GB2117381A - Vitamin E extraction - Google Patents
Vitamin E extraction Download PDFInfo
- Publication number
- GB2117381A GB2117381A GB08303777A GB8303777A GB2117381A GB 2117381 A GB2117381 A GB 2117381A GB 08303777 A GB08303777 A GB 08303777A GB 8303777 A GB8303777 A GB 8303777A GB 2117381 A GB2117381 A GB 2117381A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tocotrienol
- tocopherols
- aliphatic
- leaves
- organic solvent
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Abstract
Tocopherols and tocotrienols are extracted from the leaves of the palm tree, banana, pineapple and/or sugar cane with one or more organic solvents. Further treatment of the obtained extract solution by means of low-temperature fractionation, adsorption by use of an adsorbent or molecular distillation, or a combination of these treatments, gives a concentrate of tocopherols and tocotrienols.
Description
SPECIFICATION
Method for separating tocopherols and tocotrienol
This invention relates to a method for separating tocopherols and tocotrienol, and more particularly it relates to a method for extracting tocopherols and tocotrienol contained in leaves of palm tree, banana or the like with an organic solvent or solvents and concentrating said substances.
It is known that tocopherols and tocotrienols have a vitamin E activity, and they have long been utilized as an antisterility drug for animals. It has been disclosed lately that these substances further possess an antioxidizing action for oil- or fat-derived foods as well as a medicinal action of preventing adult diseases and senility, and their demand for use as food additives, pharmaceuticals, nourishing foods and cosmetics has increased sharply.
Hitherto, tocopherols and tocotrienols have been separated from deodorized distillates of soybean oil, cotton seel oil or the like. However, because of their relatively low content in said raw materials and also the complicated processes for separation and refining, said substances have been relatively costly and also their supply could hardly meet the rushing demand.
If it is made possible to separate tocopherols and tocotrienols from more inexpensive natural products by a more simple process, then it will become possible to supply said substances at lower cost and in greater amounts to well meet the growing demand.
The present invention has been contemplated under these circumstances and its object is to provide a method for extracting tocopherols and tocotrienol from inexpensive natural products by a simple procedure.
Another object of this invention is to provide a method for concentrating extracts of tocopherols and tocotrienol obtained from such inexpensive natural products.
Thus, the present invention, in one aspect thereof, is characterized by extracting tocopherols and tocotrienol from leaves of palm tree, banana, pineapple or sugar cane (Saccharum officinarum) by treating leaves of one of said plants or mixed leaves of two or more of said plants with a single organic solvent or a mixture of organic solvents.
In another aspect, the present invention is characterized by treating leaves of one of palm tree, banana, pineapple and sugar cane or mixed of leaves of two or more of said plants with a single or mixed organic solvent and further treating the extract by means of low-temperature fractionation, adsorption by use of an adsorbent or molecular distillation, or a combination of said treating means, to thereby concentrate tocopherols and tocotrienol.
The tocopherols to be extracted in this invention are a-tocopherol, P-tocopherol, y-tocopherol and b-tocopherol. The tocotrienol, which is another substance to be extracted in this invention, is atocotrienol. Of these substances, p- and 8-tocopherols and a-tocotrienol are minor components and atocopherol which has the strongest vitamin E activity is the principal component.
Shown in the following table are contents of said substances in the leaves of palm tree, banana or sugar cane.
Toco Tocopherols trienol 2 V Y 6 a Total Palm tree 14,805 44 84 12 18 14,963 Banana 1,687 13 1,250 12 - 2,952 Sugar cane 3,984 - 402 - - 4,386 Unit: dug/g of extract
The leaves of palm tree, banana, pineapple or sugar cane to be used for extracting said objective substances in this invention include those of said plants which are growing or after harvesting or reaping.For instance, leaves cut out when harvesting fruits of said plants or leaves of sugar cane cut down when reaping it may be used. Also, leaves of all species of palm tree, banana, pineapple and sugar cane can be used. These leaves are usually chopped, crushed or pulverized, and in some cases further dried thereafter, in order to facilitate the extraction treatment by an organic solvent or solvents.
Also, leaves of only one of said plants, for example, palm tree alone, or leaves of two or more of said plants, for example mixed leaves of palm tree and banana may be used for the extraction treatment of this invention.
