersInfo
- Publication number
- EP1147167A1 EP1147167A1 EP00901675A EP00901675A EP1147167A1 EP 1147167 A1 EP1147167 A1 EP 1147167A1 EP 00901675 A EP00901675 A EP 00901675A EP 00901675 A EP00901675 A EP 00901675A EP 1147167 A1 EP1147167 A1 EP 1147167A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hode
- esters
- acid
- oil
- oxidation
- 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.)
- Withdrawn
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 28
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 18
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 18
- 239000000194 fatty acid Substances 0.000 title claims abstract description 18
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 18
- 235000020778 linoleic acid Nutrition 0.000 title claims abstract description 18
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims abstract description 18
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims description 22
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 27
- 230000003647 oxidation Effects 0.000 claims abstract description 23
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims abstract description 17
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims abstract description 16
- 229960004488 linolenic acid Drugs 0.000 claims abstract description 16
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 7
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 6
- 235000015872 dietary supplement Nutrition 0.000 claims abstract description 5
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- 239000003921 oil Substances 0.000 claims description 21
- 235000019198 oils Nutrition 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 13
- 208000008589 Obesity Diseases 0.000 claims description 12
- 235000020824 obesity Nutrition 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- -1 but Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000003626 triacylglycerols Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 206010033307 Overweight Diseases 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 244000025254 Cannabis sativa Species 0.000 claims description 3
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 3
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 3
- 244000020518 Carthamus tinctorius Species 0.000 claims description 3
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 3
- 241000408747 Lepomis gibbosus Species 0.000 claims description 3
- 241000219925 Oenothera Species 0.000 claims description 3
- 235000004496 Oenothera biennis Nutrition 0.000 claims description 3
- 240000001890 Ribes hudsonianum Species 0.000 claims description 3
- 235000016954 Ribes hudsonianum Nutrition 0.000 claims description 3
- 235000001466 Ribes nigrum Nutrition 0.000 claims description 3
- 241000209140 Triticum Species 0.000 claims description 3
- 235000021307 Triticum Nutrition 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 235000009120 camo Nutrition 0.000 claims description 3
- 235000005607 chanvre indien Nutrition 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000011487 hemp Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 235000020236 pumpkin seed Nutrition 0.000 claims description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- 240000004355 Borago officinalis Species 0.000 claims description 2
- 235000007689 Borago officinalis Nutrition 0.000 claims description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 2
- 240000006240 Linum usitatissimum Species 0.000 claims description 2
- 244000020551 Helianthus annuus Species 0.000 claims 1
- 230000009467 reduction Effects 0.000 abstract description 11
- NPDSHTNEKLQQIJ-UHFFFAOYSA-N dimorphecolic acid Natural products CCCCCC=CC=CC(O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-UHFFFAOYSA-N 0.000 abstract description 6
- NPDSHTNEKLQQIJ-ZJHFMPGASA-N alpha-dimorphecolic acid Chemical compound CCCCC\C=C/C=C/C(O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-ZJHFMPGASA-N 0.000 abstract description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 11
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 10
- 210000001789 adipocyte Anatomy 0.000 description 9
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 9
- 235000019486 Sunflower oil Nutrition 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002600 sunflower oil Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 6
- 229960001948 caffeine Drugs 0.000 description 6
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000004130 lipolysis Effects 0.000 description 6
- 210000000689 upper leg Anatomy 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 235000019577 caloric intake Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NOCWDMQAHCQAKS-UHFFFAOYSA-N 2-hydroxyoctadeca-2,4-dienoic acid Chemical class CCCCCCCCCCCCCC=CC=C(O)C(O)=O NOCWDMQAHCQAKS-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000002366 lipolytic effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NPDSHTNEKLQQIJ-KRWDZBQOSA-N Dimorphecolsaeure Natural products CCCCCC=CC=C[C@H](O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-KRWDZBQOSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000208818 Helianthus Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- HNICUWMFWZBIFP-KDFHGORWSA-N alpha-Artemisic acid Chemical compound CCCCCC(O)\C=C\C=C\CCCCCCCC(O)=O HNICUWMFWZBIFP-KDFHGORWSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000035924 thermogenesis Effects 0.000 description 2
- 230000000476 thermogenic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 1
- MHEIOCYNLPDFHV-UHFFFAOYSA-N 9-hydroxyoctadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCCC(O)CC=CC=CC=CC(O)=O MHEIOCYNLPDFHV-UHFFFAOYSA-N 0.000 description 1
- CUHJQOVOXFVMSQ-UHFFFAOYSA-N 9-hydroxyoctadeca-2,4-dienoic acid Chemical compound CCCCCCCCCC(O)CCCC=CC=CC(O)=O CUHJQOVOXFVMSQ-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000021324 borage oil Nutrition 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015111 chews Nutrition 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- 229940031016 ethyl linoleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000019138 food restriction Nutrition 0.000 description 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
- HBOQXIRUPVQLKX-UHFFFAOYSA-N linoleic acid triglyceride Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC HBOQXIRUPVQLKX-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 235000020845 low-calorie diet Nutrition 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940126703 systemic medication Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940126702 topical medication Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/06—Preparations for care of the skin for countering cellulitis
Definitions
- the present invention relates to a process for the preparation of hydroxyoctadecadienoic acids, more particularly 9-hydroxy-10, 12-octadecadienoic acid and 13-hydroxy-9, 11-octadecadienoic acid, and their mixture, as well as their isomers such as 9 (R / S) -hydroxy-10E, 12Z-octadecadienoic acid, optionally in the form of their esters, more particularly in the form of their ethyl ester.
