JP3163364B2 - N-acyl-2-pyrrolidone-5-carboxylate - Google Patents
N-acyl-2-pyrrolidone-5-carboxylateInfo
- Publication number
- JP3163364B2 JP3163364B2 JP29491992A JP29491992A JP3163364B2 JP 3163364 B2 JP3163364 B2 JP 3163364B2 JP 29491992 A JP29491992 A JP 29491992A JP 29491992 A JP29491992 A JP 29491992A JP 3163364 B2 JP3163364 B2 JP 3163364B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidone
- carboxylic acid
- acyl
- alcohol
- ester
- 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
Landscapes
- Pyrrole Compounds (AREA)
- Cosmetics (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は例えば化粧料、外用医薬
品等の油性原料として有用なＮ−アシル−２−ピロリド
ン−５−カルボン酸エステルに関する。The present invention relates to an N-acyl-2-pyrrolidone-5-carboxylic acid ester which is useful as an oily raw material for, for example, cosmetics and external medicines.
【０００２】[0002]
【従来の技術】化粧料及び外用医薬品の油性原料として
は、各種のエステル類が広く使用されているが、中でも
２−ピロリドン−５−カルボン酸誘導体は安全性が高い
などの利点を有している。2. Description of the Related Art Various esters are widely used as oily raw materials for cosmetics and external medicines. Among them, 2-pyrrolidone-5-carboxylic acid derivatives have advantages such as high safety. I have.
【０００３】２−ピロリドン−５−カルボン酸誘導体と
しては２−ピロリドンカルボン酸イソステアリン酸ポリ
オキシエチレングリセリル、２−ピロリドン−５−カル
ボン酸オレイン酸グリセリル、２−ピロリドン−５−カ
ルボン酸ラウリルエステル等が公知である。Examples of the 2-pyrrolidone-5-carboxylic acid derivative include 2-pyrrolidonecarboxylic acid polyoxyethylene glyceryl isostearate, 2-pyrrolidone-5-carboxylic acid glyceryl oleate, and 2-pyrrolidone-5-carboxylic acid lauryl ester. It is known.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、化粧
料及び外用医薬品等への安全性の高い油性原料となりう
る、新規な２−ピロリドン−５−カルボン酸エステル誘
導体を提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel 2-pyrrolidone-5-carboxylic acid ester derivative which can be used as a highly safe oily raw material for cosmetics and external medicines. .
【０００５】[0005]
【問題点を解決する為の手段】本発明者らは、下記一般
式（Ｉ）で表わされるＮ−アシル−２−ピロリドン−５
−カルボン酸エステルが上記目的にかなうことを見いだ
し、このような知見に基づき本発明を完成させた。Means for Solving the Problems The present inventors have developed N-acyl-2-pyrrolidone-5 represented by the following general formula (I).
-It has been found that a carboxylic acid ester meets the above object, and the present invention has been completed based on such findings.
【０００６】[0006]
【化２】 （式中、ＲＣＯは炭素数８〜２２の長鎖アシル基であ
り、Ｘは炭素数８〜３８の高級アルキルもしくはアルケ
ニルアルコール、高級アルコール部分の炭素数が８〜３
８であるポリオキシアルキレン高級アルコールエーテル
またはステロールのエステル生成残基である。）Embedded image (Wherein, RCO is a long-chain acyl group having 8 to 22 carbon atoms, X is a higher alkyl or alkenyl alcohol having 8 to 38 carbon atoms, and the higher alcohol moiety has 8 to 3 carbon atoms.)
8 is an ester-forming residue of a polyoxyalkylene higher alcohol ether or sterol. )
【０００７】即ち、本発明は上記一般式（Ｉ）で表され
るＮ−アシル−２−ピロリドン−５−カルボン酸エステ
ルに関するものである。That is, the present invention relates to an N-acyl-2-pyrrolidone-5-carboxylic acid ester represented by the above general formula (I).
