RU2015127022A - Композиция на основе флавоноидов для фармацевтического, диетического или косметического применения, обладающая усиленным антиоксидантным действием - Google Patents
Композиция на основе флавоноидов для фармацевтического, диетического или косметического применения, обладающая усиленным антиоксидантным действием Download PDFInfo
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- RU2015127022A RU2015127022A RU2015127022A RU2015127022A RU2015127022A RU 2015127022 A RU2015127022 A RU 2015127022A RU 2015127022 A RU2015127022 A RU 2015127022A RU 2015127022 A RU2015127022 A RU 2015127022A RU 2015127022 A RU2015127022 A RU 2015127022A
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- Prior art keywords
- extract
- seeds
- composition according
- catechin
- range
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- 239000000203 mixture Substances 0.000 title claims 35
- 229930003935 flavonoid Natural products 0.000 title claims 11
- 235000017173 flavonoids Nutrition 0.000 title claims 11
- 230000003078 antioxidant effect Effects 0.000 title claims 5
- 150000002215 flavonoids Chemical class 0.000 title claims 3
- 239000002537 cosmetic Substances 0.000 title claims 2
- 239000000284 extract Substances 0.000 claims 21
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 claims 18
- REFJWTPEDVJJIY-UHFFFAOYSA-N quercetin Natural products C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims 18
- 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 claims 14
- 235000005487 catechin Nutrition 0.000 claims 14
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims 14
- 229950001002 cianidanol Drugs 0.000 claims 14
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims 14
- 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 claims 13
- 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 claims 13
- 235000005875 quercetin Nutrition 0.000 claims 13
- 229960001285 quercetin Drugs 0.000 claims 13
- 240000006365 Vitis vinifera Species 0.000 claims 11
- 235000014787 Vitis vinifera Nutrition 0.000 claims 11
- 235000002532 grape seed extract Nutrition 0.000 claims 11
- 235000003248 hydroxytyrosol Nutrition 0.000 claims 9
- 229940095066 hydroxytyrosol Drugs 0.000 claims 9
- -1 quercetin flavonoids Chemical class 0.000 claims 8
- 240000007817 Olea europaea Species 0.000 claims 5
- 230000000699 topical effect Effects 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 229920002770 condensed tannin Polymers 0.000 claims 4
- 235000002725 Olea europaea Nutrition 0.000 claims 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 3
- 229940114496 olive leaf extract Drugs 0.000 claims 3
- 239000011669 selenium Substances 0.000 claims 3
- 229910052711 selenium Inorganic materials 0.000 claims 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 2
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims 2
- 235000013824 polyphenols Nutrition 0.000 claims 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 claims 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims 1
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 claims 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 claims 1
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- DBLDQZASZZMNSL-QMMMGPOBSA-N L-tyrosinol Natural products OC[C@@H](N)CC1=CC=C(O)C=C1 DBLDQZASZZMNSL-QMMMGPOBSA-N 0.000 claims 1
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 claims 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 1
- 229930003427 Vitamin E Natural products 0.000 claims 1
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 claims 1
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 claims 1
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229940074360 caffeic acid Drugs 0.000 claims 1
- 235000004883 caffeic acid Nutrition 0.000 claims 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 229940108928 copper Drugs 0.000 claims 1
- 235000015872 dietary supplement Nutrition 0.000 claims 1
- 235000015428 diosmetin Nutrition 0.000 claims 1
- MBNGWHIJMBWFHU-UHFFFAOYSA-N diosmetin Chemical compound C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 MBNGWHIJMBWFHU-UHFFFAOYSA-N 0.000 claims 1
- 229960001876 diosmetin Drugs 0.000 claims 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims 1
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- 235000009498 luteolin Nutrition 0.000 claims 1
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 claims 1
- 235000011576 oleuropein Nutrition 0.000 claims 1
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 claims 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims 1
- 235000005493 rutin Nutrition 0.000 claims 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 claims 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims 1
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- 239000000126 substance Substances 0.000 claims 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 claims 1
- 235000004330 tyrosol Nutrition 0.000 claims 1
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Classifications
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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Claims (55)
1. Композиция для фармацевтического применения, обладающая антиоксидантной активностью против свободных радикалов, содержащая:
a) экстракт семян или семян и листьев Vitis vinifera, содержащий комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 6:1 до 3:1, или
а') экстракт семян или семян и листьев Vitis vinifera, содержащий комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 4:1, или
а'') смесь экстрактов Vitis vinifera а) и а'), или
а''') смесь катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 3:1,
вместе с
b) экстрактом листьев маслин Olea europaea L., содержащим гидрокситирозол в количестве в диапазоне от 1% до 30% по массе экстракта, или
b') гидрокситирозол в количестве, равном количеству, содержащемуся в экстракте b).
