ES2628178T3 - Procedimiento de producción de 9-decen-2-ona natural por bioconversión de ácido undecilénico con ayuda de un moho - Google Patents
Procedimiento de producción de 9-decen-2-ona natural por bioconversión de ácido undecilénico con ayuda de un moho Download PDFInfo
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- ES2628178T3 ES2628178T3 ES09757695.3T ES09757695T ES2628178T3 ES 2628178 T3 ES2628178 T3 ES 2628178T3 ES 09757695 T ES09757695 T ES 09757695T ES 2628178 T3 ES2628178 T3 ES 2628178T3
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- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 241000235545 Rhizopus niveus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
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- 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
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 238000011138 biotechnological process Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- NUQDJSMHGCTKNL-UHFFFAOYSA-N cyclohexyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1CCCCC1 NUQDJSMHGCTKNL-UHFFFAOYSA-N 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- JRPDANVNRUIUAB-UHFFFAOYSA-N dec-3-en-2-one Chemical compound CCCCCCC=CC(C)=O JRPDANVNRUIUAB-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000004864 galbanum Substances 0.000 description 1
- OALYTRUKMRCXNH-QMMMGPOBSA-N gamma-Nonalactone Natural products CCCCC[C@H]1CCC(=O)O1 OALYTRUKMRCXNH-QMMMGPOBSA-N 0.000 description 1
- 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 1
- 231100001261 hazardous Toxicity 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000007959 natural flavoring substance Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- ZZRQJJJPUWSDBN-UHFFFAOYSA-N pentyl 2-hydroxyacetate Chemical compound CCCCCOC(=O)CO ZZRQJJJPUWSDBN-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N trans-isoeugenol Chemical compound COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/29—Fruit flavours
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- Nutrition Science (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0853672A FR2931839B1 (fr) | 2008-06-03 | 2008-06-03 | Procede de production de la 9-decen-2-one naturelle par bioconversion de l'acide undecylenique a l'aide d'une moisissure et utilisation en parfumerie et aromatique alimentaire |
| FR0853672 | 2008-06-03 | ||
| PCT/FR2009/000646 WO2009147319A2 (fr) | 2008-06-03 | 2009-06-03 | Procede de production de la 9-decen-2-one naturelle par bioconversion de l'acide undecylenique a l'aide d'une moisissure et utilisation en parfumerie et aromatique alimentaire |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2628178T3 true ES2628178T3 (es) | 2017-08-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09757695.3T Active ES2628178T3 (es) | 2008-06-03 | 2009-06-03 | Procedimiento de producción de 9-decen-2-ona natural por bioconversión de ácido undecilénico con ayuda de un moho |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8481789B2 (enExample) |
| EP (1) | EP2297328B1 (enExample) |
| JP (2) | JP2011521664A (enExample) |
| KR (1) | KR101694672B1 (enExample) |
| CN (1) | CN102057047B (enExample) |
| BR (1) | BRPI0913339B1 (enExample) |
| DK (1) | DK2297328T3 (enExample) |
| ES (1) | ES2628178T3 (enExample) |
| FR (2) | FR2931839B1 (enExample) |
| MX (1) | MX2010013197A (enExample) |
| PL (1) | PL2297328T3 (enExample) |
| PT (1) | PT2297328T (enExample) |
| RU (1) | RU2542388C2 (enExample) |
| WO (1) | WO2009147319A2 (enExample) |
| ZA (1) | ZA201008529B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102703527A (zh) * | 2012-05-16 | 2012-10-03 | 深圳波顿香料有限公司 | 一种c5~c13的脂肪族甲基酮的制备方法 |
| JP2015534053A (ja) * | 2012-09-07 | 2015-11-26 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッドＴｈｅ Ｂｒｉｇｈａｍ ａｎｄ Ｗｏｍｅｎ’ｓ Ｈｏｓｐｉｔａｌ， Ｉｎｃ． | 侵襲性アスペルギルス症の診断及び治療 |
