NO159665B - Fremgangsmaate for fremstilling av en oljeekstrakt. - Google Patents
Fremgangsmaate for fremstilling av en oljeekstrakt. Download PDFInfo
- Publication number
- NO159665B NO159665B NO831336A NO831336A NO159665B NO 159665 B NO159665 B NO 159665B NO 831336 A NO831336 A NO 831336A NO 831336 A NO831336 A NO 831336A NO 159665 B NO159665 B NO 159665B
- Authority
- NO
- Norway
- Prior art keywords
- oil
- linolenic acid
- extracted
- seeds
- ground
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 10
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims abstract description 7
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- 235000020664 gamma-linolenic acid Nutrition 0.000 abstract 1
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
- A23C11/04—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing non-milk fats but no non-milk proteins
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- A—HUMAN NECESSITIES
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- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/003—Compositions other than spreads
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
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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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
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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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
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- 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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
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- 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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
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- 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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
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Description
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av en oljeekstrakt inneholdende -y-linolensyre fra frukter av Genus Ribes.
De fleste vegetabilske oljer inneholder linolen-(6,9-oktadekadien) og a-linolen-(9,12,15-oktadecatrien) polyumet-tede fettsyrer. Kun oljer av frøene av humle (Humulus), hamp (Cannabis), agurk (Borage) og nattlys (Oenothera) er kjent å inneholde -y-linolen-C6 ,9 ,12-oktadekatrien )syre , idet nattlys er den eneste tilgjengelige kilde til i tillegg høy pris.
"Y-linolensyre er en essensiell fettsyre som metaboliseres av organismen til prostaglandiner via dihomo-^-linolensyre og arakidonsyre-(5,8,11,14-eikosatetraensyre ), som i seg selv er en bestanddel av cellemembraner, mens cx-linolensyre ikke tar del på samme måte i denne metabolske prosess. Linolensyre-omdanningen til ^-linolensyre i vevet er ufullstendig (4-10$ sammenlignet med 90-98$ for omdanningen av "y-linolensyre til arakidonsyre) og kan ikke engang eksistere (f. eks. hos katter) ved fravær av inaktiveringen av enzymet A-6-desatu-rase.
Således resulterer en mangel på essensielle fettsyrer i en næringsmangel som påvirker alle de metabolske prosesser som er nevnt ovenfor og som kan resultere i biokjemiske mangler eller de organiske skader (f. eks. koaguleringsuregelmessig-heter, dermatologiske sår, endokrinale mangler, myokardiale sår og hepatitiske, artikulære, neurologiske og mentale mangler). Derfor er det mulig å se de fordeler som til-veiebringes ved en tilførsel av 7-1inolensyre for å forhindre eller for behandling av disse anomalier.
Muligheten for å benytte ^-linolensyre og arakidonsyre som terapeutisk og næringsmiddel er nevnt f. eks. i FR-PS 2 197 605 og 1 603 383, idet ^-linolensyren er av syntetisk opprinnelse eller ekstraheres fra oljen fra frø av nattlys (Oenothera) eller agurkurt (Borage officinalis).
I tillegg angår FR-PS 2 255 055 kosmetiske eller farma-søytiske preparater basert på oljen fra bringebærkjerner, den anti-inflammatoriske aktivitet nevnes men uten indikasjon på sammensetning. Fordi olje fortrinnsvis ekstraheres ved bruk av kloroform (et polart oppløsningsmiddel), skyldes den anti-inf lammatoriske virkning sannsynligvis nærværet av mindre komponenter. Videre har en analyse av denne olje vist at den inneholdt ca. 54 vekt-# linolensyre og 30$ av en a-linolensyre, men at den ikke inneholdt -Y-linolensyre.
