JPH042593B2 - - Google Patents
Info
- Publication number
- JPH042593B2 JPH042593B2 JP10890283A JP10890283A JPH042593B2 JP H042593 B2 JPH042593 B2 JP H042593B2 JP 10890283 A JP10890283 A JP 10890283A JP 10890283 A JP10890283 A JP 10890283A JP H042593 B2 JPH042593 B2 JP H042593B2
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- acid
- added
- formula
- dissolved
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 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 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 229960005070 ascorbic acid Drugs 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000011668 ascorbic acid Substances 0.000 description 9
- 235000010323 ascorbic acid Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 150000000996 L-ascorbic acids Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000000069 L-ascorbic acid Nutrition 0.000 description 4
- 239000002211 L-ascorbic acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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
- 238000001816 cooling Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 6-(perfluorooctanoyl)ascorbic acid Chemical compound 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000001188 anti-phage Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- POXUQBFHDHCZAD-UHFFFAOYSA-N 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2h-furan-5-one Chemical compound O1C(C)(C)OCC1C1C(O)=C(O)C(=O)O1 POXUQBFHDHCZAD-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
【発明の詳細な説明】
本発明は、アスコルビン酸誘導体に関し、更に
詳しくは２−、５−および／または６−Ｏ−ポリ
フルオロアシルアスコルビン酸誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to ascorbic acid derivatives, and more particularly to 2-, 5- and/or 6-O-polyfluoroacylascorbic acid derivatives.
Ｌ−アスコルビン酸、すなわちビタミンＣは、
古くから知られた化合物であるが、近年、医薬品
としての用途が注目を集めている。しかし、Ｌ−
アスコルビン酸自体は、酸化分解を受けやすいの
で、誘導体、たとえばエステル体に変換すること
が提案されている（たとえば、薬学雑誌第86巻第
５号376〜383頁（1966年））。 L-ascorbic acid, or vitamin C, is
It is a compound that has been known for a long time, but in recent years, its use as a pharmaceutical has been attracting attention. However, L-
Since ascorbic acid itself is susceptible to oxidative decomposition, it has been proposed to convert it into a derivative, such as an ester (for example, Pharmaceutical Journal, Vol. 86, No. 5, pp. 376-383 (1966)).
本発明者らは、さらに新規なＬ−アスコルビン
酸誘導体を開発すべく研究を重ねた結果、ポリフ
ルオロアシルアスコルビン酸は、抗フアージ剤、
抗菌剤および酸化防止剤としての活性にすぐれ、
しかも安定性もよいことを見い出し、本発明を完
成するに至つた。 As a result of repeated research to develop further novel L-ascorbic acid derivatives, the present inventors found that polyfluoroacylascorbic acid is an antiphage agent.
Excellent activity as an antibacterial agent and antioxidant,
Moreover, they discovered that it has good stability and completed the present invention.
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
て水素または炭素数２〜21のポリフルオロアシル
基を表わし、そのうち少くとも１つはパリフルオ
ロアシル基である。〕
で示されるアスコルビン酸誘導体に存する。 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 or a polyfluoroacyl group having 2 to 21 carbon atoms, and at least one of them is a polyfluoroacyl group. ] It exists in ascorbic acid derivatives shown by.
ポリフルオロアシル基は、一般に式：
RfCO− （）
〔式中、Rfは炭素数１〜20のポリフルオロアル
キル基を表わす。〕
で示される。Rfとしては炭素数１〜20、好まし
くは１〜８のものが望ましい。 The polyfluoroacyl group generally has the formula: R f CO- ( ) [wherein R f represents a polyfluoroalkyl group having 1 to 20 carbon atoms. ] It is indicated by. It is desirable that R f has 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms.
本発明の誘導体（）は、前掲薬学雑誌に記載
された方法に準じて容易に製造することができ
る。 The derivative () of the present invention can be easily produced according to the method described in the aforementioned pharmaceutical journal.
たとえば、６−エステル体は、Ｌ−アスコルビ
ン酸と式：RfCOOH〔式中、Rf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。 For example, the 6-ester form is L-ascorbic acid and the formula: R f COOH [wherein R f has the same meaning as above. ] It is obtained by reacting the carboxylic acid represented by the following in concentrated sulfuric acid, for example, at room temperature.
