JPS58144382A - Separation of tocopherol and tocotrienol - Google Patents
Separation of tocopherol and tocotrienolInfo
- Publication number
- JPS58144382A JPS58144382A JP2551982A JP2551982A JPS58144382A JP S58144382 A JPS58144382 A JP S58144382A JP 2551982 A JP2551982 A JP 2551982A JP 2551982 A JP2551982 A JP 2551982A JP S58144382 A JPS58144382 A JP S58144382A
- Authority
- JP
- Japan
- Prior art keywords
- leaves
- tocopherol
- extract
- organic solvent
- tocotrienols
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明はノシーム、バナ＼、パイナツプル及びサトウキ
ビ等の葉に含まれるトコフェロール類及びトコトリエノ
ール類の分離方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating tocopherols and tocotrienols contained in leaves of noseem, banana, pineapple, sugarcane, etc.
トコフェロール類はビタミンＥ活性を有し、励動の抗不
妊薬として利用されてきたが、最近油脂食品の酸化防止
、成人病の予防、老゛化の防止等の作用が明らかになり
、食品添加物、医薬品、栄養食品及び化粧品等への需要
が急速に増大している。Tocopherols have vitamin E activity and have been used as active anti-infertility drugs, but recently it has been revealed that they have the ability to prevent the oxidation of fats and oils, prevent adult diseases, and prevent aging. Demand for products, pharmaceuticals, nutritional foods, cosmetics, etc. is rapidly increasing.
本発明者らはパーム、バナＮ、パイナツプル及びサトウ
キビ等の葉を粉砕又は細断後乾燥するか又はしないで、
アルコール、エーテル、ケトン等の有機溶剤を単独又は
混合したもので抽出するが、これらの有機溶剤と手工溶
性有機溶剤との混合溶剤を用いて抽出することにより、
トコフェロール類並びにトコトリエノール類を分離し得
ることｒ見出した。さらに、この抽出物について、低温
分別、シリカ、アルぐす、イオン交換樹脂等を用いる吸
着処理並びに分子蒸留等を単独又は組合せて用いる仁と
により、トコフェロール類並びにトコトリエノール類を
濃縮し得ることを見出し、本発明を完成した。The inventors have discovered that the leaves of palm, Bana N, pineapple, sugarcane, etc. are crushed or shredded and then dried or not.
Extraction is performed using organic solvents such as alcohol, ether, ketone, etc. alone or in combination, but by extraction using a mixed solvent of these organic solvents and a hand-soluble organic solvent,
It has been found that tocopherols and tocotrienols can be separated. Furthermore, it has been discovered that tocopherols and tocotrienols can be concentrated in this extract by low-temperature fractionation, adsorption treatment using silica, argus, ion exchange resin, etc., and molecular distillation alone or in combination, The invention has been completed.
本発明におけ？コフエロール類はα−トコフェロール、
β−トコフェロール、γ−トコフェロール及ヒδ−トコ
フェロール等でアル。’７７’（、トコトリエノール類
ハα−トコトリエノール、β−トコトリエノール、γ−
トコトリエノール及ヒδ−トコトリエノール等であろう
これらの８種の成分Ｏａｔ、、δ−トコフェロール、α
−１β−及ヒＪ−トコトリエノールは少量成分であり、
ビタミンＥ活性の最も強いα−トコフェロール及びγ−
トコフェロールが主成分として含まれている。In the present invention? Copherols are α-tocopherol,
Al such as β-tocopherol, γ-tocopherol and human δ-tocopherol. '77' (Tocotrienols α-tocotrienol, β-tocotrienol, γ-
These eight components may include tocotrienol and δ-tocotrienol, δ-tocopherol, α
-1β- and H-J-tocotrienol are minor components,
α-tocopherol and γ- have the strongest vitamin E activity.
Contains tocopherol as the main ingredient.
