JPH013119A - L-ascorbic acid preparation - Google Patents
L-ascorbic acid preparationInfo
- Publication number
- JPH013119A JPH013119A JP62-156679A JP15667987A JPH013119A JP H013119 A JPH013119 A JP H013119A JP 15667987 A JP15667987 A JP 15667987A JP H013119 A JPH013119 A JP H013119A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- acid
- ascorbic acid
- fatty acid
- parts
- 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
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title claims description 90
- 229960005070 ascorbic acid Drugs 0.000 title claims description 45
- 239000002211 L-ascorbic acid Substances 0.000 title claims description 39
- 235000000069 L-ascorbic acid Nutrition 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 22
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 52
- 229930195729 fatty acid Natural products 0.000 claims description 52
- 239000000194 fatty acid Substances 0.000 claims description 52
- -1 glycerin fatty acid ester Chemical class 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 31
- 239000003921 oil Substances 0.000 claims description 30
- 235000019198 oils Nutrition 0.000 claims description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 28
- 238000000576 coating method Methods 0.000 claims description 28
- 235000011187 glycerol Nutrition 0.000 claims description 27
- 150000004665 fatty acids Chemical class 0.000 claims description 23
- 235000019197 fats Nutrition 0.000 claims description 19
- 239000002245 particle Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 10
- 235000021355 Stearic acid Nutrition 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 9
- 239000008117 stearic acid Substances 0.000 claims description 9
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- 239000005639 Lauric acid Substances 0.000 claims description 6
- 235000021314 Palmitic acid Nutrition 0.000 claims description 6
- 235000010323 ascorbic acid Nutrition 0.000 claims description 6
- 239000011668 ascorbic acid Substances 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 6
- 235000021360 Myristic acid Nutrition 0.000 claims description 5
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 5
- 235000015278 beef Nutrition 0.000 claims description 5
- 239000003760 tallow Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 241000287828 Gallus gallus Species 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 239000008173 hydrogenated soybean oil Substances 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
- 239000010698 whale oil Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 description 13
- 239000011162 core material Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000000787 lecithin Substances 0.000 description 4
- 235000010445 lecithin Nutrition 0.000 description 4
- 229940067606 lecithin Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 206010047623 Vitamin C deficiency Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000010233 scurvy Diseases 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は、食品や飼料などの添加剤として使用する際の
使用条件下で安定なＬ−アスコルビン酸またはその塩類
の製剤およびその製造法に関し、とくに、水分等を含有
する媒体中で溶出し難いようなＬ−アスコルビン酸また
はその塩類の製剤に関する。Detailed Description of the Invention "Field of Industrial Application" The present invention relates to a formulation of L-ascorbic acid or its salts that is stable under the conditions of use when used as an additive for foods, feeds, etc., and a method for producing the same. In particular, the present invention relates to formulations of L-ascorbic acid or its salts that are difficult to dissolve in a medium containing moisture or the like.
「従来の技術」
Ｌ−アスコルビン酸及びその塩類は栄養学上極めて重要
であり、これが欠乏すると人においては貧血を起こし、
歯茎、皮膚、粘膜より出血し、いわゆる壊血病の原因に
なり、また人のみではなく、陸上動物、水産動物におい
てもその欠乏は重大なる疾病の原因となることは公知で
あり、その予防のために人には栄養補給剤として、家畜
や養殖においてはその配合飼料へ添加されている。"Prior art" L-ascorbic acid and its salts are extremely important nutritionally, and a deficiency thereof causes anemia in humans.
Bleeding from the gums, skin, and mucous membranes causes what is called scurvy, and its deficiency is known to cause serious diseases not only in humans but also in terrestrial and aquatic animals. For this reason, it is used as a nutritional supplement for humans, and is added to mixed feed for livestock and aquaculture.
Ｌ−アスコルビン酸は人や動物の栄養面のみでなく、食
品工業において有機酸の一つとして酸味１Ｌ酸化防止剤
、小麦粉の改質剤としても使用される。L-ascorbic acid is used not only for human and animal nutrition, but also as an organic acid in the food industry, as a sour 1L antioxidant, and as a wheat flour modifier.