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。 The 6-ester can also be obtained by reacting L-ascorbic acid with the acid chloride of the above acid in the presence of an ion exchange resin in a solvent such as dimethylformamide or acetonitrile.
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。 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,
such as pyridine, picoline or triethylamide)
It can be obtained by reacting in the presence of at room temperature to ice-cooling.
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。 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.
本発明の新規Ｌ−アスコルビン酸誘導体は、抗
フアージ剤、抗菌剤、酸化防止剤などとして有用
であり、その安定性は既知のＬ−アスコルビン酸
誘導体に比べて優れている。 The novel L-ascorbic acid derivative of the present invention is useful as an antiphage agent, antibacterial agent, antioxidant, etc., and its stability is superior to known L-ascorbic acid derivatives.
次に実施例を示し、本発明を具体的に説明す
る。 Next, examples will be shown to specifically explain the present invention.
実施例 １
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（体積比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℃。Example 1 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℃.
元素分析値、計算値：Ｃ、27.29％；Ｈ、0.62
％；Ｆ、58.86％、実測値：Ｃ、27.53％；Ｈ、
0.70％；Ｆ、58.12％。 Elemental analysis value, calculated value: C, 27.29%; H, 0.62
%; F, 58.86%, actual value: C, 27.53%; H,
0.70%; F, 58.12%.
赤外吸収スペクトル、3400、1785、1760、
1675、1240、1205および1145cm-1に特性吸収。 Infrared absorption spectrum, 3400, 1785, 1760,
Characteristic absorption at 1675, 1240, 1205 and 1145 cm -1 .
実施例 ２
パーフルオロオクタン酸クロライドの代りにＨ
（CF2CF2）3COClを用いる以外は同様の手順を繰
返して２，６−ジ（ドデカフルオロヘプタノイ
ル）アスコルビン酸を得た。融点122〜４℃。Example 2 H instead of perfluorooctanoyl chloride
The same procedure was repeated except that (CF 2 CF 2 ) 3 COCl was used to obtain 2,6-di(dodecafluoroheptanoyl)ascorbic acid. Melting point 122-4℃.
赤外吸収スペクトル、3400、1770、1750、
1670、1655、1195、1140cm-1に特性吸収。 Infrared absorption spectrum, 3400, 1770, 1750,
Characteristic absorption at 1670, 1655, 1195, 1140 cm -1 .
実施例 ３
５，６−Ｏ−イソプロピリデン−Ｌ−アスコル
ビン酸（例えばJ.Amer.Chem.Soc.、102、6304に
記載）11.6ｇをアセトニトリル40mlに溶解し、ピ
リジン４mlを加えたのち、水冷下にパーフルオロ
オクタン酸クロリド23.6ｇを滴下した。滴下終了
後15時間撹拌を続けた後、減圧下で溶媒を留去し
た。あめ状残留物を実施例１と同様に処理して、
白色ないし淡黄色固体を得た。この固体をエタノ
ールに溶解し、15％塩酸を加えて30分撹拌し、減
圧下に濃縮した。次に、エーテルを加えて溶解さ
せ、ｎ−ヘキサンを加えて生じた粉末を２〜３回
再結晶させることにより、２−（パーフルオロオ
クタノイル）アスコルビン酸8.4ｇを得た。融点
155〜８℃。Example 3 11.6 g of 5,6-O-isopropylidene-L-ascorbic acid (for example, described in J. Amer. Chem. Soc., 102, 6304) was dissolved in 40 ml of acetonitrile, 4 ml of pyridine was added, and the mixture was cooled with water. 23.6 g of perfluorooctanoic acid chloride was added dropwise to the bottom. After the dropwise addition was completed, stirring was continued for 15 hours, and then the solvent was distilled off under reduced pressure. The candy-like residue was treated in the same manner as in Example 1,
A white to pale yellow solid was obtained. This solid was dissolved in ethanol, 15% hydrochloric acid was added, stirred for 30 minutes, and concentrated under reduced pressure. Next, ether was added and dissolved, and n-hexane was added and the resulting powder was recrystallized two to three times to obtain 8.4 g of 2-(perfluorooctanoyl)ascorbic acid. melting point
155-8℃.
