WO2011095839A1 - Procédé pour l'obtention d'ester éthylique de l'acide docosahexaénoïque et compositions pharmaceutiques comprenant de l'ester éthylique de l'acide stéaridonique - Google Patents

Procédé pour l'obtention d'ester éthylique de l'acide docosahexaénoïque et compositions pharmaceutiques comprenant de l'ester éthylique de l'acide stéaridonique Download PDF

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Publication number
WO2011095839A1
WO2011095839A1 PCT/IB2010/050449 IB2010050449W WO2011095839A1 WO 2011095839 A1 WO2011095839 A1 WO 2011095839A1 IB 2010050449 W IB2010050449 W IB 2010050449W WO 2011095839 A1 WO2011095839 A1 WO 2011095839A1
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WO
WIPO (PCT)
Prior art keywords
ethyl ester
stearidonic acid
acid ethyl
weight
ranging
Prior art date
Application number
PCT/IB2010/050449
Other languages
English (en)
Inventor
Fernando Moreno Egea
Laura Gil Puig
Original Assignee
Soluciones Extractivas Alimentarias, S.L.
Fernandez Montes, Mario
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Soluciones Extractivas Alimentarias, S.L., Fernandez Montes, Mario filed Critical Soluciones Extractivas Alimentarias, S.L.
Priority to PCT/IB2010/050449 priority Critical patent/WO2011095839A1/fr
Publication of WO2011095839A1 publication Critical patent/WO2011095839A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption

Definitions

  • Stearidonic is an essential fatty acid of the n-3 series. It is known that essential fatty acids of the n-3 series (nomenclature defined by the position of the first double bond from the methyl group) lead by a chain reaction to series 3 prostaglandins that inhibit the aggregation of blood platelets.
  • the first element of this chain is a-linolenic acid (ALA, C 18:3 cis 9,12,15) of which the conversion into stearidonic acid (SA, C 18:4 cis 6,9,12,15) is attributable to the activity of the enzyme.
  • DELTA.6 desaturase that is shown to weaken with age and as a result of certain diseases. The synthesis of the series 3 prostaglandins is thus compromised. To overcome this weakness of the organism, it is proposed to introduce stearidonic acid directly into the body.
  • the allergic type such as asthma
  • the cutaneous type such as acne, psoriasis and eczema
  • the rheumatic type as well as those following traumatisms
  • states of shock or pathologies such as mucoviscidose for example, leukotrienes are formed mainly by oxidation by the lipoxygenases of arachidonic acid (AA, C20:4 . DELTA.5,8,11,14) which is released from cell membranes.
  • LTB4 poly-morphonucleated human leukocytes transform AA into leukotrienes more particularly into stable (5S,12R)-5, 12-dihydroxy-6,14-cis-8,10-trans- eicosatetraenoicacid (LTB4), by way of 5-lipoxygenase.
  • LTB4 plays a predominant part in various inflammatory processes.
  • SA has the property of inhibiting the biosynthesis of leukotrienes and can be used alone or in combination with one or more polyunsaturated fatty acids, which inhibit the oxygenated metabolism of AA.
  • This unsaturated fatty acid may be a 5- lipoxygenase-inhibiting polyunsaturated fatty acid of the n-3 series, for example EPA, docosahexaenoic acid (DHA, C22:6 ⁇ 4,7,10,13,16,19),
  • Japanese patent application 86 050 752 relates to a process for the separation of stearidonic acid from fish oil which comprises the steps of converting the fatty acids present therein into their ethyl esters, treating the ethyl esters by molecular distillation and collecting the head fraction, reacting it with urea in methanol, collecting the unreacted fraction and, finally, separating a fraction enriched with ethyl ester from the stearidonic acid by two successive operations of reverse-phase partition
  • European patent 178 442 relates to the enrichment of blackcurrant seed oil with ⁇ -linolenic acid (GLA, C 18:3 ⁇ 6, 9, 12) by the double complexing with urea of a mixture of fatty acids eminating from the saponification of blackcurrant oil, followed by high-performance reversephase liquid chromatography. According to this patent, separation appeared particularly difficult, enrichment of the mixture only appearing possible in regard to its major constituent, ⁇ -linolenic acid.
  • SA stearidonic acid
  • present invention relates to presents clear advantages over the methods above mentioned.
  • the present invention does not use any organic solvent and allows obtaining a product with at least 40% by weight purity of SA.
  • This method is characterized by a starting point of a mixture of ethyl esters of fatty acids in which it is present as a minor constituent that is subjected to a supercritical chromatography using a supercritical C0 2 as mobile phase and irregular porous silicon oxide impregnated with (3-aminopropyl)-triethoxysilane as stationary phase.
  • Stationary phase used in the supercritical chromatography object of the present invention is irregular porous silicon oxide impregnated with (3-aminopropyl)- triethoxysilane in a proportion of 10% roughly and a pore size of 6 to 7 nanometers. This is a commercial stationary phase and can be supplied by different suppliers (for instance ProntoPreg. Bischoff Analysentechnick und gerate GMBH, D-7250 Leonburg, Alemania).
  • Stationary phase quantity ranges from 180 to 300 kg, preferably from 200 to 240 Kg and is contained between drilled plaques with filtration paper.
  • Supercritical C0 2 circulates through the column pumped using membrane pumps at a pressure ranges from 95 to 150 bars, preferably ranging from 97 to 110 bars, at a temperature ranging from 40 ⁇ to 60 ⁇ Celsius, preferably from 45 ⁇ to 50 ⁇ and at a flow rate ranging from 4000 to 7000Kg/h, preferably from 5000 to 6000 Kg/h.
  • Mixture of ethyl esters where SA is present is pumped at a discontinuous pace to the column in the current of C0 2 at a flow rate ranging from 0.1 to 1 Kg/s, using membrane pumps.
  • a cylindrical column of 540 mm diameter and 2745 mm length with opening and closure devices at the top and with drilled plaques with filtrating paper inside is used. It contains 220 Kg of stationary phase consisting in irregular porous silicon oxide impregnated with (3-aminopropyl)-triethoxysilane with pore size of 6.5 nanometers (ProntoPreg, Bischoff Analysentechnick und gerate GMBH, D-7250 Leonburg, Alemania).
  • Supercritical C0 2 circulates through the column at a pressure ranging 97 to 99 bars, at a temperature ranging from 45 ⁇ to 50 ⁇ and at a flow rate ranging from 5000 to 6000 Kg/h. With the C0 2 current, the mixture of esters is pumped into the column at a flow rate ranging from 8 to 15 Kg in 20-30 seconds through membrane pumps.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Cette invention porte sur la production d'ester éthylique de l'acide docosahexaénoïque à partir d'un mélange d'esters éthyliques d'acides gras essentiels dans lequel il est présent comme constituant minoritaire. L'acide stéaridonique isolé est utilisé pour préparer des compositions pharmaceutiques, qui sont administrées pour traiter des affections inflammatoires, et pour préparer des compositions cosmétiques pour le traitement de la peau.
PCT/IB2010/050449 2010-02-02 2010-02-02 Procédé pour l'obtention d'ester éthylique de l'acide docosahexaénoïque et compositions pharmaceutiques comprenant de l'ester éthylique de l'acide stéaridonique WO2011095839A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/IB2010/050449 WO2011095839A1 (fr) 2010-02-02 2010-02-02 Procédé pour l'obtention d'ester éthylique de l'acide docosahexaénoïque et compositions pharmaceutiques comprenant de l'ester éthylique de l'acide stéaridonique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2010/050449 WO2011095839A1 (fr) 2010-02-02 2010-02-02 Procédé pour l'obtention d'ester éthylique de l'acide docosahexaénoïque et compositions pharmaceutiques comprenant de l'ester éthylique de l'acide stéaridonique