このように栄養上、または食品加工上有意義であるＬ−
アスコルビン酸及びその塩類の欠点は非常に酸化されや
すいことである。とくに水溶液であったり、金属質、各
種ミネラル類が共存＝３−
すると分解し易い。In this way, L-
The disadvantage of ascorbic acid and its salts is that they are highly susceptible to oxidation. It is particularly easy to decompose if it is in an aqueous solution or if metals or various minerals coexist = 3-.
とくに近年、魚類などの養殖が盛んになるにつれて、人
工的な養魚用配合飼料の使用が増大し、普及してきた。Particularly in recent years, as the cultivation of fish and the like has become more popular, the use of artificial compound feed for fish cultivation has increased and become widespread.
一般に、魚類においては陸上動物のように腸内にビタミ
ン類を生合成する固有細菌群を保有していないため、養
殖時にその飼料中に各種ビタミン類を配合することが必
要である。Generally, unlike land animals, fish do not have indigenous bacterial groups that biosynthesize vitamins in their intestines, so it is necessary to mix various vitamins into their feed during cultivation.
しかしながら、この場合に添加されたＬ−アスコルビン
酸（いわゆるビタミンＣ）はとくに飼料中においては含
有肝臓粉末、水分、ミネラルの共存などの影響で極めて
不安定であり、容易に分解消失してしまい栄養学的目的
が達せられないことになる。However, the L-ascorbic acid (so-called vitamin C) added in this case is extremely unstable, especially in feed due to the coexistence of liver powder, water, and minerals, and is easily decomposed and lost, resulting in nutritional nutrition. The academic purpose will not be achieved.
この対策として従来から、Ｌ−アスコルビン酸またはそ
の塩類を油脂または油脂と乳化剤などの被覆剤により被
覆することにより、水分、ミネラル、空気などから遮断
してＬ−アスコルビン酸およびその塩類の分解を防止す
る試みがなされてきた。例えばこの被覆剤としては、油
脂とレシチンまたは油脂、レシチンとグリセリン脂肪酸
モノエステルの溶融物（特開昭５３−１２７８１９）、
油脂と蔗糖脂肪酸エステルとの溶融物（特開昭５４−１
０９９６２）が挙げられる。Conventionally, as a countermeasure against this problem, L-ascorbic acid or its salts are coated with a coating agent such as oil or fat and oil and an emulsifier to prevent decomposition of L-ascorbic acid and its salts by blocking moisture, minerals, air, etc. Attempts have been made to do so. For example, this coating material includes a melt of oil and fat and lecithin, or a melt of oil and fat, lecithin and glycerin fatty acid monoester (Japanese Patent Application Laid-open No. 127819-1983),
Melt of oil and fat and sucrose fatty acid ester (JP-A-54-1
09962).
「発明が解決しようとする問題点」
しかしながら、これらの特許出願において油脂とレシチ
ンとを被覆剤として併用した被覆物はレシチンを含有す
るため長時間保存すると変色することがしばしばであり
、一方油脂と蔗糖脂肪酸エステルとを併用した被覆剤は
蔗糖脂肪酸エステルが高価であるなどの欠点がある。ま
た、動植物油硬化油を単独に被覆剤として使用する場合
は被覆性能が充分でなく、水分があるとＬ−アスコルビ
ン酸は容易に溶出し、被覆性能が充分でない欠点がある
。``Problems to be Solved by the Invention'' However, in these patent applications, coatings that use both oil and lecithin as coating agents often change color when stored for a long time because they contain lecithin; Coating agents that use sucrose fatty acid esters in combination have drawbacks such as the high cost of sucrose fatty acid esters. Furthermore, when a hardened animal or vegetable oil is used alone as a coating agent, the coating performance is insufficient, and in the presence of moisture, L-ascorbic acid easily dissolves, resulting in insufficient coating performance.
