EP1624046A1 - Process for the extraction of omega 3-rich glycolipides starting from food vegetables and omega 3-rich powder obtained by said process - Google Patents

Process for the extraction of omega 3-rich glycolipides starting from food vegetables and omega 3-rich powder obtained by said process Download PDF

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Publication number
EP1624046A1
EP1624046A1 EP05300648A EP05300648A EP1624046A1 EP 1624046 A1 EP1624046 A1 EP 1624046A1 EP 05300648 A EP05300648 A EP 05300648A EP 05300648 A EP05300648 A EP 05300648A EP 1624046 A1 EP1624046 A1 EP 1624046A1
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Prior art keywords
rich
omega
glycolipids
use according
under vacuum
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German (de)
French (fr)
Inventor
Yves Guattari
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Laboratoires Elysee
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Laboratoires Elysee
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B1/00Production of fats or fatty oils from raw materials
    • C11B1/10Production of fats or fatty oils from raw materials by extracting

Definitions

  • the present invention relates to a process for extracting glycolipids rich in omega 3 (linolenic acid) from vegetable food materials containing large quantities of such compounds such as wheat, potatoes, rice bran or vegetables. green.
  • ⁇ -linolenic acid or omega 3 especially as regards the fight against cholesterol or the prevention of cardiovascular diseases are well known to nutritionists who advise their patients to consume as much as possible foods rich in these substances. compounds such as oily fish or green vegetables.
  • omega 3-rich pulverulent preparations which are obtained by fixing animal oil generally extracted from fish on different powdery carriers (proteins, sugars, ).
  • the idea underlying the invention was to overcome this disadvantage by proposing powdery preparations rich in omega 3 obtained by direct extraction of this essential fatty acid from natural food materials in the form of glycolipids.
  • Such compounds whose molecule contains sugars have the advantage of being naturally in powder form more stable to oxidation than a triglyceride.
  • the stability of the essential fatty acids in the form of glycolipids is indeed particularly good because the sugar portion of the glycolipid contributes to this stabilization.
  • the subject of the invention is therefore a process for extracting omega-3-rich glycolipids from food plant materials containing large quantities of such compounds.
  • This process therefore has the advantage of making it possible to obtain a preparation rich in omega 3 from natural raw materials from the plant world available in very large quantities, in a directly very stable form, and without requiring other solvents that a hydroalcoholic medium; such a medium has the advantage of being compatible with the regulations specific to products intended for the food industry, and is further advantageous from a microbiological point of view and easy to eliminate.
  • the omega-3-rich glycolipids are predominantly mono- and / or trigalactosyldiglycerides, that is to say compounds consisting of the attachment of one, two or three sugar molecules to a skeletal branch. triglyceride.
  • omega-3-rich glycolipids are rich in monogalactosyldiglycerides which are insoluble in water.
  • the omega-3-rich glycolipids are washed with demineralized water in order to purify the monogalactosyldiglyceride which precipitates and then subjected to a filtration or centrifugation step followed by second vacuum drying to obtain a monogalactosyldiglyceride rich in omega 3 with a purity greater than 80 ° in powder form.
  • Such a monogalactosyldiglyceride rich in omega 3 can advantageously be obtained from apple skin.
  • glycolipids are mainly present in chloroplasts; however, in the apple chloroplasts are mainly found in the skin.
  • the process according to the invention thus makes it possible to obtain a glycolipid rich in omega 3 which is particularly advantageous for health in stable form, without the use of expensive chromatographic technique. and requiring dangerous chemical solvents and incompatible with products intended for the food industry.
  • the glycolipid rich in omega 3 thus obtained has a H.L.B. (Hydrophilic Lipophilic Balance) of 8.
  • omega-3-rich glycolipids are rich in water-soluble digalactosyldiglycerides.
  • the omega-3-rich glycolipids are washed with demineralized water or they are treated by osmosis, then the aqueous solution recovered is distilled off under vacuum and the product obtained is dried. under vacuum so as to obtain a digalactosyldiglyceride rich in omega 3 with a purity of the order of 80% in powder form.
  • Such a digalactosyldiglyceride rich in omega 3 can advantageously be obtained from dehydrated spinach or most green vegetables (green lettuce leaves, lamb's lettuce ).
  • Such a water-soluble glycolipid exhibits H.L.B. (Hydrophilic Lipophilic Balance) of 12.
  • omega-3-rich glycolipids are rich in trigalactosyldiglycerides which are very soluble in water.
  • the omega-3-rich glycolipids are taken up in demineralised water, and then the aqueous solution recovered is dehydrated after filtration under vacuum or by lyophilization so as to obtain a trigalactosyl diglyceride. rich in omega 3 with a purity of the order of 80% in the form of a white powder.
  • Such trigalactosyl diglyceride which can advantageously be obtained from dehydrated potatoes or rice bran has a H.L.B. (Hydrophilic Lipophilic Balance) 14-15 and is perfectly soluble in water and alcohol.
  • the invention also relates to a powder rich in omega 3 derived from vegetable food materials obtained following the implementation of the aforementioned method.
  • Such a powder consists of a preparation based on mono- and / or trigalactosyldiglycerides with a purity of at least about 80%.

