JPH07116002B2 - Antibacterial agent - Google Patents
Antibacterial agentInfo
- Publication number
- JPH07116002B2 JPH07116002B2 JP62234139A JP23413987A JPH07116002B2 JP H07116002 B2 JPH07116002 B2 JP H07116002B2 JP 62234139 A JP62234139 A JP 62234139A JP 23413987 A JP23413987 A JP 23413987A JP H07116002 B2 JPH07116002 B2 JP H07116002B2
- Authority
- JP
- Japan
- Prior art keywords
- active ingredient
- antibacterial agent
- medium
- abbreviated
- oligoester
- 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.)
- Expired - Lifetime
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、ジカルボン酸のグリコールオリゴエステルを
抗菌活性成分として利用することに関する。TECHNICAL FIELD OF THE INVENTION The present invention relates to the use of glycol oligoesters of dicarboxylic acids as antibacterial active ingredients.
従来技術 最近、ジカルボン酸もしくはそのアルカリ金属塩を活性
成分とする抗菌剤が提案されている（特開昭53−124622
号）。この抗菌剤は、炭素数が８〜20のジカルボン酸も
しくはそのアルカリ金属塩を活性成分として利用するも
のであつて、これらの化合物の抗菌性は認められるもの
の、該化合物はいずれも油脂類に対する溶解性（脂溶
性）が非常に低いため、その利用面での制約がある。例
えば、上記抗菌剤を、変質し易い油脂含有食品や油脂含
有化粧品の保存に適用した場合、活性成分であるジカル
ボン酸並びにそのアルカリ金属塩が経時的に結晶化して
抗菌作用が著しく低下するようになる。2. Description of the Related Art Recently, an antibacterial agent containing a dicarboxylic acid or an alkali metal salt thereof as an active ingredient has been proposed (JP-A-53-124622).
issue). This antibacterial agent utilizes a dicarboxylic acid having 8 to 20 carbon atoms or its alkali metal salt as an active ingredient, and although the antibacterial properties of these compounds are recognized, all of these compounds dissolve in oils and fats. Since its solubility (fat solubility) is extremely low, there are restrictions in its use. For example, when the above-mentioned antibacterial agent is applied to the storage of oil-and-fat-containing foods and oil-and-fat-containing cosmetics that are easily altered, the dicarboxylic acid and its alkali metal salt as active ingredients are crystallized over time so that the antibacterial activity is significantly reduced. Become.
発明が解決しようとする課題 本発明は、炭素数10個以上を有するジカルボン酸をグリ
コールオリゴエステルの形態にしたものを活性成分とす
る抗菌・抗かび活性を示す抗菌剤を提供することを課題
とする。DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present invention aims to provide an antibacterial agent having antibacterial / antifungal activity, which comprises a dicarboxylic acid having 10 or more carbon atoms in the form of a glycol oligoester as an active ingredient. To do.
以下本発明を詳しく説明する。The present invention will be described in detail below.
発明の構成 本発明の特徴は、下記一般式（Ｉ）で示されるジカルボ
ン酸のグリコールオリゴエステルを活性成分とする抗菌
剤にある。Structure of the Invention A feature of the present invention is an antibacterial agent containing a glycol oligoester of a dicarboxylic acid represented by the following general formula (I) as an active ingredient.
（但し、式中、ｍは８以上、ｎは２〜６、ｓは１〜３を
表わし、Ｒは低級アルキレン基を表わす） なお、上記一般式におけるｍの上限は特に規定されない
が、20程度が好ましい。また、該グリコールオリゴエス
テルにおいて、グリコールに由来する低級アルキレン基
は、炭素数２〜５が好ましく、分枝を有していてもよ
い。 (However, in the formula, m is 8 or more, n is 2 to 6, s is 1 to 3, and R is a lower alkylene group.) The upper limit of m in the above general formula is not particularly specified, but about 20. Is preferred. In the glycol oligoester, the lower alkylene group derived from glycol preferably has 2 to 5 carbon atoms and may have a branch.
課題を解決するための手段 本発明において、活性成分として利用する上記一般式
（Ｉ）で表わされる化合物としては、下記式を有するネ
オペンチルグリコールブラシル酸オリゴエステル、ジエ
チレングリコールブラシル酸オリゴエステルを例示し得
る。Means for Solving the Problems In the present invention, examples of the compound represented by the general formula (I) used as an active ingredient include neopentylglycol brassic acid oligoester and diethylene glycol brassic acid oligoester having the following formulas. .
ネオペンチルグリコールブラシル酸オリゴエステル： ジエチレングリコールブラシル酸オリゴエステル： これらの化合物は、それ自体公知物質であつて良好な脂
溶性を示し、毒性も認められない。Neopentyl glycol brassylic acid oligoester: Diethylene glycol brassylic acid oligoester: These compounds are substances known per se, exhibit good lipophilicity, and show no toxicity.