「問題点を解決するための手段」
本発明者らはこれらのいわゆる乳化剤などを使用しなく
ても、十分な被覆性能を有する油脂で被覆されたＬ−ア
スコルビン酸および塩類の製剤をを開発することを目的
として鋭意研究した結果、油脂、グリセリン脂肪酸モノ
エステルおよびステアリン酸などの脂肪酸とからなる混
合物を被覆剤として使用し、Ｌ−アスコルビン酸を被覆
したところ、レシチンや蔗糖脂肪酸エステルなどの乳化
剤を使用しないでも被覆性能（芯物質の溶出率で判断す
る。）が向上するという驚くべき効果を見出し本発明を
完成した。"Means for Solving the Problems" The present inventors have developed a formulation of L-ascorbic acid and salts coated with oil and fat that has sufficient coating performance without using these so-called emulsifiers. As a result of intensive research aimed at this purpose, we used a mixture of fats and oils, glycerin fatty acid monoester, and fatty acids such as stearic acid as a coating agent, and coated L-ascorbic acid. The present invention was completed after discovering the surprising effect that the coating performance (judged by the elution rate of the core substance) is improved even without using it.
本発明は、Ｉ、−アスコルビン酸またはその塩類を、融
点５０〜８０℃の油脂、グリセリン脂肪酸モノエステル
またはジエステルより成る群から選択されたグリセリン
脂肪酸エステルおよび常温で固体の脂肪酸とからなる被
覆剤により被覆してなるＬ−アスコルビン酸製剤に存す
る。The present invention applies I,-ascorbic acid or its salts to a coating agent consisting of an oil or fat having a melting point of 50 to 80°C, a glycerin fatty acid ester selected from the group consisting of glycerin fatty acid monoesters or diesters, and a fatty acid that is solid at room temperature. It consists in an L-ascorbic acid preparation formed by coating.
本発明において用いられるＬ−アスコルビン酸製剤の芯
物質としてはＬ−アスコルビン酸は勿論のこと、その塩
類も使用される。Ｌ−アスコルビン酸の塩類としてはそ
のナトリウム塩またはカルシウム塩などのアルカリ金属
またはアルカリ土類金属塩である。これらのし−アスコ
ルビン酸およびその塩類は単独でも混合物でも使用でき
この芯物質の粒径は、平均粒径として一般に８０μｍ以
下、好ましくは３０μｍ以下、さらに好ましくは３〜２
０μｍである。粒径が大きいと被覆が不充分であり、小
さすぎても経済的ではない。As the core substance of the L-ascorbic acid preparation used in the present invention, not only L-ascorbic acid but also its salts are used. Salts of L-ascorbic acid include alkali metal or alkaline earth metal salts such as its sodium salt or calcium salt. These ascorbic acids and their salts can be used alone or in mixtures, and the particle size of the core material is generally 80 μm or less, preferably 30 μm or less, and more preferably 3 to 2 μm as an average particle size.
It is 0 μm. If the particle size is large, the coating will be insufficient, and if the particle size is too small, it is not economical.
本発明において用いられる融点５０〜８０℃の油脂とは
、牛脂硬化油、チキン油硬化油、菜種油硬化油、ひまし
油硬化油、鯨油硬化油、パーム油硬化油、大豆油硬化油
、ヤシ油などである。The fats and oils with a melting point of 50 to 80°C used in the present invention include hydrogenated beef tallow oil, hydrogenated chicken oil, hydrogenated rapeseed oil, hydrogenated castor oil, hydrogenated whale oil, hydrogenated palm oil, hydrogenated soybean oil, coconut oil, etc. be.
