ITMI20100691A1 - Composti dotati di attivita' antiossidante nei confronti dei radicali liberi, e composizioni farmaceutiche e cosmetiche che li contengono - Google Patents
Composti dotati di attivita' antiossidante nei confronti dei radicali liberi, e composizioni farmaceutiche e cosmetiche che li contengono Download PDFInfo
- Publication number
- ITMI20100691A1 ITMI20100691A1 IT000691A ITMI20100691A ITMI20100691A1 IT MI20100691 A1 ITMI20100691 A1 IT MI20100691A1 IT 000691 A IT000691 A IT 000691A IT MI20100691 A ITMI20100691 A IT MI20100691A IT MI20100691 A1 ITMI20100691 A1 IT MI20100691A1
- Authority
- IT
- Italy
- Prior art keywords
- composition according
- active principle
- compounds
- free radicals
- general formula
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 230000003078 antioxidant effect Effects 0.000 title claims description 11
- 239000002537 cosmetic Substances 0.000 title claims description 10
- IAAPVNQZSBLWKH-ICDJNDDTSA-N (2e,4e,6e)-octa-2,4,6-trienoic acid Chemical group C\C=C\C=C\C=C\C(O)=O IAAPVNQZSBLWKH-ICDJNDDTSA-N 0.000 claims description 13
- IAAPVNQZSBLWKH-UHFFFAOYSA-N octatrienoic acid Natural products CC=CC=CC=CC(O)=O IAAPVNQZSBLWKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 4
- 210000004761 scalp Anatomy 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000018977 lysine Nutrition 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 230000004962 physiological condition Effects 0.000 claims description 3
- 210000003491 skin Anatomy 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 150000008163 sugars Chemical class 0.000 claims description 3
- 210000002615 epidermis Anatomy 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 125000001176 L-lysyl group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 9
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- 239000003642 reactive oxygen metabolite Substances 0.000 description 6
- 239000002304 perfume Substances 0.000 description 5
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 4
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 4
- 239000002158 endotoxin Substances 0.000 description 4
- 229920006008 lipopolysaccharide Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 4
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
- NCZPCONIKBICGS-UHFFFAOYSA-N 3-(2-ethylhexoxy)propane-1,2-diol Chemical compound CCCCC(CC)COCC(O)CO NCZPCONIKBICGS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940071160 cocoate Drugs 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940100524 ethylhexylglycerin Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 229960005323 phenoxyethanol Drugs 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- TWAMIPJUDRVMJD-DFASFAQMSA-M potassium;(2e,4e,6e)-octa-2,4,6-trienoate Chemical compound [K+].C\C=C\C=C\C=C\C([O-])=O TWAMIPJUDRVMJD-DFASFAQMSA-M 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- XDFNWJDGWJVGGN-UHFFFAOYSA-N 2-(2,7-dichloro-3,6-dihydroxy-9h-xanthen-9-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1C2=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C21 XDFNWJDGWJVGGN-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 Diethylhexyl Chemical group 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 2
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 241001135917 Vitellaria paradoxa Species 0.000 description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 235000010389 delta-tocopherol Nutrition 0.000 description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000003859 lipid peroxidation Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000002248 lipoperoxidative effect Effects 0.000 description 2
- 229940100573 methylpropanediol Drugs 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229960001285 quercetin Drugs 0.000 description 2
- 235000005875 quercetin Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 2
- 239000002446 δ-tocopherol Substances 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- AAOFEMJZTYQZRH-UHFFFAOYSA-N 2-(1-butoxypropan-2-yloxy)ethanol Chemical compound CCCCOCC(C)OCCO AAOFEMJZTYQZRH-UHFFFAOYSA-N 0.000 description 1
- DWHIUNMOTRUVPG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCO DWHIUNMOTRUVPG-UHFFFAOYSA-N 0.000 description 1
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 description 1
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- 241001519274 Ajuga reptans Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 238000009010 Bradford assay Methods 0.000 description 1
- 235000005320 Coleus barbatus Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- 229920002884 Laureth 4 Polymers 0.000 description 1
