JPH0437802B2 - - Google Patents
Info
- Publication number
- JPH0437802B2 JPH0437802B2 JP58112330A JP11233083A JPH0437802B2 JP H0437802 B2 JPH0437802 B2 JP H0437802B2 JP 58112330 A JP58112330 A JP 58112330A JP 11233083 A JP11233083 A JP 11233083A JP H0437802 B2 JPH0437802 B2 JP H0437802B2
- Authority
- JP
- Japan
- Prior art keywords
- antibacterial agent
- formula
- ascorbic acid
- carbon atoms
- transition metal
- 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
- 229910052723 transition metal Inorganic materials 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 150000003624 transition metals Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- -1 transition metal salts Chemical class 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000011572 manganese Substances 0.000 claims 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 16
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 229960005070 ascorbic acid Drugs 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 150000000996 L-ascorbic acids Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000000069 L-ascorbic acid Nutrition 0.000 description 4
- 239000002211 L-ascorbic acid Substances 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001522878 Escherichia coli B Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- AQQBRCXWZZAFOK-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(Cl)=O AQQBRCXWZZAFOK-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000199866 Lactobacillus casei Species 0.000 description 1
- 235000013958 Lactobacillus casei Nutrition 0.000 description 1
- 241000515012 Micrococcus flavus Species 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000405383 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940017800 lactobacillus casei Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
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
本発明は、抗菌剤に関し、更に詳しくはＬ−ア
スコルビン酸誘導体および要すれば二価の遷移金
属の塩から成る抗菌剤に関する。
Ｌ−アスコルビン酸、すなわちビタミンＣは、
二価の遷移金属の塩の共存下に抗菌活性を示すこ
とは知られている。
本発明者らは、Ｌ−アスコルビン酸誘導体につ
いて研究を進めるうち、ある種の誘導体は自体抗
菌活性を有し、その活性は二価の遷移金属の塩の
存在により高められることを見い出し、本発明を
完成するに至つた。
すなわち、本発明の要旨は、式：
〔式中、X1、X2およびX3は、同一または異なつ
て水素、炭素数２〜21のアシル基もしくはポリフ
ルオロアシル基または炭素数７〜21の芳香族アシ
ル基を表わし、そのうち少くとも１つは水素では
ない。〕
で示されるアスコルビン酸誘導体から成る抗菌剤
に存する。
式（）中のアシル基は、一般に式：
RCO− （）
〔式中、Ｒは炭素数１〜20のアルキル基もしくは
ポリフルオロアルキル基または炭素数６〜20のア
リール基を表わす。〕
で示される。
本発明の誘導体（）のうち、フツ素を含まな
いアシル誘導体は、たとえば薬学雑誌第86巻第５
号376〜383頁（1966年）に記載され、あるいは同
文献に記載の方法に準じて製造される。また、ポ
リフルオロアシル誘導体は、同文献に記載の方法
に準じて容易に製造することができる。
たとえば、６−エステル体は、Ｌ−アスコルビ
ン酸と式：RCOOH〔式中、Ｒは前記と同意義。〕
で示されるカルボン酸とを、濃硫酸中、たとえば
室温において反応させることにより得られる。ま
た、６−エステル体は、ジメチルホルムアミド、
アセトニトリルなどの溶媒中、イオン交換樹脂の
存在下、Ｌ−アスコルビン酸と上記酸の酸クロラ
イドとを反応させることによつても得られる。
２，６−ジエステル体および２，５，６−トリ
エステル体は、上記酸の酸クロライドまたは酸無
水物とＬ−アスコルビン酸とを塩基（たとえば、
ピリジン、ピコリンまたはトリエチルアミンな
ど）の存在下、室温ないし氷冷下で反応させるこ