As the examples of the organic solvents usable in this invention, there may be cited aliphatic alcohols such as methanol, ethanol, or isopropanol, aliphatic ethers such as ethyl ether or isopropyl ether, aliphatic ketones such as methyl ethyl ketone, aliphatic carboxylic acid esters such as methyl formate, ethyl formate, or ethyl acetate, aliphatic and aromatic hydrocarbons such as petroleum ether, hexane, heptane, benzene, toluene, or oxylene, and halogenated aliphatic hydrocarbons such as chloroform, methylene chloride, or ethylene chloride. These organic solvents may be used either alone or in admixture. Also, mixtures of these organic solvents with water-insoluble organic solvents may be used.
The extraction is usually carried out at room temperature, or between 20 and 250 C. For instance, chopped leaves of palm tree, banana, pineapple or sugar cane are immersed in an organic solvent or a mixture of the organic solvents mentioned above and, after 1 - to 3-hour standing, the leaves are filtered off to obtain an extract solution of tocopherols and tocotrienol.
Further, according to this invention, the thus obtained extract solution of tocopherols and tocotrienol can be concentrated by subjecting said extract solution to low-temperature fractionation, adsorption by use of an adsorbent or molecular distillation or a combination of such treatments.
The low-temperature fractionation is accomplished by cooling the extract solution of tocopherols and tocotrienol to a temperature of-10 to -400C, this cooling being usually conducted after further adding an organic solvent or solvents for facilitating the fractionation, and separating an organic solvent insoluble portion from a soluble portion, followed by the removal of the organic solvent(s), as by distillation, from the soluble portion to obtain concentrated tocopherols and tocotrienol as a residue.
The adsorption treatment by use of an adsorbent in this invention can be accomplished by first adding a non-polar organic solvent to said extract solution of tocopherols and tocotrienol, passing the solution through an alumina- or silica-packed column, subsequently passing a non-polar organic solvent and/or an alcohol, an ether, a ketone, an ester, an aromatic compound and/or an organic chloride either alone or as a mixed solution, and then removing the solvent(s) from eluted fractions to obtain a tocopherol and tocotrienol concentrate as a residue. Hydrocarbons such as petroleum ether, hexane, or heptane may be used as the non-polar organic solvent in this treatment.Alternatively, the treatment may be accomplished by passing the extract solution and a mixed solution of non-polar and polar organic solvents through a column packed with an ion exhcange resin instead of alumina or silica, then further passing an acidic organic solvent such as an acetic acid-ethanol solution, washing the obtained fraction with water and distilling off the organic solvents, whereby a desired tocopherol and tocotrienol concentrate is given as a residue.
Further, in accordance with this invention, a similar concentrate of tocopherols and tocotrienol can be obtained by subjecting said extract solution to molecular distillation under a vacuum of 10-2 to
10-3 mmHg or below and recovering a fraction which distils out at 1900 to 2300C.
As described above, it is possible according to this invention to separate tocopherols and tocotrienol by a simple operation involving extraction with an organic solvent or solvents by using inexpensive material such as leaves of palm tree, banana, pineapple or sugar cane.
Further, in accordance with this invention, a concentrate of tocopherols and tocotrienol can be obtained with ease by subjecting the extract solution of tocopherols and tocotrienol to lowtemperature fractionation, adsorption treatment or molecular distillation.
It will thus be appreciated that the present invention makes it possible to produce tocopherols and tocotrienol, which have a vitamin E activity, at low cost and in great quantities and can well comply with the expanding demand for said substances.
The present invention will be described in further detail hereinbelow in accordance with the examples thereof.
Example 1
2 kg of palm leaves (water content: 42%) were chopped and extracted with a hexane-ethanol (1:1 v/v) mixed solution at room temperature (22-240C) to obtain 102 g of an extract. 800 ml of ethanol was added to this extract and the mixture was mixed well by shaking and then cooled to -200C to fractionate a soluble portion. Ethanol was distilled off from said soluble portion to obtain 15 g of a residue. High performance liquid chromatography of this residue (1) showed that it contained 81,000 ,ug/g of a-tocopherol, 350 *4gig of tocophernl, 4,240 ,ug/g of y-tocopherol and 200 4g/g of y-tocotrienol, or total 85,790 yg/g of tocopherols and tocotrienol combined.
Examples 2
1 kg of sugar cane leaves (water content: 73%) were chopped and extracted by using a hexaneethanol (1:1 v/v) mixed solution aroom temperature (20--220C) to obtain 15 g of an extract. This extract was well mixed with 200 ml of ethanol by stirring and then cooled to -200C to fractionate a soluble portion, followed by distilling-off of ethanol from said soluble portion to obtain 3 g of a residue.