Abstract

Use of chloroplasts of vegetable matter (A) (corn, potatoes or green vegetables) containing omega 3 to obtain glycolipids (I) by the process of extraction comprising: drying (A); hydroalcoholic extracting (A) with high degree of alcohol (higher than 80[deg]); eliminating the insoluble substances by filtration or centrifugation; distilling the alcoholic solution; and concentrating and drying (I) by vacuum. Use of chloroplasts of vegetable food matter (A) (corn, potatoes or green leaves) containing omega 3 to obtain glycolipids (I) rich in omega 3 by the process of extraction comprising: drying (A); hydroalcoholic extracting (A) with high degree of alcohol (preferably higher than 80[deg]); eliminating the insoluble substances (fibres, proteins or sugars) by filtration or centrifugation; and distilling the alcoholic solution; concentrating and drying (I) by vacuum. An independent claim is included for the powders rich in omega 3 comprising mono-, di- and/or trigalactosyl diglyceride with a purity of about 80%.

Description

La présente invention concerne un procédé d'extraction de glycolipides riches en oméga 3 (acide linolénique) à partir de matières végétales alimentaires renfermant d'importantes quantités de tels composés telles que du blé, des pommes de terre, du son de riz ou des végétaux verts.The present invention relates to a process for extracting glycolipids rich in omega 3 (linolenic acid) from vegetable food materials containing large quantities of such compounds such as wheat, potatoes, rice bran or vegetables. green.

Les propriétés bénéfiques de l'acide α linolénique ou oméga 3 notamment en ce qui concerne la lutte contre le cholestérol ou la prévention des maladies cardio-vasculaires sont bien connues des nutritionnistes qui conseillent à leurs patients de consommer autant que possible des aliments riches en ces composés tels que les poissons gras ou les légumes verts.The beneficial properties of α-linolenic acid or omega 3 especially as regards the fight against cholesterol or the prevention of cardiovascular diseases are well known to nutritionists who advise their patients to consume as much as possible foods rich in these substances. compounds such as oily fish or green vegetables.

Pour tenter de tirer partie au maximum de ces propriétés bénéfiques, les spécialistes dans le domaine agro-alimentaire ont déjà eu l'idée d'incorporer des préparations riches en cet acide gras essentiel à divers produits alimentaires ou diététiques tels que du pain ou des biscuits.To try to make the most of these beneficial properties, specialists in the agri-food sector have already had the idea of incorporating preparations rich in this essential fatty acid to various food or dietetic products such as bread or biscuits. .

A cet effet, on a déjà proposé des préparations pulvérulentes riches en oméga 3 qui sont obtenues par fixation d'huile animale en règle générale extraite de poisson sur différents supports pulvérulents (protéines, sucres, ...).For this purpose, it has already been proposed omega 3-rich pulverulent preparations which are obtained by fixing animal oil generally extracted from fish on different powdery carriers (proteins, sugars, ...).

De telles préparations présentent toutefois l'inconvénient d'être instables et sensibles à l'oxydation du fait de l'obtention des oméga 3 sous forme de triglycérides.However, such preparations have the disadvantage of being unstable and sensitive to oxidation because of the production of omega 3 in the form of triglycerides.

L'idée à la base de l'invention a consisté à remédier à cet inconvénient en proposant des préparations pulvérulentes riches en oméga 3 obtenues par extraction directe de cet acide gras essentiel de matières végétales alimentaires naturelles sous forme de glycolipides.The idea underlying the invention was to overcome this disadvantage by proposing powdery preparations rich in omega 3 obtained by direct extraction of this essential fatty acid from natural food materials in the form of glycolipids.

