IE84659B1 - Transesterified corn oil products - Google Patents
Transesterified corn oil products Download PDFInfo
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- IE84659B1 IE84659B1 IE1996/0603A IE960603A IE84659B1 IE 84659 B1 IE84659 B1 IE 84659B1 IE 1996/0603 A IE1996/0603 A IE 1996/0603A IE 960603 A IE960603 A IE 960603A IE 84659 B1 IE84659 B1 IE 84659B1
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- 239000002285 corn oil Substances 0.000 title claims description 18
- 235000005687 corn oil Nutrition 0.000 title claims description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 70
- 150000003626 triacylglycerols Chemical class 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 13
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 12
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 9
- 235000021313 oleic acid Nutrition 0.000 claims description 9
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000005642 Oleic acid Substances 0.000 claims description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 8
- 235000020778 linoleic acid Nutrition 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- 235000021355 Stearic acid Nutrition 0.000 claims description 5
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 4
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000008117 stearic acid Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 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 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 2
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- DVWSXZIHSUZZKJ-UHFFFAOYSA-N 18:3n-3 Natural products CCC=CCC=CCC=CCCCCCCCC(=O)OC DVWSXZIHSUZZKJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- -1 CW0 fatty acid Chemical class 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- QGBRLVONZXHAKJ-UHFFFAOYSA-N methyl arachidate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC QGBRLVONZXHAKJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DVWSXZIHSUZZKJ-YSTUJMKBSA-N methyl linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC DVWSXZIHSUZZKJ-YSTUJMKBSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Description
TRANSESTERIFIED CORN OIL PRODUCTS This application is derived from J application number 923082.
The present invention relates to transesterified corn oil products.
In one aspect, this invention provides a trans—esterif'1cation product of corn oil and glycerol comprising predominately of linoleic acid and oleic acid mono-, di- and tri-glycerides, and having a free glycerol content less than 10% by weight, treated so as to reduce the saturated fatty acid component content of mono-, di- and tri-glycerides, and to enhance the unsaturated fatty acid component content of mono-, di- and tri-glycerides so that the linoleic acid and oleic acid mono-, di- and tri-glyceride content is in total 85% by weight or more of the whole composition.
A pharmaceutical composition is disclosed in IE 932082 comprising a cyclosporin as active ingredient in a carrier medium comprising: ) 1,2—propylene glycol; 2) a mixed mono-, di-, tri-glyceride; and 3) a surfactant.
Components (2) in the compositions disclosed in IE 922032 comprise mixtures of CW0 fatty acid mono-, di- and tri-glycerides. especially CW3 fatty acid mono-, di- and triglycerides. The fatty acid component of said mixed mono-, di- and tri-glycerides may comprise both saturated and unsaturated fatty acid residues. Preferably however they will predominantly be comprised of unsaturated fatty acid residues in particular, Cm unsaturated fatty acid residues for example linolenic, linoleic and oleic acid residues. Suitably component (2) will comprise at least 60%, preferably at least 75%, more preferably 85% or more by weight Cw unsaturated fatty acid, e.g. linolenic, linoleic and oleic acid mono-, di- and tri-glycerides. Suitably they will comprise less than 20%, e.g. ca. 15% or 10% by weight or less, saturated fatty acid, e.g. palmitic and stearic acid mono-, di- and tri-glycerides. .4559 Components (2) in the above-mentioned compositions will preferably be predominantly comprised of mono— and di-glycerides, e.g. comprise at least 50%, more preferably at least 70%, e.g. 75%, 80%, 85% by weight or more, mono— and di-glycerides, based on the total weight of component (2).
Components (2) in the compositions will suitably comprise from about 25 to about 50%, preferably from about 30 to about 40%, e.g. 35 to 40%, monoglycerides, based on the total weight of component (2).
Components (2) in the composition will suitably comprise from about 30 to about 60%, preferably from about 40 to about 55%, e.g. about 48 to 50%, di-glycerides, based on the total weight of component (2).