- hydroxyoctadecadienoic acid is called HODE.
- the invention relates to a process for preparing HODE by controlled oxidation of linoleic acid and / or linolenic acid, then reduction.
- the invention further relates to a process for the preparation of HODE from triglycerides rich in linoleic acid and / or linolenic acid or from linoleic acid and / or linolenic acid in the form of free fatty acid or in the form of an ester or a salt, for example in the form of an ethyl ester.
- the invention further relates to a medicament, in particular for the treatment of obesity, containing as active ingredient HODE and pharmacologically acceptable carriers.
- the invention also relates to a food supplement containing HODE, in particular for the treatment of obesity.
- the invention further relates to a cosmetic product containing HODE and cosmetologically acceptable supports, more particularly for the localized treatment of overweight and its consequences on the appearance of the skin, such as orange peel, dimples, horse breeches.
- a cosmetic product containing HODE and cosmetologically acceptable supports more particularly for the localized treatment of overweight and its consequences on the appearance of the skin, such as orange peel, dimples, horse breeches.
- lipids cannot be reduced to less than 30% of energy intake since they not only play an important role in the texture and taste perception of food, but also that a minimum amount is necessary in food, especially for the biosynthesis of essential fatty acids and hormones, and the renewal of membrane phospholipids.
- One of the objectives of the invention was to find a molecule allowing the regulation of the lipolytic activity of the adipocyte, that is to say, capable of hydrolyzing the triglycerides stored in adipocytes into free fatty acids and glycerols .
- adrenaline and caffeine are two molecules known for their lipolytic effects. These molecules in particular increase the levels of adenosine cyclic mono phosphate (cAMP), the first step in activating lipolysis.
- cAMP adenosine cyclic mono phosphate
- Another object of the invention is to provide a lipolytic molecule synthesized from products commonly found in nature, in a simple and effective manner.
- HODE hydroxyoctadecadienoic fatty acid
- the invention therefore relates to a process for obtaining an oil enriched with hydroxyoctadecadienoic fatty acid (HODE) and in particular 9-hydroxyoctadecadienenoic acid (9-HODE), or its esters or its salts, from a oily mixture containing linoleic acid and / or linolenic acid, or their esters or their salts, characterized in that a controlled oxidation of linoleic acid and / or linolenic acid is carried out, or of their esters, in the presence of an oxidation catalyst, the oxidation being stopped when the total content of HODE, or of its esters, is greater than at least 5% and / or the content of 9-hydroxy- acid isomer 10, 12-octadecad ⁇ eno ⁇ que (9- HODE), or its esters, is greater than at least 1.5% and in that the hydroperoxides formed during "- of the oxidation reaction are reduced by a reducing agent.
- the starting oily mixture is a vegetable oil containing more than 40% by weight of linoleic acid and / or linolenic acid in the form of triglycerides, such as oil of corn, borage, safflower, soybeans, evening primrose, sunflower, blackcurrant seeds, wheat germ, hemp, pumpkin seeds, flaxseed.
- the starting oily mixture is an oily mixture containing more than 40% by weight of linoleic acid and / or linolenic acid, preferably containing 75% of ethyl linoleate.
- the final content in the oil enriched in total HODE or in 9-HODE is at least 5%, respectively 1.5% by weight.
- the final content in the oil enriched in total HODE or in 9-HODE is respectively between 10 and 12% by weight and between 2.2 and 2.5% by weight.
- the oxidation catalyst is a halogen of iron, copper, preferably FeCl 3 .
- the reducing agent is preferably NaBH 4 .