- 241001072282 Limnanthes Species 0.000 description 1
- 241000144217 Limnanthes alba Species 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000131459 Plectranthus barbatus Species 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 229960005193 avobenzone Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940076810 beta sitosterol Drugs 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 1
- 229960002079 calcium pantothenate Drugs 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 description 1
- 229960001630 diethylamino hydroxybenzoyl hexyl benzoate Drugs 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 229940079868 disodium laureth sulfosuccinate Drugs 0.000 description 1
- GLSRFBDXBWZNLH-UHFFFAOYSA-L disodium;2-chloroacetate;2-(4,5-dihydroimidazol-1-yl)ethanol;hydroxide Chemical compound [OH-].[Na+].[Na+].[O-]C(=O)CCl.OCCN1CCN=C1 GLSRFBDXBWZNLH-UHFFFAOYSA-L 0.000 description 1
- YGAXLGGEEQLLKV-UHFFFAOYSA-L disodium;4-dodecoxy-4-oxo-2-sulfonatobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOC(=O)CC(C([O-])=O)S([O-])(=O)=O YGAXLGGEEQLLKV-UHFFFAOYSA-L 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ASAFWGADVGGPDB-HBJGMSRDSA-N ethyl (2e,4e,6e)-octa-2,4,6-trienoate Chemical compound CCOC(=O)\C=C\C=C\C=C\C ASAFWGADVGGPDB-HBJGMSRDSA-N 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000008524 evening primrose extract Nutrition 0.000 description 1
- 229940089020 evening primrose oil Drugs 0.000 description 1
- 239000010475 evening primrose oil Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 229940060384 isostearyl isostearate Drugs 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940061515 laureth-4 Drugs 0.000 description 1
- 229940031674 laureth-7 Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- OAIQHKWDTQYGOK-UHFFFAOYSA-L magnesium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O.CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O OAIQHKWDTQYGOK-UHFFFAOYSA-L 0.000 description 1
- 229940118019 malondialdehyde Drugs 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 108700019599 monomethylolglycine Proteins 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 229960000601 octocrylene Drugs 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940100460 peg-100 stearate Drugs 0.000 description 1
- 229940029223 peg-200 hydrogenated glyceryl palmate Drugs 0.000 description 1
- 229940086539 peg-7 glyceryl cocoate Drugs 0.000 description 1
- 229940057874 phenyl trimethicone Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229940047663 ppg-26-buteth-26 Drugs 0.000 description 1
- 210000004765 promyelocyte Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
- 229940096792 quaternium-15 Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 229940096501 sodium cocoamphoacetate Drugs 0.000 description 1
- 229940101011 sodium hydroxymethylglycinate Drugs 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- CITBNDNUEPMTFC-UHFFFAOYSA-M sodium;2-(hydroxymethylamino)acetate Chemical compound [Na+].OCNCC([O-])=O CITBNDNUEPMTFC-UHFFFAOYSA-M 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- DRTSUYUYJLRPLC-UHFFFAOYSA-M sodium;octa-2,4,6-trienoate Chemical compound [Na+].CC=CC=CC=CC([O-])=O DRTSUYUYJLRPLC-UHFFFAOYSA-M 0.000 description 1
- 229950011392 sorbitan stearate Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- RLNWRDKVJSXXPP-UHFFFAOYSA-N tert-butyl 2-[(2-bromoanilino)methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CNC1=CC=CC=C1Br RLNWRDKVJSXXPP-UHFFFAOYSA-N 0.000 description 1
- 229940061605 tetrasodium glutamate diacetate Drugs 0.000 description 1
- UZVUJVFQFNHRSY-OUTKXMMCSA-J tetrasodium;(2s)-2-[bis(carboxylatomethyl)amino]pentanedioate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CC[C@@H](C([O-])=O)N(CC([O-])=O)CC([O-])=O UZVUJVFQFNHRSY-OUTKXMMCSA-J 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- LINXHFKHZLOLEI-UHFFFAOYSA-N trimethyl-[phenyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=CC=CC=C1 LINXHFKHZLOLEI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- 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
- A61P17/18—Antioxidants, e.g. antiradicals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Description
Descrizione dell’invenzione industriale dal titolo
“Composti dotati di attività antiossidante nei confronti dei radicali liberi, e composizioni farmaceutiche e cosmetiche che li contengono†.
DESCRIZIONE
Oggetto della presente invenzione sono composti dotati di attività antiossidante nei confronti dei radicali lìberi, utili quali princìpi attivi per la preparazione di composizioni farmaceutiche o cosmetiche.