Til slutt beskriver HU-PS T 13226 at tilsetning av en masse eller en råolje ekstrahert fra paprika-, tomat- eller ripskjerner til kosmetiske produkter eller bordoljer ville inhibere disses oksydasjon. Ekstraheringen slik den beskrives tillater ikke separering av uønskede vokser og fargestoffer i produktet og sammensetningen av ekstrakten er ikke nevnt.
Overraskende er det funnet at oljen fra kjerner fra frukter av Ribes-slekten inneholder en betydelig andel og minst 4 vekt-$ "Y-linolensyre. Videre er disse kjerner tilgjengelige i store mengder i kakene som oppstår fra pressede fruktsafter, fra fremstilling av syltetøy og geléer eller fra fermenteringsmoster fra fremstilling av forskjellige typer brennevin, biprodukter som hittil har vært brukt som brennstoff eller f6r.
Det kan fremstilles et næringspreparat som inneholder fra 1 til 80 vekt-$ av et fettstoff ekstrahert fra kjerner fra Ribes-slekten, inneholdende minst 4 vekt-$ -Y-linolensyre som praktisk talt er fri for luktforbindelser, frie fettsyrer, fargestoffer og voksene fra disse frukter.
Slik uttrykket benyttes betyr "næringspreparat" kosmetiske, dermatologlske (korrektive kosmetiske), eller topiske (f. eks. oftalmiske) sammensetninger og dietiske næringsmidler eller matsupplementer, eller farmasøytiske preparater for oral, enteral eller parenteral næring.
Fettstoffene som går inn i næringspreparatet stammer i praksis fra solbær (Ribes nigrum), rips (Ribes rubrum), stikkelsbær (Ribes ovacrispa eller glossularia) eller fra hybridfrukter av disse arter. Selvfølgelig kan en blanding av disse frukter benyttes.
Lipidinnholdet i biproduktene som er nevnt ovenfor er fra 12-30 vekt-#, avhengig av utgangsmaterialet. For sin del inneholder lipidfasen fra 4-19 vekt-$ "Y-linolensyre.
Som en indikasjon inneholder oljen fra kjernene av disse frukter triglyserider av de følgende fettsyrer på vektbasis:
Solbærolje som er foretrukket på grunn av det høye innhold av "Y-linolensyre inneholder også fra 1-2 vekt-$ uforsåpbare stoffer, slik som alifatiske alkoholer, hydrokarboner, tokoferoler, skvalen, e-sitosterol, kampesterol og a-7-stigmasterol. Densiteten er 0,9215 g/cm<3> Centipoise ved 20°C.
Et kosmetisk eller dermatolgisk preparat kan presenteres i form av fluid vann-i-olje- eller olje-i-vann-emulsjon (melk, lotion, shampo, barberskum osv.) eller i form av en tykkere emulsjon (krem, ansiktsmaske), og inneholder generelt fra 1 til 20 vekt-$ av det ovenfor nevnte fettstoff. Den kan i det vesentlige omfatte en oljefase (balsam, badolje, osv.), inneholdende opptil 80% av fettstoffet nevnt ovenfor, eller det kan ha en overveiende vannfase (kapillært skylleprodukt, osv.). Til slutt kan det være i det vesentlige fast (make-up produkter, øyeskygge, grunning, leppestift, osv.) og kan inneholde fra 1 til 30 $ av det ovenfor nevnte fettstoff.
I tillegg til å inneholde fettstoffet som nevnt ovenfor kan fettfasen i preparatet inneholde vegetabilske, animalske, mineralske eller syntetiske oljer, vokser, langkjedede alkoholer og polymerer som i dag benyttes i kosmetika.
Hvis emulsjoner er ønsket, inneholder preparatene fra 1 til 20 vekt-# emulgeringsmiddel.
I tillegg kan preparatene inneholde fargestoffer, parfymer, preserveringsmidler, pigmenter, antioksydanter, strekkmidler, osv.