2. Композиция по п. 1, отличающаяся тем, что указанная композиция выбрана из следующих:
а)+b);
а')+b);
а'')+b);
а''')+b);
а)+b');
а')+b');
а'')+b');
а''')+b').
3. Композиция по п. 2, отличающаяся тем, что представляет собой а'')+b) или а'')+b'), в которой катехин и кверцетин присутствуют в молярном соотношении в диапазоне, соответственно, от 7:1 до 3:1.
4. Композиция по п. 1, отличающаяся тем, что указанный экстракт b) листьев маслин Olea europaea L. содержит гидрокситирозол в количестве, по меньшей мере, 10%.
5. Композиция по п. 1, отличающаяся тем, что композиция, содержащая b'),
содержит гидрокситирозол в количестве, по меньшей мере, 10%.
6. Композиция по п. 1, отличающаяся тем, что указанный экстракт b) листьев маслин содержит следующие флавоноиды с соответствующим процентным содержанием в пересчете на абсолютно сухое вещество (% d.s.):
7. Композиция по п. 1, отличающаяся тем, что указанный экстракт а) семян или семян и листьев Vitis vinifera содержит комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 6:1 до 3:1, общее содержание полифенолов составляет выше 60% и олигомерных проантоцианидинов (ОРС) от 15% до 20%, при этом указанный экстракт получен при помощи экстрагирующего раствора, представляющего собой смесь этанол/вода.
8. Композиция по п. 1, отличающаяся тем, что указанный экстракт а') семян или семян и листьев Vitis vinifera, содержащий комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 4:1, представляет собой сухой экстракт, имеющий общее содержание полифенолов выше 95% и олигомерных проантоцианидинов (ОРС) выше 30%, при этом экстрагирующим раствором является смесь этанол/вода.
9. Композиция по п. 1, отличающаяся тем, что в указанных а), а'), а''), а''') комбинация флавоноидов катехина и кверцетина присутствует в молярном соотношении, равном приблизительно 5:1 соответственно.
10. Композиция по п. 1, отличающаяся тем, что содержит селен.
11. Композиция по п. 10, отличающаяся тем, что содержит селен в форме
обогащенных селеном дрожжей.
12. Композиция по п. 1, отличающаяся тем, что содержит, по меньшей мере, один антиоксидант, выбранный из цеаксантина, рутина, аскорбиновой кислоты, витамина Е, цинка, меди.
13. Композиция по п. 1, отличающаяся тем, что изготовлена для перорального применения.
14. Композиция по п. 1, отличающаяся тем, что изготовлена для местного применения.
15. Композиция по п. 14, отличающаяся тем, что изготовлена для местного нанесения на кожу.
16. Композиция по п. 14, отличающаяся тем, что изготовлена для местного нанесения на волосы.
17. Косметическое применение композиции для обеспечения антиоксидантной активности против свободных радикалов, отличающееся тем, что композиция содержит:
a) экстракт семян или семян и листьев Vitis vinifera, содержащий комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 6:1 до 3:1, или
а') экстракт семян или семян и листьев Vitis vinifera, содержащий комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 4:1, или
а'') смесь экстрактов Vitis vinifera а) и а'), или
а''') смесь катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 3:1,
вместе с
b) экстрактом листьев маслин Olea europaea L., содержащим гидрокситирозол в количестве в диапазоне от 1% до 30% по массе экстракта, или
b') гидрокситирозол в количестве, равном количеству, содержащемуся в экстракте b).
18. Применение композиции в качестве пищевой диетической добавки для обеспечения антиоксидантной активности против свободных радикалов, отличающееся тем, что композиция содержит:
а) экстракт семян или семян и листьев Vitis vinifera, содержащий комбинацию флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 6:1 до 3:1, или
а') экстракт семян или семян и листьев Vitis vinifera, содержащий комбинацию
флавоноидов катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 4:1, или
а'') смесь экстрактов Vitis vinifera а) и а'), или
а''') смесь катехина и кверцетина в молярном соотношении в диапазоне, соответственно, от 7:1 до 3:1,
вместе с
b) экстрактом листьев маслин Olea europaea L., содержащим гидрокситирозол в количестве в диапазоне от 1% до 30% по массе экстракта, или
b') гидрокситирозол в количестве, равном количеству, содержащемуся в экстракте b).
