JPH1179988A - Antifungal agent - Google Patents
Antifungal agentInfo
- Publication number
- JPH1179988A JPH1179988A JP26510897A JP26510897A JPH1179988A JP H1179988 A JPH1179988 A JP H1179988A JP 26510897 A JP26510897 A JP 26510897A JP 26510897 A JP26510897 A JP 26510897A JP H1179988 A JPH1179988 A JP H1179988A
- Authority
- JP
- Japan
- Prior art keywords
- acid ester
- antifungal agent
- present
- diglycerin
- monofatty acid
- 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.)
- Withdrawn
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ジグリセリンモノ
脂肪酸エステルを含有する抗真菌剤に関する。さらに詳
しくは、皮膚刺激性の少ない、安全性の高い抗真菌剤に
関する。[0001] The present invention relates to an antifungal agent containing diglycerin monofatty acid ester. More specifically, the present invention relates to a highly safe antifungal agent having little skin irritation.
【０００２】[0002]
【従来の技術】本発明は、抗真菌作用、特に白癬菌に対
し優れた作用を有する抗真菌剤に関する。わが国では、
夏特に梅雨の時期に高温多湿の気候となり、白癬菌の繁
殖が活発になる環境となる。また、生活様式の変化によ
り、靴を長時間着用する機会が多くなっている。更に、
靴下の素材が吸湿性の少ない合成繊維が多用されるよう
になり、水虫にかかる人が増加している。最近は、抗菌
剤を含浸させた抗菌靴下が市販されているが、抗菌効果
が充分であるとは言えない。BACKGROUND OF THE INVENTION The present invention relates to an antifungal agent having an excellent antifungal activity, particularly an excellent activity against Trichophyton. In our country,
In summer, especially during the rainy season, the climate becomes hot and humid, and the breeding of Trichophyton becomes active. In addition, due to changes in lifestyles, there are many opportunities to wear shoes for a long time. Furthermore,
As a material for socks, synthetic fibers with low hygroscopicity are frequently used, and the number of people suffering from athlete's foot is increasing. Recently, antibacterial socks impregnated with an antibacterial agent are commercially available, but their antibacterial effect is not sufficient.
【０００３】一般に水虫と言われているものは白癬菌が
皮膚に寄生する事によって発病するものであり、水虫に
かかるとかゆみ、疼痛、発疹、水疱等のいろいろな症状
が皮膚に現われ、重傷の場合には爪まで侵されてくる。
一度水虫にかかると毎年夏場になると水虫の症状が再発
し、多くの人が悩まされている。すなわち、水虫の治療
に従来からの薬を使用すると、白癬菌の菌糸はなくなる
が胞子のみが生存し、一見水虫が治った様な状態になる
が、その胞子は生き残るため、適した温度と湿度の条件
下では再び白癬菌が活動しはじめ水虫の症状が現われ
る。[0003] Athlete's foot, which is generally called athlete's foot, is caused by the disease caused by Trichophyton, and various symptoms such as itching, pain, rash, and vesicles appear on the skin when the athlete's foot is affected. In some cases, even the nails are affected.
Once athlete's foot is affected, the symptoms of athlete's foot recur every summer, and many people are troubled. In other words, if conventional drugs are used to treat athlete's foot, the hyphae of Trichophyton will disappear, but only the spores will survive, and at first glance it will be in a state where the athlete's foot has healed. Under the conditions described above, Trichophyton starts to act again, and the symptoms of athlete's foot appear.
【０００４】このような水虫を治療するため従来より数
多くの薬が発明されているが、いまだに効果的なものが
ないのが現状である。低級及び中級脂肪酸が白癬菌に対
して殺菌力がある事は知られているが、不快臭や皮膚刺
激性があるために使用感が極めて悪いと言う欠点があ
る。また、抗生物質や有機水銀剤のような水虫を完治さ
せる薬が開発されてはいるが、これらは毒性が強く、患
部がその薬によってただれたり、副作用を伴う場合が多
い。[0004] Although many drugs have been invented for treating such athlete's foot, there are no effective drugs at present. It is known that lower and intermediate fatty acids have bactericidal activity against Trichophyton, but they have a drawback that the feeling of use is extremely poor due to unpleasant odor and skin irritation. Although drugs that cure athlete's foot, such as antibiotics and organic mercury drugs, have been developed, they are highly toxic and often cause the affected area to be eroded by the drug or have side effects.
