JPH04202599A - Production of oil and fat having low cholesterol content - Google Patents

Production of oil and fat having low cholesterol content

Info

Publication number
JPH04202599A
JPH04202599A JP33899890A JP33899890A JPH04202599A JP H04202599 A JPH04202599 A JP H04202599A JP 33899890 A JP33899890 A JP 33899890A JP 33899890 A JP33899890 A JP 33899890A JP H04202599 A JPH04202599 A JP H04202599A
Authority
JP
Japan
Prior art keywords
oil
cholesterol
acid
layer
oils
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
Application number
JP33899890A
Other languages
Japanese (ja)
Other versions
JPH0832908B2 (en
Inventor
Mitsumune Takatsu
高津 光宗
Naoyoshi Abe
安部 直義
Manabu Sato
学 佐藤
Hideyuki Tsujino
辻野 秀行
Shohei Matsuyama
昌平 松山
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nissin Food Products Co Ltd
Original Assignee
Nissin Food Products Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nissin Food Products Co Ltd filed Critical Nissin Food Products Co Ltd
Priority to JP2338998A priority Critical patent/JPH0832908B2/en
Publication of JPH04202599A publication Critical patent/JPH04202599A/en
Publication of JPH0832908B2 publication Critical patent/JPH0832908B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Abstract

PURPOSE:To efficiently, inexpensively and safely remove cholesterol while utilizing a conventional facilities by adding a fatty acid to a cholesterol- containing oil and fat and then adding an alkaline aqueous solution thereto and separating the mixture into an oil layer and soap layer and collecting the oil layer. CONSTITUTION:>=0.5% (preferably 1-5%) fatty acid such as palmitic acid, stearic acid, oleic acid or linoleic acid is added to a cholesterol-containing oil and fat such as fish oil, pig oil or cow oil and then an alkaline aqueous solution is preferably added thereto, preferably at an amount of 2-10% and the mixture is stirred. Then the mixture is separated into an oil layer and soap layer by centrifugal separation, etc., and then the oil layer is collected.

Description

【発明の詳細な説明】 [産業上の利用分野] 本発明は油脂からコレステロールを除去する方法に関す
るものである。
DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for removing cholesterol from fats and oils.

[従来の技術1 コレステロールの過剰摂取が、動脈硬化症や心筋梗塞等
の成人病の原因の1つとなっていることから、食餌性コ
レステロールの摂取を抑えることが、重大な関心事とな
ってきている。実際に、病院等で実施されている栄養指
導でも、血中コレステロール値の高い人には、コレステ
ロール値多く含む動物性脂肪や卵製品が制限されている
。しかし一方では、動物性食品は官能的な魅力に富むば
かりでなく、アミノ酸バランスが優れているなど栄養学
的にも貴重な栄養源である。また、魚油の場合、コレス
テロールを多く含んではいるが、逆にコレステロール低
下作用のあるエイコサペンクエン酸等の多価不飽和脂肪
酸が豊富で、コレステロールが低減されればさらに用途
の拡大が期待できる。このため従来から、動物性油脂の
コレステロールを除去することを目的として、多くの研
究がなされてきた。例えば、ラード・ヘッド・魚油など
に含まれるコレステロールは、−射的な油脂精製工程で
の脱酸または脱臭工程で、ある程度除去されることが知
られている。またその他の方法としては、活性炭・ケイ
ソウ土・白土等の吸着剤でコレステロールを吸着除去す
る方法(特開昭6l−136598)および、ロドコッ
カス属の微生物により油脂に含まれるコレステロールを
分解する方法(特開平1−229097)等が知られて
いる。
[Prior art 1] Excessive intake of cholesterol is one of the causes of adult diseases such as arteriosclerosis and myocardial infarction, so reducing intake of dietary cholesterol has become a serious concern. There is. In fact, even in nutritional guidance provided in hospitals, people with high blood cholesterol levels are restricted from eating animal fats and egg products that contain high cholesterol levels. However, on the other hand, animal foods are not only rich in sensual appeal, but are nutritionally valuable sources of nutrients, such as their excellent amino acid balance. In addition, although fish oil contains a lot of cholesterol, it is also rich in polyunsaturated fatty acids such as eicosapencitric acid, which has a cholesterol-lowering effect, so if the cholesterol content can be reduced, further expansion of its uses can be expected. . For this reason, many studies have been conducted with the aim of removing cholesterol from animal fats and oils. For example, it is known that cholesterol contained in lard, head, fish oil, etc. can be removed to some extent during the deacidification or deodorization process in the aerosol refining process. Other methods include a method in which cholesterol is adsorbed and removed using adsorbents such as activated carbon, diatomaceous earth, and white clay (Japanese Unexamined Patent Application Publication No. 61-136598), and a method in which cholesterol contained in fats and oils is decomposed by microorganisms of the genus Rhodococcus (Japanese Patent Application Laid-open No. 61-136598). Kaihei 1-229097), etc. are known.