- the invention further relates to the oil enriched in hydroxyoctadecadienoic fatty acid (HODE) or its esters or its salts, obtained as described above.
- HODE hydroxyoctadecadienoic fatty acid
- the invention relates to a medicament for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its salts, acceptable pharmacologically, preferably in the form of enriched oil obtained as described above.
- the invention further relates to a food supplement for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its pharmacologically acceptable salts, preferably in the form of enriched oil obtained as described above.
- a food supplement for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its pharmacologically acceptable salts, preferably in the form of enriched oil obtained as described above.
- the invention further relates to a cosmetic product for the treatment of obesity containing as active principle the fatty acid 9-hydroxyoctadecad ⁇ eno ⁇ que (9-HODE) or its esters or its cosmetically acceptable salts, preferably in the form of enriched oil obtained as described above.
- hydroxyoctadecadienoic acid HODE
- fatty acids are present in many vegetable oils.
- the following vegetable oils contain more than 40% linoleic acid in the form of triglycerides: borage oil, safflower, soybeans, evening primrose, sunflower, blackcurrant seeds, wheat germ, hemp, pumpkin seeds, flax.
- the HODE can be obtained from triglycerides rich in linoleic and / or linolenic acid. This process is advantageous insofar as it makes it possible to use a natural vegetable oil, therefore perfectly suitable for use by the oral route, but has the drawback of considerably limiting the final content of the 9-HODE isomer.
- the structure of the starting product is a linoleic acid triglyceride or a linoleic acid ester of the following general formula (I):
- Linolenic acid exists in two forms: ⁇ -linolenic acid (or acid (Z, Z, Z) 9, 12, 15-octadecatrienoic) and ⁇ -linolenic acid (or acid (Z, Z, Z) 6, 9, 12- octadecat ⁇ enoic).
- the oxidation reaction is carried out in the presence of an oxygenation catalyst such as an iron or copper halide, preferably FeCl 3 .
- the reaction has a variable duration from 12 to 78 hours and at a temperature between -20 ° C and 40 ° C, at atmospheric pressure and / or under reduced pressure.
- the degree of oxidation is followed by different criteria:
- the mixture is reduced, namely, the hydroperoxides formed during the oxidation are reduced.
- An ethanolic solution of NaBH 4 or an ethanolic solution of any other reducing agent is used which is added in parts to the reaction mixture.
- the temperature of the mixture is maintained between 4 and 25 ° C.
- the reduction is complete when the temperature becomes constant.
- the reaction medium is neutralized to pH6-7 by adding an acid solution, preferably a solution of an acid which is pharmacologically and / or cosmetologically acceptable, for example citric acid.
- the compounds (II) and (III) are extracted with hexane or any other organic solvent capable of dissolving them.
- the organic phase is washed with water until neutral.
- the organic phase is then dried over sodium sulfate or anhydrous magnesium sulfate. Then the filtrate is evaporated under vacuum.
- the product obtained is a light yellow oily liquid with a slightly aromatic odor. It has a total content of compounds (II) and (III) (determined by gas chromatography) greater than 5% by weight and a content of compound (II) [acid 9 (R / S) hydroxy-lOE, 12Z- octadecad ⁇ eno ⁇ que or ester of 9 (R / S) hydroxy-10E, 12Z-octadecad ⁇ eno ⁇ que acid] greater than 1.5% by weight.
- the starting product is an oily mixture containing 75% by weight of ethyl moleate.
- Oxygen is bubbled (technical quality) in the reaction medium using a stainless steel or bronze filter, with a porosity of 2 to 4 ⁇ m (of the HPLC filter type or particle filter for gases ). This fine bubbling is maintained at a flow rate of 1 liter / m for 48 to 72 hours.
- the oxidation rate is controlled either:
- the reduction phase is completed when the temperature is constant when the stirring is maintained at room temperature (approximately 1 hour).
- the reduction reaction releases hydrogen.
- the object of the invention is to find a molecule having an activity on lipolysis, that is to say, capable of promoting the hydrolysis of the triglycerides stored in the edipocytes, the free fatty acids thus released being then metabolized.
- the purpose of this study is to study the effect of 9-HODE on the production of cAMP (cyclic adenos e monophosphate) which is a activator of lipolysis, in human adipocytes.
- cAMP cyclic adenos e monophosphate
- the concentration of cAMP is 10 times greater than that obtained with caffeine (7,940 fentomoles of cAMP / million adipocytes against 799).
- 9-HODE is, in vitro, a potent activator of lipolysis thanks to a stimulation of the adipocyte production of cAMP greater than that of the caffeine and adrenaline molecules.