De tels composés dont la molécule contient des sucres ont en effet l'avantage de se présenter naturellement sous forme de poudre plus stable à l'oxydation qu'un triglycéride.Such compounds whose molecule contains sugars have the advantage of being naturally in powder form more stable to oxidation than a triglyceride.

La stabilité des acides gras essentiels sous forme de glycolipides est en effet particulièrement bonne car la partie sucre du glycolipide contribue à cette stabilisation.The stability of the essential fatty acids in the form of glycolipids is indeed particularly good because the sugar portion of the glycolipid contributes to this stabilization.

L'invention a donc pour objet un procédé d'extraction de glycolipides riches en oméga 3 à partir de matières végétales alimentaires renfermant d'importantes quantités de tels composés.The subject of the invention is therefore a process for extracting omega-3-rich glycolipids from food plant materials containing large quantities of such compounds.

Ce procédé est caractérisé par les étapes suivantes :

  • on sèche les matières végétales de départ,
  • on soumet ces matières à une extraction en milieu hydroalcoolique à haut degré d'alcool, de préférence supérieur à 80°,
  • on élimine les substances insolubles telles que fibres, protéines ou sucres par filtration ou centrifugation,
  • on distille la solution alcoolique récupérée sous vide de façon à obtenir des glycolipides riches en oméga 3 sous forme concentrée, et
  • on sèche les glycolipides riches en oméga 3 ainsi obtenus sous vide.
This process is characterized by the following steps:
  • the starting vegetable matter is dried,
  • these substances are subjected to extraction in a hydroalcoholic medium with a high degree of alcohol, preferably greater than 80 °,
  • insoluble substances such as fibers, proteins or sugars are removed by filtration or centrifugation,
  • the alcoholic solution recovered under vacuum is distilled to obtain glycolipids rich in omega 3 in concentrated form, and
  • the omega-3-rich glycolipids thus obtained are dried under vacuum.

Ce procédé présente donc l'avantage de permettre d'obtenir une préparation riche en oméga 3 à partir de matières premières naturelles issues du monde végétal disponibles en très grande quantité, ce sous une forme directement très stable, et sans nécessiter d'autres solvants qu'un milieu hydroalcoolique ; un tel milieu présente l'avantage d'être compatible avec les réglementations propres aux produits destinés à l'industrie agro-alimentaire, et est en outre avantageux du point de vue microbiologique et facile à éliminer.This process therefore has the advantage of making it possible to obtain a preparation rich in omega 3 from natural raw materials from the plant world available in very large quantities, in a directly very stable form, and without requiring other solvents that a hydroalcoholic medium; such a medium has the advantage of being compatible with the regulations specific to products intended for the food industry, and is further advantageous from a microbiological point of view and easy to eliminate.

Selon l'invention, les glycolipides riches en oméga 3 sont majoritairement des mono- di- et/ou trigalactosyldiglycérides c'est-à-dire des composés constitués par la fixation d'une, deux ou trois molécules de sucre sur une branche du squelette triglycéride.According to the invention, the omega-3-rich glycolipids are predominantly mono- and / or trigalactosyldiglycerides, that is to say compounds consisting of the attachment of one, two or three sugar molecules to a skeletal branch. triglyceride.

Selon une première variante de l'invention, les glycolipides riches en oméga 3 sont riches en monogalactosyldiglycérides insolubles dans l'eau.According to a first variant of the invention, omega-3-rich glycolipids are rich in monogalactosyldiglycerides which are insoluble in water.

Selon cette première variante, après l'étape de séchage sous vide on lave les glycolipides riches en oméga 3 à l'eau déminéralisée de façon à purifier le monogalactosyldiglycéride qui précipite puis on le soumet à une étape de filtration ou de centrifugation suivie d'un second séchage sous vide de façon à obtenir un monogalactosyldiglycéride riche en oméga 3 avec une pureté supérieure à 80° sous forme pulvérulente.According to this first variant, after the vacuum drying step, the omega-3-rich glycolipids are washed with demineralized water in order to purify the monogalactosyldiglyceride which precipitates and then subjected to a filtration or centrifugation step followed by second vacuum drying to obtain a monogalactosyldiglyceride rich in omega 3 with a purity greater than 80 ° in powder form.