前述のように、油脂に含まれるコレステロールは、一般
的な油脂精製工程での脱酸工程で、ある程度除去するこ
とが出来る。
As mentioned above, cholesterol contained in fats and oils can be removed to some extent through the deacidification step in the general fats and oils refining process.

以下、参考のため、一般的な脱酸工程の概略を説明する
Hereinafter, for reference, an outline of a general deoxidizing process will be explained.

まず原油の酸価、リン脂質含量を測定してアルカリ所要
量を求めておく。次に、油脂に対して0.1〜0.2%
(重量)の75%リン酸を添加し、リン脂質などのガム
質が凝集して沈降しやすい状態にする。次にリン酸を含
めた酸価当量の110〜120%量に相当する水酸化ナ
トリウムを添加し、ラインミキサーで混合して遊離脂肪
酸を石鹸層かすとし、遠心分離機にて油層と石鹸層に分
離する。該油層を分取し、順次、水酸化ナトリウム溶液
および熱湯で洗浄し、微量に残存するガム質や、色素成
分を除去する。水洗後の油を減圧乾燥機に送り、減圧下
に加熱して水分を除去し、脱酸工程を終了する。この工
程中、コレステロールなどの不ケン化物は石鹸層かすと
共に除去される。例えば、日本食品油脂検査協会の報告
によれば、未精製魚油に含まれる5、0mg/g程度の
コレステロールが脱酸工程を経ることによって4.2m
g7g程度に減少する旨報告されている(「食用加工油
脂技術研究会・会報第5号」、第23頁表1.(財)全
日本マーガリン協会/食用加工油脂技術研究会、昭和4
8年9月26日発行)。
First, measure the acid value and phospholipid content of crude oil to determine the required amount of alkali. Next, 0.1 to 0.2% based on fats and oils
(by weight) of 75% phosphoric acid is added to create a state in which gummy substances such as phospholipids tend to aggregate and settle. Next, add sodium hydroxide equivalent to 110-120% of the acid value equivalent including phosphoric acid, mix with a line mixer to convert free fatty acids into soap layer cake, and separate the oil layer and soap layer with a centrifuge. To separate. The oil layer is separated and sequentially washed with a sodium hydroxide solution and hot water to remove trace amounts of remaining gum and pigment components. The oil after being washed with water is sent to a vacuum dryer and heated under reduced pressure to remove moisture and complete the deoxidation process. During this step, unsaponifiables such as cholesterol are removed along with the soap scum. For example, according to a report by the Japan Food Oil and Fat Inspection Association, approximately 5.0 mg/g of cholesterol contained in unrefined fish oil is reduced to 4.2 m
It has been reported that the amount decreases to about 7g ("Edible Processed Oils and Fats Technology Study Group Bulletin No. 5", page 23 Table 1. All Japan Margarine Association/Edible Processed Oils and Fats Technology Study Group, 1939)
(Published September 26, 2008).

[発明が解決しようとする課題1 しかしながら、前記脱酸工程の本来の目的は遊離脂肪酸
の除去であり、コレステロールの除去という点からはそ
の効果は低く、前述の魚油の場合でも、依然として約8
0%のコレステロールが残存している。また、吸着剤で
コレステロールを吸着除去する方法や、コレステロール
を微生物で分解する方法では、コストや安全性の点で問
題があり、工場規模での実施は困難である。
[Problem to be Solved by the Invention 1] However, the original purpose of the deacidification step is to remove free fatty acids, and its effectiveness in terms of removing cholesterol is low, and even in the case of the above-mentioned fish oil, it still
0% cholesterol remains. Furthermore, the methods of adsorbing and removing cholesterol with an adsorbent and decomposing cholesterol with microorganisms have problems in terms of cost and safety, and are difficult to implement on a factory scale.