High performance liquid chromatography conducted on said residue showed an a-tocopherol content of 12,000 ,ug/g and a y-tocophernl content of 4,500 yglg, or a total tocopherol content of 1 6,500 ssg/g.
Example 3
10 g of residue (1) obtained in Example 1 was dissolved in 50 ml of an ethanol-hexane (1:1) mixed solution and the mixture was passed through a layer of Amberlite IRA 401, an OH type basic anion exchange resin, packed in a 5 cm-diameter and 100 cm-long glass-made chromatographic tube to a height of 50 cm to have tocopherols and tocotrienol adsorbed in said layer, and then 300 ml of hexane was flown therethrough to let the neutral matter run away. Then 200 ml of a 5% acetic acid ethanol solution was passed and the solvents were distilled off from the eluate to obtain 0.8 g of a tocopherol concentrate (purity: 65%).
Example 4
1 kg of pineapple leaves (water content: 45%) were chopped and extracted with acetone at room temperature (23--240C) to obtain 45.2 g of an extract. This extract was dissolved in 400 ml of ethanol and then cooled to -200C to fractionate a soluble portion. Then ethanol was distilled off from said soluble portion to obtain 8.6 g of a residue. This residue contained 48,000 jt4g/g of a-tocopherol, 12,800 ,ug/g of y-tocopherol, 650 jug/g of a-tocotrienol and 1 ,1 jug/g of y-tocotrienol, or total 62,550 ,ug/g of tocopherols and tocotrienols.
Example 5
20 kg of banana leaves (water content: 65%) were chopped and extracted by using a hexaneethanol (1 :1 v/v) mixed solution at room temperature (24-250C). The extract solution contained 22,000 4g of a a-tocopherol and 1,060 g of y-tocopherol, totalling 23,060,us of tocopherols.
Example 6
4 kg of palm leaves (water content: 48%) were crushed down by using a roller and then chopped, and the chopped leaves were added to 12 litres of a hexane-ethanol (1:1 v/v) mixed solution and allowed to stand overnight at room temperature (22--240C), followed by the fractionation of the extract solution to obtain 1 86 g of an extract. This extract was well mixed with 1 litre of methanol by shaking and cooled to OOC to fractionate a soluble portion. Methanol was distilled off from this soluble portion to obtain 48 g of a residue.To 20 g of this resude was added 20 g of refined palm oil and the mixture was subjected to molecular distillation under 5x 10-3 mmHg to fractionate the mixture into four fractions: a first fraction at 1 900C or below, a second fraction at 1 90--2000C, a third fraction at 200-2200C and a final residue. The tocopherol content of each fraction was as follows: 23.5% in the first fraction,8.1 in the second fraction, 2.5% in the third fraction and 0.6% in the final residue.
Example 7
2.3 kg of palm leaves (water content: 42%) were chopped and extracted with a hexane-ethanol (1:1 v/v) mixed solution at room temperature (22-240C) to obtain 116 g of an extract. 51 of hexaneethanol (1:1 v/v) mixed solution of hexane was added to this extract and mixed well. This mixture was washed with large amount of hot water to remove water soluble matters from said mixture and then dried completely followed by cooling to -200C to fractionate a hexane soluble portion. This hexane soluble portion was passed through a silica-packed column (Bio Sil A, 100-200 mesh), subsequently hexane was passed. Hydrocarbons were eluted first and then c-tocopheral was eluted by hexane. By collecting cg-tocopherol fraction and removing solvent from said fraction, 2.5 g of a-tocopherol concentrate was obtained as a residue. A concentration and a recovery of ce-tocopherol of said residue were 68.4% and 83.3%, respectively.
Claims (9)
1. A method for separating tocopherols and tocotrienol which comprises treating leaves of palm tree, of banana, of pineapple and/or of sugar cane either alone or in admixture with a single or mixed organic solvent and extracting tocopherols and tocotrienol.
2. The method for separating tocopherols and tocotrienol according to Claim 1, wherein the organic solvent is selected from the group consisting of aliphatic alcohols, aliphatic ethers, aliphatic ketones, aliphatic carboxylic acid esters, aliphatic hydrocarbons, aromatic hydrocarbons and halogenated aliphatic hydrocarbons.
3. The method for separating tocopherols and tocotrienol according to Claim 1, wherein the leaves of palm tree, of banana, cf pineapple and/or of sugar cane are used after chopping or pulverizing them.