本発明の出発物質はパーム、バナ＼、パイナツプル及び
サトウキビの葉で、生育中並びに収穫後の葉を含むもの
であり、例えば果実を収穫する時に切り取った葉及びサ
トウキビを収穫する時に刈取った葉もあげられる。The starting materials of the present invention are palm, banana, pineapple and sugarcane leaves, including both growing and harvested leaves, such as leaves cut when harvesting fruit and leaves cut when harvesting sugarcane. You can also give
本発明によれば、メタノール、エタノール、インプロパ
ツール等のアルコール、エチルエーテル、インプロピル
エーテル等のエーテル、アセトン、メチルエチルケトン
等のケトン、ギ酸メチル、ギ酸エチル、酢酸メチル、酢
酸エチル等のカルボン酸エステル、石油エーテル、ヘキ
サン、ヘプタン、ベンゼン、トルエン、キシレン等の炭
化水素及ヒクロロホルム、塩化メチレン、□塩化エチレ
ン等のハロゲン化炭化水素等の有機溶剤を単独又は混合
物を抽出溶剤として用いて葉を抽出処理することにより
、トコフェロール類並びにトコトリエノール類を含む抽
出物が得られる。According to the present invention, alcohols such as methanol, ethanol, and impropanol; ethers such as ethyl ether and impropyl ether; ketones such as acetone and methyl ethyl ketone; and carboxylic acid esters such as methyl formate, ethyl formate, methyl acetate, and ethyl acetate. Extract the leaves using organic solvents such as hydrocarbons such as , petroleum ether, hexane, heptane, benzene, toluene, and xylene, and halogenated hydrocarbons such as dichloroform, methylene chloride, and ethylene chloride, alone or in combination, as extraction solvents. The treatment yields an extract containing tocopherols and tocotrienols.
本発明における抽出物を有機溶剤の存在下で低温分別を
行い、可溶部にトコフェロール類並びにトコトリエノー
ル類の濃縮物が得られる。The extract in the present invention is subjected to low-temperature fractionation in the presence of an organic solvent, and a concentrate of tocopherols and tocotrienols is obtained in the soluble portion.
また、本発明における抽出物を無極性有機溶剤に溶解し
、アルミナ又はシリカを充填したカラムに流し、続いて
、アルコール、エーテル、ケトン、エステル、芳香族化
合物及び有機塩素化物等を単独又は混合溶液として流し
、後者の流出区分から溶剤を除去して、残留物中にトコ
フェロール及びトコトリエノール濃縮物を得ることがで
きる。上記方法のアルミナ又はシリカの代りに、イオン
交換体をカラムにつめ、これに抽出物の有機溶剤の溶液
を流し、続いて酸性の有機溶剤を流して得られる区分を
水洗、蒸留後、残留物中にトコフェロール類及びトコト
リエノール類の濃縮物を得ることができる。In addition, the extract in the present invention is dissolved in a nonpolar organic solvent and passed through a column packed with alumina or silica, and then alcohol, ether, ketone, ester, aromatic compound, organic chloride, etc. are added as a single or mixed solution. The solvent can be removed from the latter effluent section to obtain tocopherol and tocotrienol concentrates in the residue. Instead of alumina or silica in the above method, an ion exchanger is packed in a column, and an organic solvent solution of the extract is poured into the column, followed by an acidic organic solvent.The resulting section is washed with water, and after distillation, the residue is Concentrates of tocopherols and tocotrienols can be obtained therein.
さらに、本発明層おける抽出物を１０−２〜１Ｏ−３−
Ｕ以下の真空度で分子蒸留を行い、１９０℃〜２３０℃
で留出する区分を回収して、トコフェロール類及びトコ
トリエノール類の濃縮物を得ることがで・きる。Furthermore, the extract in the present invention layer is 10-2 to 1O-3-
Molecular distillation is carried out at a vacuum degree of U or below, and the temperature is 190℃ to 230℃.
The fraction distilled in can be collected to obtain a concentrate of tocopherols and tocotrienols.
以下実施例により本発明の詳細な説明する。The present invention will be explained in detail below with reference to Examples.
実施例１゜
パームの葉２ｋｌｉｌ（水分４２％）を細断した後、ヘ
キサン、エタノール（Ｖ／Ｖ、１：１）混合溶液を用い
、室温２２〜２４℃で抽出した。抽出物１０２ｇを得た
。この抽出物にエタノール８００１１１１加え、よく振
りまぜた後、−２０°Ｃに冷却し、可溶部を分別した。Example 1 Two kilograms of palm leaves (water content 42%) were shredded and extracted at room temperature of 22 to 24°C using a mixed solution of hexane and ethanol (V/V, 1:1). 102 g of extract was obtained. Ethanol 8001111 was added to this extract, and after shaking well, it was cooled to -20°C and the soluble portion was separated.
可溶部からエタノールを留去し、残留物２５１を得た。Ethanol was distilled off from the soluble portion to obtain residue 251.