[課題を解決するための手段1 そこで、本発明者らは前述のような課題を解決するため
、効率的に、安価に、安全に、しかも従来の設備を利用
して油脂中のコレステロールを除去する方法を研究した
結果、通常の脱酸工程の中に脂肪酸を添加する工程を加
えることにより、より効果的にコレステロールが除去さ
れることを見いだし、本発明に至った。
[Means for Solving the Problems 1] Therefore, in order to solve the above-mentioned problems, the present inventors removed cholesterol from fats and oils efficiently, inexpensively, safely, and using conventional equipment. As a result of research into a method for this purpose, it was discovered that cholesterol can be removed more effectively by adding a step of adding fatty acids to the normal deacidification step, leading to the present invention.

即ち、本発明の構成要旨とするところは、コレステロー
ル含有油脂に脂肪酸を添加後、アルカリ性水溶液を加え
て混合撹拌し、次いで油層と石鹸層に分離した後、該油
層を分取することを特徴とする、低コレステロール油脂
の製造方法である。
That is, the gist of the present invention is that after fatty acids are added to cholesterol-containing fats and oils, an alkaline aqueous solution is added, mixed and stirred, and then separated into an oil layer and a soap layer, and then the oil layer is fractionated. This is a method for producing low-cholesterol fats and oils.

以下、本発明の内容を工程順に詳しく説明する。Hereinafter, the content of the present invention will be explained in detail in the order of steps.

まず、油脂に脂肪酸を添加後、アルカリ水溶液を添加し
混合撹拌する。本発明が対象とする油脂は、コレステロ
ールを含む油脂であり、例えば魚油、豚油、牛油等の動
物性油脂が適している。また、添加する脂肪酸は、安全
性の面から油脂の構成成分が望ましく、パルミチン酸・
ステアリン酸・オレイン酸・リノール酸などの脂肪酸が
適している。脂肪酸の添加量は、油脂に対して帆5%以
上、好ましくは1〜5%が望ましい。 アルカリ水溶液
の濃度および添加量は、添加する脂肪酸を含めた酸化当
量の110%量以上に相当する量が好ましく、水酸化ナ
トリウムの場合10〜30°Beの濃度で、油脂に対し
て2〜lO%(重量)程度の添加量が望ましい。
First, after adding fatty acids to fats and oils, an aqueous alkaline solution is added and mixed and stirred. The fats and oils targeted by the present invention are fats and oils containing cholesterol, and animal fats and oils such as fish oil, pork oil, and beef oil are suitable, for example. In addition, from the viewpoint of safety, the fatty acids to be added are desirably constituents of fats and oils, such as palmitic acid and
Fatty acids such as stearic acid, oleic acid, and linoleic acid are suitable. The amount of fatty acid added is preferably 5% or more, preferably 1 to 5% based on the fat and oil. The concentration and amount of the alkaline aqueous solution is preferably equivalent to 110% or more of the oxidation equivalent including the fatty acid to be added, and in the case of sodium hydroxide, the concentration is 10 to 30°Be, and the amount is 2 to 1O % (weight) is desirable.

撹拌は、油脂と添加した脂肪酸およびアルカリ水溶液が
充分に混合されればよく、また、撹拌中の温度について
は、必ずしも通常の脱酸工程のような高温(70〜90
℃)である必要はなく、油脂を液状に保てる温度であれ
ばよい。
Stirring is sufficient as long as the fats and oils, added fatty acids, and alkaline aqueous solution are sufficiently mixed, and the temperature during stirring is not necessarily higher than the high temperature (70 to 90℃
℃), any temperature that can keep the oil in a liquid state is sufficient.