本発明におけるグリセリン脂肪酸エステルはグリセリン
脂肪酸モノエステルまたはジエステルまたはその１種ま
たは２種以上のものから選択することができる。その脂
肪酸成分の炭素数としては８〜２２までが好ましく、グ
リセリン脂肪酸エステルの脂肪酸は飽和でも不飽和でも
かまわないが、−船釣には飽和脂肪酸のグリセライドが
用いられる。このグリセリン脂肪酸エステルとしては、
例えばラウリン酸モノエステル、ミリスチン酸モノエス
テル、パルミチン酸モノエステル、ステアリン酸モノエ
ステルなどのモノエステルまたはラウリン酸ジエステル
、ミリスチン酸ジエステル、パルミチン酸ジエステル、
ステアリン酸ジエステルなどのジエステルが挙げられる
が、一般の実用的な市販品は食用油脂とグリセリンとの
エステル交換法で製造される。The glycerin fatty acid ester in the present invention can be selected from glycerin fatty acid monoesters, diesters, or one or more thereof. The number of carbon atoms in the fatty acid component is preferably 8 to 22, and the fatty acid in the glycerin fatty acid ester may be saturated or unsaturated, but - for boat fishing, saturated fatty acid glycerides are used. As this glycerin fatty acid ester,
For example, monoesters such as lauric acid monoester, myristic acid monoester, palmitic acid monoester, stearic acid monoester, or lauric acid diester, myristic acid diester, palmitic acid diester,
Examples include diesters such as stearic acid diester, but general practical commercial products are produced by transesterification of edible fats and oils and glycerin.
この方法ではモノエステル含有Ｎ４８〜６９χ、残部は
主としてジグリセライドのものが得られ、さらにモノエ
ステル含量を高めるには分子蒸留することにより９０％
以上のものが得られる。これら市販品は上記脂肪酸成分
の２種類以上の混合モノグリセライドである。本発明の
グリセリン脂肪酸エステルとしては、これらのモノエス
テルまたはモノエステルとジエステルとの混合物のいず
れのものでも使用することができるが、主成分がモノエ
ステルのものが好ましい。In this method, monoester-containing N48-69χ, the remainder being mainly diglyceride, can be obtained, and to further increase the monoester content, 90% can be obtained by molecular distillation.
You can get more than that. These commercially available products are mixed monoglycerides of two or more of the above fatty acid components. As the glycerin fatty acid ester of the present invention, any of these monoesters or mixtures of monoesters and diesters can be used, but those whose main component is a monoester are preferred.
本発明に使用される脂肪酸は、常温で固体のもの、通常
融点４０℃以上で炭素数１２〜２２のものが適しており
、これらの脂肪酸の中でとくにステアリン酸、パルミチ
ン酸、ミリスチン酸、ラウリン酸が適当であるが、これ
らの混合物であっても差し支えがない。Suitable fatty acids used in the present invention are those that are solid at room temperature, and those that have a melting point of 40°C or higher and a carbon number of 12 to 22, and among these fatty acids, stearic acid, palmitic acid, myristic acid, and lauric acid are particularly suitable. Acids are suitable, but mixtures thereof may also be used.
グリセリン脂肪酸エステルおよび脂肪酸の使用量は、油
脂１００重量部に対してグリセリン脂肪酸エステルが１
〜３０重量部と脂肪酸が２〜２０重量部、通常グリセリ
ン脂肪酸エステルが４〜２０重量部と脂肪酸が２〜１０
重量部、好ましくはグリセリン脂肪酸エステルが４〜１
０重量部と脂肪酸が２〜８重量部である。グリセリン脂
肪酸エステルと脂肪酸の使用量が少ないと被覆効果（例
えば水に芯物質が溶出する程度を調べる、いわゆる溶出
試験の結果）が悪く、多すぎても逆に溶出率が低下する
。脂肪酸はグリセリン脂肪酸エステルの使用量が脂肪１
００重量部に対して４重量部以上使用したときに被覆性
能の向上にとくに効果がある。The amount of glycerin fatty acid ester and fatty acid used is 1 glycerin fatty acid ester per 100 parts by weight of oil and fat.
~30 parts by weight and 2 to 20 parts by weight of fatty acids, usually 4 to 20 parts by weight of glycerin fatty acid ester and 2 to 10 parts by weight of fatty acids.