Blant de dietiske næringsmidler eller næringsmiddelsupple-menter som er nevnt, skal spesielt nevnes spebarnmelk og mere spesielt melk med morsmelkens sammensetning, sauser, majones og oljer for salater. I disse produkter er fettstoffene tilstede slik at de tilveiebringer en ekvivalent av fra 0,35 til 2,5 vekt-# -y-linolensyre og utgjør fra 2 til 15 vekt-$. Fettstoffene vil fordelaktig beskyttes fra oksydasjon ved tilsetning av fettsyreestere av askorbinsyre, f. eks. askorbylpalmitat.
Det er også mulig å benytte de ovenfor nevnte fettstoffer i animal næring, f. eks. kattemat.
Til slutt kan fettstoffene som nevnt ovenfor gå inn i blandinger av medikamenter som har en formulering tilpasset inngivelsesmetoden og som f. eks. inngis i form av sirup eller kapsler eller okulær isotoniske emulsjoner, eller de kan være en bestanddel av oljefasen i emulsjoner eller kombineres med oljer ment for parenteral næring, og de kan utgjøre fra 5 til 80 vekt-# av preparatet.
I ethvert tilfelle vil den farmasøytiske blanding være fysikalsk og kjemisk stabilisert (spesielt mot oksydasjon) og de for parenteral bruk presenteres i steril, pyrogenfri form.
Foreliggende oppfinnelse angår således en fremgangsmåte for fremstilling av en oljeekstrakt inneholdende -y-linolensyre, fra frø av frukten av slekten Ribes, hvor frøene males og vaskes med et polart oppløsningsmiddel med etterfølgende ekstraksjon av frøoljen med et ikke polart oppløsningsmiddel, og denne fremgangsmåte karakteriseres ved at frømaterialet fraskilles etter forvasking med det polare oppløsningsmidlet og finmales, fuktes og omdannes til et granulat eller pellets, før det ekstaheres med det ikkepolare ekstraksjonsmidlet.
Uttrykket "vegetabilsk materiale" omfatter de biprodukter som er nevnt ovenfor. Utgangsmaterialet er generelt i form av en sterkt farget kake inneholdende vokser fra 5 til 7 vekt-$ av råoljen som vil ekstraheres derfra, f. eks. ved bruk av heksan. Voksene er mettede og monoumettede estere av langkjedede fettsyrer med fettalkoholer som er faste ved omgivelsestemperatur. De angjeldende vokser og fargestoffer er ikke ønsket i en olje som innarbeides i et næringsmiddel.
Et foretrukket utgangsmateriale er den kake som oppnås ved pressing av fruktsafter, spesielt solbærsaft. Kaken tørkes først, f. eks. i luft i ca. 1 time ved ca. 60°C. Den grovmales og siktes for å oppnå partikler med størrelse fra 1-1,5 mm, Idet siktutbyttet ligger fra 60-80 vekt-$ av kakene. Det er med fordel mulig å separere kjernene fra resten ved hjelp av tyngdekraften i en luftstrøm eller ved elutrering med et utbytte på vektbasis fra 80 til 90$. 1 henhold til en foretrukket utførelsesform ifølge oppfinnelsen blir frøene vasket med et konvensjonelt polart opp-løsningsmiddel for å befri dem fra voksene, fargestoffer og frie fettsyrer. For kosmetiske formål er det mulig f. eks. å benytte metanol, isopropanol, aceton, etanol eller en blanding av disse oppløsningsmidler, eller et superkritisk fluid, f. eks. karbondioksyd under betingelser som gir betingelsen polar karakter. For nærings- og farmasøytiske formål vil et oppløsningsmiddel av næringsmiddelkvalitet benyttes, f. eks. etanol eller superkritisk karbondioksyd.
F. eks. kan vaskingen utføres ved å ekstrahere frøene med etanol under tilbakeløp, enten satsvis, f. eks. først i ca. 2 timer og deretter i ca. 30 - 60 minutter, eller kontinuerlig i ca. 2 timer, hvoretter resten helles av.