この残留物（１）はα−トコフェロール８１，０００ｇ
ｇ／ｇ、ｐ−）コフエロール３５０μ９７９、γ−トコ
フェロール４，２４０μ９／９、γ−トコト１ノエノー
ル２００μｇ／ｇ、合計８５，７９０μ、！ｉＩ／ｇを
含有していた。This residue (1) contains 81,000 g of α-tocopherol.
g/g, p-) Copherol 350μ979, γ-tocopherol 4,240μ9/9, γ-tocoto1 noenol 200μg/g, total 85,790μ,! It contained iI/g.
実施例２゜
サトウキビの葉１ｋｇ（水分７３襲）を細断した後、ヘ
キサ／、エタノール（Ｖ／Ｖ、 １ ： １）混合溶液
を用い、室温２０〜２２°Ｃで抽出した。抽出物１５ｇ
を得た。この抽出物にエタノール２００ｍ１をカロえ、
よくかきまぜた後、−２０℃に冷却し、可溶部を分別し
た。可溶部からエタノールを留去し、残留物３ｇを得た
。この残留物はα−トコフェロール１２．０００ ｔｔ
ｌ／１１及びｒ−）：７フエｏ−ル４，５００μ、９／
ｇ、合計１６，５００μ９／９を含有していた。Example 2 1 kg of sugarcane leaves (water content: 73%) were shredded and extracted at room temperature of 20-22°C using a mixed solution of hexa/ethanol (V/V, 1:1). 15g extract
I got it. Add 200ml of ethanol to this extract,
After stirring thoroughly, the mixture was cooled to -20°C and the soluble portion was separated. Ethanol was distilled off from the soluble portion to obtain 3 g of residue. This residue contains 12,000 tt of α-tocopherol.
l/11 and r-): 7 fer o-le 4,500μ, 9/
g, a total of 16,500 μ9/9.
実施例３゜
実施例３で得られた残留物（１） １０ｇ ’ｋ ５０
ｍｌのエタノールに溶解し、これをＯＨ型塩基性陰イオ
ン交換樹脂アンバーライトＩＲＡ４０１を径５ｃｒＩＬ
、長さ１００ａｎのガラス製クロマト管に５０ｃｍの高
さに充填した層に流し、トコフェロール類及びトコトリ
エノール類を吸着させた後、３ＱＱｍｌのヘキサンを流
して、中性物質を流去した。次に５％酢酸エタノール２
００１１を流し、流出液から溶剤金留去するとトコフェ
ロール濃縮物ｏ、ｓｙｃ純度６５％）が得られた。Example 3゜Residue obtained in Example 3 (1) 10g 'k 50
ml of ethanol, and add the OH type basic anion exchange resin Amberlite IRA401 to a diameter of 5crIL.
The mixture was poured into a layer packed in a glass chromatography tube with a length of 100 ann to a height of 50 cm to adsorb tocopherols and tocotrienols, and then 3QQml of hexane was poured to wash away neutral substances. Next, 5% acetic acid ethanol 2
0011 was poured, and the solvent gold was distilled off from the effluent to obtain a tocopherol concentrate (O, syc purity 65%).
実施例４、
パイナツプルの葉１ｋｇ（水分４５％）を細断した後、
アセトンを用い室温２３〜２４℃で抽出した。Example 4: After shredding 1 kg of pineapple leaves (45% moisture),
Extraction was performed using acetone at room temperature of 23-24°C.
抽出物４５．２．Ｆを得た。この抽出物をエタノール４
００ｍ１に溶解後、−２０℃で冷却し、可溶部を分取し
た。可溶部からエタノールを留去し、残留物８．６ｇを
得光。この残留物はα−トコフェロール。Extract 45.2. I got an F. This extract was added to ethanol 4
After dissolving in 00ml, it was cooled at -20°C and the soluble portion was separated. Ethanol was distilled off from the soluble portion to obtain 8.6 g of a residue. This residue is α-tocopherol.
４８．０００ ｔｔｌ／／ｌ！、ｒ −） コ７工ａ−
ル１２，８００ａｌｌ／ｇ１ α−トコトリエノール６
５０μｇ／Ｅｌ、γ−トコトリエ／−ル１．ｉ ｏｏｔ
ｔ９／９、合計６２．５ ｓ ｏ ｔｔｉ／１を含有し
ていた。48.000 ttl//l! , r -) ko7 engineering a-
12,800all/g1 α-tocotrienol 6
50 μg/El, γ-tocotriol/-1. i oot
t9/9, containing a total of 62.5 s o tti/1.