4. A method for separating tocopherols and tocotrienol which comprises treating leaves of palm tree, of banana, of pineapple and/or of sugar cane either alone or in admixture with a single or mixed organic solvent, and subjecting the obtained extract solution to one of the following treatments or a combination thereof: low-temperature fractionation, adsorption by use of an adsorbent, and molecular distillation, to thereby obtain a concentrate of tocopherols and tocotrienol.
5. The method for separating tocopherols and tocotrienol according to Claim 4, wherein the organic solvent is selected from the group consisting of aliphatic alcohols, aliphatic ethers, aliphatic ketones, aliphatic carboxylic acid esters, aliphatic hydrocarbons, aromatic hydrocarbons and halogenated aliphatic hydrocarbons.
6. The method for separating tocopherols and tocotrienol according to Claim 4, wherein the leaves of palm tree, of banana, of pineapple and/or of sugar cane are used after chopping or pulverizing them.
7. The method for separating tocopherols and tocotrienol according to Claim 4 wherein the adsorbent is silica, alumina or an ion exchange resin.
8. The method for separating tocopherols and tocotrienol according to Claim 4 wherein the adsorption treatment by use of an adsorbent is conducted after adding a non-polar organic solvent to the extract solution.
9. A method for separating tocopherols and tocotrienol as claimed in claim 1 and substantially as described in any of Examples 1 to 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2551982A JPS58144382A (en) | 1982-02-19 | 1982-02-19 | Separation of tocopherol and tocotrienol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8303777D0 GB8303777D0 (en) | 1983-03-16 |
| GB2117381A true GB2117381A (en) | 1983-10-12 |
| GB2117381B GB2117381B (en) | 1985-07-10 |
Family
ID=12168302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08303777A Expired GB2117381B (en) | 1982-02-19 | 1983-02-11 | Vitamin e extraction |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58144382A (en) |
| GB (1) | GB2117381B (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4603142A (en) * | 1984-06-01 | 1986-07-29 | Wisconsin Alumni Research Foundation | Cholesterol lowering method of use |
| WO1991017985A1 (en) * | 1990-05-23 | 1991-11-28 | Lipogenics, Inc. | Processes for recovering tocotrienols, tocopherols and tocotrienol-like compounds |
| FR2669032A1 (en) * | 1990-11-14 | 1992-05-15 | Cecchi Georges | Process for the manufacture of a d- alpha -tocopherol preparation |
| US5138075A (en) * | 1983-07-05 | 1992-08-11 | Kuraray Co., Ltd. | Extractive separation method |
| US5190618A (en) * | 1988-03-16 | 1993-03-02 | Bioindustry Development Centre (Bidec) | Production of high concentration tocopherols and tocotrienols from palm-oil by-products |
| US5348974A (en) * | 1989-10-04 | 1994-09-20 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| EP0941671A2 (en) | 1998-03-12 | 1999-09-15 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Taste agent from Saccharum Officinarum, process for preparing it, products containing it |
| US5985344A (en) * | 1997-09-02 | 1999-11-16 | The Ricex Company | Process for obtaining micronutrient enriched rice bran oil |
| EP1043051A2 (en) * | 1999-01-25 | 2000-10-11 | F. Hoffmann-La Roche Ag | Process for preparing an adsorbent which is loaded with an oil |
| EP1163235A2 (en) * | 1999-01-26 | 2001-12-19 | Archer-Daniels-Midland Company | Methods for separating a tocopherol from a tocopherol-containing mixture and compositions thereof |
| WO2009110782A1 (en) * | 2008-03-06 | 2009-09-11 | Nova Laboratories Sdn Bhd | Extract from oil palm leaves comprising phenolic acids |
| WO2010110640A1 (en) * | 2009-03-24 | 2010-09-30 | Universiti Putra Malaysia | Anti-diabetic nutraceutical composition from palm leaf extract |
| US20150259370A1 (en) * | 2014-03-11 | 2015-09-17 | Ecotech Development LLC | Integrated process extraction of pineapple biomass into fibers and natural products |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3582904D1 (en) * | 1984-08-02 | 1991-06-27 | Henkel Corp | CLEANING TOCOPHEROLS BY EXTRACTION. |