次いで、前記撹拌工程により得られた混合物を油層と石
鹸層に分離し、該油層を分取する。分離方法としては、
通常、遠心分離法が用いられ、現在多くの製油工場で脱
酸工程に使用されている連続を遠心機をそのまま使用す
ることができる。バッチ式の遠心分離機を使用する場合
でも、100OGにて5分間程度遠心分離すれば充分で
ある。また、分取された油脂に脂肪酸が残存する場合、
必要に応じて、アルカリ性水溶液または熱湯を加えて撹
拌し、再度遠心分離によって油層を分取する。以上の工
程によって、低コレステロール油脂が製造できる。
Next, the mixture obtained in the stirring step is separated into an oil layer and a soap layer, and the oil layer is separated. The separation method is
Usually, a centrifugal separation method is used, and the continuous centrifuge currently used in many oil refineries for the deacidification process can be used as is. Even when using a batch type centrifuge, centrifugation at 100OG for about 5 minutes is sufficient. In addition, if fatty acids remain in the separated fats and oils,
If necessary, add an alkaline aqueous solution or hot water, stir, and separate the oil layer by centrifugation again. Through the above steps, low cholesterol fats and oils can be produced.

F実験例フ 以下、実験例に基づき本発明を説明する。F Experiment example F The present invention will be explained below based on experimental examples.

く実験例1〉 精製魚油(コレステロール含量2.3mg/g) 40
gに、バルミチン酸・ステアリン酸・オレイン酸・リノ
ール酸を、それぞれ1.6g添加し、ホモジナイザーに
て11000rpで撹拌しながら、20%水酸化ナトリ
ウム溶液(約26°Be)を2ml加えた。次いで、2
5℃で(パルミチン酸の場合は液状とするため80℃)
30分間撹拌した後、得られた混合物を3000rpm
で5分間遠心分離し、油層を分取した。分取した魚油の
コレステロール含量を測定した。その結果を表1に示し
た。
Experimental Example 1> Refined fish oil (cholesterol content 2.3 mg/g) 40
1.6 g of each of valmitic acid, stearic acid, oleic acid, and linoleic acid were added to g, and 2 ml of 20% sodium hydroxide solution (approximately 26°Be) was added while stirring at 11,000 rpm with a homogenizer. Then 2
At 5℃ (80℃ for palmitic acid to make it liquid)
After stirring for 30 minutes, the resulting mixture was heated at 3000 rpm.
The mixture was centrifuged for 5 minutes and the oil layer was separated. The cholesterol content of the fractionated fish oil was measured. The results are shown in Table 1.

(以下余白) 表1 本実験結果より、脂肪酸を添加せずに同様の処理を行っ
た場合(試料:対照)、コレステロールは除去されず、
脂肪酸を添加することによって(本発明試料No、1.
2.3.4)、効果的にコレステロールが除去されるこ
とが明らかである。
(Margins below) Table 1 From the results of this experiment, when the same treatment was performed without adding fatty acids (sample: control), cholesterol was not removed;
By adding fatty acids (invention sample No. 1.
2.3.4), it is clear that cholesterol is effectively removed.

〈実験例2〉 精製魚油(コレステロール含量2−1mg/g) 、精
製牛脂(コレステロール含量0.8mg/g) 、精製
豚脂(コレステロール含量0.3mg/g)各々40g
にオレイン酸1.6gを加え、実験例1と同様にアルカ
リ水溶液を加えた後、80’C11000rpで20分
間混合撹拌し、次いで遠心分離を行い、油層を分取した
。分取した各油脂のコレステロール含量を測定した。
<Experimental Example 2> 40 g each of purified fish oil (cholesterol content 2-1 mg/g), purified beef tallow (cholesterol content 0.8 mg/g), and purified pork fat (cholesterol content 0.3 mg/g)
After adding 1.6 g of oleic acid and adding an alkaline aqueous solution in the same manner as in Experimental Example 1, the mixture was mixed and stirred at 80'C11000 rpm for 20 minutes, and then centrifuged to separate the oil layer. The cholesterol content of each fractionated fat and oil was measured.

その結果を表2に示した。The results are shown in Table 2.