- the study is carried out on twelve rats which are first subjected to a food restriction (simulation of a diet) for two weeks, then who receive a normal diet (weight gain) associated or not with the administration of a sunflower oil treated according to the process of the present invention and containing 2% by weight of 9-HODE.
- a control group is used which receives sunflower oil devoid of 9-HODE. After eleven days of treatment, the fat mass is measured in the two groups.
- a skin penetration study is carried out in vitro on human skin with FRANZ cells. These cells comprise a surface of human skin of 1.76 cm 2 on which 800 ⁇ g of 9-HODE are deposited. After 6 hours of contact, a 9-HODE assay is carried out by gas chromatography on the surface of the sample of human skin, in the epidermis, in the dermis and in the receptor phase.
- 9-HODE therefore has significant skin penetrating power allowing it to act directly at the level of adipocytes.
- Clinical study evaluating the effectiveness of a cosmetic gel containing 0.5% of 9-HODE A clinical study is carried out in twenty women with excess fatty tissue in the thighs ("horse breeches"). The volunteers applied for a month, twice a day, a gel containing 0.5% of 9-HODE on each thigh. The efficiency criterion is the measurement of the thigh circumference on two levels.
- thermogenesis The difference in energy expenditure after treatment is statistically significant (p ⁇ 0.01). This increase in thermogenesis of almost 8% is particularly interesting for the treatment of obesity. 4863
- 9-HODE can be administered as an acid or as a triglyceride.
- 9-HODE is preferably administered in the form of free acid.
- 9-HODE can be administered as a dietary supplement in the form of capsules, tablets, oral solution, lozenges, chews, etc. and / or in food. You can use 9-HODE pure or diluted in creams, gels, sticks, ointments, etc.
- 9-HODE can be administered as a systemic or topical medication for the treatment of obesity.
- the administration doses are, for example, orally, 50 to 5,000 mg / day and locally, 0.1 to 100%.
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Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9901078 | 1999-01-29 | ||
FR9901078A FR2789085B1 (fr) | 1999-01-29 | 1999-01-29 | Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode), ou de ses esters a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters |
PCT/FR2000/000208 WO2000044863A1 (fr) | 1999-01-29 | 2000-01-28 | Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters |
Publications (1)
Publication Number | Publication Date |
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EP1147167A1 true EP1147167A1 (fr) | 2001-10-24 |
Family
ID=9541426
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Application Number | Title | Priority Date | Filing Date |
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EP00901675A Withdrawn EP1147167A1 (fr) | 1999-01-29 | 2000-01-28 | Procede d'obtention d'une huile enrichie en acides gras hydroxyoctadecadienoiques (hode) ou de ses esters, a partir d'un melange huileux contenant de l'acide linoleique, ou ses esters |
Country Status (17)
Country | Link |
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US (1) | US6348609B1 (fr) |
EP (1) | EP1147167A1 (fr) |
JP (1) | JP2002535479A (fr) |
KR (1) | KR20010102995A (fr) |
CN (1) | CN1342193A (fr) |
AU (1) | AU2299900A (fr) |
BR (1) | BR0007861A (fr) |
CA (1) | CA2325887A1 (fr) |
FR (1) | FR2789085B1 (fr) |
HK (1) | HK1043605A1 (fr) |
IL (1) | IL144573A0 (fr) |
MX (1) | MXPA01007680A (fr) |
NZ (1) | NZ513136A (fr) |
PL (1) | PL364225A1 (fr) |
RU (1) | RU2245358C2 (fr) |
WO (1) | WO2000044863A1 (fr) |
ZA (1) | ZA200106098B (fr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2844454B1 (fr) * | 2002-09-12 | 2006-05-19 | Marc Schwaller | Composition comprenant en association au moins une huile de courge et au moins une huile de bourrache,son utilisation comme medicament, comme agent dermatologique ou dermato-cosmetique |