実施例５゜
バチ５０葉２ｋｇ（水分６５チ）を細断した後、ヘキサ
ン、エタノール（Ｖ／Ｖ、 １ ： １）混合溶液を用
い、室温２４〜２５℃で抽出した。この抽出液はα−ト
コフェロール２２，０００μｍ１７９、γ−トコフェロ
ール１，０６０μｇ、Ｑ 、合計２３，０６０ｇｇＺＩ
を含有していた。Example 5 After 2 kg of 50 ゜ Wasp leaves (water content: 65 g) were shredded, they were extracted at room temperature of 24 to 25°C using a mixed solution of hexane and ethanol (V/V, 1:1). This extract contains α-tocopherol 22,000μm179, γ-tocopherol 1,060μg, Q, total 23,060ggZI
It contained.
：′７．−１〜・′−二゛。:'7. −1〜・′−2゛.
！ｊ ” ｌ’、’ Ｉ ’＋ 、−
手続補正書（自発）
５囮技研第３５７号
昭和５８年３ 月８ 日
特許庁長官 若 杉 和 夫 殿
１、事件の表示 昭和５７年特許願第２５５１９
号事件との関係特許出願人
住 所 東京都千代田区霞が関１丁目３番１号玩
名 （１１り工業技術院長 石 坂 誠 −４、指定
代理人
６、補正によ町増加する発明の数 Ｏ８、補正の内容
本願明細書中において、次のとおり補正します。! j ” l', ' I ' + , - Procedural amendment (spontaneous) 5 Decoy Giken No. 357 March 8, 1980 Commissioner of the Patent Office Kazuo Wakasugi 1, Indication of case Patent application No. 25519 of 1988
Patent applicant address related to case No. 1, 1-3-1 Kasumigaseki, Chiyoda-ku, Tokyo Name (11) Makoto Ishizaka, Director of the Agency of Industrial Science and Technology -4, Designated Agent 6, Number of inventions increased by amendment O8 , Contents of the amendment The following amendments will be made in the specification of the present application.
（１）第１頁下から第５行〜第４行の「励動」を「動物
」に訂正します。(1) Correct "excitation" to "animal" in lines 5 and 4 from the bottom of page 1.
（２）第２頁第５行の「不溶性有機溶剤」を「水不溶性
有機溶剤」に訂正します。(2) Correct “insoluble organic solvent” in line 5 of page 2 to “water-insoluble organic solvent”.
（３）第４頁第７行の「芳香族化合物及び」を「芳香族
化合物、無極性有機溶剤及び」に訂正します。(3) "Aromatic compounds and" in line 7 of page 4 will be corrected to "aromatic compounds, non-polar organic solvents and".
（４）第５頁第１Ｏ行の［２５，１をｒ１５．９Ｊに訂
正します。(4) Correct [25,1 on page 5, line 1O] to r15.9J.
（５）第７頁第７行〜第１３行の実施例５を次のように
訂正します。(5) Example 5 on page 7, lines 7 to 13 is corrected as follows.
「実施例５゜
バナ＼の葉２０ｋｇ（水分６５チ）を細断した後、ヘキ
サン・エタノール（Ｖ／Ｖ、［１）混合溶液を用い、室
温２４〜２５℃で抽出した。この抽出液はα−トコフェ
ロール２２，０００μｙ、γ−トコフェロール１，０６
０μｇ、合計２３，０６０ｇｇを含有していた。``Example 5'' After cutting 20 kg of Banana leaves (65 g water) into pieces, they were extracted using a hexane-ethanol (V/V, [1) mixed solution at room temperature of 24-25°C. α-tocopherol 22,000 μy, γ-tocopherol 1,06
It contained 0 μg, a total of 23,060 gg.
（６）第５頁第１Ｏ行の次に実施例６及び実施例７を追
加し、ます。(6) Add Example 6 and Example 7 next to page 5, line 1 O.