L’attività antiossidante nei confronti dei radicali liberi à ̈ stata ed à ̈ oggetto di numerosi studi sia in campo farmaceutico sia cosmetico. Ad esempio EP1328268 B1 della stessa Richiedente riguarda una composizione dotata di tale genere di attività svolta da determinati flavonoidi estratti dal vino rosso, in particolare una combinazione dei principi attivi quercetina e catechina formulata per uso orale, utile in svariate applicazioni in campo farmaceutico o nutrizionale o cosmetico essenzialmente basate su tale attività antiossidante nei confronti dei radicali liberi. Secondo la presente invenzione, si à ̈ ora sorprendentemente trovato che una rimarchevole attività antiossidante nei confronti dei radicali liberi à ̈ svolta da composti di formula generale (I):
CH3(-CH=CH)3-R (I)
in cui R à ̈ scelto tra CO-O-R’ oppure CO-O^, essendo R' scelto tra H, alchile o alchenile da Ci a C22, oppure zuccheri, e loro sali farmaceuticamente accettabili, quali preferibilmente sali di sodio, potassio, lisina.
Uno studio sperimentale riportato nel seguito della presente descrizione ha infatti sorprendentemente mostrato per i detti composti dell’invenzione che à ̈ possibile ottenere in modo rilevante tale attività antiossidante nei confronti dei radicali liberi. Oggetto dell’invenzione sono anche le composizioni farmaceutiche e cosmetiche che ne derivano, ciascun composto di formula generale (I) essendo usato in tali composizioni come tale oppure in miscela con gli altri.
L’invenzione pertanto si riferisce all’uso dei composti di formula (I) quali principi attivi per ogni applicazione terapeutica o cosmetica in cui tale attività antiossidante nei confronti dei radicali liberi produce un effetto vantaggioso. In particolare ci si riferisce alle applicazioni sulla cute e sullo scalpo umani per contrastare l'azione ossidante dei radicali liberi e preservare le condizioni fisiologiche dell’epidermide e dei capelli soggetti a tale azione.
Sono di seguito riportati dati di caratterizzazione e formule di alcuni dei composti preferiti di formula generale (I), riferiti all'acido ottatrienoico e suoi sali oppure esteri:
o
C8H10O2MW 138.17
2E,4E,6E-Octa-214,6-trienoic acid
CAS #: 5205-32-3
o
K
C8H902-K MW 176.26
2E,4E,6E-Octa-2,4,6-trienoic acid potassium salt
CAS #: 1147842-10-1
o
Na
C8H902-Na MW 160.15
2E,4E,6E-Octa-214I6-trienoic acid sodium salt
CAS #: not available
OH
NH 2
C8H9O2O6H15N2O2 MW 284.36
2E,4E,6E-Octa-2,4,6-trienoic acid L-lysine salt
CAS #: not available
o
C-10H14O2 MW 166.22
2E,4E,6E-Octa-2,4,6-trienoic acid ethyl ester
CAS #5941-49-1
Una composizione dell’invenzione à ̈ formulata preferibilmente per una somministrazione topica sulla pelle 0 sullo scalpo, e comprende detto principio attivo in quantità compresa nell’intervallo da 0.0003 a 0.0036 mol/100g.
Tale intervallo corrisponde a un intervallo da 0,04 a 0,6% in peso percentuale della composizione per l’acido ottatrienoico, oppure per il corrispondente sale di sodio, di potassio o per il corrispondente etilestere, mentre corrisponde a un intervallo da 0.11% a 1.4% in peso percentuale della composizione nel caso del corrispondente sale di lisina.
Seguono esempi, da non intendersi in alcun modo limitativi, di composizione adatta in particolare all’uso cosmetico ivi specificato.
Le quantità dei componenti, identificati secondo nomenclatura INCI, sono espresse come percentuali in peso variabili negli intervalli descritti:
Esempio 1
SHAMPOO
Componente (nome INCI) . Quantità p/p (%)
Disodium Laureth Sulfosuccinate . 1 ,00-5,00
Magnesium Laureth Sulfate . 5,00-9,00
PEG-7 Glyceryl Cocoate . 0,50-1,00 Cocamide MIPA . 0,50-2,00 PEG-200 Hydrogenated Glyceryl Palmate . 0,50-2,00 Polyquaternium-10 . 0,10-0,50 Tetrasodium EDTA . 0,05-0,20 Sodium Lauroyl Sarcosinate . 1,00-4,00 Tetrasodium EDTA . 0,05-0,20 Sodium octatrienoate . 0,048-0,6 BHA . 0,005-0,015 Potassium Undecilenoyl Wheat Protein . 0,50-1 ,00 Phenyl Trimethicone . 0,5-1 ,50 Silicone Quaternium-15 . 0,01-0,07 Laureth-4 . 0,01-0,80 Parfum . 0,10-0,80 Glycol Distearate . 0,50-1,00 Laureth-7 . 0,50-0,80 Sodium Cocoamphoacetate . 0,05-3,00 Cocamidopropyl Betaine . 0,01-2,00 Sodium Laureth Sulfate . 0.01-3,00 Sodium Hydroxymethylglycinate . 0,20-0,45 Benzoic acid . 0,005-0,10 Citric acid . q.b.
