JP6216769B2 - 微細藻類により産生されるスクアレンを精製する方法 - Google Patents

微細藻類により産生されるスクアレンを精製する方法 Download PDF

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Publication number
JP6216769B2
JP6216769B2 JP2015506284A JP2015506284A JP6216769B2 JP 6216769 B2 JP6216769 B2 JP 6216769B2 JP 2015506284 A JP2015506284 A JP 2015506284A JP 2015506284 A JP2015506284 A JP 2015506284A JP 6216769 B2 JP6216769 B2 JP 6216769B2
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Prior art keywords
squalene
composition
biomass
extract
supercritical
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Expired - Fee Related
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JP2015506284A
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Japanese (ja)
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JP2015516152A (ja
JP2015516152A5 (enExample
Inventor
ローテン，フィリップ
パティニール，サミュエル
ペリュ，ミシェル
ペリュ，ヴァンサン
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Roquette Freres SA
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Roquette Freres SA
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Publication of JP2015516152A5 publication Critical patent/JP2015516152A5/ja
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    • 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
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/60—Edible seaweed
    • 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
    • C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
    • C12P5/02—Preparation of hydrocarbons or halogenated hydrocarbons acyclic
    • 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
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61K31/01—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/02—Algae
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9706—Algae
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9706—Algae
    • A61K8/9711—Phaeophycota or Phaeophyta [brown algae], e.g. Fucus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
    • B01D3/40—Extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
    • C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/12—Unicellular algae; Culture media therefor
    • 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
    • C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
    • C12P5/007—Preparation of hydrocarbons or halogenated hydrocarbons containing one or more isoprene units, i.e. terpenes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/10—Preparation or pretreatment of starting material
    • A61K2236/19—Preparation or pretreatment of starting material involving fermentation using yeast, bacteria or both; enzymatic treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/37—Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/85—Products or compounds obtained by fermentation, e.g. yoghurt, beer, wine
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/86—Products or compounds obtained by genetic engineering
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Epidemiology (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Birds (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Water Supply & Treatment (AREA)
  • Analytical Chemistry (AREA)
  • Cell Biology (AREA)
  • Toxicology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
JP2015506284A 2012-04-16 2013-04-15 微細藻類により産生されるスクアレンを精製する方法 Expired - Fee Related JP6216769B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR1253496A FR2989373B1 (fr) 2012-04-16 2012-04-16 Procede de raffinage du squalene produit par microalgues
FR1253496 2012-04-16
FR1253614 2012-04-19
FR1253614 2012-04-19
PCT/FR2013/050812 WO2013156720A2 (fr) 2012-04-16 2013-04-15 Procédé de raffinage du squalène produit par microalgues

Publications (3)

Publication Number Publication Date
JP2015516152A JP2015516152A (ja) 2015-06-11
JP2015516152A5 JP2015516152A5 (enExample) 2017-06-22
JP6216769B2 true JP6216769B2 (ja) 2017-10-18

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JP2015506284A Expired - Fee Related JP6216769B2 (ja) 2012-04-16 2013-04-15 微細藻類により産生されるスクアレンを精製する方法

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Country Link
US (1) US9346722B2 (enExample)
EP (1) EP2838630A2 (enExample)
JP (1) JP6216769B2 (enExample)
KR (1) KR102192410B1 (enExample)
CN (2) CN105296552A (enExample)
CA (1) CA2869358C (enExample)
IN (1) IN2014DN08554A (enExample)
WO (1) WO2013156720A2 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2523546Y2 (ja) 1991-07-01 1997-01-29 本田技研工業株式会社 傘歯車用把持装置