Un tel monogalactosyldiglycéride riche en oméga 3 peut avantageusement être obtenu à partir de peau de pomme.Such a monogalactosyldiglyceride rich in omega 3 can advantageously be obtained from apple skin.

Il est en effet connu des spécialistes que dans le monde végétal les glycolipides sont surtout présents dans les chloroplastes ; or, dans la pomme les chloroplastes se trouvent majoritairement dans la peau.It is indeed known specialists that in the plant world glycolipids are mainly present in chloroplasts; however, in the apple chloroplasts are mainly found in the skin.

Le procédé conforme à l'invention permet donc d'obtenir un glycolipide riche en oméga 3 particulièrement intéressant pour la santé sous forme stable, sans utilisation de technique chromatographique coûteuse et nécessitant des solvants chimiques dangereux et incompatibles avec des produits destinés à l'industrie agro-alimentaire.The process according to the invention thus makes it possible to obtain a glycolipid rich in omega 3 which is particularly advantageous for health in stable form, without the use of expensive chromatographic technique. and requiring dangerous chemical solvents and incompatible with products intended for the food industry.

Le glycolipide riche en oméga 3 ainsi obtenu présente une H.L.B. (Hydrophile Lipophile Balance) de 8.The glycolipid rich in omega 3 thus obtained has a H.L.B. (Hydrophilic Lipophilic Balance) of 8.

Selon une seconde variante de l'invention, les glycolipides riches en oméga 3 sont riches en digalactosyldiglycérides solubles dans l'eau.According to a second variant of the invention, omega-3-rich glycolipids are rich in water-soluble digalactosyldiglycerides.

Conformément à cette seconde variante, après l'étape de séchage sous vide, on lave les glycolipides riches en oméga 3 à l'eau déminéralisée ou on les traite par osmose, puis on distille la solution aqueuse récupérée sous vide et on sèche le produit obtenu sous vide de façon à obtenir un digalactosyldiglycéride riche en oméga 3 avec une pureté de l'ordre de 80 % sous forme pulvérulente.According to this second variant, after the vacuum drying step, the omega-3-rich glycolipids are washed with demineralized water or they are treated by osmosis, then the aqueous solution recovered is distilled off under vacuum and the product obtained is dried. under vacuum so as to obtain a digalactosyldiglyceride rich in omega 3 with a purity of the order of 80% in powder form.

Un tel digalactosyldiglycéride riche en oméga 3 peut avantageusement être obtenu à partir d'épinards déshydratés ou de la plupart des végétaux verts (feuilles de laitue vertes, de mâche ...).Such a digalactosyldiglyceride rich in omega 3 can advantageously be obtained from dehydrated spinach or most green vegetables (green lettuce leaves, lamb's lettuce ...).

Conformément à cette variante, il est avantageux d'utiliser pour l'extraction un milieu alcoolique ayant un degré d'alcool supérieur à 95°.According to this variant, it is advantageous to use for the extraction an alcoholic medium having an alcohol degree greater than 95 °.

Un tel glycolipide soluble dans l'eau présente une H.L.B. (Hydrophile Lipophile Balance) de 12.Such a water-soluble glycolipid exhibits H.L.B. (Hydrophilic Lipophilic Balance) of 12.

Selon une troisième variante de l'invention, les glycolipides riches en oméga 3 sont riches en trigalactosyldiglycérides très solubles dans l'eau.According to a third variant of the invention, omega-3-rich glycolipids are rich in trigalactosyldiglycerides which are very soluble in water.

Conformément à cette troisième variante, après l'étape de séchage sous vide, on reprend les glycolipides riches en oméga 3 à l'eau déminéralisée, puis on déshydrate la solution aqueuse récupérée après filtration sous vide ou par lyophilisation de façon à obtenir un trigalactosyl diglycéride riche en oméga 3 avec une pureté de l'ordre de 80% sous la forme d'une poudre blanche.According to this third variant, after the vacuum drying step, the omega-3-rich glycolipids are taken up in demineralised water, and then the aqueous solution recovered is dehydrated after filtration under vacuum or by lyophilization so as to obtain a trigalactosyl diglyceride. rich in omega 3 with a purity of the order of 80% in the form of a white powder.