力實施例６゜
パームの葉４に９Ｃ水分４８％）をローラーを用いて圧
片した後細断し、ヘキサンーエタ／ −ル（Ｖ／Ｖ、１
：１）、混合溶液１２Ｊを加え、−夜室温２２〜２４℃
に放置後、抽出液を分別した。抽出物１８６ｇを得た。Power Example 6 Palm leaves (9C moisture 48%) were crushed using a roller and then shredded, and hexane-ethanol (V/V, 1
:1), add 12J of mixed solution, -night room temperature 22-24℃
After being left to stand, the extract was separated. 186 g of extract was obtained.
この抽出物にメタノール１１を加え、よく振りまぜた後
、０℃に冷却し、可溶部を分別した。可溶部からメタノ
ールを留去し、残留物４８ｇを得た。Methanol 11 was added to this extract, and after shaking well, it was cooled to 0° C. and the soluble portion was separated. Methanol was distilled off from the soluble portion to obtain 48 g of residue.
残留物２０．９に精製パーム油２０，９を加え、分子蒸
留を行い、５ｘｌＱ ｍｍＨ９で、第１留分（〜１９
０℃）、第２留分１９０〜２００℃、第３留分２００℃
〜２２０°Ｃ１残留分の４区分に分別した。それぞれの
区分のトコフェロール含有量は第１区分２３．５チ、第
２区分８．１％、第３区分２．５％、残留分０．６チで
あった。Refined palm oil 20.9 was added to the residue 20.9, molecular distillation was carried out, and the first fraction (~19
0°C), 2nd distillate 190-200°C, 3rd distillate 200°C
It was divided into 4 categories of ~220°C 1 residue. The tocopherol content in each category was 23.5% in the first category, 8.1% in the second category, 2.5% in the third category, and 0.6% in the residual content.
実施例７゜
パームの葉（水分４２チ）２．３ｋｇを細断し、室温（
２２〜２４℃）において、ヘキサン−エタノール（１：
１、Ｖ／Ｖ）混合溶媒で抽出を行なうと、抽出物１１６
ｇが得られた。この抽出物に５１のヘキサン−エタノー
ル（１：１、Ｖ／Ｖ）混合溶媒あるいは５１のヘキサン
を加えてよく攪拌する。次に、上記混合物を大量の温水
で洗い、水溶性の物質を除去する。充分に乾燥した後、
−２０°Ｃに冷却し、ヘキサン可溶部を分取した。この
ヘキサン可溶部をシリカカラム（８１０８１１人、１０
０〜２００メツシユ）を通し、ひき続いてヘキサンで溶
出すると、最初に炭化水素類が溶出され、次に、α−ト
コフェロールが溶出された。得られたα−トコフェロー
ル画分は２５ｇで、α−トコフェロール濃ｉハロｓ、４
チであり、α−トコフェロールの回収率は８３．３％で
あった。」Example 7 2.3 kg of palm leaves (water content: 42 g) were shredded and
22-24°C), hexane-ethanol (1:
1. When extraction is performed with a mixed solvent (V/V), the extract 116
g was obtained. Add 51 hexane-ethanol (1:1, V/V) mixed solvent or 51 hexane to this extract and stir well. The mixture is then washed with plenty of warm water to remove water-soluble substances. After drying thoroughly,
It was cooled to -20°C, and the hexane soluble portion was separated. This hexane-soluble part was collected in a silica column (810,811 people, 10
0-200 mesh) and subsequent elution with hexane, the hydrocarbons were eluted first, followed by the alpha-tocopherol. The α-tocopherol fraction obtained was 25 g, containing α-tocopherol concentration ihalos, 4
The recovery rate of α-tocopherol was 83.3%. ”
Claims (1)
サトウキビの葉の中のトコフェロール類並びにトコトリ
エノール類を分離する方法において、該植物の葉を有機
溶剤を単独又は混合物で用いて、抽出処理することを特
徴とするトコフェロール及びトコトリエノールの分離方
法っ(1) In a method for separating tocopherols and tocotrienols in balm leaves, banana leaves, pineapple leaves, and sugarcane leaves, the leaves of the plants are subjected to extraction treatment using an organic solvent alone or in a mixture. A method for separating tocopherols and tocotrienols, characterized by
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2551982A JPS58144382A (en) | 1982-02-19 | 1982-02-19 | Separation of tocopherol and tocotrienol |
| GB08303777A GB2117381B (en) | 1982-02-19 | 1983-02-11 | Vitamin e extraction |
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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS58144382A true JPS58144382A (en) | 1983-08-27 |
| JPH029590B2 JPH029590B2 (en) | 1990-03-02 |
Family
ID=12168302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2551982A Granted JPS58144382A (en) | 1982-02-19 | 1982-02-19 | Separation of tocopherol and tocotrienol |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58144382A (en) |