とにより得られる。
２−エステル体は、５，６−イソプロピリデン
−アスコルビン酸と上記酸クロライドとを、塩
基、たとえばピリジンなどの存在下に反応させる
ことにより得られる。
Ｌ−アスコルビン酸誘導体（）のうち、ポリ
フルオロアシル基を含むエステル誘導体は、昭和
58年６月16日出願の特許願（アスコルビン酸誘導
体）に記載されている。
Ｌ−アスコルビン酸誘導体（）は、自体抗菌
活性を有するが、二価の遷移金属の塩を共存させ
ると、活性が高くなり、あるいは抗菌スペクトル
が拡大されうる。
二価の遷移金属の塩としては、銅、鉄、マンガ
ン、亜鉛などの硫酸塩、硝酸塩、ハロゲン化物
（たとえば塩化物および臭化物）が好ましく例示
でき、就中、銅の塩、たとえばCuSO4、Cu
（NO3）2、CuCl2、CuBr2などが特に好ましい。
二価の遷移金属の塩を共存させる場合、その添
加量は、誘導体（）の種類および濃度、菌の種
類などに応じて適且定めることができる。
次に製造例を示し、誘導体（）のうちポリフ
ルオロアシル基を含むエステル体の製造方法を例
示する。
製造例
アスコルビン酸4.7ｇをアセトニトリル40mlお
よびピリジン4.5ml混合物中に加え、次いで水冷
下にパーフルオロオクタン酸クロライド24.2ｇを
滴下した。滴下終了後、10時間撹拌を続けた。溶
媒を減圧下に留去し、あめ状残渣をエーテル／ク
ロロホルム（容積比１：２）混合溶媒に溶解し、
希塩酸水溶液および続いて水で洗浄し、次いで硫
酸ナトリウムで乾燥した。ｎ−ヘキサンを加え、
析出した粉末をエーテル／ｎ−ヘキサンで再沈殿
させることにより２，６−ジ（パーフルオロオク
タノイル）アスコルビン酸13.5ｇを得た。融点
162〜５℃。
次に実施例を示し、本発明の誘導体（）の抗
菌活性を説明する。
実施例 １
第１表に示す化合物と細菌とを組み合せて次の
様にして抗菌活性を試験した。
試験菌を0.22Mトリス塩酸緩衝液（PH7.4）に
１〜４×107cells／mlとなる様に加え、これに化
合物溶液を濃度１×10-3Mまたは３×10-4Mとな
る様に混合した。次いで１×10-6MのCu2+の存在
下または非存在下、37℃で60分間インキユベート
した。その後、液の一部を採り、希釈液（NaCl
１ｇ、MgSO4・7H2O 0.25ｇ、ゼラチン0.03ｇ、
0.01Mリン酸緩衝液（PH7.0）１）で100倍以上
に希釈して反応を停止した。
反応前後のコロニー数を通常の方法により測定
し、細菌の残存率を計算して化合物の抗菌活性を
評価した。なお、１×10-6MのCu+2単独では抗菌
活性はなかつた。
結果を第１表に示す。
表中、菌の略号は次の細菌を示す：
Ｂ：Escherichia coli Ｂ
S1：Lactobacillus casei S1
101：Escherichia coli NIHJ JC−２
102：Proteus vulgaris IFO 3988
103：Proteus morganii IFO 3168
106：Salmonella typhimurium LT−２
110：Micrococcus flavus LFO 3242
111：Staphylococcus aureus FAO 209P
The present invention relates to an antibacterial agent, and more particularly to an antibacterial agent comprising an L-ascorbic acid derivative and optionally a salt of a divalent transition metal. L-ascorbic acid, or vitamin C, is
It is known that it exhibits antibacterial activity in the coexistence of divalent transition metal salts. While conducting research on L-ascorbic acid derivatives, the present inventors discovered that certain derivatives themselves have antibacterial activity, and that this activity is enhanced by the presence of salts of divalent transition metals. I was able to complete it. That is, the gist of the present invention is that the formula: [In the formula, X 1 , X 2 and X 3 are the same or different and represent hydrogen, an acyl group or polyfluoroacyl group having 2 to 21 carbon atoms, or an aromatic acyl group having 7 to 21 carbon atoms, and at least One is not hydrogen. ] An antibacterial agent consisting of an ascorbic acid derivative shown in the following. The acyl group in formula () generally has the formula: RCO- () [wherein R represents an alkyl group or polyfluoroalkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms. ] It is indicated by. Among the derivatives () of the present invention, acyl derivatives that do not contain fluorine are, for example, Pharmaceutical Journal, Vol. 86, 5.