I en variant er det mulig å vaske frøene ved ekstrahering f. eks. med karbondioksyd under et trykk på 250 - 350 bar og ved 60 - 80°C i en kontinuerlig cyklus, idet oppløsningsmidlet gjenvinnes i gassform ved å redusere trykket, hvoretter det komprimeres igjen og tilbakeføres. Det er funnet at ekstraksjonen gjør det mulig å fjerne mesteparten av fargestoffene og voksene som er tilstede i skinnet og rundt kjernene. Videre felles voksene ut ved avkjøling fra det alkoholiske ekstraksjonsmiddel, mens nevnte ekstrakt er meget sterkt farget.
Den oppnådde rest males (partikkelstørrelse fra 100 til 300 pm), det tilsettes ca. 10 - 15 vekt-$ vann og det hele omdannes til pellets eller granulat ved ekstrudering av pastaen og kutting av strengen. I en variant er det mulig å flakdanne frøene på en utflatningssylinder fra den ikke oppmalte oppnådde rest. Denne form forhindrer tilstopping og letter etterfølgende ekstraksjon av oljen ved å tilveie-bringe produktet med en porøsitet som tillater god penetrer-ing av oppløsningsmidlet og flakene motstår spesielt knusing.
Det neste trinn omfatter ekstrahering av oljen med et ikke-polart oppløsningsmiddel, f. eks. heksan, i en andel på ca. 250 vekt-$ heksan med henblikk på resten. I en variant er det likeledes mulig i dette trinn å benytte flytende karbondioksyd eller fortrinnsvis superkritisk karbondioksyd under betingelser der forbindelsene er lett polar, f. eks. under trykk på 200 - 300 bar og ved 40 - 60"C. Selvfølgelig er det f. eks. mulig å benytte superkritisk karbondioksyd i vasketrinnet og i det etterfølgende ekstraheringstrinn, eller kun ett av disse trinn, mens det andre utføres f. eks. ved bruk av etanol eller heksan.
Etter ekstrahering er det mulig, selv om disse forholdsregler kun er foretrukne, å nøytralisere oppløsningen for å fjerne gjenværende frie fettsyrer, etter partielt å ha fordampet oppløsningsmidlet, f. eks. når det gjelder heksan, slik at resten inneholder ca. 10 vekt-$ olje, ved bruk av (2N) konsentrert kalium- eller natriumhydroksyd, og avkjøle oppløsningen til ca. 0 - 4°C i ca. 24 timer og å filtrere den ved denne temperatur for helt å fjerne restvoksen. På samme måte er de etterfølgende avfargnings- og avluktningstrinn foretrukne: oppløsningen avfarges ved bruk av 2-8 vekt-$ aktivkull med henblikk på oljen som behandles, ved ca. 20-60°C, hvoretter heksanet fordampes. Oljen deodoriseres deretter ved hjelp av dampstripping ved 120 - 220°C og fortrinnsvis ved ca. 180°C under et vakuum tilsvarende eller mindre enn 1 torr.
I enkelte tilfelle blir en fettsubstans anriket med -y-linolenolje. For å gjøre dette forsåpes oljen som er befridd for vokser og frie fettsyrer med et alkalihydroksyd, f. eks. kaliumhydroksyd, i et medium av metanol og vann i en konsentrasjon på ca. 11$, idet de resulterende salter surgjøres ved bruk av en mineralsyre, f. eks. 2N svovelsyre, de frie fettsyrer ekstraheres med heksan og den organiske fase separeres og tørkes, f. eks. ved tilsetning av natrium-sulfat. I en variant er det mulig direkte å behandle den oppmalte kake med et alkalihydroksyd, og surgjøre den med en mineralsyre, og ekstrahere de frie fettsyrer med heksan og å tørke den organiske fase som antydet ovenfor. Den organiske fase fraksjoneres ved høytrykkskromatografi 1 flytende fase ved føring over kolonner av silikagel med sølvnitrat og eluering fortrinnsvis med en blanding av diklormetan, toluen og dietyleter i forhold 70:25:5 til 65:30:5 på isokratisk måte, det vil si med tilbakeføring av oppløsningsmiddelbland-ingen av fastsatt sammensetning og en fraksjon inneholdende ca. 60 vekt-$ -Y-linolensyre og ca. 40 vekt-$ a-linolensyre oppnås på denne måte.