表2 本実験結果より、魚油、牛脂、豚脂いずれの油脂の場合
でも、本発明によれば脂肪酸の添加によって効果的に、
コレステロールが除去されることが明らかである。
Table 2 From the results of this experiment, it was found that, according to the present invention, the addition of fatty acids can effectively
It is clear that cholesterol is removed.

〈実験例3〉 精製魚油(コレステロール含量2.6mg/g) 20
0gにオレイン酸 0.5g、 Ig、 2g、 4g
、 6g、 8g、 lOg。
<Experimental Example 3> Refined fish oil (cholesterol content 2.6 mg/g) 20
Oleic acid 0.5g, Ig, 2g, 4g to 0g
, 6g, 8g, lOg.

15gを加え、ホモジナイザーにて撹拌しながら、オレ
イン酸の添加量に応じて適量のアルカリ水溶液を添加し
た。すなわち、オレイン酸0.5〜Igに対して20%
水酸化ナトリウム溶液5m1.オレイン酸2g−1og
に対して20%水酸化ナトリウム溶液10+ol、オレ
イン酸15gに対して20%水酸化ナトリウム溶液20
m lを添加した。次いで、25℃。
15 g was added, and while stirring with a homogenizer, an appropriate amount of alkaline aqueous solution was added depending on the amount of oleic acid added. i.e. 20% for 0.5-Ig of oleic acid
5ml of sodium hydroxide solution. 2g-1og oleic acid
20% sodium hydroxide solution 10+ ol for oleic acid, 20% sodium hydroxide solution 20+ for oleic acid 15g
ml was added. Then, 25°C.

11000rpにて20分間撹拌後、遠心分離を行い、
油層を分取した。分取した各油脂のコレステロール含量
を測定した。その結果を表3に示した。
After stirring at 11,000 rpm for 20 minutes, centrifugation was performed.
The oil layer was separated. The cholesterol content of each fractionated fat and oil was measured. The results are shown in Table 3.

(以下余白) 本実験結果より、コレステロールの除去効率および経済
性等を考慮すれば、オレイン酸の添加量は油脂に対して
0.5%以上、好ましくは1〜5%程度が適当と思われ
る。
(Left below) Based on the results of this experiment, it seems appropriate to add oleic acid at 0.5% or more, preferably 1 to 5%, based on fats and oils, considering cholesterol removal efficiency and economic efficiency. .

〈実験例4〉 精製魚油(コレステロール含量2.3+ng/g) 4
0gにオレイン酸1.6gを添加し、実施例1と同様に
アルカリ水溶液を加え、4℃、24℃、80℃にてlo
oorpmで20分間撹拌後、遠心分離を行い、油層を
分取した。分取した各油脂のコレステロール含量を測定
した。その結果を表4に示した。
<Experimental Example 4> Refined fish oil (cholesterol content 2.3+ng/g) 4
1.6 g of oleic acid was added to 0 g, an aqueous alkali solution was added in the same manner as in Example 1, and the lo
After stirring at oorpm for 20 minutes, centrifugation was performed to separate the oil layer. The cholesterol content of each fractionated fat and oil was measured. The results are shown in Table 4.

本実験結果より、油脂と、脂肪酸およびアルカリ水溶液
との混合撹拌温度は、常法よる脱酸工程のような高温(
70〜90℃)である必要はなく、低温でもコレステロ
ールの除去効率が改善されていることが明らかである。
From the results of this experiment, it was found that the mixing temperature of fats and oils, fatty acids, and aqueous alkaline solutions was not as high as in the conventional deoxidation process (
It is clear that the cholesterol removal efficiency is improved even at low temperatures.

[実施例] 精製魚油(コレステロール含量2.3mg/g) 40
gにオレイン酸1.6gを添加し、実験例1と同様にア
ルカリ水溶液を加え、24℃にて1000rp+m 2
0分間撹拌後、遠心分離を行い、油層を分取した。得ら
れた油脂を再度アルカリ水溶液および熱湯にて洗浄し、
真空乾燥機にて60℃30分間乾燥し、水分を除去して
低コレステロール魚油を得た。本処理前の精製魚油と前
記本発明により得られた低コレステロール魚油について
コレステa−ル含量、AV。
[Example] Refined fish oil (cholesterol content 2.3 mg/g) 40
Add 1.6 g of oleic acid to
After stirring for 0 minutes, centrifugation was performed to separate the oil layer. The obtained fats and oils are washed again with an alkaline aqueous solution and boiling water,
It was dried in a vacuum dryer at 60° C. for 30 minutes to remove water and obtain low cholesterol fish oil. Cholesterol content and AV of the purified fish oil before this treatment and the low-cholesterol fish oil obtained according to the present invention.