No. 376-383 (1966), or produced according to the method described in the same document. Moreover, polyfluoroacyl derivatives can be easily produced according to the method described in the same document. For example, the 6-ester form is L-ascorbic acid and the formula: RCOOH [wherein R has the same meaning as above]. ]
It can be obtained by reacting the carboxylic acid represented by in concentrated sulfuric acid, for example, at room temperature. In addition, the 6-ester body is dimethylformamide,
It can also be obtained by reacting L-ascorbic acid with the acid chloride of the above acid in a solvent such as acetonitrile in the presence of an ion exchange resin. The 2,6-diester and 2,5,6-triester are obtained by combining the acid chloride or acid anhydride of the above acid with L-ascorbic acid with a base (for example,
pyridine, picoline, triethylamine, etc.) at room temperature or under ice-cooling. The 2-ester is obtained by reacting 5,6-isopropylidene-ascorbic acid with the above acid chloride in the presence of a base such as pyridine. Among L-ascorbic acid derivatives (), ester derivatives containing polyfluoroacyl groups are
It is described in a patent application (ascorbic acid derivative) filed on June 16, 1958. L-ascorbic acid derivatives () themselves have antibacterial activity, but when divalent transition metal salts coexist, the activity can be increased or the antibacterial spectrum can be expanded. Preferred examples of salts of divalent transition metals include sulfates, nitrates, and halides (e.g., chlorides and bromides) of copper, iron, manganese, zinc, etc. Among them, copper salts, e.g., CuSO 4 , Cu
(NO 3 ) 2 , CuCl 2 , CuBr 2 and the like are particularly preferred. When a salt of a divalent transition metal is present, the amount added can be appropriately determined depending on the type and concentration of the derivative (), the type of bacteria, etc. Next, a production example will be shown to illustrate a method for producing an ester containing a polyfluoroacyl group among the derivatives (). Production Example 4.7 g of ascorbic acid was added to a mixture of 40 ml of acetonitrile and 4.5 ml of pyridine, and then 24.2 g of perfluorooctanoic acid chloride was added dropwise while cooling with water. After the dropwise addition was completed, stirring was continued for 10 hours. The solvent was distilled off under reduced pressure, and the candy-like residue was dissolved in a mixed solvent of ether/chloroform (volume ratio 1:2).
Washed with dilute aqueous hydrochloric acid and then water, then dried over sodium sulfate. Add n-hexane,
The precipitated powder was reprecipitated with ether/n-hexane to obtain 13.5 g of 2,6-di(perfluorooctanoyl)ascorbic acid. melting point
162~5℃. Next, Examples will be shown to explain the antibacterial activity of the derivative () of the present invention. Example 1 The antibacterial activity of the compounds shown in Table 1 was tested in the following manner in combination with bacteria. Test bacteria were added to 0.22M Tris-HCl buffer (PH7.4) at a concentration of 1 to 4 × 10 7 cells/ml, and the compound solution was added to this at a concentration of 1 × 10 -3 M or 3 × 10 -4 M. Mixed so that. It was then incubated at 37° C. for 60 minutes in the presence or absence of 1×10 −6 M Cu 2+ . Then, take a portion of the solution and dilute it (NaCl
1g, MgSO 4 7H 2 O 0.25g, gelatin 0.03g,
The reaction was stopped by diluting it 100 times or more with 0.01M phosphate buffer (PH7.0) 1). The number of colonies before and after the reaction was measured by a conventional method, and the residual rate of bacteria was calculated to evaluate the antibacterial activity of the compound. Note that 1×10 -6 M Cu +2 alone had no antibacterial activity. The results are shown in Table 1. In the table, the bacterial abbreviations indicate the following bacteria: B: Escherichia coli B S1: Lactobacillus casei S1 101: Escherichia coli NIHJ JC-2 102: Proteus vulgaris IFO 3988 103: Proteus morganii IFO 3168 106: Salmonella typhimurium LT-2 110: Micrococcus flavus LFO 3242 111: Staphylococcus aureus FAO 209P
【表】【table】
【表】
実施例 ２
実施例１と同様の手順により、各種化合物の
Escherichia coli Ｂ(B)および
Lactobaccilluscasei S1（S1）に対するCu2+（１×
10-6M）存在下の抗菌性を調べた。
結果を第２表に示す。[Table] Example 2 Using the same procedure as in Example 1, various compounds were
Escherichia coli B(B) and
Cu 2+ (1×
The antibacterial properties were investigated in the presence of 10 -6 M). The results are shown in Table 2.