Praktisk talt all -Y-linolensyre kan isoleres ved høytrykks-væskefasekromatografi med en Cg eller C^g-bærer i invers fase med en gradient av en oppløsningsmiddelblanding acetonitril-/vann, metanol/vann eller isopropanol/vann.
De følgende eksempler illustrerer oppfinnelsen. Andeler og prosentandeler er basert på vekt.
EKSEMPEL 1
100 kg rest oppnådd ved ekstraksjon av solbærsaft og tørking behandles en første gang i 2 timer under tilbakeløp med 250 kg etanol og en andre gang i 1 time under tilbakeløp med 250 kg etanol. Ekstrakten helles av og tørkes to ganger ved 80"C i 30 minutter i en lufttørker og males til slutt i en hammermølle.
Etter fukting med fra 10 til 15$ vann og etter ekstrudering av pastaen i form av pellets, oppnås 89 kg produkt som ekstraheres to ganger med 205 kg heksan under tilbakeløp i 3 timer, hvoretter det hele avkjøles og filtreres. Heksanet fordampes og det oppnås 14,3 kg av en klar gul olje hvis innhold av frie fettsyrer er 0,16$.
Eksempel 2
100 kg tørket solbærmasse fra saftpressing males i en skyvemølle og det malte produkt siktes for å oppnå 60,5 kg partikler med partikkelstørrelse 1 - 1,5 mm. Produktet innføres i en elutriator og det gjenvinnes 49,5 kg av en tung fraksjon i det vesentlige omfattende frø. Fraksjonen vaskes to ganger med hver gang 120 kg etanol under tilbakeløp. Prosessen fortsettes som angitt i eksempel 1 bortsett fra at 2 x 120 kg etanol benyttes for vaskingen, den tørkede ekstrakt omgjøres til flak ved bruk av en flaksylindermølle istedet for ekstruderen og flakene ekstruderes med 1 x 102,5 kg heksan. Det oppnås 11,1 kg av en klar gul olje.
Claims (3)
1.
Fremgangsmåte for fremstilling av en oljeekstrakt inneholdende "y-linolensyre, fra frø av frukten av slekten Ribes, hvor frøene males og vaskes med et polart oppløsningsmiddel med etterfølgende ekstraksjon av frøoljen med et ikke-polart oppløsningsmiddel.karakterisert ved at frømaterialet fraskilles etter forvasking med det polare oppløsningsmidlet og finmales, fuktes og omdannes til et granulat eller pellets, før det ekstraheres med det ikkepolare ekstraksjonsmidlet.
2.
Fremgangsmåte ifølge krav 1, karakter 1 sert ved at det oppmalte vegetabilske materiale vaskes med etanol under tilbakeløp.
3.