Components (2) in the compositions will suitably comprise at least 5%, e.g. from about 7.5 to about 15%, e.g. 9 to 12%, by weight of triglycerides.
Components (2) in the compositions may be prepared by admixture of individual mono—, di- or tri-glycerides in appropriate relative proportion. Conveniently however they will comprise transesterification products of vegetable oils, for example almond oil, ground nut oil, olive oil, peach oil, palm oil or, preferably. corn oil, sunflower oil or safflower oil and most preferably corn oil, with glycerol.
In another aspect, this invention provides a transesterification product of corn oil and glycerol having a saturated fatty acid content of mono-, di-, and trl-glycerides, and having a free glycerol content less than 10% by weight, which product comprises i) from about 25% to about 50% by weight of mono-glycerides, from about 30% to about 60% by weight of di-glycerides, and at least 5% by weight of tri-glycerides; and ii) a linoleic acid, oleic acid and linolenic acid mono-, di- and tri-glyceride content of at least 85% by weight; wherein the total saturated fatty acid content of mono-, di-. and tri-glycerides is less than % by weight.
Such transesterification products are generally obtained by heating of the selected vegetable oil with glycerol, at high temperature in the presence of an appropriate catalyst under an inert atmosphere with continuous agitation, eg. in a stainless steel reactor. to effect trans—esterif1cation or glycerolysis. In addition to their mono-, di- and tri-glyceride components, such transesterification products will also generally comprise minor amounts of free glycerol. The amount of free glycerol present in components (2) for use in the compositions of the invention will preferably be less than 10%, more preferably less than %, most preferably ca. 1 or 2% by weight based on the total weight of free glycerol plus mono-, di- and tri-glycerides.
Preferably some of the glycerol is first removed e.g. by distillation (to give a substantially glycerol free batch), when soft gelatine capsules are to be made.
Components (2) thus preferably contain lesser quantities of saturated fatty acids (e.g. palmitic and stearic acids) and relatively greater quantities of unsaturated fatty acids (e.g. oleic and linoleic acids) than for the starting material.
Typical preferred components (2) preferably contain: -36% mono-glycerides, 45-55% di-glyccrides and 12-20% tri-glycerides by weight based on the total weight of component (2).
Further preferred characteristics include the following: Fatty acid content as determined as the methyl ester by chromatography Methyl linoleatc 53-63% Methyl oleate 24-34% Methyl linolenate 0- 3% Methyl arachate 0- 3% Methyl palmitate 6-12% Methyl stearate 1- 3% Relative Density 0.94-0.96 Hydroxyl Value 140-210 Iodine Value 110-120 Peroxide Value <4.0 Free Glycerol Acid value max. ca. 2 Saponiftcation no. ca. 150-185 Components (2) complying with the above outlined features are referred to herein as "refined glycerol-transesterified corn oils". Freshly prepared components (2) according to the preferred embodiments are of clear appearance and stay clear at storage temperature of °C - 25°C for more than 20 days.
The refined glycerol-transesterified corn oils have especially been proposed for the preparation of the compositions disclosed in IE 922082. They may also have uses for the solubilization of other active agents and have the advantage of remaining stable, e.g. clear, for a long time.
The following example illustrates the present invention.
EXAMPLE 1: Preparation of refined glycerol-transesterified corn oil.
Substantially-glycerol free glycerol-transesterified corn oil (if necessary after heating to give a clear mixture) is slowly cooled to a temperature of -t-20°C and kept at this temperature for one night. In a first-step centrifugation, at an acceleration of 12 000 G and (62 kg/h) and a sediment-containing phase (41 kg/h) are obtained. The liquid phase is slowly cooled to a flow rate of 103 kg/h in a continuous flow centrifuge, a liquid phase +8°C and kept at this temperature for one night. In a second-step centrifugation at an G and a flow rate of 112 kg/h a liquid phase (76.2 kg/h) and a sediment-containing phase (35.8 kg/h) are obtained. The liquid phase is "refined glycerol—transesterifted corn oil". Alternatively an improved product may be obtained by acceleration of effecting the centrifugation in three steps, e.g. at +20°C, +10°C and +S°C.