【０００５】また、低級及び中級脂肪酸の刺激性等の欠
点を少なくする目的で、これら脂肪酸をグリセリンとエ
ステル化したグリセリドが抗白癬菌剤として提案されて
いる（特公昭６４−１１６１８）。グリセリンとのエス
テル化物は、常温において液状あるいは半固体状の化合
物で、無色、無臭で、また皮膚への刺激性がなく、皮膚
への浸透力が強く、水虫等の白癬菌のほか、他のカビに
対しても強力な殺菌作用を有しているとしている。しか
し、これらのグリセリドでも皮膚への刺激性及び不快臭
が多少あり、実用性に全く問題ないとは言えない。[0005] Further, glycerides obtained by esterifying these fatty acids with glycerin have been proposed as anti-tineamycosis agents for the purpose of reducing the drawbacks such as irritation of lower and middle fatty acids (JP-B 64-11618). Esterified with glycerin is a liquid or semi-solid compound at room temperature, colorless, odorless, non-irritating to the skin, has a strong penetration into the skin, and, in addition to ringworm such as athlete's foot, It also has a strong bactericidal action against mold. However, even with these glycerides, there are some irritation to the skin and unpleasant odor, and it cannot be said that there is no problem in practicality.
【０００６】[0006]
【発明が解決しようとする課題】本発明者らは、上記の
従来技術の問題点を克服し、皮膚刺激性のない抗真菌剤
を開発すべく、鋭意研究を重ねた結果、本発明を完成し
た。DISCLOSURE OF THE INVENTION The present inventors have made intensive studies to overcome the above-mentioned problems of the prior art and to develop an antifungal agent having no skin irritation, and as a result, completed the present invention. did.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、炭素数が
８ないし１６の範囲にある飽和もしくは不飽和の脂肪酸
から構成されるジグリセリンモノ脂肪酸エステルが白癬
菌に対して強い抗菌力を有すること、また脂肪酸単体や
グリセリンモノ脂肪酸エステル等に比較して刺激臭は少
なく、かつ皮膚刺激性も殆どなく抗白癬菌治療剤として
優れた物性を有することを見出し本発明に到ったもので
ある。本発明に用いられるジグリセリンモノ脂肪酸エス
テルの含量は構成されるエステル中の５０重量％以上で
あればよく、また脂肪酸は単独もしくは２種以上の併用
物であっても構わない。DISCLOSURE OF THE INVENTION The present inventors have found that diglycerin monofatty acid esters composed of saturated or unsaturated fatty acids having 8 to 16 carbon atoms have strong antibacterial activity against Trichophyton. In addition, the present invention has been found to have less irritating odor than fatty acid simple substance and glycerin monofatty acid ester and the like, and has excellent physical properties as an anti-ringworm treatment agent with little skin irritation. is there. The content of the diglycerin monofatty acid ester used in the present invention may be 50% by weight or more in the constituting ester, and the fatty acid may be used alone or in combination of two or more kinds.