Aqua . q.b. 100,00
Esempio 2
PROTETTIVO SOLARE MEDIA PROTEZIONE
Componente (nome INCI) . Quantità p/p (%) Aqua . 40,00-60,00 C12-15 alkyl benzoate . 5,00-7,00 Ethylexyl methoxycinnamate . 3,00-7,00 Isostearil isostearate . 2,00-8,00 Styrene/Acrylates Copolymer . 1 ,00-5,00 Acrylates/C10-30 Alkyl Acrylate Crosspolymer . 0.05-0,70 Butylene glycol cocoate . 1 ,00-5,00 Butyl methoxydibenzoylmethane . 1,00-5,00 Diethylamino Hydroxybenzoyl Hexyl Benzoate . 1,00-5,00 Ethylhexyl Triazone . 1 ,00-5,00 Octocrylene . 1 ,00-5,00 Polyurethane - 34. 1 ,00-5,00 PPG-15 staeryl ether . 1 ,00-5,00 Diethylhexyl syringylidene maionate . 0,10-1,00 Sorbityl furfural . 0.05-0,10 Octatrienoic acid . 0,04-0,5 Quercetin . 0,001-0.005 Ethylhexylglycerin . 0,15-0,60 Coleus forskohlii root extrtact . 0,005-0,50 Polyperfluoroethoxymethoxy Difluoroethyl PEG Phosphate...0.2-1 ,50 Parfum . 0,1 -0,5 Phenoxyethanol . 0,80-1 ,00 Sodium Hydroxide . q.b
Esempio 3
LOZIONE ANTl CADUTA
Componente (nome INCI) . Quantità p/p (%) Alcohol denat . 10,00-30,00 Disodium EDTA . 0,025-0,20 Octatrienoic acid . 0,04-0,5 Biotin . 0,001-0,005 Parfum . 0,30
Ajuga reptans leaf extract . 0,01-0,05 Calcium pantothenate . 0,05-0,40 PEG-40 Hydrogenated Castor Oil . 0,20-1 ,00 Aqua . q.b. 100,00 Esempio 4
LATTE DOPO SOLE CORPO
Componente (nome INCI) . Quantità p/p (%) Glycerin . 1,00-6,00 Methylpropanediol . 1 ,00-6,00 Cetyl hydroxyethylceliulose . 0,10-0,40 Xanthan gum . 0,10-0,40 Tapioca starch . 1 ,00-2,00 Disodium EDTA . 0,025-0,20 Octatrienoic acid . 0,04-0,5 Sorbitan stearate . 2,00-5,00 Sucrose cocoate . 0,10-1,00 Ethyiexyl palmitate . 1 ,00-5,00 Hydrogenated polydecene . 100-5,00 Caprilic/capric triglycerides . 1 ,00-5,00 Butyrospermum parkii . 1 ,00-5,00 Meadowfoam (Limnanthes alba) seed oil . 1,00-3,00 Dimethicone . 1 ,00-3,00 Sodium hydroximethylgiycinate . 0-10-0,20 Phenoxyethanol . 0,70-0,90 Lactic acid . q.b.