Fremgangsmåte ifølge krav 1 eller 2,karakterisert ved at den vaskede rest ekstraheres med heksan under tilbakeløp.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO852357A NO165525C (no) | 1982-04-16 | 1985-06-11 | Kosmetiske preparater. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH231482 | 1982-04-16 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO831336L NO831336L (no) | 1983-10-17 |
NO159665B true NO159665B (no) | 1988-10-17 |
NO159665C NO159665C (no) | 1989-01-25 |
Family
ID=4230898
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO831336A NO159665C (no) | 1982-04-16 | 1983-04-15 | Fremgangsm te for fremstilling av en oljeekstrakt. |
NO831335A NO831335L (no) | 1982-04-16 | 1983-04-15 | Lipidnaeringsmiddel |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO831335A NO831335L (no) | 1982-04-16 | 1983-04-15 | Lipidnaeringsmiddel |
Country Status (22)
Country | Link |
---|---|
US (4) | US4526793A (no) |
EP (2) | EP0092076B1 (no) |
JP (2) | JPS58192828A (no) |
AT (2) | ATE24266T1 (no) |
AU (2) | AU567091B2 (no) |
CA (2) | CA1195172A (no) |
CS (1) | CS277394B6 (no) |
DE (2) | DE3368377D1 (no) |
DK (1) | DK171649B1 (no) |
DZ (1) | DZ529A1 (no) |
ES (3) | ES8500987A1 (no) |
FI (2) | FI76678C (no) |
GB (1) | GB2118567B (no) |
GR (2) | GR78211B (no) |
HK (1) | HK83286A (no) |
HU (1) | HU185359B (no) |
IL (2) | IL68275A0 (no) |
MA (2) | MA19772A1 (no) |
MY (1) | MY8700142A (no) |
NO (2) | NO159665C (no) |
NZ (1) | NZ203828A (no) |
ZA (2) | ZA832367B (no) |
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JP6059859B2 (ja) * | 2009-11-16 | 2017-01-11 | ビーエーエスエフ ビューティ ケア ソリューションズ フランス エスエーエスBASF Beauty Care Solutions France S.A.S. | 弾性繊維の形成を刺激するための、loxl(リシルオキシダーゼ類似)アイソフォームの合成及び活性の刺激 |
US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
US9861605B2 (en) | 2011-10-24 | 2018-01-09 | Stable Solutions Llc | Enriched injectable emulsion containing selected fatty acid triglycerides |
MY171747A (en) | 2012-11-13 | 2019-10-27 | Rrip Llc | Method to recover free fatty acids from fats and oils |
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WO2018167038A1 (en) * | 2017-03-15 | 2018-09-20 | Aalborg Universitet | Method for extracting cannabinoids from cannabis plant material |
CN112494441A (zh) * | 2020-12-24 | 2021-03-16 | 迪沙药业集团有限公司 | 一种盐酸二甲双胍组合物 |
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US2611706A (en) * | 1949-12-21 | 1952-09-23 | Wyeth Corp | Fat composition for infants' food |
GB1082624A (en) * | 1965-02-26 | 1967-09-06 | Calmic Ltd | Improvements in or relating to therapeutically active compounds |
US3542560A (en) * | 1967-12-06 | 1970-11-24 | American Home Prod | Infant formula with fat composition like human milk |
GB1240513A (en) * | 1968-09-13 | 1971-07-28 | Ono Pharmaceutical Co | Poly-unsaturated fatty acid ester composition and its preparation |
US3649295A (en) * | 1970-06-01 | 1972-03-14 | American Home Prod | Humanized fat compositions and infant formulas thereof |
GB1446431A (en) * | 1972-04-20 | 1976-08-18 | Williams J | Nutritional supplement |
FR2197605A1 (en) * | 1972-09-06 | 1974-03-29 | Williams John | Foodstuff or skin nutrient to combat cholesterolaemia - contains arachidonic acid or gamma linolenic acid or esters and salts thereof |
FR2255055A1 (en) * | 1973-12-19 | 1975-07-18 | Pourrat Henri | Raspberry seed oil compsns - with antiinflammatory activity, for cosmetic and pharmaceutical use |