【０００８】以下、本発明の詳細について説明する。グ
リセリン脂肪酸エステル、及びポリグリセリン脂肪酸エ
ステルは、食品添加物として、使用食品、使用量に規制
が設けられていない安全な化合物である。これら化合物
の中で、グリセリンモノ脂肪酸エステル、トリグリセリ
ン脂肪酸エステル、ヘキサグリセリン脂肪酸エステル、
及びデカグリセリン脂肪酸エステルに抗菌性がある事は
知られている(Antimicrobial Agents and Chemotherap
y, Nov.1973, p.501〜506)。この文献では、これらポリ
グリセリン脂肪酸エステルの抗菌性評価をStreptococcu
s sp., Staphyrococcus aureus, Corynebacterium sp.,
Nocardia asteroides, Micrococcus sp. の５種類のグ
ラム陽性菌について最小発育阻止濃度（ＭＩＣ）を測定
したものであり、各菌でのＭＩＣ値はグリセリン脂肪酸
エステルに比べ大幅に小さいものであり、また、グラム
陰性菌、酵母、真菌での抗菌性の効果の記述はない。本
発明に用いるジグリセリンモノ脂肪酸エステルの抗菌特
性については知られておらず、しかも抗真菌性について
も、全く知られていなかった。Hereinafter, the present invention will be described in detail. Glycerin fatty acid esters and polyglycerin fatty acid esters are safe compounds for which no restrictions are imposed on foods to be used and usage amounts as food additives. Among these compounds, glycerin monofatty acid ester, triglycerin fatty acid ester, hexaglycerin fatty acid ester,
And decaglycerin fatty acid esters are known to have antibacterial properties (Antimicrobial Agents and Chemotherap
y, Nov. 1973, p. 501-506). In this document, the antibacterial evaluation of these polyglycerin fatty acid esters is described in Streptococcu.
s sp., Staphyrococcus aureus, Corynebacterium sp.,
Nocardia asteroides, Micrococcus sp. 5 types of gram-positive bacteria were measured for minimum inhibitory concentration (MIC), the MIC value of each bacterium is significantly smaller than that of glycerin fatty acid ester. No description of antibacterial effects on negative bacteria, yeast, and fungi. No antibacterial properties of the diglycerin monofatty acid ester used in the present invention were known, and no antifungal properties were known at all.
【０００９】本発明に用いるジグリセリンモノ脂肪酸エ
ステルは、モノ脂肪酸エステルを５０重量％以上含むも
のである。本発明に用いられるジグリセリンモノ脂肪酸
エステルは、モノ脂肪酸エステルが５０重量％未満では
抗真菌性が劣る、又はない。The diglycerin monofatty acid ester used in the present invention contains the monofatty acid ester in an amount of 50% by weight or more. The diglycerin monofatty acid ester used in the present invention has poor or no antifungal activity when the monofatty acid ester is less than 50% by weight.
【００１０】一般に、ジグリセリン脂肪酸エステルは、
ジグリセリンと脂肪酸とを無触媒又は触媒存在下１８０
〜２４０℃で加熱混合して得られる。エステル化反応
は、無差別分布に沿って進行し、反応生成物として未反
応ジグリセリン、ジグリセリンモノ脂肪酸エステルの他
に、同ジエステル、同トリエステル、同テトラエステル
が存在する。これらの存在比率は、ジグリセリンと脂肪
酸の反応モル比により決定される。具体的に、ジグリセ
リンとパルミチン酸とを混合し未反応脂肪酸がなくなる
まで反応した場合、反応生成物はほぼ次表のようにな
る。Generally, diglycerin fatty acid ester is
Diglycerin and a fatty acid are reacted with or without a catalyst in the presence of 180
Obtained by heating and mixing at ~ 240 ° C. The esterification reaction proceeds along an indiscriminate distribution, and the reaction products include unreacted diglycerin, diglycerin monofatty acid ester, diester, triester, and tetraester as reaction products. The proportion of these is determined by the reaction molar ratio of diglycerin and fatty acid. Specifically, when diglycerin and palmitic acid are mixed and reacted until there is no unreacted fatty acid, the reaction products are almost as shown in the following table.