| JP5312731B2 (en) * | 2006-08-30 | 2013-10-09 | 株式会社ノエビア | Topical skin preparation |
| EP2209392B1 (en) * | 2007-10-05 | 2014-01-01 | Horizon Science Pty Ltd | Natural preservatives and antimicrobial agents |
| JP5566677B2 (en) * | 2008-12-05 | 2014-08-06 | 株式会社 ヒロインターナショナル | An androgen action inhibitor, prostate enlargement inhibitor, and androgen-dependent hair loss inhibitor containing whole plants other than banana fruit as active ingredients |
| AU2012214104C1 (en) | 2011-02-08 | 2017-08-03 | Poly Gain Pte Ltd | Sugar extracts |
| WO2014032100A1 (en) | 2012-08-28 | 2014-03-06 | Phytolin Pty Ltd | Extraction method |
| EP3035949B1 (en) | 2013-08-16 | 2023-10-04 | Poly Gain Pte Ltd | Sugar cane derived extracts and uses |
-
1982
- 1982-02-19 JP JP2551982A patent/JPS58144382A/en active Granted
-
1983
- 1983-02-11 GB GB08303777A patent/GB2117381B/en not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138075A (en) * | 1983-07-05 | 1992-08-11 | Kuraray Co., Ltd. | Extractive separation method |
| US4603142A (en) * | 1984-06-01 | 1986-07-29 | Wisconsin Alumni Research Foundation | Cholesterol lowering method of use |
| US5190618A (en) * | 1988-03-16 | 1993-03-02 | Bioindustry Development Centre (Bidec) | Production of high concentration tocopherols and tocotrienols from palm-oil by-products |
| US5348974A (en) * | 1989-10-04 | 1994-09-20 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| WO1991017985A1 (en) * | 1990-05-23 | 1991-11-28 | Lipogenics, Inc. | Processes for recovering tocotrienols, tocopherols and tocotrienol-like compounds |
| AU666464B2 (en) * | 1990-05-23 | 1996-02-15 | Lipogenics, Inc. | Processes for recovering tocotrienols, tocopherols and tocotrienol-like compounds |
| US5908940A (en) * | 1990-05-23 | 1999-06-01 | Lipogenics, Inc. | Processes for recovering tocotrienols, tocopherols and tocotrienol-like compounds |
| FR2669032A1 (en) * | 1990-11-14 | 1992-05-15 | Cecchi Georges | Process for the manufacture of a d- alpha -tocopherol preparation |
| US5985344A (en) * | 1997-09-02 | 1999-11-16 | The Ricex Company | Process for obtaining micronutrient enriched rice bran oil |
| US6706898B2 (en) | 1998-01-29 | 2004-03-16 | Archer-Daniels-Midland Company | Methods for separating a tocopherol from a tocopherol-containing mixture |
| EP0941671A3 (en) * | 1998-03-12 | 2001-08-01 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Taste agent from Saccharum Officinarum, process for preparing it, products containing it |
| EP0941671A2 (en) | 1998-03-12 | 1999-09-15 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Taste agent from Saccharum Officinarum, process for preparing it, products containing it |
| EP1043051A2 (en) * | 1999-01-25 | 2000-10-11 | F. Hoffmann-La Roche Ag | Process for preparing an adsorbent which is loaded with an oil |
| EP1043051A3 (en) * | 1999-01-25 | 2002-12-11 | F. Hoffmann-La Roche Ag | Process for preparing an adsorbent which is loaded with an oil |
| EP1163235A2 (en) * | 1999-01-26 | 2001-12-19 | Archer-Daniels-Midland Company | Methods for separating a tocopherol from a tocopherol-containing mixture and compositions thereof |
| EP1163235A4 (en) * | 1999-01-26 | 2002-06-26 | Archer Daniels Midland Co | Methods for separating a tocopherol from a tocopherol-containing mixture and compositions thereof |
| WO2009110782A1 (en) * | 2008-03-06 | 2009-09-11 | Nova Laboratories Sdn Bhd | Extract from oil palm leaves comprising phenolic acids |
| WO2010110640A1 (en) * | 2009-03-24 | 2010-09-30 | Universiti Putra Malaysia | Anti-diabetic nutraceutical composition from palm leaf extract |
| US9937220B2 (en) | 2009-03-24 | 2018-04-10 | Universiti Putra Malaysia | Anti-diabetic nutraceutical composition from palm leaf extract |
| US20150259370A1 (en) * | 2014-03-11 | 2015-09-17 | Ecotech Development LLC | Integrated process extraction of pineapple biomass into fibers and natural products |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH029590B2 (en) | 1990-03-02 |
| JPS58144382A (en) | 1983-08-27 |
| GB2117381B (en) | 1985-07-10 |
| GB8303777D0 (en) | 1983-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |