JP2012188602A - Oil-and-fat composition, and process for producing the same - Google Patents
Oil-and-fat composition, and process for producing the same Download PDFInfo
- Publication number
- JP2012188602A JP2012188602A JP2011054863A JP2011054863A JP2012188602A JP 2012188602 A JP2012188602 A JP 2012188602A JP 2011054863 A JP2011054863 A JP 2011054863A JP 2011054863 A JP2011054863 A JP 2011054863A JP 2012188602 A JP2012188602 A JP 2012188602A
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- Prior art keywords
- oil
- water
- soluble substance
- fat composition
- fat
- Prior art date
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 229940093633 tricaprin Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
本発明は、水溶性物質を、油脂中に、相分離なく可溶化させた、油脂組成物及びこの油脂組成物の製造方法に関する。 The present invention relates to an oil and fat composition in which a water-soluble substance is solubilized in oil and fat without phase separation, and a method for producing the oil and fat composition.
医薬品、化粧品、食品に用いられる水溶性物質の活性成分の中には、水中で化学的に不安定なものが存在するため、水溶性物質の活性成分を油脂中に溶解させることが行われる。 Some active ingredients of water-soluble substances used in pharmaceuticals, cosmetics, and foods are chemically unstable in water, so that the active ingredients of water-soluble substances are dissolved in fats and oils.
骨粗鬆症治療に効能があるラロキシフェンは、経口投与した際に消化管内で代謝を受けやすく、経口バイオアベイラビリティが２％と極めて低いという問題がある。この問題を回避するためには、軟膏などの油性剤形によりラロキシフェンを皮下及び／又は皮膚へ投与することが有効であると考えられている。 Raloxifene, which is effective in treating osteoporosis, is susceptible to metabolism in the gastrointestinal tract when administered orally, and has a problem that oral bioavailability is as low as 2%. In order to avoid this problem, it is considered effective to administer raloxifene subcutaneously and / or dermally by an oily dosage form such as an ointment.
食品分野では、機能性食品の商品形態やサプリメント剤形の多様化に伴い、水溶性の食品添加物の主剤や機能性食品の有効成分などの水溶性物質の活性成分を、マーガリンやサラダ油などの食用油脂や油脂を内封するソフトカプセルなどに安定的に配合する技術が要求されている。 In the food sector, with the diversification of product forms and supplement dosage forms of functional foods, active ingredients of water-soluble substances such as main ingredients of water-soluble food additives and active ingredients of functional foods, margarine, salad oil, etc. There is a demand for a technique for stably blending edible oils and fats and soft capsules enclosing oils and fats.
水溶性物質を、油脂中に、一定時間以上可溶化させる手法としては、例えば、特許文献１及び特許文献２に記載されているように、乳化装置や高圧ホモジナイザーなどを使用し、油脂中に水型エマルションを形成させて、水溶性物質を物理的に油脂中へ分散させる方法が挙げられ、特許文献３に開示されているように、油脂への溶解性を改善するため、エステル化など活性成分の分子構造中に高脂溶性の官能基を付加する方法などが知られている。 As a method for solubilizing a water-soluble substance in fats and oils for a certain period of time or more, as described in Patent Document 1 and Patent Document 2, for example, an emulsifier or a high-pressure homogenizer is used. A method in which a water-soluble substance is physically dispersed in an oil or fat by forming a mold emulsion. As disclosed in Patent Document 3, an active ingredient such as esterification is used to improve the solubility in an oil or fat. A method of adding a highly fat-soluble functional group to the molecular structure is known.
しかしながら、特許文献１及び特許文献２に記載された手法では、水溶性物質を油脂中に長期間可溶化させるため、多量の乳化剤を混合することから、風味、皮膚への刺激などの問題があり、特許文献３に開示された方法では、高脂溶性の官能基を付加することが可能な化合物が限定され、かつ、化合物の安全性などの問題もある。 However, in the methods described in Patent Document 1 and Patent Document 2, in order to solubilize water-soluble substances in fats and oils for a long period of time, a large amount of emulsifier is mixed. In the method disclosed in Patent Document 3, compounds capable of adding a highly lipophilic functional group are limited, and there are also problems such as compound safety.