【０００８】以下、本発明について詳細に説明する。上
記の一般式（Ｉ）において、長鎖アシル基としては炭素
数８〜２２の飽和または不飽和脂肪酸より誘導されるア
シル基で、例えばラウリン酸、パルミチン酸、ステアリ
ン酸、オレイン酸等の単一組成の脂肪酸によるアシル基
が挙げられ、この他にヤシ油脂肪酸、牛脂脂肪酸、硬化
牛脂脂肪酸等の天然より得られる混合脂肪酸あるいは合
成により得られる脂肪酸（分岐脂肪酸を含む）のアシル
基であってもよい。Hereinafter, the present invention will be described in detail. In the above general formula (I), the long-chain acyl group is an acyl group derived from a saturated or unsaturated fatty acid having 8 to 22 carbon atoms, such as lauric acid, palmitic acid, stearic acid or oleic acid. An acyl group of a fatty acid having a composition may be mentioned. In addition, an acyl group of a mixed fatty acid obtained from nature such as coconut oil fatty acid, tallow fatty acid, and hardened tallow fatty acid or a fatty acid (including branched fatty acid) obtained by synthesis may be used. Good.
【０００９】エステル基としては、例えば２−オクチル
ドデシルアルコール、イソステアリルアルコール等の分
岐アルコール、オレイルアルコール等の不飽和アルコー
ルまたはセチルアルコール、ベヘニルアルコール等の炭
素数８〜３８の天然または合成脂肪族アルコール；前記
の脂肪族アルコールにポリオキシエチレンなどのポリオ
キシアルキレンを付加したポリオキシアルキレン高級ア
ルコールエーテル；コレステロール、ラノステロール、
フィトステロール及びこれらの水添物（動物由来のもの
でも植物由来のものでも差し支えない。）等のステロー
ルである。Examples of the ester group include branched alcohols such as 2-octyldodecyl alcohol and isostearyl alcohol; unsaturated alcohols such as oleyl alcohol; and natural or synthetic aliphatic alcohols having 8 to 38 carbon atoms such as cetyl alcohol and behenyl alcohol; A polyoxyalkylene higher alcohol ether obtained by adding a polyoxyalkylene such as polyoxyethylene to the aliphatic alcohol; cholesterol, lanosterol,
Sterols such as phytosterols and their hydrogenated products (animal-derived or plant-derived).
【００１０】本発明のＮ−アシル−２−ピロリドン−５
−カルボン酸エステルの製造に当たっては公知の方法を
用いればよく、例えば２−ピロリドン−５−カルボン酸
と脂肪酸クロライドとの反応により、Ｎ−アシル−２−
ピロリドン−５−カルボン酸を合成した後、アルコール
と脱水縮合することで目的物を得ることができる。また
Ｎ−アシルグルタミン酸とアルコールとを反応しエステ
ル化と環化を同時に行うことによっても得ることができ
る。さらに、グリタミン酸とアルコールとを反応させ、
２−ピロリドン−５−カルボン酸エステルを合成した
後、アシル化することによっても得ることができる。反
応混合物から目的のエステルを単離するにはカラムクロ
マトグラフィー、蒸留、濃縮、結晶化、抽出等の常法を
用いればよい。The N-acyl-2-pyrrolidone-5 of the present invention
A known method may be used for the production of the carboxylic acid ester, for example, by reacting 2-pyrrolidone-5-carboxylic acid with a fatty acid chloride to form N-acyl-2-
After synthesizing pyrrolidone-5-carboxylic acid, the desired product can be obtained by dehydration condensation with an alcohol. It can also be obtained by reacting N-acylglutamic acid with an alcohol to simultaneously perform esterification and cyclization. In addition, the reaction between the glutamic acid and the alcohol,
It can also be obtained by synthesizing 2-pyrrolidone-5-carboxylic acid ester followed by acylation. The desired ester can be isolated from the reaction mixture by a conventional method such as column chromatography, distillation, concentration, crystallization, or extraction.
【００１１】[0011]
【発明の効果】本発明のＮ−アシル−２−ピロリドン−
５−カルボン酸エステルは、安全性の高い油性原料とし
て化粧料及び外用医薬品に利用することができる。According to the present invention, the N-acyl-2-pyrrolidone-
5-Carboxylic acid esters can be used in cosmetics and external medicines as highly safe oily raw materials.
【００１２】[0012]
【実施例】以下、実施例により本発明を更に詳細に説明
する。The present invention will be described in more detail with reference to the following examples.