次に、各活性成分について、その抗菌力を試験した結果
を下記に示す。Next, the results of testing the antibacterial activity of each active ingredient are shown below.
試験方法： 供試菌として下記10種類のものを対象とし、培地に下記
組成のブイヨン培地（Ｂ培地と略記する）とツアペツク
培地（Cz培地と略記する）を用い、検体としての各活性
成分が供試菌の発育を抑制するのに必要な最低有効濃度
を測定してそれらの抗菌力とした。Test method: The following 10 types of test bacteria were used, and broth medium (abbreviated as B medium) and Tuapetsk medium (abbreviated as Cz medium) having the following compositions were used as the medium, and each active ingredient as a sample was tested. The minimum effective concentration required to suppress the growth of the test bacteria was measured and used as their antibacterial activity.
供試菌 細菌： バチルス・ズブチリスIF0−3134 （Bacillus subtilis、B.sと略記する） エシエリヒア・コリIFO−3806 （Escherichia coli、E.cと略記する） エアロバクター・エロゲナスIFO−3319 （Aerobacter aerogenes、A.aと略記する） シュードモーナス・アエルギノーザIFO−12689 （Pseudomonas aeruginosa、P.aと略記する） ミクロコツカス・ピオゲネスFDA−2099 （Micrococcus pyogenes、M.pと略記する） 糸状菌： アスペルギルス・ニガーIFO−6341 （Aspergillus niger、A.nと略記する） ペニシリウム・チトリウムIFO−6352 （Penicillum citrinum、P.cと略記する） 酵母： トリコデルマ・Ｔ−1 IFO−6355 （Trichoderma T−１、Ｔ・Ｔ−１と略記する） トルロプシス・キヤンデイタIFO−1084 （Torulopsis candida、T.cと略記する） ジオトリチウム・キヤンデイデムIFO−4958 （Geotrichum candidum、G.cと略記する） 培地組成 細菌用ブイヨン培地（Ｂ培地） 寒天末 18.0 g 肉汁 5.0 g ペプトン 10.0 g 食塩 5.0 g 蒸留水 1000 ml 糸状菌、酵母用ツアペツク培地（Cz培地） 寒天末 20.0 ｇ シヨ糖 30.0 ｇ NaNO3 2.0 ｇ K2HPO4 1.0 ｇ KCl 0.5 ｇ MgSO4・7H2O 0.5 ｇ FeSO4 0.01 ｇ 蒸留水 1000 ml 検査活性成分の濃度調整 各活性成分の濃度は、シヤーレ中の培地10mlに対して上
限が10,000ppm、下限が1ppmの範囲で下記の各濃度にな
るように調整して添加したものを用意して試験に供し
た。Test bacteria Bacteria: Bacillus subtilis IF0-3134 (abbreviated as Bacillus subtilis, Bs) Escherichia coli IFO-3806 (abbreviated as Escherichia coli, Ec) Aerobic aerogenes IFO-3319 (abbreviated as Aerobacter aerogenes, Aa) ) Pseudomonas aeruginosa IFO-12689 (abbreviated as Pseudomonas aeruginosa, Pa) Micrococcus pyogenes FDA-2099 (abbreviated as Micrococcus pyogenes, Mp) Filamentous fungus: Aspergillus niger IFO-6341 (abbreviated as Aspergillus niger, An) ) Penicillium citrium IFO-6352 (abbreviated as Penicillum citrinum, Pc) Yeast: Trichoderma T-1 IFO-6355 (abbreviated as Trichoderma T-1, T.T-1) Torlopsis canandida IFO-1084 (Torulopsis candida) , Tc) Geotritium candeidum IFO-4958 (Geotrichum candidum, abbreviated as Gc) Medium set Bacteriological broth (B medium) agar powder 18.0 g broth 5.0 g peptone 10.0 g NaCl 5.0 g Distilled water 1000 ml fungi, Tsuapetsuku medium (Cz medium) yeast agar powder 20.0 g sucrose 30.0 g NaNO 3 2.0 g K 2 HPO 4 1.0 g KCl 0.5 g MgSO 4 / 7H 2 O 0.5 g FeSO 4 0.01 g Distilled water 1000 ml Adjusting the concentration of the test active ingredient The maximum concentration of each active ingredient is 10,000 ppm, and the lower limit is 10 ml of the medium in the dish. Was added and adjusted so as to have the following respective concentrations within a range of 1 ppm, and the test was prepared.