赤外吸収スペクトル、3550、3350、1780、
1680、1660、1200、1140cm-1。 Infrared absorption spectrum, 3550, 3350, 1780,
1680, 1660, 1200 , 1140cm -1 .
実施例 ４
アスコルビン酸10.1ｇをＮ，Ｎ−ジメチルホル
ムアミド50mlに溶解し、イオン交換樹脂
（Amberlite IRA−402OH-型）4.0ｇを加え、パ
ーフルオロオクタン酸クロリド24.8ｇを滴下し
た。50〜55℃で15時間反応させた後イオン交換樹
脂を別し、実施例１と同様に処理することによ
り６−（パーフルオロオクタノイル）アスコルビ
ン酸5.8ｇを得た。融点150〜３℃。Example 4 10.1 g of ascorbic acid was dissolved in 50 ml of N,N-dimethylformamide, 4.0 g of ion exchange resin (Amberlite IRA-402OH - type) was added, and 24.8 g of perfluorooctanoic acid chloride was added dropwise. After reacting at 50 to 55°C for 15 hours, the ion exchange resin was separated and treated in the same manner as in Example 1 to obtain 5.8 g of 6-(perfluorooctanoyl)ascorbic acid. Melting point: 150-3℃.
赤外吸収スペクトル、3350、3250、1775、
1760、1670、1210、1140cm-1。 Infrared absorption spectrum, 3350, 3250, 1775,
1760, 1670, 1210 , 1140cm -1 .
実施例 ５
アスコルビン酸2.9ｇをアセトニトリル35mlに
溶解し、ピリジン4.5mlを加え、水冷下にパーフ
ルオロオクタン酸クロリド25.0ｇを滴下した。室
温で10時間撹拌した後、45〜50℃に加熱し、２〜
３時間撹拌を続けた。Example 5 2.9 g of ascorbic acid was dissolved in 35 ml of acetonitrile, 4.5 ml of pyridine was added, and 25.0 g of perfluorooctanoic acid chloride was added dropwise while cooling with water. After stirring at room temperature for 10 hours, heat to 45-50℃ and
Stirring was continued for 3 hours.
実施例１と同様に処理することにより、２，
５，６−トリ（パーフルオロオクタノイル）アス
コルビン酸5.4ｇを得た。 By processing in the same manner as in Example 1, 2,
5.4 g of 5,6-tri(perfluorooctanoyl)ascorbic acid was obtained.
赤外吸収スペクトル、1780、1755、1675、
1200、1140cm-1。 Infrared absorption spectrum, 1780, 1755, 1675,
1200, 1140cm -1 .
実施例 ６
実施例４で得た６−（パーフルオロオクタノイ
ル）アスコルビン酸6.3ｇをアセトニトリルに溶
解し、ピリジン1.2mlを加え、Ｈ
（CF2CF2）3COOl4.7ｇを滴下し、15時間反応させ
た。以下同様の処理を行なうことにより６位に
C7F15CO2、２位にＨ（CF2CF2）3CO2基が導入され
た誘導体3.5ｇを得た。Example 6 6.3 g of 6-(perfluorooctanoyl)ascorbic acid obtained in Example 4 was dissolved in acetonitrile, 1.2 ml of pyridine was added, and H
4.7 g of (CF 2 CF 2 ) 3 COOl was added dropwise and reacted for 15 hours. By performing the same process below, we will be ranked 6th.
3.5 g of a C 7 F 15 CO 2 derivative having an H(CF 2 CF 2 ) 3 CO 2 group introduced at the 2-position was obtained.
赤外吸収スペクトル、3400、1780、1760、
1670、1655、1200、1140cm-1。 Infrared absorption spectrum, 3400, 1780, 1760,
1670, 1655, 1200 , 1140cm -1 .
