JPS5934681B2 - microbial inhibitor - Google Patents
microbial inhibitorInfo
- Publication number
- JPS5934681B2 JPS5934681B2 JP6538575A JP6538575A JPS5934681B2 JP S5934681 B2 JPS5934681 B2 JP S5934681B2 JP 6538575 A JP6538575 A JP 6538575A JP 6538575 A JP6538575 A JP 6538575A JP S5934681 B2 JPS5934681 B2 JP S5934681B2
- Authority
- JP
- Japan
- Prior art keywords
- mold
- present
- microbial inhibitor
- observed
- octagenyl
- 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
Links
- 239000003112 inhibitor Substances 0.000 title claims description 4
- 230000000813 microbial effect Effects 0.000 title claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 7
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000004334 sorbic acid Substances 0.000 description 5
- 235000010199 sorbic acid Nutrition 0.000 description 5
- 229940075582 sorbic acid Drugs 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- -1 freelfuramide Chemical class 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Description
【発明の詳細な説明】
本発明は食品又は其の他の資材の新規な微生物抑制剤に
係るものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel microbial inhibitor for foods or other materials.
一般に食品又はその他の資材、例えば塗料、化粧品など
の微生物による悪質の影響は極めて大きく、このためそ
の防止方法がつとに望まれている。In general, the harmful effects of microorganisms on foods or other materials, such as paints and cosmetics, are extremely large, and therefore methods for preventing them are highly desired.
この防止法としては理論上無菌状態に保つ事が正しいが
現実的には全く不可能な事であり、従つて殺菌剤、殺カ
ビ剤による簡易な方法で防止する事が現実的には好まし
い方法となる。Theoretically, the correct way to prevent this is to maintain it in a sterile state, but in reality this is completely impossible.Therefore, the preferred method is to use simple methods such as disinfectants and fungicides. becomes.
併しながら従来の殺カビ剤、殺菌剤は効果の変動性、毒
性などにおいて欠点のあるものが多かった。However, many conventional fungicides and fungicides have drawbacks such as variability in effectiveness and toxicity.
例えばソルビン酸はpHの変動によって、その効果が2
0係にも低下し、そのため最適状態での使用しか実用的
でなく従って使用範囲が制限せられる。For example, the effect of sorbic acid can be reduced by changing the pH.
Therefore, it is only practical to use it in the optimum condition, and the range of use is therefore limited.
又食品防腐剤として最も有効なニトロフラン誘導体、特
にフリールフラマイドは毒性が強く、極く微量の添加し
か有用性がなかった。Furthermore, nitrofuran derivatives, particularly freelfuramide, which are the most effective food preservatives, are highly toxic and are useful only when added in extremely small amounts.
又ペンタクロルフェノールなどは塗料の防カビ剤として
有効であるが、毒性が強くまた残溜蓄積性も犬なるため
、環境汚染の原因となり好ましくない。Although pentachlorophenol and the like are effective as antifungal agents for paints, they are highly toxic and have a tendency to accumulate residue, so they are undesirable as they cause environmental pollution.
本発明は上記の従来品の欠点を克服した有用な化合物を
提供する事に係るものである。The present invention is directed to providing useful compounds that overcome the drawbacks of the conventional products mentioned above.
即ち下記構造式で示され礼
2・7−シメチルー1・7−オクタジェニル−3−オー
ル
即ちこの化合物を有効成分とする微生物抑制剤に係るも
のである。That is, it relates to a microbial inhibitor containing 2,7-dimethyl-1,7-octagenyl-3-ol, a compound represented by the following structural formula, as an active ingredient.
本発明に係る物質は従来品と異り、毒性が少く、使用状
態でのpH弯動による効果の低下性がなく、残溜蓄積性
も少ない化合物である。Unlike conventional products, the substance according to the present invention is a compound that is less toxic, has no tendency to reduce its effectiveness due to pH fluctuations during use, and has less tendency to accumulate residue.