それ故、乳化装置や高圧ホモジナイザーなどの特殊な装置を使用せず、エステル化などの特殊な操作を行わず、かつ多量の乳化剤を配合することなく、油脂に溶解しない水溶性物質を、医薬品、化粧品、食品などの用途に使用される油脂中に、少なくとも１週間以上、相分離なく可溶化させることは、現時点では困難といわざるを得ず、新規の医薬品開発、化粧品開発、食品開発において、障害となっている。 Therefore, without using a special device such as an emulsifier or a high-pressure homogenizer, without performing a special operation such as esterification, and adding a large amount of emulsifier, a water-soluble substance that does not dissolve in fats and oils Solubilization in oils and fats used for cosmetics, foods, etc. for at least a week or more without phase separation is difficult at this time. In the development of new drugs, cosmetics, and foods, It is an obstacle.
本発明の目的とするところは、特殊な装置を使用せず、特殊な操作を行わず、かつ、多量の乳化剤を配合することなく、油脂に溶解しない水溶性物質を、油脂中に、相分離なく可溶化させて、水溶性物質の活性成分を油脂中に溶解させた、油脂組成物及びこの油脂組成物の製造方法を提供することにある。 The object of the present invention is to use a water-soluble substance that does not dissolve in fats and oils, phase separation, without using special equipment, without performing special operations, and without adding a large amount of emulsifier. An object of the present invention is to provide an oil / fat composition and a method for producing the oil / fat composition in which the active ingredient of the water-soluble substance is dissolved in the oil / fat.
本発明の発明者は、前記課題を解決するため、鋭意検討を重ねた結果、水溶性物質と、プロピレングリコールと、トリアセチンと、特定の炭素数の脂肪酸とを含有して成る油脂組成物などにより、上記目的を達成することを見出し、本発明をするに至った。 The inventor of the present invention has made extensive studies to solve the above problems, and as a result, an oil and fat composition comprising a water-soluble substance, propylene glycol, triacetin, and a fatty acid having a specific number of carbon atoms. The inventors have found that the above object can be achieved and have come to the present invention.
即ち、本発明の油脂組成物は、水溶性物質と、プロピレングリコールと、トリアセチンと、炭素数８〜２２の脂肪酸とを含有して成り、相分離せず、相溶性を有することを特徴とする。 That is, the oil-and-fat composition of the present invention comprises a water-soluble substance, propylene glycol, triacetin, and a fatty acid having 8 to 22 carbon atoms, and is compatible with no phase separation. .
本発明の好適態様は、上記油脂組成物は、乳化剤を含まず、上記水溶性物質の含有量は、上記油脂組成物に対し、０．０１〜２０重量％である。 As for the suitable aspect of this invention, the said oil-fat composition does not contain an emulsifier, and content of the said water-soluble substance is 0.01-20 weight% with respect to the said oil-fat composition.
本発明の油脂組成物の製造方法は、水溶性物質をプロピレングリコールに溶解させた後、トリアセチンと、炭素数８〜２２の脂肪酸とを添加することを特徴とする。 The method for producing an oil or fat composition of the present invention is characterized in that after a water-soluble substance is dissolved in propylene glycol, triacetin and a fatty acid having 8 to 22 carbon atoms are added.
本発明の油脂組成物は、水溶性物質の活性成分（有効成分）が、油脂中に溶解し、少なくとも１週間以上、溶解状態を維持するため、経口投与による医薬品や機能性食品においては、当該活性成分の胃内における分解抑制や消化管酵素による代謝抑制などの効果が期待され、経皮投与型の医薬品や化粧品においては、当該活性成分の安定性向上や皮膚透過性の亢進などの効果が期待される。 In the oil and fat composition of the present invention, the active ingredient (active ingredient) of the water-soluble substance dissolves in the oil and fat and maintains the dissolved state for at least one week. It is expected to have effects such as inhibition of decomposition of the active ingredient in the stomach and inhibition of metabolism by gastrointestinal enzymes, and transdermal pharmaceuticals and cosmetics are effective in improving the stability of the active ingredient and enhancing skin permeability. Be expected.
本発明の油脂組成物の製造方法を用いることにより、水溶性物質が油脂中に可溶化しやすくなるため、油脂組成物の製造時間の短縮化が図られる。 By using the method for producing an oil / fat composition of the present invention, the water-soluble substance is easily solubilized in the oil / fat, so that the production time of the oil / fat composition can be shortened.
本発明の油脂組成物は、水溶性物質と、水溶性溶剤としてのプロピレングリコールと、トリアセチンと、炭素数８〜２２の脂肪酸とを含有して成る。 The oil and fat composition of the present invention comprises a water-soluble substance, propylene glycol as a water-soluble solvent, triacetin, and a fatty acid having 8 to 22 carbon atoms.
本発明に用いる水溶性物質としては、水溶性溶剤としてのプロピレングリコールに溶解可能なものであれば、特に限定されないが、水溶性溶剤の活性成分（有効成分）が注目され、目的や効能等により適宜選択される。 The water-soluble substance used in the present invention is not particularly limited as long as it is soluble in propylene glycol as a water-soluble solvent. However, the active component (active ingredient) of the water-soluble solvent has attracted attention, depending on the purpose and efficacy. It is selected appropriately.
本発明に用いる水溶性物質として、医薬品分野においては、例えば、アシクロビル、アモキシリン、アトロピン、ビスホスホネート、エリスロマイシン、ファモジチン、メトフォルミン、プラバスタチン、ペニシリン、ラロキシフェン、ラニチジン、テトラサイクリン、バルサルタンが挙げられる。これらの水溶性物質は、特に膜透過性が低いため、水溶性物質の活性成分が体内に吸収されにくいが、油脂中に溶解させることにより、当該活性成分の体内への吸収性が向上する。 Examples of the water-soluble substance used in the present invention include acyclovir, amoxiline, atropine, bisphosphonate, erythromycin, famoditine, metformin, pravastatin, penicillin, raloxifene, ranitidine, tetracycline and valsartan in the pharmaceutical field. Since these water-soluble substances have particularly low membrane permeability, the active ingredients of the water-soluble substances are not easily absorbed into the body, but by dissolving them in fats and oils, the absorbability of the active ingredients into the body is improved.
本発明に用いる水溶性物質として、化粧品分野においては、例えば、アルブチン、リン酸アスコルビルマグネシウム、プラセンタエキス、トラネキサム酸、ルシノール、アデノシン三リン酸二ナトリウム、コウジ酸、エラグ酸が挙げられる。これらの水溶性物質は、皮膚透過性が低いため、水溶性物質の活性成分が皮膚などに作用しにくいが、油脂中に溶解させることにより、当該活性成分の皮膚透過性が向上するため、当該活性成分の化粧品としての効能が改善される。 Examples of the water-soluble substance used in the present invention include arbutin, ascorbyl magnesium phosphate, placenta extract, tranexamic acid, lucinol, adenosine triphosphate disodium, kojic acid, and ellagic acid in the cosmetic field. Since these water-soluble substances have low skin permeability, the active ingredients of the water-soluble substances are unlikely to act on the skin, etc., but by dissolving in oils and fats, the skin permeability of the active ingredients is improved. The efficacy of the active ingredient as a cosmetic is improved.
本発明に用いる水溶性物質として、食品分野においては、例えば、水溶性ビタミン類、コラーゲン、ヒアルロン酸、カルニチン、各種水溶性ペプチド、各種アミノ酸、メチルサルフォニルメタン、コンドロイチン、グルコサミン、カテキン類、レスベラトロールに代表されるポリフェノール類が挙げられる。これらの水溶性物質は、そのままマーガリン、サラダ油等の油性食品やソフトカプセル内の溶液などに配合した場合には、分離や沈殿を生じ、商品価値を損なうが、油脂中に溶解させることにより、良好な品質が保たれる。 As the water-soluble substance used in the present invention, in the food field, for example, water-soluble vitamins, collagen, hyaluronic acid, carnitine, various water-soluble peptides, various amino acids, methylsulfonylmethane, chondroitin, glucosamine, catechins, les Examples include polyphenols typified by veratrol. When these water-soluble substances are blended as they are in oily foods such as margarine and salad oil or solutions in soft capsules, they cause separation and precipitation, which impairs the commercial value, but are good by dissolving in fats and oils. Quality is maintained.
本発明に用いる水溶性物質は、油脂組成物中に０．０１〜２０重量％含有されているのが好ましい。油脂組成物中の水溶性物質の濃度が０．０１重量％未満の場合には、水溶性物質の活性成分のもつ効能が発揮されない可能性があるため、好ましくないからであり、逆に、油脂組成物中の水溶性物質の濃度が２０重量％を超えると、プロピレングリコールに十分溶解しなくなり、形成された油脂組成物中で沈殿するおそれがあるため、好ましくないからである。 The water-soluble substance used in the present invention is preferably contained in the oil / fat composition in an amount of 0.01 to 20% by weight. This is because if the concentration of the water-soluble substance in the oil / fat composition is less than 0.01% by weight, the efficacy of the active ingredient of the water-soluble substance may not be exhibited. If the concentration of the water-soluble substance in the composition exceeds 20% by weight, it is not preferable because it is not sufficiently dissolved in propylene glycol and may be precipitated in the formed oil and fat composition.
本発明において用いられる水溶性溶剤は、プロピレングリコールに限定される。水、グリセリン、糖、アルコールなどは、脂肪酸及び／又はトリアセチンとの相溶性に乏しいため、たとえ、油脂中に水溶性物質の活性成分を溶解できたとしても、短時間で相分離するため、相溶性を有する状態を維持することは困難だからである。 The water-soluble solvent used in the present invention is limited to propylene glycol. Since water, glycerin, sugar, alcohol, etc. are poorly compatible with fatty acids and / or triacetin, even if the active ingredients of water-soluble substances can be dissolved in fats and oils, phase separation takes place in a short time. This is because it is difficult to maintain a soluble state.
本発明に用いるトリアセチンは、グリセリンの酢酸トリエステルである。トリアセチンに類似する組成物としては、脂肪酸鎖長が異なるグリセリントリエステルである、トリカプリン、トリオレインなどが挙げられるが、これらは、プロピレングリコールとの相溶性が悪く、混合によって可溶化状態を得ることはできないため、本発明の油脂組成物の含有物として適さない。 The triacetin used in the present invention is glycerol acetic acid triester. Examples of compositions similar to triacetin include tricaprin and triolein, which are glycerin triesters with different fatty acid chain lengths, but these are poorly compatible with propylene glycol and can be solubilized by mixing. Therefore, it is not suitable as a content of the oil and fat composition of the present invention.
本発明に用いる脂肪酸の炭素数が８〜２２に限定されるのは、酪酸、吉草酸、カプロン酸、エナント酸などの炭素数が８未満の脂肪酸については、刺激性が強く、悪臭を有するため、医薬品、化粧品及び飲食料品への配合が困難であるからであり、逆に、リグノセリン酸、ペンタコサン酸、セロチン酸、ヘプタコサン酸、モンタン酸、メリシン酸などの炭素数が２２を越える脂肪酸については、概ね融点が極めて高いため、加熱下においても混合が困難となるからである。 The reason why the number of carbon atoms in the fatty acid used in the present invention is limited to 8 to 22 is that fatty acids having a carbon number of less than 8 such as butyric acid, valeric acid, caproic acid, and enanthic acid have strong irritation and bad odor. This is because it is difficult to blend into pharmaceuticals, cosmetics and foods and beverages, and conversely, for fatty acids having more than 22 carbon atoms such as lignoceric acid, pentacosanoic acid, serotic acid, heptacosanoic acid, montanic acid, and melicic acid. This is because the melting point is generally extremely high, so that mixing becomes difficult even under heating.
本発明に用いる脂肪酸としては、炭素数が８〜２２であれば、直鎖であっても、分枝状であってもよく、飽和脂肪酸であっても、不飽和脂肪酸であってもよく、例えば、カプリン酸、ペラルゴン酸、カプリル酸、ラウリン酸、ミリスチン酸、パルミチン酸、パルミトレイン酸、マルガリン酸、ステアリン酸、オレイン酸、リノール酸、リノレン酸、アラキジン酸、アラキドン酸、ベヘン酸が挙げられる。 As the fatty acid used in the present invention, if it has 8 to 22 carbon atoms, it may be linear, branched, saturated fatty acid, unsaturated fatty acid, Examples thereof include capric acid, pelargonic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, margaric acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, arachidonic acid, and behenic acid.
本発明の油脂組成物においては、乳化剤を含まないのが好ましい。乳化剤を使用すると、皮膚に塗布する医薬品及び化粧品においては皮膚刺激性を亢進する可能性があり、経口投与する医薬品及び食品においては、消化管刺激や好ましくない味を呈するおそれがあるからであり、本発明の油脂組成物においては、混合した水溶性物質の活性成分が油脂に溶解して相分離しないため、例えば、水と油への親和性の程度を表すＨＬＢ値が低い界面活性剤をさらに配合する必要性もないからである。しかしながら、さらなる溶解安定性が要求される場合には、油脂組成物において、少量の乳化剤（例えば、油脂組成物中に０．０１〜５重量％）が配合されていてもよい。 The oil and fat composition of the present invention preferably contains no emulsifier. The use of emulsifiers may increase skin irritation in pharmaceuticals and cosmetics applied to the skin, and in orally administered pharmaceuticals and foods, there is a risk of exhibiting gastrointestinal irritation and undesirable taste, In the oil and fat composition of the present invention, since the active component of the mixed water-soluble substance dissolves in the oil and fat and does not phase-separate, for example, a surfactant having a low HLB value representing the degree of affinity for water and oil is further added. This is because there is no need for blending. However, when further dissolution stability is required, a small amount of an emulsifier (for example, 0.01 to 5% by weight in the oil or fat composition) may be blended in the oil or fat composition.
本発明の油脂組成物は、混合した水溶性物質が油脂中に十分溶解するため、本発明の油脂組成物を製造する際には、乳化装置や高圧ホモジナイザーなどの特別な装置を使用する必要がなく、エステル化などの特殊な操作を行う必要もない。 In the oil and fat composition of the present invention, the mixed water-soluble substance is sufficiently dissolved in the oil and fat. Therefore, when producing the oil and fat composition of the present invention, it is necessary to use a special device such as an emulsifying device or a high-pressure homogenizer. There is no need for special operations such as esterification.
本発明の油脂組成物には、水溶性物質の活性成分の効能や製品価値を維持するため、水溶性物質、プロピレングリコール、トリアセチン、脂肪酸以外の成分として、例えば、酸化防止剤、香料、増粘安定剤、保存料、保湿剤などを添加してもよい。なお、本発明の油脂組成物は、水を含まない無水状態であることはいうまでもない。 In the oil and fat composition of the present invention, in order to maintain the efficacy and product value of the active ingredient of the water-soluble substance, as an ingredient other than the water-soluble substance, propylene glycol, triacetin and fatty acid, for example, antioxidant, fragrance, thickening agent Stabilizers, preservatives, humectants and the like may be added. In addition, it cannot be overemphasized that the oil-fat composition of this invention is an anhydrous state which does not contain water.
本発明の油脂組成物は、水溶性物質の活性成分が、油脂中に、少なくとも１週間以上、相分離なく溶解された状態となるが、特に、油脂組成物中の水溶性物質の濃度が低い場合や油脂組成物が、水溶性物質、プロピレングリコール、トリアセチン、脂肪酸のみから構成される場合には、本発明の油脂組成物は、水溶性物質の活性成分が、３年以上の極めて長期にわたり、相分離なく溶解されるため、当該活性成分の安定状態が維持される。 In the oil and fat composition of the present invention, the active ingredient of the water-soluble substance is dissolved in the oil and fat for at least one week without phase separation. In particular, the concentration of the water-soluble substance in the oil and fat composition is low. In the case where the oil and fat composition is composed only of a water-soluble substance, propylene glycol, triacetin, and a fatty acid, the oil and fat composition of the present invention has an active ingredient of the water-soluble substance for an extremely long period of 3 years or more, Since it is dissolved without phase separation, the stable state of the active ingredient is maintained.
本発明の油脂組成物の製造方法は、水溶性物質をプロピレングリコールに溶解させた後、トリアセチンと、炭素数８〜２２の脂肪酸とを添加する。本発明の油脂組成物の製造方法は、油脂組成物の製造時間を短縮したい場合や油脂組成物の品質を向上させたい場合に有効である。プロピレングリコールにトリアセチン及び炭素数８〜２２の脂肪酸を添加した後、水溶性物質を混合すると、水溶性物質の油脂中への可溶化に時間がかかり、水溶性物質の活性成分が油脂中に十分溶解しないおそれもあるからである。 In the method for producing an oil and fat composition of the present invention, a water-soluble substance is dissolved in propylene glycol, and then triacetin and a fatty acid having 8 to 22 carbon atoms are added. The method for producing an oil / fat composition of the present invention is effective when it is desired to shorten the production time of the oil / fat composition or to improve the quality of the oil / fat composition. After adding triacetin and a fatty acid having 8 to 22 carbon atoms to propylene glycol and mixing a water-soluble substance, it takes time to solubilize the water-soluble substance in the fat and oil, and the active ingredient of the water-soluble substance is sufficient in the fat and oil This is because it may not dissolve.
（実施例１）
水溶性物質としてラロキシフェンを選択した。プロピレングリコール１００重量部に１重量部のラロキシフェンを溶解して混合物１を作成した。混合物１に、トリアセチン１００重量部とオレイン酸１００重量部とを添加して混合し、乳化剤を含まず、水溶性物質を０．３重量％含有する、透明な外観の液状組成物１を得た。液状組成物１は、１ヶ月以上経過しても安定な可溶化状態を維持し、ラロキシフェンの結晶生成や相分離などの不具合は確認されなかった。
Example 1
Raloxifene was selected as the water soluble substance. 1 part by weight of raloxifene was dissolved in 100 parts by weight of propylene glycol to prepare a mixture 1. To the mixture 1, 100 parts by weight of triacetin and 100 parts by weight of oleic acid were added and mixed to obtain a liquid composition 1 having a transparent appearance and containing 0.3% by weight of a water-soluble substance without containing an emulsifier. . The liquid composition 1 maintained a stable solubilized state even after a lapse of one month or more, and problems such as raloxifene crystal formation and phase separation were not confirmed.
（実施例２）
オレイン酸をカプリン酸に代えた以外は実施例１と同様の操作を繰り返し、乳化剤を含まず、水溶性物質を０．３重量％含有する、透明な外観の液状組成物２を得た。液状組成物２は、１ヶ月以上経過しても安定な可溶化状態を維持し、ラロキシフェンの結晶生成や相分離などの不具合は確認されなかった。
(Example 2)
Except that oleic acid was replaced with capric acid, the same operation as in Example 1 was repeated to obtain a liquid composition 2 having a transparent appearance and not containing an emulsifier and containing 0.3% by weight of a water-soluble substance. The liquid composition 2 maintained a stable solubilized state even after 1 month or more, and no defects such as raloxifene crystal formation and phase separation were confirmed.
（実施例３）
オレイン酸をリノール酸に代えた以外は実施例１と同様の操作を繰り返し、乳化剤を含まず、水溶性物質を０．３重量％含有する、透明な外観の液状組成物３を得た。液状組成物３は、１ヶ月以上経過しても安定な可溶化状態を維持し、ラロキシフェンの結晶生成や相分離などの不具合は確認されなかった。
(Example 3)
Except that oleic acid was replaced with linoleic acid, the same operation as in Example 1 was repeated to obtain a liquid composition 3 having a transparent appearance and containing 0.3% by weight of a water-soluble substance without containing an emulsifier. The liquid composition 3 maintained a stable solubilized state even after 1 month or more, and no defects such as raloxifene crystal formation and phase separation were confirmed.
（実施例４）
トリアセチン１００重量部をトリアセチン５０重量部に代え、オレイン酸１００重量部をオレイン酸５０重量部に代えた以外は実施例１と同様の操作を繰り返し、乳化剤を含まず、水溶性物質を０．５重量％含有する、透明な外観の液状組成物４を得た。液状組成物４は、１ヶ月以上経過しても安定な可溶化状態を維持し、ラロキシフェンの結晶生成や相分離などの不具合は確認されなかった。
Example 4
The same operation as in Example 1 was repeated except that 100 parts by weight of triacetin was replaced with 50 parts by weight of triacetin and 100 parts by weight of oleic acid was replaced with 50 parts by weight of oleic acid. A liquid composition 4 having a transparent appearance and containing% by weight was obtained. The liquid composition 4 maintained a stable solubilized state even after 1 month or more, and no defects such as crystal formation of raloxifene and phase separation were confirmed.
（実施例５）
ラロキシフェンをリン酸アスコルビルマグネシウムに代えた以外は実施例１と同様の操作を繰り返し、乳化剤を含まず、水溶性物質を０．３重量％含有する、透明な外観の液状組成物５を得た。液状組成物５は、１ヶ月以上経過しても安定な可溶化状態を維持し、リン酸アスコルビルマグネシウムの結晶生成や相分離などの不具合は確認されなかった。
(Example 5)
Except that raloxifene was replaced with ascorbyl magnesium phosphate, the same operation as in Example 1 was repeated to obtain a liquid composition 5 having a transparent appearance and not containing an emulsifier and containing 0.3% by weight of a water-soluble substance. The liquid composition 5 maintained a stable solubilized state even after 1 month or more, and no defects such as crystal formation or phase separation of ascorbyl magnesium phosphate were confirmed.
（実施例６）
ラロキシフェンをカルニチンに代えた以外は実施例１と同様の操作を繰り返し、乳化剤を含まず、水溶性物質を０．３重量％含有する、透明な外観の液状組成物６を得た。液状組成物６は、１ヶ月以上経過しても安定な可溶化状態を維持し、カルニチンの結晶生成や相分離などの不具合は確認されなかった。
(Example 6)
Except that raloxifene was replaced with carnitine, the same operation as in Example 1 was repeated to obtain a liquid composition 6 having a transparent appearance and containing 0.3% by weight of a water-soluble substance without containing an emulsifier. The liquid composition 6 maintained a stable solubilized state even after 1 month or more, and no defects such as carnitine crystal formation and phase separation were confirmed.
（実施例７）
トリアセチン１００重量部とオレイン酸１００重量部を、トリアセチン１００重量部とオレイン酸１００重量部と乳化剤としてのテトラグリセリン縮合リシノレイン酸エステル１重量部に代えた以外は実施例１と同様の操作を繰り返し、水溶性物質を０．３重量％含有する、透明な外観の液状組成物７を得た。液状組成物７は、１ヶ月以上経過しても安定な可溶化状態を維持し、ラロキシフェンの結晶生成や相分離などの不具合は確認されなかった。
(Example 7)
The same operation as in Example 1 was repeated except that 100 parts by weight of triacetin and 100 parts by weight of oleic acid were replaced with 100 parts by weight of triacetin, 100 parts by weight of oleic acid and 1 part by weight of tetraglycerin condensed ricinoleate as an emulsifier, A transparent liquid composition 7 containing 0.3% by weight of a water-soluble substance was obtained. The liquid composition 7 maintained a stable solubilized state even after 1 month or more, and no defects such as raloxifene crystal formation and phase separation were confirmed.