【００１１】[0011]
【表１】 [Table 1]
【００１２】本発明に用いられるジグリセリンモノ脂肪
酸エステルの含量は構成するエステル組成物中の５０重
量％以上であればよい。５０重量％を充せば反応物をそ
のまま使用できる。反応物中のモノ脂肪酸エステル含量
が５０重量％に充たない場合は適当な方法で濃縮して用
いられる。未反応のジグリセリンはジグリセリンモノ脂
肪酸エステルの抗菌力を阻害するものでなく組成物中に
残存しても構わない。モノ脂肪酸エステルを５０重量％
以上含有する組成物は、反応物を溶剤分別法、分子蒸留
法等の方法等により得ることができる。これら溶剤分別
法、分子蒸留法には公知の技術を採用できる。The content of the diglycerin monofatty acid ester used in the present invention may be at least 50% by weight in the constituent ester composition. If the content is 50% by weight, the reactant can be used as it is. When the content of the monofatty acid ester in the reaction product is less than 50% by weight, it is concentrated and used by an appropriate method. Unreacted diglycerin does not inhibit the antibacterial activity of diglycerin monofatty acid ester and may remain in the composition. 50% by weight of mono fatty acid ester
The composition contained above can be obtained by a method such as a solvent fractionation method or a molecular distillation method of the reactant. Known techniques can be used for the solvent fractionation method and the molecular distillation method.
【００１３】本発明に用いられるモノ脂肪酸エステルを
５０重量％以上含有するジグリセリンモノ脂肪酸エステ
ルは、脂肪酸炭素数が８から１６が好ましい。脂肪酸炭
素数が８より小さいジグリセリンモノエステルは、不快
臭の発生、皮膚刺激性が強くなる。また、脂肪酸炭素数
が１６より大きいジグリセリンモノエステルは、抗真菌
性が劣るか、又はない。The diglycerin monofatty acid ester containing 50% by weight or more of the monofatty acid ester used in the present invention preferably has 8 to 16 fatty acid carbon atoms. Diglycerin monoester having a fatty acid carbon number of less than 8 causes generation of unpleasant odor and increased skin irritation. Diglycerin monoesters having more than 16 fatty acid carbon atoms have poor or no antifungal properties.
【００１４】本発明に用いられるジグリセリンモノ脂肪
酸エステルは、常温に於いて液体又は半固体状の化合物
であり、無色、無臭であり、また皮膚に対して刺激性が
極めて弱いか、又はない。皮膚に対する浸透力が強く、
水虫等の白癬菌等のほか、他のカビに対しても強力な殺
菌作用を有している。The diglycerin monofatty acid ester used in the present invention is a liquid or semi-solid compound at room temperature, is colorless and odorless, and has little or no irritation to the skin. Strong penetration into the skin,
In addition to ringworm such as athlete's foot, it has a strong bactericidal action against other molds.
【００１５】更に本発明のジグリセリンモノ脂肪酸エス
テルは、抗真菌剤としての作用効果だけでなく、抗真菌
剤の溶剤及び乳化剤としての性能も優れており、従来か
ら用いられている殺菌、消毒用医薬品、溶剤又は軟膏配
合剤として利用する事も可能である。上記の医薬品の例
としては、サリチル酸、サリチル酸メチル、塩化ベンザ
ルコニウム、ほう酸、Ｎ−ウンデシレノイルアミノ酸、
ニコチン酸、クレゾール等がある。Further, the diglycerin monofatty acid ester of the present invention is excellent not only in the action and effect as an antifungal agent, but also in the performance as a solvent and an emulsifier for the antifungal agent. It can also be used as a pharmaceutical, solvent or ointment compound. Examples of the above pharmaceuticals include salicylic acid, methyl salicylate, benzalkonium chloride, boric acid, N-undecylenoyl amino acid,
Nicotinic acid, cresol and the like.