Publications (1)

Publication Number Publication Date
WO2011095839A1 true WO2011095839A1 (fr) 2011-08-11

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PCT/IB2010/050449 WO2011095839A1 (fr) 2010-02-02 2010-02-02 Procédé pour l'obtention d'ester éthylique de l'acide docosahexaénoïque et compositions pharmaceutiques comprenant de l'ester éthylique de l'acide stéaridonique

Country Status (1)

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WO (1) WO2011095839A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102391111A (zh) * 2011-10-24 2012-03-28 赵永俊 一种生产二十二碳六烯酸乙酯（dha-ee）的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5362895A (en) * 1992-03-02 1994-11-08 K.D. Pharma Gmbh Method of recovering unsaturated fatty acids
WO2001036369A1 (fr) * 1999-11-19 2001-05-25 Kd. Iqa, S.L. Nouveau procede de preparation de l'ester ethylique de l'acide eicosa-pentaenoique
US20070207223A1 (en) * 2006-03-03 2007-09-06 Dirienzo Maureen A Means for improving cardiovascular health
WO2007147554A2 (fr) * 2006-06-19 2007-12-27 K.D. Pharma Bexbach Gmbh Procédé amélioré servant à récupérer une substance ou un groupe de substances à partir d'un mélange

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5362895A (en) * 1992-03-02 1994-11-08 K.D. Pharma Gmbh Method of recovering unsaturated fatty acids
WO2001036369A1 (fr) * 1999-11-19 2001-05-25 Kd. Iqa, S.L. Nouveau procede de preparation de l'ester ethylique de l'acide eicosa-pentaenoique
US20070207223A1 (en) * 2006-03-03 2007-09-06 Dirienzo Maureen A Means for improving cardiovascular health
WO2007147554A2 (fr) * 2006-06-19 2007-12-27 K.D. Pharma Bexbach Gmbh Procédé amélioré servant à récupérer une substance ou un groupe de substances à partir d'un mélange

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102391111A (zh) * 2011-10-24 2012-03-28 赵永俊 一种生产二十二碳六烯酸乙酯（dha-ee）的方法

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