| Publication number | WO1996023420 A1 |
| Publication type | Application |
| Application number | PCT/EP1996/000373 |
| Publication date | Aug 8, 1996 |
| Filing date | Jan 30, 1996 |
| Priority date | Jan 31, 1995 |
| Also published as | CA2211107A1, EP0812135A1 |
| Publication number | PCT/1996/373, PCT/EP/1996/000373, PCT/EP/1996/00373, PCT/EP/96/000373, PCT/EP/96/00373, PCT/EP1996/000373, PCT/EP1996/00373, PCT/EP1996000373, PCT/EP199600373, PCT/EP96/000373, PCT/EP96/00373, PCT/EP96000373, PCT/EP9600373, WO 1996/023420 A1, WO 1996023420 A1, WO 1996023420A1, WO 9623420 A1, WO 9623420A1, WO-A1-1996023420, WO-A1-9623420, WO1996/023420A1, WO1996023420 A1, WO1996023420A1, WO9623420 A1, WO9623420A1 |
| Inventors | Peter Moldt |
| Applicant | Neurosearch A/S |
| Export Citation | BiBTeX, EndNote, RefMan |
| Patent Citations (6), Referenced by (15), Classifications (11), Legal Events (12) | |
| External Links: Patentscope, Espacenet | |
ASTAXAMTHIN SUSPENSION
This invention relates to a stable oil suspension of astaxanthin with high bioavailability, and the use thereof.
PRIOR ART
Astaxanthin belongs to the carotenoids, which is a group of compounds exhibiting a wide range of yellow to red colour nuances. Carotenoids give rise to several of the colour characteristics of plants, and aquatic animals, for example.
Carotenoids are insoluble in water and are only slightly fat soluble which means that solutions of carotenoids for direct application are unavailable. Furthermore, carotenoids are very sensible to oxidation.
The colouring effect of crystalline carotenoids, which can be isolated in laboratories, is very low due to the insolubility and the particle size of the crystals.
In order to increase the colouring effect and the resorbability of carotenoids, it is necessary to reduce the particle size of the carotenoids and to protect the carotenoids from oxidation.
Astaxanthin is used in fish-farming to impart a pink colour to shrimp, trout, salmon etc.
Currently, two gelatine-coated products (Carophyll Pink™) containing 5% and 8% astaxanthin, respectively, are commercially available. These products are given in the feed.
These products, however, suffer from the disadvantages of having a reduced bio- availability due to a very slow dissolution rate of gelatine at low temperatures, and a limited storage time due to a hardening of the gelatine capsule; furthermore, there is a considerable waste of the products (approximately 15%) during production of feed by extrusion. OBJECTS OF THE INVENTION
It is an object of the invention to provide a stable suspension of astaxanthin with a high bioavailability even at low temperatures. Furthermore, it is an object of the invention to provide a product that can be added to the feed after extrusion and thereby obviating the loss of colour pigment in feed production.
Additional objects will be obvious to a person skilled in the art.
SUMMARY OF THE INVENTION
The invention comprises thus the following:
A suspension of astaxanthin in oil wherein a majority of the astaxanthin particles have a particle size less than 2 μm;
such a suspension wherein a majority of the astaxanthin particles have a particle size less than less than 1μm;
such a suspension wherein the concentration of astaxanthin is between 0.03% and 50%;
such a suspension wherein the concentration of astaxanthin is between 5% and 20%;
such a suspension containing an antioxidant;
the use of such a suspension in the manufacture of feed for aquatic animals;
and such use whereby the oil suspension is absorbed into the feed after extrusion.
The suspension according to the invention can be prepared by milling of astaxanthin, if desired in the presence of oil. Suitably, astaxanthin is milled without oil, whereafter oil is added and the milling continued, if desired. Oxidation of astaxanthin during the dry milling operation can be reduced by the application of an inert gas atmosphere.
Another method by which astaxanthin could be obtained in finely divided form is by abrupt precipitation from a solution of astaxanthin in a solvent.
The astaxanthin particles in the suspension of the invention have a particle size less than 2 μm, especially less than 1μm. More preferred is an astaxanthin particle size less than 0.5 μm, especially less than 0J μm.
The oil can be any animal or vegetable oil suitable for use in feed for aquatic animals. Such oil includes fish oil, such as for example mackerel oil, sprat oil and launce oil.
Antioxidants, such as for example tocopherols, especially α-tocopherol, butylhydroxyanisole (BHA), butylhydroxytoluene (BHT), ascorbylpalmitate or ethoxyquin, can be added to the suspension to avoid oxidation.
Further stabilisation of the solution of the invention can be obtained by keeping the suspension at temperatures below the solidification temperature.
Feed for aquatic animals suitably contains 15-30 % fat. Fat can be added by absorption of oil into the feed after extrusion, if desired using vacuum. The oil suspension of the invention could suitably be added to the feed using the same procedure, whereby an addition of fat and astaxanthin is obtained in one step.
Preferably, the suspension of the invention has a high concentration of astaxanthin and is diluted with additional oil before use.
The final concentration of astaxanthin in fish feed is suitable between 25 and 100 ppm. Detailed Description of the Invention
The invention will now be described in greater detail with reference to the following example, which are given by way of illustration and are not to be construed as limiting.
Milling of Astaxanthin
Astaxanthin (OJ g) is milled for one hour totally in a Fritsen planetary micro mill pulverisette 7, speed 6. 5 ml of Launce oil ( Esbjerg Fiskeindustri ) is added and milling is continued for 15 min, speed 1.5. Particle size is measured by microscopy and found to be less than 2 μm for the majority of the particles. This suspension is poured on to a glass and placed in the dark at room temperature for 14 days.