【００１６】本発明に係わるモノ脂肪酸エステル純度が
５０重量％以上であるジグリセリンモノ脂肪酸エステル
からなる抗真菌剤は、抗菌性の要求される物質、物品の
いずれに添加、含有せしめてもよい。尚、本発明に係わ
る抗真菌剤は、他の抗真菌剤（他の有機系抗真菌剤、無
機系抗真菌剤等）の１又は２種以上と併用してもよい。The antifungal agent comprising the diglycerin monofatty acid ester having a monofatty acid ester purity of 50% by weight or more according to the present invention may be added to or contained in any substance or article requiring antibacterial properties. The antifungal agent according to the present invention may be used in combination with one or more other antifungal agents (other organic antifungal agents, inorganic antifungal agents, etc.).
【００１７】[0017]
【実施例】以下に実施例を挙げて本発明を説明するが、
本発明はこれらの実施例に限定されるものではない。EXAMPLES The present invention will be described below with reference to examples.
The present invention is not limited to these examples.
【００１８】（実施例１）表２に示す本発明品であるジ
グリセリンモノ脂肪酸エステル、及び比較例を用いて抗
菌性の評価を行った。Example 1 Antibacterial properties were evaluated using diglycerin monofatty acid esters of the present invention shown in Table 2 and Comparative Examples.
【００１９】[0019]
【表２】 [Table 2]
【００２０】上記本発明品を用いて、下記方法で抗菌性
について評価した。菌株としてTrichophyton rubrum(IF
O9185)を用いた。ジグリセリンモノ脂肪酸エステルの添
加濃度を５０ｐｐｍ、１００ｐｐｍ、２００ｐｐｍ、４
００ｐｐｍ、８００ｐｐｍに調製した SABOURAUDの寒天
平板培地（表３に成分を示した）を作成した。The antibacterial properties of the product of the present invention were evaluated by the following method. Trichophyton rubrum (IF
O9185). The concentration of the diglycerin monofatty acid ester added was 50 ppm, 100 ppm, 200 ppm,
SABOURAUD agar plate media (components shown in Table 3) were prepared at 00 ppm and 800 ppm.
【００２１】[0021]
【表３】 [Table 3]
【００２２】上記寒天平板培地に、一定量の菌体を含む
菌液を接種し、通常行われる真菌の形態観察を行い抗菌
性を評価した。接種後２週間経過時の真菌の発育抑制力
を評価し、最小発育阻止濃度（ＭＩＣ）を求めた。その
結果を表４に示した。The above agar plate medium was inoculated with a bacterial solution containing a certain amount of bacterial cells, and the morphological observation of fungi, which is usually performed, was performed to evaluate antibacterial activity. Two weeks after the inoculation, the ability to inhibit the growth of the fungus was evaluated, and the minimum inhibitory concentration (MIC) was determined. Table 4 shows the results.
【００２３】[0023]
【表４】 [Table 4]
【００２４】表４の結果より、本発明品は抗真菌剤とし
て有効である事が判る。The results in Table 4 show that the product of the present invention is effective as an antifungal agent.
【００２５】（実施例２）表２に示すジグリセリンモノ
脂肪酸エステルを用いて抗菌性の評価を行った。実施例
１と同様な下記方法で抗菌性について評価した。菌株と
して Aspergillus nigerを用いた。ジグリセリンモノ脂
肪酸エステルの添加濃度を５０ｐｐｍ、１００ｐｐｍ、
２００ｐｐｍ、４００ｐｐｍ、８００ｐｐｍに調製した
SABOURAUDの寒天平板培地（表２に成分を示した）を作
成した。上記寒天平板培地に、一定量の菌体を含む菌液
を接種し、通常行われる真菌の形態観察を行い抗菌性を
評価した。接種後２週間経過時の真菌の発育抑制力を評
価し、最小発育阻止濃度（ＭＩＣ）を求めた。その結果
を表５に示した。Example 2 Antibacterial properties were evaluated using diglycerin monofatty acid esters shown in Table 2. The antibacterial property was evaluated by the following method as in Example 1. Aspergillus niger was used as a strain. The addition concentration of diglycerin mono fatty acid ester is 50 ppm, 100 ppm,
Adjusted to 200ppm, 400ppm, 800ppm
SABOURAUD agar plate medium (the components are shown in Table 2) was prepared. The agar plate medium was inoculated with a bacterial solution containing a certain amount of cells, and the fungal morphology observed in a usual manner was evaluated to evaluate the antibacterial activity. Two weeks after the inoculation, the ability to inhibit the growth of the fungus was evaluated, and the minimum inhibitory concentration (MIC) was determined. Table 5 shows the results.