Parts by weight, preferably 4 to 1 part by weight of glycerin fatty acid ester
0 parts by weight and 2 to 8 parts by weight of fatty acids. If the amount of glycerin fatty acid ester and fatty acid used is small, the coating effect (for example, the result of a so-called elution test, which examines the extent to which the core material dissolves in water) will be poor, and if it is too large, the elution rate will decrease. For fatty acids, the amount of glycerin fatty acid ester used is 1 fat.
It is particularly effective in improving coating performance when it is used in an amount of 4 parts by weight or more per 00 parts by weight.
被覆剤は融点５０〜８０℃の油脂、グリセリン脂肪酸モ
ノエステルおよび脂肪酸とからなるが、これは通常混合
し、加熱溶融して使用する。The coating material is composed of an oil or fat having a melting point of 50 to 80 DEG C., a glycerin fatty acid monoester, and a fatty acid, which are usually mixed and used by heating and melting.
この被覆物の使用量は芯物質であるし−アスコルビン酸
またはその塩類に対して０．５〜２０重景倍、通常１〜
１０重量倍、好ましくは２〜５重量倍である。The amount of this coating used is 0.5 to 20 times, usually 1 to 20 times, relative to the core material - ascorbic acid or its salts.
The amount is 10 times by weight, preferably 2 to 5 times by weight.
本発明のＬ−アスコルビン酸製剤の製造法としては、噴
霧冷却法または芯物質を流動させた中に有機溶媒に溶解
した被覆剤溶液を噴霧し溶媒を蒸発させながら造粒する
方法など公知の被覆方法が挙げられるが、工業的には噴
霧冷却法が好ましい。例えば、被覆剤を７０〜８０℃に
加熱溶融し、これに芯物質を加え、均一に分散させた後
、回転円盤型造粒装置により４０℃以下、好ましくは３
５℃以下に調整された室内に噴霧し、大部分が粒径約２
００〜７００μｍ、好ましくは２００〜５００μｍの微
粒状に造粒する方法が採られる。被覆物の粒径を揃える
には、得られた被覆物を求める粒径範囲に篩別すること
もできる。The L-ascorbic acid preparation of the present invention can be produced by known coating methods, such as a spray cooling method or a method in which a coating solution dissolved in an organic solvent is sprayed into a fluidized core material and granulated while the solvent is evaporated. Although various methods can be mentioned, the spray cooling method is industrially preferred. For example, the coating material is heated and melted at 70 to 80°C, the core material is added thereto, and the core substance is uniformly dispersed.
Sprayed into a room adjusted to 5 degrees Celsius or below, with most of the particles having a particle size of about 2.
A method of granulating into fine particles of 00 to 700 μm, preferably 200 to 500 μm is adopted. In order to make the particle size of the coating uniform, the obtained coating can be sieved into the desired particle size range.
「作用」
本発明のＬ−アスコルビン酸製剤は、医薬、食品、家畜
用および養殖魚類の飼料の品質改良剤またはＬ−アスコ
ルビン酸（ビタミンＣ）補強剤などとして使用すること
ができるが、被添加物、例えば食品や飼料原料が乾燥状
態または水分を含んだ状態のものでも容易に添加混合す
ることにより充分その目的を達成することができる。"Function" The L-ascorbic acid preparation of the present invention can be used as a quality improver for medicines, foods, feed for livestock and farmed fish, or as an L-ascorbic acid (vitamin C) supplement. The purpose can be sufficiently achieved by easily adding and mixing even dry or moist materials such as foods and feed materials.
しかもミネラルなどＬ−アスコルビン酸を分解するよう
な他の基材を添加することが可能である。Moreover, it is possible to add other base materials such as minerals that decompose L-ascorbic acid.
Ｕ発明の効果コ
本発明のＬ−アスコルビン酸製剤は、従来よりも安価な
原料で高価な乳化剤を使用しないで、油脂本来の被覆効
果を有効に発揮しうる極めて工業的に重要な効果を奏す
ることができる。U Effects of the Invention The L-ascorbic acid preparation of the present invention has extremely industrially important effects in that it can effectively exhibit the inherent coating effect of fats and oils using cheaper raw materials than conventional ones and without using expensive emulsifiers. be able to.