Parfum . 0,30
Delta tocopherol . 0,02-0,25 Sorbityl furfural . 0,10-0,90 Aqua . q.b. 100,00
Esempio 5
CREMA VISO
Componente (nome INCI) . Quantità p/p (%) Glycerin . 2,00-5,00 Diglycerin . 0,20-2,00 Cetearyl alcohol . 0,20-2,50 Cetearyl glucoside . 0,20-2,50 PEG-100 Stearate . 0,20-1 ,00 Sorbityl furfural . 0,5-1 ,00 Tetrasodium Glutamate Diacetate . 0,10-0,50 Octatrienoic acid . 0,04-0,5 Palm butter . 0,50-3,00 Hydrogenated Evening Primrose Oil . 0,50-3,00 Octyldodecanol . 0,50-3,00 Hydrogenated castor oil . 1 ,00-4,00 Ethylhexyl cocoate . 1 ,00-4,00 Acrylates/C 10-30 Alkyl acrylate crosspolymer . 1,00-2,00 Butyrospermum parkii . 1,00-5,00 Beta sitosterol . 0,10-0,50 Delta tocoferol . 0,05-0,20 Dimethicone . 0,50-1,50 Dimethicone crosspolymer . 0,10-1,50 Ethylhexylglycerin . 0-25-0,50 Phenoxyethanol . 0,50-0,99 Parfum . q.b.
Aqua . q.b. 100,00
Esempio 6
STRUCCANTE LEAVE-ON
Componente (nome INCI) . Quantità p/p (%) Glycerin . 2,00-5,00 Ethylhexylglycerin . 0-25-0,50 Potassium octatrienoate . 0,05-0,6 Trehalose . 0,50-1,00 PPG-26 Buteth-26. 2,00-15,00 PEG-40 Hydrogenated Castor Oil . 2,00-15,00 Methylpropanediol . 1 ,00-6,00 Aqua . 60,00-80,00 Le figure 1 e 2 dei disegni allegati mostrano grafici tratti da uno studio sperimentale come di seguito descritto.
Studio sperimentale: valutazione in vitro degli effetti antiossidanti dei composti dell’invenzione
Scopo dello studio à ̈ stato quello di valutare in vitro la modulazione della produzione di ROS (Reactive oxygen species), oggetto della fig. 1, e la lipoperossidazione lipidica, oggetto della fig. 2, da parte dei seguenti composti dell'invenzione:
composto 1: acido 2E,4E,6E-ottatrienoico
composto 2: potassio 2E,4E,6E-ottatrienoato
composto 3: acido 2E,4E,6E-ottatrienoico sale di L-Lisina,
comparati con un controllo.
Modelli sperimentali
Sono stati utilizzati due sistemi cellulari: NCTC 2544, una linea di cheratinociti umani, e THP-1, una linea promielocitica umana. I risultati sono stati espressi come media ± deviazione standard. Ciascun esperimento à ̈ stato ripetuto almeno due volte.
Parametri valutati e risultati ottenuti
a) Modulazione della produzione di ROS
Tributilstagno (TBT) e lipopolisaccaride (LPS) sono utilizzati come induttori endogeni di specie radicaliche. La produzione di ROS Ã ̈ stata valutata mediante tecniche citofluorimetriche per la linea cellulare THP-1, utilizzando DCFH come colorante.
In esperimenti preliminari sono stati identificati i tempi e le concentrazioni ottimali per la misurazione citofluorimetrica dei ROS.
Come controllo positivo à ̈ stato utilizzato il derivato della vitamina E 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), alla concentrazione di 100 Î1⁄4Îœ.
Nel grafico di Figura 1 sono riportati i risultati ottenuti.
Le cellule THP-1 sono state trattate per 1 ora con i composti dell’invenzione 1 e 2 alla concentrazione di 100 pg/ml, con il composto 3 alla concentrazione di 200 Î1⁄49/ηηΙ e con Trolox 100 Î1⁄4Îœ in terreno senza siero, caricate negli ultimi 30 minuti con DCFH (10 Î1⁄4Îœ) e quindi trattate in presenza o in assenza di LPS (0.1 Î1⁄49/ιτιΙ) ed analizzate al citofluorimetro. Come si trae dal grafico, i composti dell'invenzione sono risultati in grado di annullare la produzione di ROS indotta da LPS 0.1 Î1⁄49/ιτιΙ in misura non inferiore al Trolox.
b) Lipoperossidazione lipidica
La perossidazione lipidica à ̈ stata valutata sulle cellule NCTC 2544 misurando il contenuto di malondialdeide, uno dei maggiori sottoprodotti della perossidazione lipidica, attraverso la sua reattività con l'acido tiobarbiturico. I risultati sono espressi come assorbanza/mg proteina. Il contenuto proteico à ̈ stato valutato mediante il metodo Bradford.
Le cellule NCTC sono state trattate per 24 ore in presenza o in assenza della concentrazione massima tollerata dei detti composti 1, 2, 3, e quindi stimolate con TBT 1-2.5 Î1⁄4Îœ per altre 24 ore.