| GB201407383D0 (en) | 2014-04-28 | 2014-06-11 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2015187938A1 (en) | 2014-06-05 | 2015-12-10 | The Brigham And Women's Hospital, Inc. | Diagnosis and treatment of invasive aspergillosis |
| CA2992805A1 (en) * | 2015-08-07 | 2017-02-16 | V. Mane Fils | Composition comprising taste modulation compounds, their use and foodstuff comprising them |
| CN112021546B (zh) * | 2020-09-04 | 2022-07-01 | 恒枫食品科技有限公司 | 一种杏仁味香精的制备方法 |
| CN115590135B (zh) * | 2022-10-12 | 2024-04-26 | 恒枫食品科技有限公司 | 一种香精及其应用、含该香精的碳酸饮料 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5939822A (ja) * | 1982-08-31 | 1984-03-05 | Meiji Milk Prod Co Ltd | ω−アルケニルメチルケトンを含有する香料組成物 |
| US4832964A (en) * | 1987-10-22 | 1989-05-23 | Nestec S.A. | Preparation of a blue cheese flavour |
| JP2826748B2 (ja) * | 1988-09-09 | 1998-11-18 | 昭和産業株式会社 | 発酵法によるメチルケトン及び／またはその対応アルコールの製造法、及び培養液の使用 |
| FR2643647B1 (fr) * | 1989-02-27 | 1991-06-21 | Sanofi Sa | Procede microbiologique d'obtention de methylcetones |
| JPH03247291A (ja) * | 1990-02-27 | 1991-11-05 | Showa Sangyo Co Ltd | 発酵法によるメチルケトン及び／またはその対応アルコールの製造法、及び培養液の使用 |
| JPH04148688A (ja) * | 1990-10-09 | 1992-05-21 | Showa Sangyo Co Ltd | メチルケトンの製造方法 |
| JP4148688B2 (ja) | 2001-03-07 | 2008-09-10 | 株式会社リコー | マルチビーム走査装置 |
| FR2877340B1 (fr) * | 2004-11-03 | 2008-10-10 | Mane Fils Sa | Preparation stereoselective de gamma-lactones |
| FR2877339B1 (fr) * | 2004-11-03 | 2008-10-31 | Mane Fils Sa V | Gamma-undecenolactone, procede de preparation et utilisations |
-
2008
- 2008-06-03 FR FR0853672A patent/FR2931839B1/fr active Active
- 2008-12-18 FR FR0858747A patent/FR2931840A1/fr active Pending
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2009
- 2009-06-03 JP JP2011512171A patent/JP2011521664A/ja active Pending
- 2009-06-03 CN CN200980120746.3A patent/CN102057047B/zh active Active
- 2009-06-03 BR BRPI0913339A patent/BRPI0913339B1/pt active IP Right Grant
- 2009-06-03 US US12/995,289 patent/US8481789B2/en active Active
- 2009-06-03 PT PT97576953T patent/PT2297328T/pt unknown
- 2009-06-03 PL PL09757695T patent/PL2297328T3/pl unknown
- 2009-06-03 EP EP09757695.3A patent/EP2297328B1/fr active Active
- 2009-06-03 RU RU2010153903/10A patent/RU2542388C2/ru active
- 2009-06-03 MX MX2010013197A patent/MX2010013197A/es active IP Right Grant
- 2009-06-03 WO PCT/FR2009/000646 patent/WO2009147319A2/fr not_active Ceased
- 2009-06-03 DK DK09757695.3T patent/DK2297328T3/da active
- 2009-06-03 ES ES09757695.3T patent/ES2628178T3/es active Active
- 2009-06-03 KR KR1020107028601A patent/KR101694672B1/ko active Active
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2010
- 2010-11-29 ZA ZA2010/08529A patent/ZA201008529B/en unknown
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2015
- 2015-03-03 JP JP2015041171A patent/JP2015130873A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201008529B (en) | 2012-01-25 |
| BRPI0913339B1 (pt) | 2018-10-09 |
| WO2009147319A2 (fr) | 2009-12-10 |
| CN102057047B (zh) | 2015-06-17 |
| EP2297328A2 (fr) | 2011-03-23 |
| PL2297328T3 (pl) | 2017-10-31 |
| JP2011521664A (ja) | 2011-07-28 |
| RU2542388C2 (ru) | 2015-02-20 |
| PT2297328T (pt) | 2017-06-26 |
| BRPI0913339A2 (pt) | 2015-11-24 |
| WO2009147319A3 (fr) | 2010-04-08 |
| RU2010153903A (ru) | 2012-07-20 |
| US20110077431A1 (en) | 2011-03-31 |
| US8481789B2 (en) | 2013-07-09 |
| FR2931840A1 (fr) | 2009-12-04 |
| CN102057047A (zh) | 2011-05-11 |
| KR101694672B1 (ko) | 2017-01-10 |
| MX2010013197A (es) | 2011-03-21 |
| JP2015130873A (ja) | 2015-07-23 |
| EP2297328B1 (fr) | 2017-03-22 |
| FR2931839A1 (fr) | 2009-12-04 |
| FR2931839B1 (fr) | 2011-07-15 |
| DK2297328T3 (da) | 2017-07-03 |
| KR20110025918A (ko) | 2011-03-14 |
| HK1156985A1 (en) | 2012-06-22 |
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