【００２６】[0026]
【表５】 [Table 5]
【００２７】表５の結果より、本発明品は抗真菌剤とし
て有効である事が判る。The results in Table 5 show that the product of the present invention is effective as an antifungal agent.
【００２８】（実施例３）本発明の抗真菌剤を水虫患者
の患部に毎朝１回塗布し、１週間毎に患部の状態と治癒
の経過を観察した。その結果を表６に示した。Example 3 The antifungal agent of the present invention was applied to the affected part of athlete's foot patients once every morning, and the condition of the affected part and the progress of healing were observed weekly. Table 6 shows the results.
【００２９】[0029]
【表６】 [Table 6]
【００３０】表６より明らかなように本発明の抗真菌剤
は、水虫治療薬として治癒効果が優れている事が判る。As is clear from Table 6, the antifungal agent of the present invention has an excellent healing effect as a remedy for athlete's foot.
【００３１】[0031]
【発明の効果】本発明により、優れた抗真菌剤が得られ
た。本発明に使用した抗真菌剤の有効成分は、食品添加
物であるポリグリセリン脂肪酸エステルであり、衛生的
に安全である。According to the present invention, an excellent antifungal agent has been obtained. The active ingredient of the antifungal agent used in the present invention is a polyglycerin fatty acid ester which is a food additive, and is hygienic and safe.
Claims (2)
上であるジグリセリンモノ脂肪酸エステルを含有するこ
とを特徴とする抗真菌剤。1. An antifungal agent comprising a diglycerin monofatty acid ester having a monofatty acid ester purity of 50% by weight or more.
構成する脂肪酸の炭素数が８から１６の範囲であること
を特徴とする請求項１記載の抗真菌剤。2. The antifungal agent according to claim 1, wherein the fatty acid constituting the diglycerin mono fatty acid ester has 8 to 16 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26510897A JPH1179988A (en) | 1997-09-12 | 1997-09-12 | Antifungal agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26510897A JPH1179988A (en) | 1997-09-12 | 1997-09-12 | Antifungal agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1179988A true JPH1179988A (en) | 1999-03-23 |
Family
ID=17412726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26510897A Withdrawn JPH1179988A (en) | 1997-09-12 | 1997-09-12 | Antifungal agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH1179988A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007510746A (en) * | 2003-11-11 | 2007-04-26 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | Regulation of cell membrane-mediated effects |
| JP2010260814A (en) * | 2009-05-07 | 2010-11-18 | Riken Vitamin Co Ltd | Agent for preventing influenza viral infection |
| US8796332B2 (en) | 2004-08-03 | 2014-08-05 | Regents Of The University Of Minnesota | Compositions and methods for controlling infections |
-
1997
- 1997-09-12 JP JP26510897A patent/JPH1179988A/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007510746A (en) * | 2003-11-11 | 2007-04-26 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | Regulation of cell membrane-mediated effects |
| US8796332B2 (en) | 2004-08-03 | 2014-08-05 | Regents Of The University Of Minnesota | Compositions and methods for controlling infections |
| US9603824B2 (en) | 2004-08-03 | 2017-03-28 | Regents Of The University Of Minnesota | Compositions and methods for controlling infections |
| US10342776B2 (en) | 2004-08-03 | 2019-07-09 | Regents Of The University Of Minnesota | Compositions and methods for controlling infections |
| JP2010260814A (en) * | 2009-05-07 | 2010-11-18 | Riken Vitamin Co Ltd | Agent for preventing influenza viral infection |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Withdrawal of application because of no request for examination |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20041207 |