Come controllo positivo à ̈ stato utilizzato Trolox 100 Î1⁄4Îœ.
Nel grafico di Figura 2 sono riportati i risultati ottenuti.
Come si vede, per le cellule trattate con i detti composti 1, 2, 3 una riduzione statisticamente significativa (p<0.05) della lipoperossidazìone indotta da TBT 2.5 Î1⁄4Îœ à ̈ stata osservata alle 24 ore, confermando l’effetto dell’invenzione.
Claims (14)
- RIVENDICAZIONI 1. Uso di composti di formula generale (I): CH3(-CH=CH)3-R (I) in cui R à ̈ scelto tra CO-O-R’ oppure CO-O^, essendo R' scelto tra H, alchile o alchenile da Ci a C22, oppure zuccheri, e loro sali farmaceuticamente accettabili, quali preferibilmente sali di sodio, potassio, lisina, ciascun composto di formula generale (I) essendo usato come tale oppure in miscela con uno o più degli altri, come principi attivi in una composizione farmaceutica o cosmetica dotata di attività antiossidante nei confronti dei radicali liberi.
- 2. Uso secondo la rivendicazione 1 per contrastare l'azione ossidante dei radicali liberi e preservare le condizioni fisiologiche deH’epidermide umana.
- 3. Uso secondo la rivendicazione 1 per contrastare l’azione ossidante dei radicali liberi sullo scalpo umano e preservare le condizioni fisiologiche dei capelli.
- 4. Uso di composti di formula generale (I): CH3(-CH=CH)3-R (I) in cui R à ̈ scelto tra CO-O-R’ oppure CO-O^, essendo R' scelto tra H, alchile o alchenile da Ci a C22, oppure zuccheri, e loro sali farmaceuticamente accettabili, quali preferibilmente sali di sodio, potassio, lisina, ciascun composto di formula generale (I) essendo usato come tale oppure in miscela con uno o più degli altri, per la preparazione di una composizione farmaceutica o cosmetica dotata di attività antiossidante nei confronti dei radicali liberi.
- 5. Composizione per un uso secondo una qualsiasi delle rivendicazioni precedenti in cui il detto principio attivo à ̈ un composto di formula generale (I) usato come tale oppure in miscela con uno o più degli altri composti.
- 6. Composizione secondo la rivendicazione 5 in cui il detto principio attivo à ̈ l’acido 2,4,6-ottatrienoico.
- 7. Composizione secondo la rivendicazione 5 in cui il detto principio attivo à ̈ un sale dell’acido 2,4,6-ottatrienoico.
- 8. Composizione secondo la rivendicazione 7 in cui il detto principio attivo à ̈ il sale sodico dell’acido 2,4,6-ottatrienoico.
- 9. Composizione secondo la rivendicazione 7 in cui il detto principio attivo à ̈ il sale di potassio dell’acido 2,4,6-ottatrienoico.
- 10. Composizione secondo la rivendicazione 7 in cui il detto principio attivo à ̈ il sale di L-lisina dell’acido 2,4,6-ottatrienoico.
- 11. Composizione secondo la rivendicazione 5 in cui il detto principio attivo à ̈ l’estere etilico dell’acido 2,4,6-ottatrienoico.
- 12. Composizione secondo la rivendicazione 5 in cui il detto principio attivo à ̈ una miscela di due o più dei composti di formula (I).
- 13. Composizione secondo una qualsiasi delle rivendicazioni precedenti comprendente detto principio attivo in quantità compresa nell’intervallo da 0.0003 a 0.0036 mol/100g.