脂肪酸組成、水分を測定し、その結果を表5に示した。The fatty acid composition and water content were measured and the results are shown in Table 5.

この結果より、コレステロールは処理前の2゜3 m 
g/gから0.6mg/g (約4分の1)に減少し、
AV、脂肪酸組成、水分については処理前の精製魚油と
有意差はなかった。また、官能的にも本発明による低コ
レステロール魚油は処理前の精製魚油とほぼ同じ風味と
なり、良好であった。
From this result, cholesterol is 2゜3 m before treatment.
g/g to 0.6 mg/g (about a quarter),
There was no significant difference in AV, fatty acid composition, and water content from the purified fish oil before treatment. In addition, the low-cholesterol fish oil according to the present invention had a flavor that was almost the same as that of the purified fish oil before treatment, and was good in sensory terms.

(以下余白) 表5 [効果] 以上、本発明によれば、油脂に含有されるコレステロー
ルを、該油脂の品質を損なうことなく効率的に且つ低コ
ストで除去することができる。
(Margins below) Table 5 [Effects] As described above, according to the present invention, cholesterol contained in fats and oils can be removed efficiently and at low cost without impairing the quality of the fats and oils.

Claims (1)

【特許請求の範囲】[Claims] コレステロール含有油脂に脂肪酸を添加後、アルカリ性
水溶液を加えて混合撹拌し、次いで油層と石鹸層に分離
した後、該油層を分取することを特徴とする、低コレス
テロール油脂の製造方法。
A method for producing low-cholesterol fats and oils, which comprises adding fatty acids to cholesterol-containing fats and oils, adding an alkaline aqueous solution, mixing and stirring, separating the mixture into an oil layer and a soap layer, and then fractionating the oil layer.
JP2338998A 1990-11-30 1990-11-30 Method for producing low-cholesterol oil Expired - Fee Related JPH0832908B2 (en)

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Application Number Priority Date Filing Date Title
JP2338998A JPH0832908B2 (en) 1990-11-30 1990-11-30 Method for producing low-cholesterol oil

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2338998A JPH0832908B2 (en) 1990-11-30 1990-11-30 Method for producing low-cholesterol oil

Publications (2)

Publication Number Publication Date
JPH04202599A true JPH04202599A (en) 1992-07-23
JPH0832908B2 JPH0832908B2 (en) 1996-03-29

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7807848B2 (en) 2005-08-26 2010-10-05 Ocean Nutrition Canada Limited Reduction of sterols and other compounds from oils
US7977498B2 (en) 2005-08-26 2011-07-12 Ocean Nutrition Canada Limited Reduction of sterols and other compounds from oils

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5315308A (en) * 1976-07-27 1978-02-13 Nippon Oil & Fats Co Ltd Collection of fatty acid esters and cholesterol
JPS60248798A (en) * 1984-05-23 1985-12-09 ミヨシ油脂株式会社 Deacidifying and decoloring method for oil and fat

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5315308A (en) * 1976-07-27 1978-02-13 Nippon Oil & Fats Co Ltd Collection of fatty acid esters and cholesterol
JPS60248798A (en) * 1984-05-23 1985-12-09 ミヨシ油脂株式会社 Deacidifying and decoloring method for oil and fat

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7807848B2 (en) 2005-08-26 2010-10-05 Ocean Nutrition Canada Limited Reduction of sterols and other compounds from oils
US7977498B2 (en) 2005-08-26 2011-07-12 Ocean Nutrition Canada Limited Reduction of sterols and other compounds from oils
US8143310B2 (en) 2005-08-26 2012-03-27 Ocean Nutrition Canada Limited Reduction of sterols and other compounds from oils

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