The process is characterised by a slight percentage reduction in the mono-glyceride component in the refined glycerol transesterified corn oil as compared to the starting material (e.g. 35.6% compared to 38.3%).
A typical analytical comparison between the sediment and clear solution is as follows: Compound Sediment (%) Clear Solution (%) . Mono palmitate 19.1 3.4 2. Mono linoleate + 23.4 27.0 Mono oleate 3. Mono stearate 5.7 <2 Dilinoleate + 35.4 44.7 Dioleate . Other di-glycerides 7.7 10.4 Tri-glycerides 8.7 12.5 Typical contents of components in the refined product obtained from these preparations are listed in the following Table: COMPOSITION OF COMPONENTS (% w/w) Components refined glycerol-trans- esterified corn oil Glycerides: mono 33.3 di 52.1 tri 14.6 Fatty acids: palrnitic acid (C16) 7.8 stearic acid (C18) 1.7 oleic acid (C1821) 31.6 linoleic acid (Cl8:2) 57.7 Glycerol content <1%
Claims (17)
1. A trans-esterification product of corn oil and glycerol comprising predominately of linoleic acid and oleic acid mono-, di- and tri-glycerides, and having a free glycerol content less than 10% by weight, wherein the product has been treated so as to a) reduce the saturated fatty acid component content of mono«, di- and tri—glycerides; and to b) enhance the unsaturated fa"v acid component content of mono-, di- and tri-glycerides so that the linoleic acid and oleic acid mono-, di- and triglyceride content is in total 85% by weight or more of the whole composition.
2. A product as claimed in claim 1 having 30% to 40% by weight of mono-glycerides.
3. A product as claimed in claim 1 or claim 2 having 45% to 55% by weight of di- glycerides.
4. A product as claimed in any preceding claim having from about 7.5 to about 15 % by weight of tri-glycerides.
5. A product as claimed in any preceding claim having a free glycerol content of less than 5% by weight.
6. A product as claimed in any preceding claim having a free glycerol content of less than 2% by weight.
7. A product as claimed in any preceding claim, having a total palmitic acid and stearic acid content of mono-, di- and tri-gylcerides of less than 10% by weight. 35 _ 7 _
8. A transesterification product of corn oil and glycerol having a saturated fatty acid content of mono-, di-, and tri-glycerides, and having a free glycerol content less than 10% by weight, which product comprises i) from about 25% to about 50% by weight of mono-glycerides, from about 30% to about 60% by weight of di-glycerides, and at least 5% by weight of tri-glycerides; and ii) a linoleic acid, oleic acid and linolenic acid mono-, di- and tri-glyceride content of at least 85% by weight; wherein the total saturated fatty acid content of mono-, di-, and tri-glycerides is less than 10% by weight.
9. A product as claimed in claim 8 having 30% to 40% by weight of mono~g1ycerides.
10. A product as claimed in claim or claim 9 having 45% to 55% by weight of di- glycerides.
11. A product as claimed in any one of claims 8 to 10 having from about 7.5 to about 15 % by weight of triglycerides.
12. A product as claimed in any one of claims 8 to 11 having a free glycerol content of less than 5% byweight.
13. A product as claimed in any one of claims 8 to 12 having a free glycerol content of less than 2% by weight.
14. A product as claimed in any one of claims 8 to 13, having a total palmitic acid and stearic acid content of mono-, di- and tri-gylcerides of less than 10% by weight.
15. A process for obtaining a refined glycerol-transesterified corn oil according to any preceding claim, comprising heating of corn oil with glycerol at high temperature in the presence of a suitable catalyst under an inert atmosphere with continuous agitation to effect glycerol-transesterification. and refining said product by freezing procedures coupled with separative techniques.
16. A transesterified corn oil substantially as hereinbefore described with reference to Example 1.
17. A process substantially as hereinbefore described with reference to Example 1. TOMKI NS 81 C0 .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBUNITEDKINGDOM27/06/19919113872 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE84659B1 true IE84659B1 (en) | 2007-08-08 |
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