| GB (1) | GB2117381B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6153280A (en) * | 1984-08-02 | 1986-03-17 | ヘンケル・コーポレイション | Purification of tocopherol by extraction |
| JP2008056587A (en) * | 2006-08-30 | 2008-03-13 | Noevir Co Ltd | Skin preparation for external use |
| WO2009043097A1 (en) * | 2007-10-05 | 2009-04-09 | Horizon Science Pty Ltd | Natural preservatives and antimicrobial agents |
| US9717771B2 (en) | 2011-02-08 | 2017-08-01 | The Product Makers (Australia) Pty Ltd | Sugar extract |
| US10350259B2 (en) | 2013-08-16 | 2019-07-16 | The Product Makers (Australia) Pty Ltd | Sugar cane derived extracts and methods of treatment |
| US11730178B2 (en) | 2012-08-28 | 2023-08-22 | Poly Gain Pte Ltd | Extraction method |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2152837B (en) * | 1983-07-05 | 1987-03-25 | Kuraray Co | Extractive separation method |
| US4603142A (en) * | 1984-06-01 | 1986-07-29 | Wisconsin Alumni Research Foundation | Cholesterol lowering method of use |
| EP0333472B1 (en) * | 1988-03-16 | 1997-10-08 | PALM OIL RESEARCH & DEVELOPMENT BOARD | Production of high concentration tocopherols and tocotrienols from palm oil by-products |
| US5217992A (en) * | 1989-10-04 | 1993-06-08 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| JPH06502844A (en) * | 1990-05-23 | 1994-03-31 | リポジェニックス，インコーポレイテッド | Recovery process for tocotrienols, tocopherols and tocotrienol-like compounds |
| FR2669032B1 (en) * | 1990-11-14 | 1993-04-23 | Cecchi Georges | PROCESS FOR THE MANUFACTURE OF A PREPARATION OF D-ALPHA-TOCOPHEROL. |
| 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 |
| ES2138951T1 (en) | 1998-03-12 | 2000-02-01 | Int Flavors & Fragrances Inc | FLAVOR AGENT FROM "SACCHARUM OFFICINARUM", PROCEDURE FOR ITS PREPARATION AND PRODUCTS THAT CONTAIN IT. |
| ES2269029T3 (en) * | 1999-01-25 | 2007-04-01 | Dsm Ip Assets B.V. | PROCESS FOR THE PREPARATION OF AN ADSORBENT THAT IS CHARGED WITH AN OIL. |
| MY157650A (en) * | 2008-03-06 | 2016-07-15 | Nova Lab Sdn Bhd | Extract from oil palm leaves comprising phenolic acids |
| 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 |
| US20120058207A1 (en) | 2009-03-24 | 2012-03-08 | 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 |
-
1982
- 1982-02-19 JP JP2551982A patent/JPS58144382A/en active Granted
-
1983
- 1983-02-11 GB GB08303777A patent/GB2117381B/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ALSTRACTS * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6153280A (en) * | 1984-08-02 | 1986-03-17 | ヘンケル・コーポレイション | Purification of tocopherol by extraction |
| JP2008056587A (en) * | 2006-08-30 | 2008-03-13 | Noevir Co Ltd | Skin preparation for external use |
| WO2009043097A1 (en) * | 2007-10-05 | 2009-04-09 | Horizon Science Pty Ltd | Natural preservatives and antimicrobial agents |
| US9717771B2 (en) | 2011-02-08 | 2017-08-01 | The Product Makers (Australia) Pty Ltd | Sugar extract |
| US10226502B2 (en) | 2011-02-08 | 2019-03-12 | The Product Makers (Australia) Pty Ltd | Sugar extract |
| US11730178B2 (en) | 2012-08-28 | 2023-08-22 | Poly Gain Pte Ltd | Extraction method |
| US10350259B2 (en) | 2013-08-16 | 2019-07-16 | The Product Makers (Australia) Pty Ltd | Sugar cane derived extracts and methods of treatment |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH029590B2 (en) | 1990-03-02 |
| GB2117381B (en) | 1985-07-10 |
| GB8303777D0 (en) | 1983-03-16 |
| GB2117381A (en) | 1983-10-12 |
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