（実施例８）
プロピレングリコール１００重量部に、トリアセチン１００重量部とオレイン酸１００重量部とを加え、混合して混合物８を作成した。混合物８に、１重量部のラロキシフェンを添加し、混合して、水溶性物質を０．３重量％含有する、透明な外観の液状組成物８を得た。ラロキシフェンの溶解は、実施例１と比べると、時間を要した。液状組成物８は、１ヶ月以上経過しても安定な可溶化状態を維持し、ラロキシフェンの結晶生成や相分離などの不具合は確認されなかった。
(Example 8)
To 100 parts by weight of propylene glycol, 100 parts by weight of triacetin and 100 parts by weight of oleic acid were added and mixed to prepare a mixture 8. 1 part by weight of raloxifene was added to the mixture 8 and mixed to obtain a liquid composition 8 having a transparent appearance and containing 0.3% by weight of a water-soluble substance. The dissolution of raloxifene took time compared to Example 1. The liquid composition 8 maintained a stable solubilized state even after 1 month or more, and no defects such as raloxifene crystal formation and phase separation were confirmed.
（比較例１）
プロピレングリコールを精製水に代えた以外は実施例１と同様の操作を繰り返し、液状組成物Ｒ１を得た。液状組成物Ｒ１は、二相に分離し、可溶化状態は得られなかった。
(Comparative Example 1)
A liquid composition R1 was obtained by repeating the same operation as in Example 1 except that propylene glycol was replaced with purified water. The liquid composition R1 was separated into two phases, and a solubilized state was not obtained.
（比較例２）
トリアセチンをトリオレインに代えた以外は実施例１と同様の操作を繰り返し、液状組成物Ｒ２を得た。液状組成物Ｒ２は、二相に分離し、可溶化状態は得られなかった。
(Comparative Example 2)
A liquid composition R2 was obtained by repeating the same operation as in Example 1 except that triacetin was replaced with triolein. The liquid composition R2 was separated into two phases, and a solubilized state was not obtained.
（比較例３）
トリアセチン１００重量部をトリアセチン０重量部に代えた以外は実施例１と同様の操作を繰り返し、液状組成物Ｒ３を得た。液状組成物Ｒ３は、可溶化状態を得ることができたが、１週間以内にラロキシフェンの結晶物が沈殿した。
(Comparative Example 3)
A liquid composition R3 was obtained by repeating the same operation as in Example 1 except that 100 parts by weight of triacetin was replaced with 0 parts by weight of triacetin. The liquid composition R3 was able to obtain a solubilized state, but raloxifene crystals were precipitated within one week.
（比較例４）
オレイン酸を大豆油に代えた以外は実施例１と同様の操作を繰り返し、液状組成物Ｒ４を得た。液状組成物Ｒ４は、二相に分離し、可溶化状態は得られなかった。
(Comparative Example 4)
A liquid composition R4 was obtained by repeating the same operation as in Example 1 except that oleic acid was replaced with soybean oil. The liquid composition R4 was separated into two phases, and a solubilized state was not obtained.
本発明は、油脂に溶解しない水溶性物質を油脂中に可溶化させることができるため、例えば、軟膏、湿布剤、ソフトカプセルなどの医薬品、ローション、乳液などの化粧品、マーガリン、ドレッシングなどの食品等に有用である。 Since the present invention can solubilize water-soluble substances that do not dissolve in fats and oils, for example, pharmaceuticals such as ointments, poultices, soft capsules, cosmetics such as lotions and emulsions, foods such as margarine and dressings, etc. Useful.
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| JPS6399008A (en) * | 1986-08-01 | 1988-04-30 | ワ−ナ−−ランバ−ト・コンパニ− | Transdermal composition |
| JPH11147835A (en) * | 1997-09-08 | 1999-06-02 | Panacea Biotec Ltd | New composition containing cyclosporin |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS6399008A (en) * | 1986-08-01 | 1988-04-30 | ワ−ナ−−ランバ−ト・コンパニ− | Transdermal composition |
| JPH11147835A (en) * | 1997-09-08 | 1999-06-02 | Panacea Biotec Ltd | New composition containing cyclosporin |
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