【００１３】製造例１ Ｎ−ココイル−２−ピロリドン−５−カルボン酸ベヘニ
ルエステルの合成 Ｎ−ココイル−２−ピロリドンカルボン酸１５５ｇ
（０．４８ｍｏｌ）及びベヘニルアルコール１５７ｇ
（０．４８ｍｏｌ）をトルエン３００ｍｌに溶解し、触
媒として硫酸０．５ｍｌを加え１３０〜１４０℃に加熱
し、約４時間エステル化反応を行った。中和後、トルエ
ンを留去し透明液状のＮ−ココイル−２−ピロリドンカ
ルボン酸ベヘニルエステルを得た。Production Example 1 Synthesis of N-cocoyl-2-pyrrolidone-5-carboxylic acid behenyl ester 155 g of N-cocoyl-2-pyrrolidonecarboxylic acid
(0.48 mol) and 157 g of behenyl alcohol
(0.48 mol) was dissolved in 300 ml of toluene, 0.5 ml of sulfuric acid was added as a catalyst, and the mixture was heated to 130 to 140 ° C. to carry out an esterification reaction for about 4 hours. After neutralization, toluene was distilled off to obtain a transparent liquid N-cocoyl-2-pyrrolidonecarboxylic acid behenyl ester.
【００１４】ＩＲ（ＫＢｒ）；１７５２、１６９５、１
４６９、１３１８、１３８４、１２１９（ｃｍ-1） ＭＳ（ＦＤ）；６１９（Ｍ+）IR (KBr); 1752, 1695, 1
469, 1318, 1384, 1219 (cm -1 ) MS (FD); 619 (M + )
【００１５】製造例２ Ｎ−ラウロイル−２−ピロリドン−５−カルボン酸２−
オクチルドデシルエステルの合成 Ｎ−ラウロイル−２−ピロリドンカルボン酸１５５ｇ
（０．４８ｍｏｌ）及び２−オクチルドデカソール１４
５ｇ（０．４８ｍｏｌ）を用いて製造例１と同様にして
白色固体を得た。Production Example 2 N-Lauroyl-2-pyrrolidone-5-carboxylic acid 2-
Synthesis of octyldodecyl ester 155 g of N-lauroyl-2-pyrrolidonecarboxylic acid
(0.48 mol) and 2-octyldodecasol 14
A white solid was obtained in the same manner as in Production Example 1 using 5 g (0.48 mol).
【００１６】製造例３ Ｎ−ラウロイル−２−ピロリドン−５−カルボン酸コレ
ステリルエステルの合成 製造例１のエステル化反応で２−オクチルドデカノール
の代わりにコレステロール１９０ｇ（０．４８ｍｏｌ）
を用いて同様にして淡黄色固体を得た。Production Example 3 Synthesis of cholesteryl N-lauroyl-2-pyrrolidone-5-carboxylate In the esterification reaction of Production Example 1, 190 g (0.48 mol) of cholesterol instead of 2-octyldodecanol.
And a pale yellow solid was obtained in the same manner.
【００１７】ＩＲ（ＫＢｒ）；１７４４、１６９７、１
４６８、１３８２、１２０７（ｃｍ-1） ＭＳ（ＦＤ）；６８０（ＭＨ+）IR (KBr); 1744, 1697, 1
468, 1382, 1207 (cm -1 ) MS (FD); 680 (MH + )
【００１８】以下、使用例を示すが、成分の配合比は重
量％である。In the following, examples of use are shown, and the mixing ratio of the components is% by weight.
【００１９】使用例１（Ｏ／Ｗ型クリーム） 下記表１に示す成分１を８０℃、成分２を７０℃まで加
温して、成分１をかき混ぜながら成分２を徐々に添加し
乳化した。水冷攪拌しながら５０℃で成分３を添加し、
３５℃まで冷却してＯ／Ｗ型クリームを得た。Use Example 1 (O / W type cream) Component 1 shown in Table 1 below was heated to 80 ° C. and component 2 was heated to 70 ° C., and while stirring the component 1, the component 2 was gradually added and emulsified. Add component 3 at 50 ° C. while stirring with water cooling,
After cooling to 35 ° C., an O / W type cream was obtained.
【００２０】[0020]
【表１】 [Table 1]
【００２１】使用例２（ミルキーローション） 下記表２に示す成分１を８５℃まで加温した。成分２を
攪拌しながら成分１を徐々に添加し、冷却攪拌して３０
℃でミルキーローションを得た。Use Example 2 (Milk lotion) Component 1 shown in Table 2 below was heated to 85 ° C. While stirring the component 2, the component 1 is gradually added.