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CA2397655C (en) 2000-01-19 2012-06-05 Craig M. Ruecker Solventless extraction process
EP2576801B1 (en) 2010-06-01 2019-10-02 DSM IP Assets B.V. Extraction of lipid from cells and products therefrom
CN102787140A (zh) 2011-05-20 2012-11-21 罗盖特兄弟公司 从微藻制备与提取角鲨烯的工艺方法
CN102787074B (zh) 2011-05-20 2016-06-08 罗盖特兄弟公司 生产角鲨烯的微藻新菌株
FR2975705B1 (fr) * 2011-05-27 2014-12-26 Roquette Freres Procede d'extraction du squalene a partir de microalgues
BR112016014517B1 (pt) 2013-12-20 2022-06-28 Dsm Ip Assets B.V. Processo para a obtenção de um óleo microbiano compreendendo um ou mais ácidos graxos poli-insaturados de uma ou mais células microbianas
JP2017500037A (ja) 2013-12-20 2017-01-05 ディーエスエム アイピー アセッツ ビー．ブイ． 微生物細胞から微生物油を入手するための方法
AU2014369042B2 (en) 2013-12-20 2020-04-30 Dsm Ip Assets B.V. Processes for obtaining microbial oil from microbial cells
AR098893A1 (es) 2013-12-20 2016-06-22 Dsm Ip Assets Bv Proceso para obtener aceite microbiano a partir de células microbianas
WO2015095696A1 (en) * 2013-12-20 2015-06-25 Dsm Ip Assets B.V. Processes for obtaining microbial oil from microbial cells
EP3307701A4 (en) * 2015-06-15 2019-01-30 White Dog Labs, Inc. METHOD FOR MANUFACTURING ONE OR MORE OIL-SOLUBLE BIOLOGICAL PRODUCTS
JP6992057B2 (ja) 2016-06-10 2022-01-13 クラリティ コスメティックス インコーポレイテッド 非面皰形成性の毛髪および頭皮ケア製剤ならびにその使用方法
CN106588542A (zh) * 2016-12-27 2017-04-26 宁波大红鹰生物工程股份有限公司 一种植物角鲨烯浓缩液及其制备方法
FR3077994B1 (fr) * 2018-02-22 2020-02-28 IFP Energies Nouvelles Separation selective des impuretes presentes dans une coupe hydroalcoolique par recyclage dans une colonne d'extraction liquide-liquide
CN110643420A (zh) * 2019-11-13 2020-01-03 贵州航天乌江机电设备有限责任公司 一种从毛叶山桐子中提取油并精炼的工艺
CN112426739A (zh) * 2020-10-16 2021-03-02 安庆缘启医药科技有限公司 一种分子蒸馏提取抗癌药物的制备工艺
CN113956125B (zh) * 2021-11-11 2022-10-11 宜春大海龟生命科学有限公司 一种植物角鲨烷的组合物及其制备方法和应用
CN120230606A (zh) * 2025-04-28 2025-07-01 大理农林职业技术学院 脂溶性迷迭香提取物在核桃油保鲜中的应用及其制备方法

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FR2584618B1 (fr) 1985-07-09 1989-11-24 Elf Aquitaine Dispositif pour la mise en oeuvre de procedes d'extraction-separation-fractionnement par fluides supercritiques
DE4137733A1 (de) * 1991-11-15 1993-05-19 Mueller Extract Co Gmbh Verfahren und vorrichtung zur herstellung von squalen aus olivenoel-rueckstaenden
DE4316620A1 (de) 1993-05-18 1994-11-24 Mueller Extract Co Gmbh Verfahren und Vorrichtung zur Herstellung von Squalen aus Olivenölrückständen
FR2803598B1 (fr) 2000-01-12 2002-04-26 Pharmascience Lab Procede d'extraction des insaponifiables des huiles vegetales au moyen de chloro-1-butane, composition comprenant ces insaponifiables
DE10031994A1 (de) * 2000-06-30 2002-01-10 Cognis Deutschland Gmbh Verfahren zur Herstellung von Squalen
MY142319A (en) * 2002-08-20 2010-11-15 Malaysian Palm Oil Board Mpob Extraction of palm vitamin e, phytosterols and squalene from palm oil
MY138963A (en) 2003-08-27 2009-08-28 Malaysian Palm Oil Board One-stage and two-stage supercritical fluid extractions of carotenes concentrate, vitamin e concentrate and other minor components concentrates
ES2238183B1 (es) * 2004-02-09 2006-12-16 Consejo Sup. Investig. Cientificas Procedimiento para obtener compuestos de alto valor añadido a partir de hoja de olivo.
ATE466065T1 (de) * 2006-02-10 2010-05-15 Carotech Sdn Bhd Verfahren zur gewinnung hochangereicherter naturstoff-fraktionen aus palmöl unter verwendung von superkritischen und beinahe superkritischen flüssigmedien
ES2308924B1 (es) * 2007-05-18 2009-11-02 Pradomudo Investigacion Y Desarrollo, S.L(Titular El 50%) Procedimiento de obtencion de escualeno.
FR2933403B1 (fr) 2008-07-07 2010-08-27 Sophim Procede d'extration de squalene, de stereols et de vitamine e contenus dans des condensats de raffinage physique et/ou dans des distillats de desodorisation d'huiles vegetales
AU2009286426B2 (en) * 2008-08-28 2013-08-22 Seqirus UK Limited Production of squalene from hyper-producing yeasts
CN102100260B (zh) * 2010-12-03 2013-07-31 滨州学院 酵母油脂及其制备方法和应用

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2523546Y2 (ja) 1991-07-01 1997-01-29 本田技研工業株式会社 傘歯車用把持装置

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Publication number Publication date
CN104245076B (zh) 2017-03-01
WO2013156720A3 (fr) 2014-01-09
US20150140030A1 (en) 2015-05-21
CA2869358C (fr) 2020-12-08
KR20150006421A (ko) 2015-01-16
JP2015516152A (ja) 2015-06-11
KR102192410B1 (ko) 2020-12-17
EP2838630A2 (fr) 2015-02-25
WO2013156720A2 (fr) 2013-10-24
CN104245076A (zh) 2014-12-24
US9346722B2 (en) 2016-05-24
IN2014DN08554A (enExample) 2015-05-15
CA2869358A1 (fr) 2013-10-24
CN105296552A (zh) 2016-02-03

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