Claims (1)
て水素または炭素数２〜21のポリフルオロアシル
基を表わし、そのうち少くとも１つはポリフルオ
ロアシル基である。〕 で示されるアスコルビン酸誘導体。 ２ ２−または６−エステル体である特許請求の
範囲第１項記載のアスコルビン酸誘導体。 ３ ２，６−ジエステル体である特許請求の範囲
第１項記載のアスコルビン酸誘導体。 ４ ２，５，６−トリエステル体である特許請求
の範囲第１項記載のアスコルビン酸誘導体。[Claims] 1 Formula: [Formula] [In the formula, X 1 , X 2 and X 3 are the same or different and represent hydrogen or a polyfluoroacyl group having 2 to 21 carbon atoms, and at least one of them represents is a polyfluoroacyl group. ] An ascorbic acid derivative represented by. 2. The ascorbic acid derivative according to claim 1, which is a 2- or 6-ester. 3. The ascorbic acid derivative according to claim 1, which is a 2,6-diester. 4. The ascorbic acid derivative according to claim 1, which is a 2,5,6-triester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10890283A JPS601175A (en) | 1983-06-16 | 1983-06-16 | Ascorbic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10890283A JPS601175A (en) | 1983-06-16 | 1983-06-16 | Ascorbic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS601175A JPS601175A (en) | 1985-01-07 |
| JPH042593B2 true JPH042593B2 (en) | 1992-01-20 |
Family
ID=14496521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10890283A Granted JPS601175A (en) | 1983-06-16 | 1983-06-16 | Ascorbic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS601175A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA852614B (en) * | 1985-05-17 | 1986-10-09 | Takeda Chemical Industries, Ltd. | Ascorbic acid ethers and their production |
| FR2602774B1 (en) * | 1986-07-29 | 1990-10-19 | Atta | NOVEL POLYHYDROXYLATED AND PERFLUOROALKYLATED AMPHIPHILIC MOLECULES HAVING SURFACTANT PROPERTIES |
| KR101119027B1 (en) | 2009-05-07 | 2012-03-14 | (주)코스몰 | Method for preparating ascorbic acid derivatives |
| TW201629077A (en) * | 2014-10-21 | 2016-08-16 | Suntory Holdings Ltd | Ascorbic acid derivative and glycoside production method using same |
-
1983
- 1983-06-16 JP JP10890283A patent/JPS601175A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS601175A (en) | 1985-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0314315B2 (en) | ||
| JPH05208978A (en) | Method for aroylating 5-position of 1,2-dihydro-3h-pyrrolo(1,2-alpha)pyrrole-1-carboxyic ester | |
| JPS59122470A (en) | Preparation of quinoline-3-carboxylic acid derivative | |
| JPH042593B2 (en) | ||
| US2767174A (en) | N-benzylidene and n-quinolylmethylene-substituted 2-aminobenzisothiazolones and processes for their preparation | |
| JPS61183286A (en) | Manufacture of 2-alkoxy-n-(1-azabicyclo (2,2,2)octan-3-yl)aminobenzamide | |
| US3787423A (en) | Beta-picolyloxy ester of(3-trifluoromethylphenoxy)(4-chlorophenyl)acetic acid and derivatives | |
| JPH0437802B2 (en) | ||
| JPH02131471A (en) | Preparation of pylidadinones | |
| JPS6049634B2 (en) | Method for producing quinoxaline-1,4-dioxide derivative | |
| SU764609A3 (en) | Method of preparing benzimidazolecarbamate derivatives | |
| JPS6261966A (en) | Propionamidine derivatives and manufacture | |
| JPH0533230B2 (en) | ||
| JPS62142159A (en) | 2-(4-((3-chloro-5-iodo-2-pyridinyl)oxy)phrnoxy)propionic acid, derivatives and manufacture | |
| JPH0128013B2 (en) | ||
| JPS5928547B2 (en) | Process for producing 3-phenyl-viridazone-(6) | |
| JPS6113474B2 (en) | ||
| JPH0557982B2 (en) | ||
| JP2937387B2 (en) | Process for producing 5-substituted 2-amino-3-cyanopyrazines | |
| JPH0523272B2 (en) | ||
| JPS5934190B2 (en) | Method for producing 3,5↓-dimethyl↓-4↓-lower alkoxycarbonyl phthalic anhydride | |
| JPS6130571A (en) | Preparation of 3-phenyl-4-cyanopyrrole | |
| JPS604165B2 (en) | Novel method for producing esters of long-chain unsaturated alcohols | |
| JPH06184112A (en) | 1-amidopyridinium salt derivative | |
| JPS625915B2 (en) |