Milky lotion was obtained at ° C.
【００２２】[0022]
【表２】 [Table 2]
【００２３】本発明のエステルを含有するミルキーロー
ションは、乳化滴の粒子が細かく、また経時安定性も優
れたエマルションであった。また皮膚親和性、付着性が
向上し、使用感のよいエマルションが得られた。The milky lotion containing the ester of the present invention was an emulsion having fine emulsion droplets and excellent stability over time. In addition, the affinity for the skin and the adhesion were improved, and an emulsion having a good feeling in use was obtained.
【００２４】使用例３（親水軟膏） 下記表３に示す成分１を８０℃で加熱溶解し、そこに７
５℃で加熱溶解した成分２を加え、固まるまで攪拌し、
親水軟膏とした。Use Example 3 (Hydrophilic ointment) Component 1 shown in Table 3 below was heated and dissolved at 80 ° C.
Add the component 2 heated and melted at 5 ° C and stir until it hardens,
A hydrophilic ointment was used.
【００２５】[0025]
【表３】 [Table 3]
【００２６】得られた親水軟膏は、皮膚との親和性が良
く感触の良いものであった。The obtained hydrophilic ointment had a good affinity for the skin and a good feel.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C07D 207/28 A61K 7/00 - 7/50 ＣＡ（ＳＴＮ) ＣＡＯＬＤ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) C07D 207/28 A61K 7/ 00-7/50 CA (STN) CAOLD (STN) REGISTRY (STN)
Claims (1)
ー２−ピロリドンー５−カルボン酸エステル。 【化１】 （式中、ＲＣＯは炭素数８〜２２の長鎖アシル基であ
り、Ｘは炭素数８〜３８の高級アルキルもしくはアルケ
ニルアルコール、高級アルコール部分の炭素数が８〜３
８であるポリオキシアルキレン高級アルコールエーテル
またはステロールのエステル生成残基である。）1. An N-acyl-2-pyrrolidone-5-carboxylic acid ester represented by the following general formula (I). Embedded image (Wherein, RCO is a long-chain acyl group having 8 to 22 carbon atoms, X is a higher alkyl or alkenyl alcohol having 8 to 38 carbon atoms, and the higher alcohol moiety has 8 to 3 carbon atoms.)
8 is an ester-forming residue of a polyoxyalkylene higher alcohol ether or sterol. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29491992A JP3163364B2 (en) | 1992-11-04 | 1992-11-04 | N-acyl-2-pyrrolidone-5-carboxylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29491992A JP3163364B2 (en) | 1992-11-04 | 1992-11-04 | N-acyl-2-pyrrolidone-5-carboxylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06145141A JPH06145141A (en) | 1994-05-24 |
| JP3163364B2 true JP3163364B2 (en) | 2001-05-08 |
Family
ID=17813957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29491992A Expired - Lifetime JP3163364B2 (en) | 1992-11-04 | 1992-11-04 | N-acyl-2-pyrrolidone-5-carboxylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3163364B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2609190A (en) * | 2021-06-18 | 2023-02-01 | Geoffrey Stott Leon | A cover for a cordless power tool |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5703104A (en) * | 1995-07-07 | 1997-12-30 | Durham Pharmaceuticals Llc | Cyclic amides and derivatives thereof |
| IT1305188B1 (en) * | 1998-11-18 | 2001-04-10 | Zschimmer & Schwarz Italiana S | N-ACYLATED DERIVATIVES OF PYROLIDONCARBOSSIC ACID AS SURFACTANTS |
| EP1980237B1 (en) * | 2006-01-06 | 2013-10-02 | Ajinomoto Co., Inc. | Gelling agent |
| JP6273695B2 (en) * | 2013-06-14 | 2018-02-07 | 味の素株式会社 | Phytosterol ester and pigment-containing composition |
-
1992
- 1992-11-04 JP JP29491992A patent/JP3163364B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2609190A (en) * | 2021-06-18 | 2023-02-01 | Geoffrey Stott Leon | A cover for a cordless power tool |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06145141A (en) | 1994-05-24 |
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