2・7−シメチルー1・7−オクタジェニル−3−オー
ルはホスフィン類を配位子としたバラジュウム系触媒を
用い、イソプレンを炭酸ガスと水の存在下で溶剤系又は
エマルジョン系で反応せしめる事により製造する事が出
来る。2,7-dimethyl-1,7-octagenyl-3-ol is produced by reacting isoprene in the presence of carbon dioxide gas and water in a solvent system or an emulsion system using a baradium catalyst with phosphines as ligands. I can do it.
この物質は下記物性を有する。沸点96〜99℃/10
#H,!i+
17.5
屈折率 ”D 1.4709
本発明物質の急性毒性は、マウス経口投与でL D5o
7 、!i’ /に9以上を示すことかられかるように
ソルビン酸と同様であり、加うるにpHによる効果の変
動も少い。This substance has the following physical properties. Boiling point 96-99℃/10
#H,! i+ 17.5 Refractive index "D 1.4709 The acute toxicity of the substance of the present invention is LD5o after oral administration to mice.
7,! It is similar to sorbic acid as it shows an i'/ of 9 or more, and in addition, its effect varies little depending on pH.
従って果汁、乳製品などの食品、化粧品、ペイントなど
に11500〜1 / 2000添加する事によりすぐ
れた効果を与える事が示された。Therefore, it has been shown that adding 11,500 to 1/2,000 to foods such as fruit juices and dairy products, cosmetics, and paints provides excellent effects.
以下実施例につき説明する。Examples will be explained below.
実施例 1
本発明に係る2・7−シメチルー1・7−オクタジェニ
ル−3−オール及び対照ソルビン酸の50%グリセリン
水溶液を作成した。Example 1 A 50% aqueous glycerin solution of 2,7-dimethyl-1,7-octagenyl-3-ol according to the present invention and a control sorbic acid was prepared.
次に供試菌として大腸菌(Escherichia c
oli)、黄色ブドウ球菌(Staphylococc
us aureus)、枯草菌(Bacillussu
btills )、パン酵母(Saccharomyc
escerevisae )、黒カビ(Aspergi
llus niger )、青カビ(Penicill
ium chrysogenum)を選択した。Next, Escherichia c.
oli), Staphylococcus aureus
us aureus), Bacillus subtilis
btills), baker's yeast (Saccharomyc
escerevisae), black mold (Aspergi
llus niger), blue mold (Penicill)
Chrysogenum) was selected.
次に細菌用の培地としては普通寒天培地pH7,0、酵
母カビ用の培地としてはバレイショー葡萄糖−寒天培地
pH7,0とし、培地中の試料濃度を1000.500
,250,125,62.5μg/mlとなる様に寒天
平板を作成した。Next, the medium for bacteria is ordinary agar medium pH 7.0, and the medium for yeast mold is potato grape sugar-agar medium pH 7.0, and the sample concentration in the medium is 1000.500.
, 250, 125, and 62.5 μg/ml.
次にこれらに上記の供試菌を夫々接種し、細菌は37℃
、2日間、酵母及びカビ類は25℃、5日間培養し生育
の有無を観察した。Next, each of the above test bacteria was inoculated into these, and the bacteria were incubated at 37°C.
The yeast and mold were cultured at 25° C. for 5 days, and the presence or absence of growth was observed.
本試験結果を第1表に示す。The results of this test are shown in Table 1.
上表より明らかな如く本発明物質は菌類に関してはソル
ビン酸と同等であるが、黒カビ、青カビ類に対してはソ
ルビン酸よりもすぐれた結果が得られた。As is clear from the above table, the substance of the present invention was equivalent to sorbic acid with respect to fungi, but superior results than sorbic acid were obtained against black mold and blue mold.