次に、実施例により、本発明の詳細な説明する。ただし
、実施例において「部」および「％」は断らない限り「
重量部」および「重量％」を表す。Next, the present invention will be explained in detail with reference to Examples. However, in the examples, "part" and "%" are used unless otherwise specified.
"parts by weight" and "% by weight".
「実施例」
実施例 １〜３
牛脂硬化油１００部とグリセリン脂肪酸モノエステル（
全モノグリセライド含量９５％以上；脂肪酸成分がミリ
スチン酸２０〜３０′Ａ、ステアリン酸６０〜７０χの
市販品）および第１表に示す割合の脂肪酸（ステアリン
酸）からなる被覆剤を融解し、温度８０℃に保持した中
に、平均粒径２０μｍのＬ−アスコルビン酸結晶粒子を
芯物質含有量が約３０％になるように加え、均一に混合
し回転円盤型噴霧装置にて、２５〜３５℃の室内に噴霧
し、篩分して３００〜４００μｍの被覆物（Ｌ−アスコ
ルビン酸製剤）を得た。"Example" Examples 1 to 3 100 parts of hydrogenated beef tallow oil and glycerin fatty acid monoester (
A coating material consisting of a total monoglyceride content of 95% or more; a commercial product with fatty acid components of 20-30'A myristic acid and 60-70x stearic acid) and a fatty acid (stearic acid) in the proportion shown in Table 1 was melted and heated at a temperature of 80%. L-ascorbic acid crystal particles with an average particle size of 20 μm were added to the mixture maintained at 20 μm so that the core material content was approximately 30%, mixed uniformly, and heated at 25 to 35° C. using a rotating disc type sprayer. It was sprayed indoors and sieved to obtain a coating (L-ascorbic acid preparation) of 300 to 400 μm.
得られた被覆物の性能は、実験例に示す溶出率の測定に
よって行った。その結果を第１表に示す。The performance of the obtained coating was determined by measuring the dissolution rate shown in Experimental Examples. The results are shown in Table 1.
比較例 １〜５
被覆剤として、牛脂硬化油にグリセリン脂肪酸モノエス
テル（実施例１と同様のもの）のみ、または脂肪酸のみ
を添加（添加割合は第２表に示す。）したもの、および
牛脂硬化油のみを使用した以外は、実施例１〜３と同様
に実施した。Comparative Examples 1 to 5 As a coating agent, only glycerin fatty acid monoester (same as in Example 1) or only fatty acid was added to hardened beef tallow (the addition ratio is shown in Table 2), and hardened beef tallow It was carried out in the same manner as Examples 1 to 3 except that only oil was used.
実験例
１２一
実施例１〜３及び比較例１〜５の被覆物を造粒から室温
で１日経過した後、この被覆物の溶出率について次の試
験を行った。Experimental Example 12 - After one day had passed since the coatings of Examples 1 to 3 and Comparative Examples 1 to 5 were granulated at room temperature, the following test was conducted on the dissolution rate of the coatings.
１１０回／分の震盪数および振幅５０ｍｍの往復振動が
できる震盪器を使用し、ガラス製容器に被覆物と約８０
倍量の安定剤人の水を入れ、３０℃で３０分間震盪し、
芯物質の溶出率を調べ、次の結果を得た。Using a shaker capable of reciprocating vibrations at a vibration frequency of 110 times/min and an amplitude of 50 mm, the coating was placed in a glass container with approximately 80 vibrations per minute.
Add double the amount of stabilizer water and shake at 30℃ for 30 minutes.
The elution rate of the core substance was investigated and the following results were obtained.
第１表
第２表
実施例 ４
実施例１〜３においてＬ−アスコルビン酸の代わりにＬ
−アスコルビン酸のカルシウム塩を使用して同様の結果
を得た。Table 1 Table 2 Example 4 In Examples 1 to 3, L-ascorbic acid was replaced with L-ascorbic acid.
- Similar results were obtained using the calcium salt of ascorbic acid.