Claims (1)
て水素、炭素数２〜21のアシル基もしくはポリフ
ルオロアシル基または炭素数７〜21の芳香族アシ
ル基を表わし、そのうち少なくとも１つは水素で
はない。］ で示されるアスコルビン酸誘導体から成る抗菌
剤。 ２ 式： ［式中、X1、X2およびX3は、同一または異なつ
て水素、炭素数２〜21のアシル基もしくはポリフ
ルオロアシル基または炭素数７〜21の芳香族アシ
ル基を表わし、そのうち少なくとも１つは水素で
はない。］ で示されるアスコルビン酸誘導体および二価の遷
移金属の塩から成る抗菌剤。 ３ 二価の遷移金属が銅、鉄、マンガンまたは亜
鉛である特許請求の範囲第２項記載の抗菌剤。 ４ 二価の遷移金属が銅である特許請求の範囲第
３項記載の抗菌剤。 ５ 二価の遷移金属の塩がCuSO4、CuCl2、
CuBr2、またはCu（NO3）2である特許請求の範囲
第４項記載の抗菌剤。[Claims] 1 Formula: [In the formula, X 1 , X 2 and X 3 are the same or different and represent hydrogen, an acyl group or polyfluoroacyl group having 2 to 21 carbon atoms, or an aromatic acyl group having 7 to 21 carbon atoms, and at least one of them represents One is not hydrogen. ] An antibacterial agent consisting of an ascorbic acid derivative. 2 formula: [In the formula, X 1 , X 2 and X 3 are the same or different and represent hydrogen, an acyl group or polyfluoroacyl group having 2 to 21 carbon atoms, or an aromatic acyl group having 7 to 21 carbon atoms, and at least one of them represents One is not hydrogen. ] An antibacterial agent consisting of an ascorbic acid derivative and a salt of a divalent transition metal. 3. The antibacterial agent according to claim 2, wherein the divalent transition metal is copper, iron, manganese or zinc. 4. The antibacterial agent according to claim 3, wherein the divalent transition metal is copper. 5 Divalent transition metal salts include CuSO 4 , CuCl 2 ,
The antibacterial agent according to claim 4, which is CuBr 2 or Cu(NO 3 ) 2 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58112330A JPS604127A (en) | 1983-06-21 | 1983-06-21 | Antibacterial agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58112330A JPS604127A (en) | 1983-06-21 | 1983-06-21 | Antibacterial agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS604127A JPS604127A (en) | 1985-01-10 |
| JPH0437802B2 true JPH0437802B2 (en) | 1992-06-22 |
Family
ID=14583975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58112330A Granted JPS604127A (en) | 1983-06-21 | 1983-06-21 | Antibacterial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS604127A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2602774B1 (en) * | 1986-07-29 | 1990-10-19 | Atta | NOVEL POLYHYDROXYLATED AND PERFLUOROALKYLATED AMPHIPHILIC MOLECULES HAVING SURFACTANT PROPERTIES |
| JPH0773597B2 (en) * | 1988-05-16 | 1995-08-09 | 俶将 猪狩 | Deodorant composition |
| AU7333996A (en) * | 1996-10-18 | 1998-05-15 | Zaidan Hojin Shiniryozaidan | Mixed bactericidal fluid |
| DE10237227B4 (en) * | 2002-08-14 | 2012-04-26 | Bode Chemie Gmbh | Use of vitamin C and / or its derivatives as antiviral agents in alcoholic disinfectants |
| EP1527777A1 (en) * | 2003-10-31 | 2005-05-04 | MERCK PATENT GmbH | Composition with antioxidant properties comprising an ester of ascorbic acid and a benzoyl rest |
| DE102006037724A1 (en) * | 2006-08-11 | 2008-02-14 | Merck Patent Gmbh | Use of ascorbic acid derivatives for the functionalization of matrices |
| US20090170932A1 (en) * | 2007-12-31 | 2009-07-02 | Tyco Healthcare Group Lp | Disinfectant compositions, methods and systems |
-
1983
- 1983-06-21 JP JP58112330A patent/JPS604127A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS604127A (en) | 1985-01-10 |
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