The above procedure is repeated, and the suspension obtained is compared with the 14-day-old suspension.
The small particles show a tendency to agglomeration but nothing indicates that the particles grow when standing. There is no sedimentation of astaxanthin.
Launce oil solidifies at -18°C.
| Cited Patent | Filing date | Publication date | Applicant | Title |
|---|---|---|---|---|
| WO1988008025A1 * | Apr 15, 1988 | Oct 20, 1988 | Danisco Bioteknologi A/S | Astaxanthin-producing yeast cells, methods for their preparation and their use |
| WO1989006910A1 * | Jan 20, 1989 | Aug 10, 1989 | Microbio Resources, Inc. | Pigmentation supplements for animal feed compositions |
| WO1991006292A1 * | Nov 2, 1990 | May 16, 1991 | Danochemo A/S | Process of preparing a water dispersible hydrophobic or aerophilic solid |
| WO1993014645A1 * | Jan 25, 1993 | Aug 5, 1993 | Gist-Brocades N.V | Method for the preparation of feed pellets |
| EP0239949A2 * | Mar 27, 1987 | Oct 7, 1987 | BASF Aktiengesellschaft | Process for the manufacture of powdery finely divided preparations of carotenoids |
| EP0551638A1 * | Dec 21, 1992 | Jul 21, 1993 | BASF Aktiengesellschaft | Stable fluid preparation of fat-soluble substances |
| Citing Patent | Filing date | Publication date | Applicant | Title |
|---|---|---|---|---|
| WO2004016099A1 * | Aug 14, 2003 | Feb 26, 2004 | Zoolife International Limited | Composition for dietary enrichment |
| WO2006034556A1 * | Sep 29, 2005 | Apr 6, 2006 | Michael Ary Bos | Caratenoid composition and method for preparation thereof |
| WO2006125591A1 * | May 22, 2006 | Nov 30, 2006 | Phares Pharmaceutical Research N.V. | Direct dissolution |
| WO2009065928A1 * | Nov 21, 2008 | May 28, 2009 | Basf Se | Method for producing carotenoid solutions |
| WO2009065929A1 * | Nov 21, 2008 | May 28, 2009 | Basf Se | Method for the production of carotenoid solutions |
| WO2014170225A1 * | Apr 11, 2014 | Oct 23, 2014 | Basf Se | Process for the preparation of an astaxanthin suspension |
| CN100558245C | Aug 14, 2003 | Nov 11, 2009 | 动物生活国际有限公司 | Composition for dietary enrichment |
| EP2266419A1 * | May 22, 2006 | Dec 29, 2010 | Phares Drug Delivery AG | Direct dissolution of carotenoids in edible oils and fats |
| EP2792246A1 | Apr 17, 2013 | Oct 22, 2014 | Basf Se | Method for producing an astaxanthin suspension |
| US5863953 * | Nov 18, 1997 | Jan 26, 1999 | Basf Aktiengesellschaft | Liquid, oil-miscible carotenoid preparations |
| US7105176 | Nov 19, 2001 | Sep 12, 2006 | Basf Aktiengesellschaft | Production of solid preparations of water-soluble, sparingly water-soluble or water-insoluble active compounds |
| US8197851 | Sep 29, 2005 | Jun 12, 2012 | Michael Ary Bos | Carotenoid composition and method for preparation thereof |
| US8632832 | Nov 21, 2007 | Jan 21, 2014 | Phares Pharmaceutical Research N.V. | Direct dissolution |
| US8809398 | Jan 15, 2008 | Aug 19, 2014 | Basf Se | Liquid formulations containing a carotinoid |
| US9375387 | Oct 1, 2009 | Jun 28, 2016 | Basf Se | Ready-to-use, stable emulsion |
| International Classification | A23K1/18, A23K1/16, A23L1/275 |
| Cooperative Classification | A23L5/44, A23K20/179, C07C403/24, A23K50/80 |
| European Classification | A23L1/275B2, A23K1/18S, A23K1/16C, C07C403/24 |
| Date | Code | Event | Description |
|---|---|---|---|
| Aug 8, 1996 | AK | Designated states | Kind code of ref document: A1 Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IS JP KE KG KP KR KZ LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN AZ BY KG KZ RU TJ TM |
| Aug 8, 1996 | AL | Designated countries for regional patents | Kind code of ref document: A1 Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE |
| Sep 26, 1996 | DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | |
| Nov 6, 1996 | 121 | Ep: the epo has been informed by wipo that ep was designated in this application | |
| Jul 11, 1997 | WWE | Wipo information: entry into national phase | Ref document number: 972961 Country of ref document: FI |
| Jul 18, 1997 | WWE | Wipo information: entry into national phase | Ref document number: 1996902947 Country of ref document: EP |
| Jul 21, 1997 | ENP | Entry into the national phase in: | Ref country code: CA Ref document number: 2211107 Kind code of ref document: A Format of ref document f/p: F Ref document number: 2211107 Country of ref document: CA |
| Jul 22, 1997 | WWE | Wipo information: entry into national phase | Ref document number: 301672 Country of ref document: NZ |
| Oct 23, 1997 | ENP | Entry into the national phase in: | Ref country code: US Ref document number: 1997 875593 Date of ref document: 19971023 Kind code of ref document: A Format of ref document f/p: F |
| Dec 4, 1997 | REG | Reference to national code | Ref country code: DE Ref legal event code: 8642 |
| Dec 17, 1997 | WWP | Wipo information: published in national office | Ref document number: 1996902947 Country of ref document: EP |
| Jun 8, 1999 | WWW | Wipo information: withdrawn in national office | Ref document number: 1996902947 Country of ref document: EP |