- 14. Composizione secondo una qualsiasi delle rivendicazioni precedenti comprendente detto principio attivo formulato con ogni adatto eccipiente per somministrazione topica sulla pelle o sullo scalpo umani.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2010A000691A IT1401289B1 (it) | 2010-04-22 | 2010-04-22 | Composti dotati di attivita' antiossidante nei confronti dei radicali liberi, e composizioni farmaceutiche e cosmetiche che li contengono |
| PL11724766T PL2560632T3 (pl) | 2010-04-22 | 2011-04-22 | Związki o działaniu przeciwutleniającym przeciwko wolnym rodnikom oraz zawierające je kompozycje kosmetyczne |
| PCT/IB2011/051767 WO2011132177A1 (en) | 2010-04-22 | 2011-04-22 | Compounds provided with antioxidant activity against free radicals, and pharmaceutical and cosmetic compositions containing them |
| CA2796592A CA2796592C (en) | 2010-04-22 | 2011-04-22 | Compounds provided with antioxidant activity against free radicals, and pharmaceutical and cosmetic compositions containing them |
| US13/642,853 US9289405B2 (en) | 2010-04-22 | 2011-04-22 | Compounds provided with antioxidant activity against free radicals, and pharmaceutical and cosmetic compositions containing them |
| EP11724766.8A EP2560632B1 (en) | 2010-04-22 | 2011-04-22 | Compounds provided with antioxidant activity against free radicals, and cosmetic compositions containing them |
| ES11724766.8T ES2528446T3 (es) | 2010-04-22 | 2011-04-22 | Compuestos provistos de actividad antioxidante contra radicales libres, y composiciones cosméticas que los contienen |
| JP2013505596A JP2013525342A (ja) | 2010-04-22 | 2011-04-22 | フリーラジカルに対する抗酸化活性を備えた化合物、およびそれらを含有する医薬および化粧品組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2010A000691A IT1401289B1 (it) | 2010-04-22 | 2010-04-22 | Composti dotati di attivita' antiossidante nei confronti dei radicali liberi, e composizioni farmaceutiche e cosmetiche che li contengono |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ITMI20100691A1 true ITMI20100691A1 (it) | 2011-10-23 |
| IT1401289B1 IT1401289B1 (it) | 2013-07-18 |
Family
ID=42669798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ITMI2010A000691A IT1401289B1 (it) | 2010-04-22 | 2010-04-22 | Composti dotati di attivita' antiossidante nei confronti dei radicali liberi, e composizioni farmaceutiche e cosmetiche che li contengono |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9289405B2 (it) |
| EP (1) | EP2560632B1 (it) |
| JP (1) | JP2013525342A (it) |
| CA (1) | CA2796592C (it) |
| ES (1) | ES2528446T3 (it) |
| IT (1) | IT1401289B1 (it) |
| PL (1) | PL2560632T3 (it) |
| WO (1) | WO2011132177A1 (it) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2407163A1 (en) * | 2010-07-16 | 2012-01-18 | Giuliani S.p.A. | Compounds with a skin pigmenting activity and pharmaceutical or cosmetic compositions containing them |
| DE102011086633A1 (de) * | 2011-11-18 | 2013-05-23 | Henkel Ag & Co. Kgaa | Haarpflegemittel mit Riechstoffen und kationischen Silikonen |
| ITMI20131475A1 (it) | 2013-09-06 | 2015-03-07 | Giuliani Spa | Composizioni utili nella prevenzione e terapia dei tumori della pelle |
| EP3116849B1 (en) | 2014-03-10 | 2018-07-25 | Giuliani S.p.A. | Compounds with a combined antioxidant activity against free radicals together with an anti-inflammatory action, and pharmaceutical and cosmetic compositions containing them for the treatment of skin and hair |
| GB2537647A (en) | 2015-04-22 | 2016-10-26 | Cosmetic Warriors Ltd | Composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050175555A1 (en) * | 2002-05-07 | 2005-08-11 | Riccardo Stradi | Polyunsaturated linear aldehydes and their derivatives with anti-radical and anti-tumoral activity |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1320080B1 (it) | 2000-10-25 | 2003-11-18 | Giuliani Spa | Composizione per uso farmaceutico o dietetico. |