特許出願人 川崎化成工業株式会社Patent applicant: Kawasaki Chemical Industries, Ltd.
Claims (1)
〜８０℃の油脂、グリセリン脂肪酸モノエステルまたは
ジエステルより成る群から選択されたグリセリン脂肪酸
エステルおよび常温で固体の脂肪酸とからなる被覆剤に
より被覆してなるＬ−アスコルビン酸製剤。 （２）被覆剤が融点５０〜８０℃の油脂１００部、グリ
セリン脂肪酸エステル１〜３０重量部および脂肪酸２〜
２０重量部である特許請求の範囲第１項記載のＬ−アス
コルビン酸製剤。 （３）被覆剤が融点５０〜８０℃の油脂１００部、グリ
セリン脂肪酸エステル４〜２０重量部および脂肪酸２〜
１０重量部である特許請求の範囲第１項記載のＬ−アス
コルビン酸製剤。 （４）被覆剤が融点５０〜８０℃の油脂１００部、グリ
セリン脂肪酸モノエステル４〜１０重量部および脂肪酸
２〜８重量部である特許請求の範囲第３項記載のＬ−ア
スコルビン酸製剤。 （５）油脂が硬化油である特許請求の範囲第１項記載の
Ｌ−アスコルビン酸製剤。 （６）油脂が牛脂硬化油、チキン油硬化油、菜種油硬化
油、ひまし油硬化油、鯨油硬化油、パーム油硬化油、大
豆油硬化油、ヤシ油である特許請求の範囲第１項記載の
Ｌ−アスコルビン酸製剤。 （７）グリセリン脂肪酸エステルがラウリン酸モノエス
テル、ミリスチン酸モノエステル、パルミチン酸モノエ
ステル、ステアリン酸モノエステルなどのモノエステル
、ラウリン酸ジエステル、ミリスチン酸ジエステル、パ
ルミチン酸ジエステル、ステアリン酸ジエステルなどの
ジエステルである特許請求の範囲第１項記載のＬ−アス
コルビン酸製剤。（８）グリセリン脂肪酸エステルの主
成分がグリセリン脂肪酸モノエステルである特許請求の
範囲第１、２、３、４または７項記載のＬ−アスコルビ
ン酸製剤。 （９）脂肪酸が炭素数が１２〜２２の脂肪酸である特許
請求の範囲第１項記載のＬ−アスコルビン酸製剤。 （１０）脂肪酸がステアリン酸、パルミチン酸、ミリス
チン酸またはラウリン酸である特許請求の範囲第１項記
載のＬ−アスコルビン酸製剤。 （１１）被覆する方法が噴霧冷却法である特許請求の範
囲第１項記載のＬ−アスコルビン酸製剤。 （１２）被覆する方法が回転円板式噴霧冷却法である特
許請求の範囲第１項記載のＬ−アスコルビン酸製剤。 （１３）アスコルビン酸またはその塩類の粒径が３〜２
０μｍである特許請求の範囲第１、１１または１２項記
載のＬ−アスコルビン酸製剤。 （１４）Ｌ−アスコルビン酸製剤の粒径が２００〜５０
０μｍである特許請求の範囲第１、１１または１２項記
載のＬ−アスコルビン酸製剤。[Claims] (1) L-ascorbic acid or its salts with a melting point of 50
An L-ascorbic acid preparation coated with a coating agent consisting of oil and fat at ~80°C, a glycerin fatty acid ester selected from the group consisting of glycerin fatty acid monoesters or diesters, and a fatty acid that is solid at room temperature. (2) The coating material is 100 parts of oil or fat with a melting point of 50 to 80°C, 1 to 30 parts by weight of glycerin fatty acid ester, and 2 to 30 parts of fatty acid.
The L-ascorbic acid preparation according to claim 1, which contains 20 parts by weight. (3) The coating material is 100 parts of oil or fat with a melting point of 50 to 80°C, 4 to 20 parts by weight of glycerin fatty acid ester, and 2 to 20 parts of fatty acid.