GB1506563A (en) * | 1974-04-25 | 1978-04-05 | Williams J | Immunosuppressive agents |
CH621048A5 (no) * | 1977-04-27 | 1981-01-15 | Nestle Sa | |
SE443711B (sv) * | 1980-03-14 | 1986-03-10 | Kimura Bed Mfg | Urineringshjelpmedel av vakuumsugningstyp |
FR2490631A1 (fr) * | 1980-09-24 | 1982-03-26 | Roussel Uclaf | Nouvelle composition lipidique utilisable en dietetique, reanimation et therapeutique |
DE3368377D1 (en) * | 1982-04-16 | 1987-01-29 | Nestle Sa | Lipid composition for oral, enteral or parenteral feeding |
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1983
- 1983-03-30 DE DE8383103149T patent/DE3368377D1/de not_active Expired
- 1983-03-30 EP EP83103149A patent/EP0092076B1/fr not_active Expired
- 1983-03-30 AT AT83103149T patent/ATE24266T1/de not_active IP Right Cessation
- 1983-03-31 AU AU13084/83A patent/AU567091B2/en not_active Ceased
- 1983-03-31 AT AT83103223T patent/ATE18572T1/de not_active IP Right Cessation
- 1983-03-31 EP EP83103223A patent/EP0092085B1/fr not_active Expired
- 1983-03-31 IL IL68275A patent/IL68275A0/xx not_active IP Right Cessation
- 1983-03-31 ZA ZA832367A patent/ZA832367B/xx unknown
- 1983-03-31 DE DE8383103223T patent/DE3362492D1/de not_active Expired
- 1983-04-06 IL IL68302A patent/IL68302A0/xx not_active IP Right Cessation
- 1983-04-06 AU AU13169/83A patent/AU555940B2/en not_active Ceased
- 1983-04-06 US US06/482,430 patent/US4526793A/en not_active Expired - Fee Related
- 1983-04-07 FI FI831173A patent/FI76678C/fi not_active IP Right Cessation
- 1983-04-07 FI FI831172A patent/FI72997C/fi not_active IP Right Cessation
- 1983-04-08 NZ NZ203828A patent/NZ203828A/en unknown
- 1983-04-08 ZA ZA832492A patent/ZA832492B/xx unknown
- 1983-04-11 DZ DZ830819A patent/DZ529A1/fr active
- 1983-04-11 GB GB08309742A patent/GB2118567B/en not_active Expired
- 1983-04-13 MA MA19992A patent/MA19772A1/fr unknown
- 1983-04-13 MA MA19991A patent/MA19771A1/fr unknown
- 1983-04-14 GR GR71088A patent/GR78211B/el unknown
- 1983-04-14 GR GR71087A patent/GR78210B/el unknown
- 1983-04-15 CA CA000426002A patent/CA1195172A/en not_active Expired
- 1983-04-15 NO NO831336A patent/NO159665C/no not_active IP Right Cessation
- 1983-04-15 CA CA000426003A patent/CA1216592A/en not_active Expired
- 1983-04-15 JP JP58066837A patent/JPS58192828A/ja active Granted
- 1983-04-15 NO NO831335A patent/NO831335L/no unknown
- 1983-04-15 HU HU831329A patent/HU185359B/hu not_active IP Right Cessation
- 1983-04-15 ES ES521524A patent/ES8500987A1/es not_active Expired
- 1983-04-15 CS CS832723A patent/CS277394B6/cs not_active IP Right Cessation
- 1983-04-15 DK DK165483A patent/DK171649B1/da not_active IP Right Cessation
- 1983-04-15 JP JP58066836A patent/JPS58189110A/ja active Granted
- 1983-04-15 ES ES521523A patent/ES8506188A1/es not_active Expired
- 1983-10-14 US US06/542,149 patent/US4703060A/en not_active Expired - Lifetime
-
1985
- 1985-03-01 ES ES540830A patent/ES540830A0/es active Granted
-
1986
- 1986-11-06 HK HK832/86A patent/HK83286A/xx not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY142/87A patent/MY8700142A/xx unknown
-
1989
- 1989-05-05 US US07/349,896 patent/US4938984A/en not_active Expired - Lifetime
- 1989-05-08 US US07/348,414 patent/US4970235A/en not_active Expired - Lifetime
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