Un tel trigalactosyl diglycéride qui peut avantageusement être obtenu à partir de pommes de terre déshydratées ou de son de riz présente une H.L.B. (Hydrophile Lipophile Balance) de 14-15 et est parfaitement soluble dans l'eau et dans l'alcool.Such trigalactosyl diglyceride which can advantageously be obtained from dehydrated potatoes or rice bran has a H.L.B. (Hydrophilic Lipophilic Balance) 14-15 and is perfectly soluble in water and alcohol.

L'invention se rapporte également à une poudre riche en oméga 3 issus de matières végétales alimentaires obtenue suite à la mise en oeuvre du procédé susmentionné.The invention also relates to a powder rich in omega 3 derived from vegetable food materials obtained following the implementation of the aforementioned method.

Une telle poudre est constituée par une préparation à base de mono- di- et/ou trigalactosyldiglycérides avec une pureté au moins de l'ordre de 80 %.Such a powder consists of a preparation based on mono- and / or trigalactosyldiglycerides with a purity of at least about 80%.

Claims (9)

Utilisation de chloroplastes de matières végétales alimentaires renfermant d'importantes quantités d'oméga 3 telles que du blé, des pommes de terre ou des végétaux verts pour l'obtention de glycolipides riches en de tels composés par un procédé d'extraction selon lequel : - on sèche les matières végétales de départ, - on soumet ces matières à une extraction en milieu hydroalcoolique à haut degré d'alcool, de préférence supérieur à 80°, - on élimine les substances insolubles telles que fibres, protéines ou sucres par filtration ou centrifugation, - on distille la solution alcoolique récupérée sous vide de façon à obtenir des glycolipides riches en oméga 3 sous forme concentrée, et - on sèche les glycolipides riches en oméga 3 ainsi obtenus sous vide. Use of chloroplasts of vegetable food materials containing large amounts of omega 3 such as wheat, potatoes or green vegetables for obtaining glycolipids rich in such compounds by an extraction process in which: - the starting vegetable matter is dried, these substances are subjected to extraction in a hydroalcoholic medium with a high degree of alcohol, preferably greater than 80 °, insoluble substances such as fibers, proteins or sugars are removed by filtration or centrifugation, the alcoholic solution recovered under vacuum is distilled to obtain glycolipids rich in omega 3 in concentrated form, and the omega-3-rich glycolipids thus obtained are dried under vacuum. Utilisation selon la revendication 1,
caractérisée en ce que
les glycolipides riches en oméga 3 sont des mono-, di- et/ou trigalactosyldiglycérides.
Use according to claim 1,
characterized in that
omega 3-rich glycolipids are mono-, di- and / or trigalactosyldiglycerides.
Utilisation selon la revendication 2,
caractérisée en ce que
les glycolipides riches en oméga 3 sont riches en monogalactosyldiglycérides insolubles dans l'eau et en ce que, après l'étape de séchage sous vide on lave les glycolipides riches en oméga 3 à l'eau déminéralisée de façon à purifier le monogalactosyldiglycéride qui précipite puis on le soumet à une étape de filtration ou de centrifugation suivie d'un second séchage sous vide de façon à obtenir un monogalactosyldiglycéride riche en oméga 3 avec une pureté supérieure à 80 % sous forme pulvérulente.
Use according to claim 2,
characterized in that
the glycolipids rich in omega 3 are rich in monogalactosyldiglycerides insoluble in water and in that , after the vacuum drying step omega 3-rich glycolipids are washed with demineralized water so as to purify the monogalactosyldiglyceride which precipitates and it is subjected to a filtration or centrifugation step followed by a second vacuum drying so as to obtain a omega 3-rich monogalactosyldiglyceride with a purity greater than 80% in powder form.
Utilisation selon la revendication 3,
caractérisée en ce que
les matières premières de départ sont des peaux de pomme.
Use according to claim 3,
characterized in that
the raw materials of departure are apple skins.
Utilisation selon la revendication 2,
caractérisée en ce que
les glycolipides riches en oméga 3 sont riches en digalactosyldiglycérides solubles dans l'eau, et en ce que, après l'étape de séchage sous vide on lave les glycolipides riches en oméga 3 à l'eau déminéralisée ou on les traite par osmose, puis on distille la solution aqueuse récupérée sous vide et on sèche le produit obtenu sous vide de façon à obtenir un digalactosyldiglycéride riche en oméga 3 avec une pureté de l'ordre de 80 % sous forme pulvérulente.
Use according to claim 2,
characterized in that
the omega-3 rich glycolipids are rich in water-soluble digalactosyldiglycerides, and in that , after the vacuum drying step, the omega-3-rich glycolipids are washed with deionized water or they are treated by osmosis, then the aqueous solution recovered is distilled off under vacuum and the product obtained is dried under vacuum to obtain a digalactosyldiglyceride rich in omega 3 with a purity of about 80% in powder form.
Utilisation selon la revendication 5,
caractérisée en ce que
les matières premières de départ sont des épinards déshydratés.
Use according to claim 5,
characterized in that
the raw materials of departure are dehydrated spinach.
Utilisation selon la revendication 2,
caractérisée en ce qu'
les glycolipides riches en oméga 3 sont riches en trigalactosyl diglycérides très solubles dans l'eau,
et en ce qu'
après l'étape de séchage sous vide, on reprend les glycolipides riches en oméga 3 à l'eau déminéralisée, puis on déshydrate la solution aqueuse récupérée après filtration sous vide ou par lyophilisation de façon à obtenir un trigalactosyl diglycéride riche en oméga 3 avec une pureté de l'ordre de 80% sous la forme d'une poudre blanche.
Use according to claim 2,
characterized in that
glycolipids rich in omega 3 are rich in trigalactosyl diglycerides very soluble in water,
and in that
after the vacuum drying step, the omega-3-rich glycolipids are taken up in demineralized water, and then the aqueous solution recovered is dehydrated after filtration under vacuum or by lyophilization so as to obtain an omega-3-rich triglycerosyl diglyceride with a purity of the order of 80% in the form of a white powder.
Utilisation selon la revendication 7,
caractérisée en ce que
les matières premières de départ sont des pommes de terre déshydratées ou du son de riz.
Use according to claim 7,
characterized in that
the starting materials are dehydrated potatoes or rice bran.
Poudre riche en oméga 3 issus de matière végétales alimentaires obtenue suite à la mise en oeuvre du procédé utilisé selon l'une quelconque des revendications 1 à 8,
caractérisée en ce qu'
elle est constituée par une préparation à base de mono-, di- et/ou trigalactosyl diglycéride avec une pureté au moins de l'ordre de 80 %.
Powder rich in omega 3 derived from plant food material obtained following the implementation of the method used according to any one of claims 1 to 8,
characterized in that
it consists of a preparation based on mono-, di- and / or trigalactosyl diglyceride with a purity of at least of the order of 80%.
EP05300648A 2004-08-06 2005-08-03 Process for the extraction of omega 3-rich glycolipides starting from food vegetables and omega 3-rich powder obtained by said process Withdrawn EP1624046A1 (en)