単位（ppm） 1,5,10,33,66,100,330,660,1000,3300,6600,10,000 供試菌の最小阻止濃度（MIC）の測定 （イ）細菌 斜面培養基中に生育した細菌の１白金耳量をブイヨン液
体培養基10mlに接種し、約37℃で24時間培養した後、そ
の培養液を滅菌した蒸留水で10-2に希釈して供試菌液と
した。Unit (ppm) 1,5,10,33,66,100,330,660,1000,3300,6600,10,000 Measurement of minimum inhibitory concentration (MIC) of test bacteria (a) Bacteria One platinum loop amount of bacteria grown in slope culture medium After inoculating 10 ml of broth liquid culture medium and culturing at about 37 ° C for 24 hours, the culture solution was diluted to 10 -2 with sterilized distilled water to prepare a test bacterial solution.
次に、検体活性成分を上記の各濃度になるように添加し
たブイヨン培地10mlの各平板寒天培養基に上記供試菌液
の１白金耳量をそれぞれ塗抹し、37℃で24時間又は48時
間培養した後、各培養基に形成したコロニーの有無によ
り最小阻止濃度を調べて抗菌力を判定した。Next, each platinum agar culture medium of 10 ml of broth medium to which the active ingredient of the sample was added so as to have each of the above concentrations was smeared with 1 platinum loop of the test bacterial solution, and incubated at 37 ° C for 24 hours or 48 hours. After that, the minimum inhibitory concentration was examined by the presence or absence of colonies formed in each culture medium to determine the antibacterial activity.
（ロ）酵母 斜面培養基中に生育した酵母の１白金耳量をサブロー液
体培養基10mlに接種し、28℃で24時間培養し、その培養
液をそのまま供試菌液とした。(B) Yeast One platinum loop amount of yeast grown in a slant culture medium was inoculated into 10 ml of Sabouraud liquid culture medium and cultured at 28 ° C. for 24 hours, and the culture solution was directly used as a test bacterial solution.
次に、検体活性成分を上記各濃度になるように添加した
ツアペツク寒天培地10mlの各平板培養基に上記供試菌液
の１白金耳量をそれぞれ塗抹し、28℃で７日間培養した
後、各培養基に形成したコロニーの有無により最小阻止
濃度を調べて抗菌力を判定した。Next, 1 platinum loop amount of the test bacterial solution was smeared on each plate culture medium of 10 ml of Tuapetsk agar medium to which the active ingredient of the sample was added so as to have the above respective concentrations, and after culturing at 28 ° C for 7 days, The minimum inhibitory concentration was examined by the presence or absence of colonies formed in the culture medium to determine the antibacterial activity.
（ハ）糸状菌 スラント中に生育した糸状菌の斜面培養基中に10mlの滅
菌蒸留水を注ぎ込み、白金釣を用いて胞子および菌糸を
十分に分散させ、バイブレーターを用いて更に激しく振
り動かして胞子および菌糸を十分に分散させた。(C) Filamentous fungus Pour 10 ml of sterile distilled water into the slant culture medium of the filamentous fungus grown in the slant, use platinum fishing to disperse the spores and mycelia sufficiently, and further shake vigorously to vibrate the spores and The hyphae were well dispersed.
次いで、上述のように分散させた培養基内容物を滅菌ガ
ーゼでこし、その瀘液を供試菌液とした。この供試菌液
を酵母の場合と同様な手段により28℃で７日間培養を行
つた後、その発育状態を観察して抗菌力を判定した。因
に発育が阻害されないものは菌糸が十分に生育してお
り、ある程度阻害されたものは菌糸の生育が不完全であ
り、完全に阻害されたものは全く生育しない。Then, the contents of the culture medium dispersed as described above were rubbed with sterile gauze, and the filtrate was used as a test bacterial solution. The test bacterial solution was cultured at 28 ° C. for 7 days by the same method as in the case of yeast, and the growth state was observed to determine the antibacterial activity. The hyphae of which growth is not inhibited are sufficiently grown, the hyphae of which are inhibited to some extent are incomplete, and the hyphae of which are completely inhibited do not grow at all.
上記試験結果は表１並びに表２に示すとおりである。な
お、各表中の活性成分の番号はそれぞれ下記式の化合物
を示す。The test results are shown in Tables 1 and 2. The numbers of the active ingredients in each table indicate the compounds of the following formulas.
No.1……ネオペンチルグリコールブラシル酸オリゴエス
テル ｎ＝2.5 No.2……ジエチレングリコールブラシル酸オリゴエステ
ル ｎ＝2.5 表１並びに表２にみられるとおり、本発明で用いる活性
成分は、細菌、酵母及び糸状菌等の多くの微生物に対
し、１重量％前後の濃度で抗菌性を有するものである。
そして、これら活性成分は前述したように無色乃至淡黄
色透明であつて、臭も殆んどなく、かつ良好な脂溶性を
示すもので、種々の脂肪含有食品及び脂性化粧品の保存
剤として有効である。No.1 …… Neopentyl glycol brushic acid oligoester n = 2.5 No.2 …… Diethylene glycol brushic acid oligoester n = 2.5 As seen in Table 1 and Table 2, the active ingredient used in the present invention has antibacterial activity against many microorganisms such as bacteria, yeast and filamentous fungi at a concentration of about 1% by weight.