| IT1391663B1 (it) * | 2008-11-10 | 2012-01-17 | Giuliani Spa | Uso di composti atti ad inibire l' attivita' dell'enzima 5alfa-reduttasi e composizioni farmaceutiche e cosmetiche che li contengono |
-
2010
- 2010-04-22 IT ITMI2010A000691A patent/IT1401289B1/it active
-
2011
- 2011-04-22 JP JP2013505596A patent/JP2013525342A/ja active Pending
- 2011-04-22 EP EP11724766.8A patent/EP2560632B1/en active Active
- 2011-04-22 US US13/642,853 patent/US9289405B2/en active Active
- 2011-04-22 ES ES11724766.8T patent/ES2528446T3/es active Active
- 2011-04-22 PL PL11724766T patent/PL2560632T3/pl unknown
- 2011-04-22 CA CA2796592A patent/CA2796592C/en active Active
- 2011-04-22 WO PCT/IB2011/051767 patent/WO2011132177A1/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050175555A1 (en) * | 2002-05-07 | 2005-08-11 | Riccardo Stradi | Polyunsaturated linear aldehydes and their derivatives with anti-radical and anti-tumoral activity |
Non-Patent Citations (1)
| Title |
|---|
| MUKHERJEE, SUBHENDU ET AL: "Cardioprotection with the Parrodiene 2,4,6-Octatrienal and Its Potassium Salt through Activation of the Akt-Bcl-2 Survival Pathway", JOURNAL OF NATURAL PRODUCTS , 72(5), 871-875 CODEN: JNPRDF; ISSN: 0163-3864, 2009, XP002599834 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011132177A1 (en) | 2011-10-27 |
| EP2560632A1 (en) | 2013-02-27 |
| PL2560632T3 (pl) | 2015-05-29 |
| IT1401289B1 (it) | 2013-07-18 |
| CA2796592A1 (en) | 2011-10-27 |
| CA2796592C (en) | 2018-08-07 |
| US20130046017A1 (en) | 2013-02-21 |
| EP2560632B1 (en) | 2014-10-29 |
| US9289405B2 (en) | 2016-03-22 |
| ES2528446T3 (es) | 2015-02-10 |
| JP2013525342A (ja) | 2013-06-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2683296T3 (es) | Composición a base de flavonoides para uso farmacéutico, nutricional o cosmético con acción antioxidante potenciada | |
| JP5693459B2 (ja) | 出穂前に収穫されたエンバク地上部の抽出物 | |
| US20050048008A1 (en) | Antiaging Cosmetic Delivery Systems | |
| JPWO2004016236A1 (ja) | 化粧料 | |
| US8501162B2 (en) | Compositions and methods for the skin and hair | |
| CA2796592C (en) | Compounds provided with antioxidant activity against free radicals, and pharmaceutical and cosmetic compositions containing them | |
| CN109453087B (zh) | 美白透肌水及其制备方法和美白化妆品添加剂 | |
| KR101425031B1 (ko) | 유자씨 및 망고씨 혼합오일을 함유하는 피부 자극완화 및 피부보습용 화장료 조성물 | |
| WO2024066643A1 (zh) | 一种防晒组合物及其应用 | |
| ES2743205T3 (es) | Composiciones cosméticas que contienen una preparación de cultivo celular de mora ártica | |
| KR101317430B1 (ko) | 진달래꽃, 사과꽃 및 함박꽃 추출물을 함유하는 보습 및 진정 화장용 조성물 | |
| CN109453088B (zh) | 美白紧致霜及其制备方法和酪氨酸酶抑制剂 | |
| ES2744173T3 (es) | Combinación de vitamina C y de ácido hialurónico para el tratamiento de los efectos del envejecimiento cutáneo | |
| KR101934793B1 (ko) | 고욤나무 잎 추출물을 유효성분으로 함유하는 피부 광노화 예방 또는 개선용 조성물 | |
| KR101063147B1 (ko) | 진세노사이드 Ｒｏ(ｇｉｎｓｅｎｏｓｉｄｅ Ｒｏ)를함유하는 조성물 | |
| KR102348707B1 (ko) | 도세탁셀 또는 이의 약학적으로 허용가능한 염을 포함하는 피부 탄력, 주름개선, 보습 또는 항염증용 화장료 또는 약학 조성물 | |
| ES2638298T3 (es) | Complejo de extractos vegetales para la protección de la piel | |
| KR20170076356A (ko) | 제니핀-1-베타-d-젠티오비오사이드를 포함하는 피부상태 개선용 조성물 | |
| ES2631191B1 (es) | Composición para la protección solar y reparación de la piel mediante complejos protectores | |
| ITMI20110503A1 (it) | Composizioni cosmetiche e dermatologiche comprendenti estratti di rhus coriaria | |
| JP2023102221A (ja) | 皮膚外用剤 | |
| KR101637935B1 (ko) | 숙근 천인국 추출물을 함유하는 피부 상태 개선용 조성물 | |
| JP2024077661A (ja) | 皮膚化粧料組成物 | |
| RO126912A0 (ro) | Compoziţie cremă antiîmbătrânire () multifuncţională | |
| ITMI20131159A1 (it) | Composizione cosmetica utile per il trattamento antieta' della pelle |