The L-ascorbic acid preparation according to claim 1, which contains 10 parts by weight. (4) The L-ascorbic acid preparation according to claim 3, wherein the coating agent is 100 parts of oil or fat having a melting point of 50 to 80°C, 4 to 10 parts by weight of glycerin fatty acid monoester, and 2 to 8 parts by weight of fatty acid. (5) The L-ascorbic acid preparation according to claim 1, wherein the fat or oil is a hydrogenated oil. (6) L according to claim 1, wherein the fat or oil is hydrogenated beef tallow oil, hydrogenated chicken oil oil, hydrogenated rapeseed oil oil, hydrogenated castor oil oil, hydrogenated whale oil oil, hydrogenated palm oil oil, hydrogenated soybean oil oil, or coconut oil. - Ascorbic acid preparations. (7) Glycerin fatty acid esters are monoesters such as lauric acid monoester, myristic acid monoester, palmitic acid monoester, and stearic acid monoester, and diesters such as lauric acid diester, myristic acid diester, palmitic acid diester, and stearic acid diester. An L-ascorbic acid preparation according to claim 1. (8) The L-ascorbic acid preparation according to claim 1, 2, 3, 4, or 7, wherein the main component of the glycerin fatty acid ester is a glycerin fatty acid monoester. (9) The L-ascorbic acid preparation according to claim 1, wherein the fatty acid has 12 to 22 carbon atoms. (10) The L-ascorbic acid preparation according to claim 1, wherein the fatty acid is stearic acid, palmitic acid, myristic acid, or lauric acid. (11) The L-ascorbic acid preparation according to claim 1, wherein the coating method is a spray cooling method. (12) The L-ascorbic acid preparation according to claim 1, wherein the coating method is a rotating disk spray cooling method. (13) The particle size of ascorbic acid or its salts is 3 to 2
The L-ascorbic acid preparation according to claim 1, 11 or 12, which has a particle size of 0 μm. (14) Particle size of L-ascorbic acid preparation is 200-50
The L-ascorbic acid preparation according to claim 1, 11 or 12, which has a particle size of 0 μm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15667987A JPH0791187B2 (en) | 1987-06-25 | 1987-06-25 | L-ascorbic acid preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15667987A JPH0791187B2 (en) | 1987-06-25 | 1987-06-25 | L-ascorbic acid preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH013119A true JPH013119A (en) | 1989-01-06 |
| JPS643119A JPS643119A (en) | 1989-01-06 |
| JPH0791187B2 JPH0791187B2 (en) | 1995-10-04 |
Family
ID=15632953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15667987A Expired - Lifetime JPH0791187B2 (en) | 1987-06-25 | 1987-06-25 | L-ascorbic acid preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0791187B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5230836A (en) * | 1991-06-20 | 1993-07-27 | Kalamazoo Holdings, Inc. | Low micron-sized ascorbic acid particles, especially a suspension thereof in a medium in which they are insoluble, and the use thereof as an antioxidant for mediums in which the particles remain insoluble |
| MY115334A (en) * | 1994-02-07 | 2003-05-31 | Shiseido Co Ltd | Method for inhibiting oxidation of oils and fats or fatty acids |
| JP2001031590A (en) | 1999-04-05 | 2001-02-06 | Takeda Chem Ind Ltd | Production and use of coated preparation |
| JP2005232089A (en) * | 2004-02-19 | 2005-09-02 | Aloe Seiyaku Kk | Orally administrable functional agent having bone quantity-increasing activity |
| JP6207934B2 (en) * | 2013-09-03 | 2017-10-04 | 株式会社松風 | Surface-coated ascorbic acid |
| WO2016136285A1 (en) * | 2015-02-26 | 2016-09-01 | 理研ビタミン株式会社 | L-ascorbic acid fatty acid ester preparation |
| JP2021141849A (en) * | 2020-03-12 | 2021-09-24 | 湯本製飴株式会社 | Method for producing vitamin c, and vitamin c |
-
1987
- 1987-06-25 JP JP15667987A patent/JPH0791187B2/en not_active Expired - Lifetime
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