And, as mentioned above, these active ingredients are colorless to pale yellow and transparent, have almost no odor, and show good fat solubility, and are effective as preservatives for various fat-containing foods and oily cosmetics. is there.
本発明に係る抗菌剤は、活性成分としての一般式（Ｉ）
で示されるジカルボン酸グリコールオリゴエステルを単
独または２種以上を配合して混合物そのままで使用する
ことができるので、取扱が容易である。また、上記活性
成分は食品添加剤や化粧用添加剤と併用することもでき
る。The antibacterial agent according to the present invention has the general formula (I) as an active ingredient.
The dicarboxylic acid glycol oligoester represented by the formula (1) can be used alone or in combination of two or more, and the mixture can be used as it is, so that it is easy to handle. Further, the above-mentioned active ingredients can be used in combination with food additives and cosmetic additives.
本発明の抗菌剤の使用量は、その活性成分の種類並びに
保存対象物により異なるも、前記表１及び２に示した抗
菌力に鑑み、１重量％前後で優れた保存効果を奏するも
のと言える。Although the amount of the antibacterial agent of the present invention used varies depending on the type of the active ingredient and the object to be preserved, considering the antibacterial activity shown in Tables 1 and 2, it can be said that an excellent preservation effect is exhibited at about 1% by weight. .
───────────────────────────────────────────────────── フロントページの続き (72)発明者 上島 卓雄 千葉県船橋市前原西７丁目15番24号 (72)発明者 小野 健 神奈川県相模原市西大沼２丁目38番25号 (72)発明者 田岡 映 東京都港区赤坂１丁目12番32号 日本鉱業 株式会社内 (72)発明者 渡辺 章夫 埼玉県戸田市新曽南３丁目17番35号 日本 鉱業株式会社内 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Takuo Uejima 7-15-24 Maebaru Nishi, Funabashi City, Chiba Prefecture (72) Inventor Ken Ono 2-38-25 Nishi Nishinuma City, Sagamihara City, Kanagawa Prefecture (72) Inventor Ei Taoka 1-12-32 Akasaka, Minato-ku, Tokyo Within Japan Mining Industry Co., Ltd. (72) Inventor Akio Watanabe 3-17-35, Shinzonan, Toda City, Saitama Prefecture Within Japan Mining Co., Ltd.
Claims (2)
表わし、Ｒは低級アルキレン基を表わす） で示されるジカルボン酸のグリコールオリゴエステルを
活性成分として含有する抗菌剤。1. A general formula (In the formula, m is 8 or more, n is 2 to 6, s is 1 to 3, and R is a lower alkylene group.) An antibacterial agent containing a glycol oligoester of a dicarboxylic acid as an active ingredient. .
エステルにおいて、該低級アルキレン基Ｒが、分枝を有
してもよい炭素数２〜５のアルキレン基であることを特
徴とする特許請求の範囲（１）に記載の抗菌剤。2. The glycol oligoester of dicarboxylic acid as described above, wherein the lower alkylene group R is an alkylene group having 2 to 5 carbon atoms which may have a branch. The antibacterial agent according to 1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62234139A JPH07116002B2 (en) | 1987-09-18 | 1987-09-18 | Antibacterial agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62234139A JPH07116002B2 (en) | 1987-09-18 | 1987-09-18 | Antibacterial agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6475420A JPS6475420A (en) | 1989-03-22 |
| JPH07116002B2 true JPH07116002B2 (en) | 1995-12-13 |
Family
ID=16966251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62234139A Expired - Lifetime JPH07116002B2 (en) | 1987-09-18 | 1987-09-18 | Antibacterial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07116002B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5303286A (en) * | 1991-03-29 | 1994-04-12 | Space Systems/Loral, Inc. | Wireless telephone/satellite roaming system |
| CA2078932C (en) * | 1991-10-10 | 2003-12-02 | Robert A. Wiedeman | Satellite telecommunications system using network coordinating gateways operative with a terrestrial communication system |
| US5526404A (en) * | 1991-10-10 | 1996-06-11 | Space Systems/Loral, Inc. | Worldwide satellite telephone system and a network coordinating gateway for allocating satellite and terrestrial gateway resources |
| JP2009057350A (en) * | 2007-09-03 | 2009-03-19 | Nippon Fine Chem Co Ltd | Antimicrobial agent, antimicrobial cosmetics and skin care preparation including the same |
-
1987
- 1987-09-18 JP JP62234139A patent/JPH07116002B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6475420A (en) | 1989-03-22 |
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