実施例 2
バニシングクリーム(ステアリン酸120、ビーズワッ
クス4.0、流動パラフィン6.0、界面活性剤4.0
、ラノリン1.0、グリセリン5.0.トリエタノール
アミン0.3、水67.7部)に2・7−ジメチ)V−
1・7−オクタジェニル−3−オールを0.2 %添加
したもの、無添加のものに青カビの胞子を接種し、27
℃、1ケ月放置した。Example 2 Vanishing cream (stearic acid 120, beeswax 4.0, liquid paraffin 6.0, surfactant 4.0
, lanolin 1.0, glycerin 5.0. (0.3 parts of triethanolamine, 67.7 parts of water) and 2,7-dimethy)V-
Blue mold spores were inoculated into those containing 0.2% of 1,7-octagenyl-3-ol and those containing no additive.
℃ for one month.
その結果は本化合物添加ものにはカビの発育は認められ
なかったが、無添加のものは旺盛なカビの発育が認めら
れた。As a result, no mold growth was observed in the product to which this compound was added, but active mold growth was observed in the product without the additive.
実施例 3
油性ペイント(日本ペイント■製、酢酸ビニル樹脂エマ
ルジョン)に本発明化合物0.1%を添加し、これを2
0べ厚さ0.9%に耐水ベニヤ合板に塗布し、27℃、
湿度80%の恒温室に放置しカビの発生を調べた。Example 3 0.1% of the compound of the present invention was added to an oil-based paint (manufactured by Nippon Paint ■, vinyl acetate resin emulsion), and this was
Coated on water-resistant veneer plywood to a thickness of 0.9% and heated at 27°C.
The samples were left in a constant temperature room with a humidity of 80% and examined for mold growth.
その結果は第2表に示す如く本発明の優秀さが示された
。The results, as shown in Table 2, demonstrate the superiority of the present invention.
夏みかんマーマレードを常法により作製し、製造最終工
程(糖度調整工程)終了時に2・7−シメチルー1・7
−オクタジェニル−3−オールを製品重量に対して0.
2%添加さ、均一に攪拌した。Summer mandarin marmalade is made by a conventional method, and at the end of the final manufacturing process (sugar content adjustment process), 2,7-dimethyl-1,7
-Octagenyl-3-ol at 0.0% relative to the weight of the product.
2% was added and stirred uniformly.
一方本化合物無添加の製品を作製し、これらの2種類の
製品に対して青カビ(Penicilliumchry
sogenum )の胞子を同一条件にて多量に接種し
、25℃で30日間放置した。On the other hand, we produced products without the addition of this compound, and tested these two products with blue mold (Penicillium chry).
sogenum) spores were inoculated in large quantities under the same conditions and left at 25°C for 30 days.
その結果、本化合物0.2%添加製品では何ら菌の発育
は認められなかったが、無添加対照製品では6日目に菌
糸の発生が認められ、100日目胞子の着生が認められ
た。As a result, no growth of bacteria was observed in the product containing 0.2% of this compound, but in the non-additive control product, the growth of mycelia was observed on the 6th day, and the settlement of spores was observed on the 100th day. .
これから本発明がすぐれていることは明瞭である。It is clear from this that the present invention is superior.
Claims (1)
ールを有効成分とすることを特徴とする微生物抑制剤。A microbial inhibitor characterized by containing 12,7-dimethyl-1,7-octagenyl-3-ol as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6538575A JPS5934681B2 (en) | 1975-06-02 | 1975-06-02 | microbial inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6538575A JPS5934681B2 (en) | 1975-06-02 | 1975-06-02 | microbial inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51142531A JPS51142531A (en) | 1976-12-08 |
| JPS5934681B2 true JPS5934681B2 (en) | 1984-08-24 |
Family
ID=13285454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6538575A Expired JPS5934681B2 (en) | 1975-06-02 | 1975-06-02 | microbial inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5934681B2 (en) |
-
1975
- 1975-06-02 JP JP6538575A patent/JPS5934681B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51142531A (en) | 1976-12-08 |
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