MXPA05008216A (es) * | 2003-01-31 | 2005-10-05 | Procter & Gamble | Medios para mejorar la apariencia del tejido queratinoso mamifero. |
JP4348452B2 (ja) * | 2003-12-16 | 2009-10-21 | 独立行政法人産業技術総合研究所 | 酸化ストレスマーカー及びその測定法 |
JP4972745B2 (ja) * | 2005-06-22 | 2012-07-11 | 国立大学法人群馬大学 | Gタンパク質共役型受容体g2aの作動薬、及びg2a活性調節薬のスクリーニング方法 |
CN100548962C (zh) * | 2007-11-27 | 2009-10-14 | 江南大学 | 一种醇-水体系中还原制备羟基共轭亚油酸的方法 |
CN101613267B (zh) * | 2008-06-27 | 2012-08-29 | 中山市尤利卡天然药物有限公司 | 双羟基油酸及它的制备方法与用途 |
GB0814105D0 (en) * | 2008-08-01 | 2008-09-10 | Springdale Sustainable Develop | Composition for accelerated production of collagen |
US11304960B2 (en) * | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
SG186234A1 (en) | 2010-07-02 | 2013-01-30 | Helix Biomedix Inc | N-acyl amino acid derivatives for treating skin conditions such as cellulite |
US20130274333A1 (en) * | 2012-04-11 | 2013-10-17 | Versitech Limited | Coriolus versicolor extracts, methods of isolating biologically-active compounds, and uses thereof |
CN110054560A (zh) * | 2019-05-23 | 2019-07-26 | 河南农业大学 | 一种医药用木本α-亚麻酸的提纯方法及其应用 |
CN111568889A (zh) * | 2020-06-12 | 2020-08-25 | 四川大学华西医院 | 羟基十八碳二烯酸在制备α-葡萄糖苷酶抑制剂类药物的用途及其分离方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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AU546872B2 (en) * | 1982-06-16 | 1985-09-26 | Unilever Plc | Skin treatment compositions containing a fatty acid or ester |
JPH0710774B2 (ja) * | 1986-01-13 | 1995-02-08 | 株式会社ツムラ | アンジオテンシンi転換酵素阻害剤 |
DE59001796D1 (de) * | 1990-01-16 | 1993-07-22 | Boots Pharma Gmbh | Verwendung einer hydroxyoctadecadiensaeure, deren zur ketoform oxidierte saeure sowie deren derivate zur therapie oestrogenabhaengiger krankheiten, sowie pharmazeutische zusammensetzungen, die diese enthalten. |
-
1999
- 1999-01-29 FR FR9901078A patent/FR2789085B1/fr not_active Expired - Fee Related
-
2000
- 2000-01-28 IL IL14457300A patent/IL144573A0/xx unknown
- 2000-01-28 CN CN00804413A patent/CN1342193A/zh active Pending
- 2000-01-28 PL PL00364225A patent/PL364225A1/xx unknown
- 2000-01-28 AU AU22999/00A patent/AU2299900A/en not_active Abandoned
- 2000-01-28 KR KR1020017009451A patent/KR20010102995A/ko not_active Application Discontinuation
- 2000-01-28 CA CA002325887A patent/CA2325887A1/fr not_active Abandoned
- 2000-01-28 JP JP2000596108A patent/JP2002535479A/ja active Pending
- 2000-01-28 WO PCT/FR2000/000208 patent/WO2000044863A1/fr not_active Application Discontinuation
- 2000-01-28 NZ NZ513136A patent/NZ513136A/en unknown
- 2000-01-28 BR BR0007861-1A patent/BR0007861A/pt not_active Application Discontinuation
- 2000-01-28 RU RU2001123944/04A patent/RU2245358C2/ru not_active IP Right Cessation
- 2000-01-28 EP EP00901675A patent/EP1147167A1/fr not_active Withdrawn
- 2000-01-28 MX MXPA01007680A patent/MXPA01007680A/es active IP Right Grant
- 2000-01-28 US US09/647,474 patent/US6348609B1/en not_active Expired - Fee Related
-
2001
- 2001-07-25 ZA ZA200106098A patent/ZA200106098B/en unknown
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2002
- 2002-07-15 HK HK02105215.6A patent/HK1043605A1/zh unknown
Non-Patent Citations (1)
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See references of WO0044863A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU2299900A (en) | 2000-08-18 |
US6348609B1 (en) | 2002-02-19 |
HK1043605A1 (zh) | 2002-09-20 |
FR2789085B1 (fr) | 2003-06-20 |
ZA200106098B (en) | 2002-05-03 |
JP2002535479A (ja) | 2002-10-22 |
KR20010102995A (ko) | 2001-11-17 |
IL144573A0 (en) | 2002-05-23 |
MXPA01007680A (es) | 2003-06-24 |
CN1342193A (zh) | 2002-03-27 |
BR0007861A (pt) | 2001-10-23 |
NZ513136A (en) | 2003-08-29 |
RU2245358C2 (ru) | 2005-01-27 |
WO2000044863A1 (fr) | 2000-08-03 |
FR2789085A1 (fr) | 2000-08-04 |
PL364225A1 (en) | 2004-12-13 |
CA2325887A1 (fr) | 2000-08-03 |
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