19. Применение по пп. 17 и 18, отличающееся тем, что композиция изготовлена для перорального применения.
20. Применение по п. 17, отличающееся тем, что композиция изготовлена для местного применения.
21. Композиция по п. 20, отличающаяся тем, что изготовлена для местного нанесения на кожу.
22. Композиция по п. 20, отличающаяся тем, что изготовлена для местного нанесения на волосы.
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IT000397A ITMI20130397A1 (it) | 2013-03-15 | 2013-03-15 | Composizione a base di flavonidi per uso farmaceutico, nutrizionale o cosmetico con potenziata azione antiossidante |
ITMI2013A000397 | 2013-03-15 | ||
PCT/EP2014/055162 WO2014140312A1 (en) | 2013-03-15 | 2014-03-14 | Flavonoid-based composition for pharmaceutical, nutritional or cosmetic use having potentiated antioxidant action |
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RU2015127022A RU2640915C2 (ru) | 2013-03-15 | 2014-03-14 | Композиция на основе флавоноидов для фармацевтического, диетического или косметического применения, обладающая усиленным антиоксидантным действием |
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ES (1) | ES2683296T3 (ru) |
HR (1) | HRP20181362T1 (ru) |
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JP6033382B1 (ja) | 2015-10-01 | 2016-11-30 | 小豆島ヘルシーランド株式会社 | オリーヴ葉エキス及びその製造方法 |
CN105726556A (zh) * | 2016-03-23 | 2016-07-06 | 中国科学院兰州化学物理研究所 | 一种具有降血脂作用的组合物 |
US10485745B2 (en) * | 2016-04-29 | 2019-11-26 | L'oreal | UV-A/UV-B sunscreen composition |
KR20200005595A (ko) * | 2017-12-15 | 2020-01-15 | 쯔카사 나가오 | 항노화 건강식품 및 화장품과 포도 종자 유래 항노화 성분의 제조 방법 |
ES2689105B8 (es) * | 2018-04-30 | 2019-05-28 | Monteloeder S L | Composición de extractos vegetales con flavonoides para paliar los múltiples efectos de la contaminación del aire sobre la piel |
IT201900015018A1 (it) * | 2019-08-26 | 2021-02-26 | Epitech Group S P A | Composizione di n-palmitoil-etanolamide e rutina in forma comicronizzata |
US11583480B2 (en) | 2019-08-27 | 2023-02-21 | L'oreal | Sunscreen composition with a high UV filter load |
IT202000015493A1 (it) | 2020-06-26 | 2021-12-26 | Fondazione St Italiano Tecnologia | Estratto di vinacce di uva bianca di vitis vinifera, relative composizioni e usi |
WO2024028283A1 (en) * | 2022-08-03 | 2024-02-08 | Nanomol Technologies, S.L. | Vesicles based on glucose-derived surfactants and phytosterols |
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FR2883884B1 (fr) * | 2005-03-30 | 2012-11-09 | Lallemand Sas | Preparation de levures a proprietes anti-oxydantes ameliorees et leurs applications |
EP1790234B1 (en) * | 2005-11-28 | 2014-07-02 | Chr. Hansen A/S | Natural antioxidant additive for feed and drinking water |
FR2942224B1 (fr) * | 2009-02-18 | 2012-11-30 | Centre De Cooperation Internationale En Rech Agronomique Pour Le Developpement Cirad | Procede d'extraction de composes phenoliques a partir d'eau de vegetation de l'olive et preparation d'extrait titre en polyphenols d'olive et de raisin |
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PL2968428T3 (pl) | 2018-11-30 |
MX363219B (es) | 2019-03-15 |
EP2968428A1 (en) | 2016-01-20 |
EP2968428B1 (en) | 2018-05-30 |
RS57563B1 (sr) | 2018-10-31 |
KR20150127578A (ko) | 2015-11-17 |
BR112015019578A2 (pt) | 2017-07-18 |
WO2014140312A1 (en) | 2014-09-18 |
CY1120628T1 (el) | 2019-12-11 |
AU2014230124B2 (en) | 2018-07-12 |
HRP20181362T1 (hr) | 2018-10-19 |
HUE039977T2 (hu) | 2019-02-28 |
ES2683296T3 (es) | 2018-09-26 |
CA2897262C (en) | 2021-03-02 |
PT2968428T (pt) | 2018-10-24 |
ITMI20130397A1 (it) | 2014-09-16 |
US9808498B2 (en) | 2017-11-07 |
KR102213351B1 (ko) | 2021-02-08 |
AU2014230124A1 (en) | 2015-07-23 |
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