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FR0451803A FR2873934B1 (en) 2004-08-06 2004-08-06 PROCESS FOR EXTRACTING GLYCOLIPIDS RICH IN OMEGA 3 FROM FOOD VEGETABLE MATERIALS AND OMEGA 3-RICH POWDER OBTAINED BY CARRYING OUT SAID METHOD

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8682005B2 (en) 1999-11-19 2014-03-25 Gentex Corporation Vehicle accessory microphone

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR889959A (en) * 1939-08-02 1944-01-25 Henkel & Cie Gmbh Process for the extraction of fats and for obtaining substances from the cells of fattened microorganisms
US4870011A (en) * 1985-01-22 1989-09-26 Director General Of Agency Of Industrial Science And Technology Method for obtaining lipids from fungus bodies
EP0535939A1 (en) * 1991-09-30 1993-04-07 Suntory Limited Process for production of omega 9 type polyunsaturated fatty acid
US20030054058A1 (en) * 2001-05-09 2003-03-20 Corley David Gregory Vitex agnus castus extract

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR889959A (en) * 1939-08-02 1944-01-25 Henkel & Cie Gmbh Process for the extraction of fats and for obtaining substances from the cells of fattened microorganisms
US4870011A (en) * 1985-01-22 1989-09-26 Director General Of Agency Of Industrial Science And Technology Method for obtaining lipids from fungus bodies
EP0535939A1 (en) * 1991-09-30 1993-04-07 Suntory Limited Process for production of omega 9 type polyunsaturated fatty acid
US20030054058A1 (en) * 2001-05-09 2003-03-20 Corley David Gregory Vitex agnus castus extract

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8682005B2 (en) 1999-11-19 2014-03-25 Gentex Corporation Vehicle accessory microphone

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FR2873934A1 (en) 2006-02-10

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