JPH01272563A - N-acylaminoalkyl glyceryl ether compound - Google Patents
N-acylaminoalkyl glyceryl ether compoundInfo
- Publication number
- JPH01272563A JPH01272563A JP10118188A JP10118188A JPH01272563A JP H01272563 A JPH01272563 A JP H01272563A JP 10118188 A JP10118188 A JP 10118188A JP 10118188 A JP10118188 A JP 10118188A JP H01272563 A JPH01272563 A JP H01272563A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydrocarbon group
- compound
- acylaminoalkyl
- present
- 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.)
- Pending
Links
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 19
- -1 Acylaminoalkyl glyceryl ether compound Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 9
- 239000002736 nonionic surfactant Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000502 dialysis Methods 0.000 abstract description 5
- 239000004094 surface-active agent Substances 0.000 abstract description 5
- 108010052285 Membrane Proteins Proteins 0.000 abstract description 4
- 102000018697 Membrane Proteins Human genes 0.000 abstract description 4
- 239000002270 dispersing agent Substances 0.000 abstract description 3
- 239000003995 emulsifying agent Substances 0.000 abstract 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 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 230000001804 emulsifying effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical group CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 abstract 1
- 230000007928 solubilization Effects 0.000 abstract 1
- 238000005063 solubilization Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000012634 fragment Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 238000006227 trimethylsilylation reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 239000000693 micelle Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000000436 anus Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000002298 terpene group Chemical group 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、新規なＮ−アシルアミノアルキルグリセリル
エーテル化合物に関する。この新規化合物は、洗浄剤、
乳化・分散剤、可溶化剤等に利用できる非イオン性界面
活性剤、特に膜タンパク質可溶化剤などの生化学用界面
活性剤として有用である。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to novel N-acylaminoalkyl glyceryl ether compounds. This new compound can be used as a cleaning agent,
It is a nonionic surfactant that can be used as an emulsifier/dispersant, a solubilizer, etc., and is particularly useful as a biochemical surfactant such as a membrane protein solubilizer.
従来の技術
非イオン界面活性剤は硬水や塩類の影響が少なく安定な
界面活性能を有することから、洗浄剤や乳化・分散剤と
して広く用いられているが、この中で、例えばオクチル
グルコシド〔「ビオヒシカ・工−ビオフィジ力・アクタ
（Ｂｉｏｃｈｉｍ、 Ｂｉｏｐｂｙｓ。Conventional technology Nonionic surfactants are widely used as detergents and emulsifying/dispersing agents because they have stable surfactant ability that is less affected by hard water and salts. Biochim, Biopbys.
Ａｃｔり、第３８２巻、第２７６〜２８５ページ（１９
７５））や、一般式
％式％（）
（ただし、Ｒはヘプチル、オクチル、ノニルである）
で表わされるＭＥＧＡ （ｒバイオケミカル・ジャーナ
ル（Ｂｉｏｅｈｅ＋ｍ、Ｊ、）Ｊ、第２０７巻、第３６
３〜３６６ページ（１９８２））は、膜タンパク質可溶
化剤として知られている。Act, Volume 382, Pages 276-285 (19
75)) or the general formula % (where R is heptyl, octyl, or nonyl).
3-366 (1982)) is known as a membrane protein solubilizer.
しかしながら、これらは合成経路が複雑である上、結晶
性が低く精製が困難であると共に、吸湿性が大きいため
保存に特別な配慮が必要であり、大量生産あるいは大量
使用に当って不利になるのを免れない。However, these have complex synthetic routes, are difficult to purify due to low crystallinity, and are highly hygroscopic, requiring special consideration for storage, which may be disadvantageous in mass production or use. I can't escape it.
また、ＭＥＧＡと同じＮ−アシルアミノアルキル構造を
有するものとして、−最大
％式％（［１）
（式中のＲは長鎖アルキル基である）
で表わされる非イオン界面活性剤も知られている〔西独
特許公開第２，６４７，９７９号明細書（＋９７５））
。Additionally, a nonionic surfactant represented by the formula % ([1) (R in the formula is a long-chain alkyl group) is also known as having the same N-acylaminoalkyl structure as MEGA. [West German Patent Publication No. 2,647,979 (+975)]
.
しかしながら、これらにおいては、エチレンオキシド又
はグリシドールの付加モル数は幅広い分布を持っている
ため、透析によって界面活性剤を除去できないという根
本的欠陥を有する。また、式（ＩＩ［）においてｎを小
さくしたものは水に溶解しないため、可溶化剤として使
用することができない。However, these have a fundamental defect that the surfactant cannot be removed by dialysis because the number of moles of ethylene oxide or glycidol added has a wide distribution. Further, formula (II[) in which n is small does not dissolve in water and cannot be used as a solubilizer.
他方、トリトンＸ−１００のような非イオン界面活性剤
は臨界ミセル濃度が小さく、やはり透析による界面活性
剤の脱離は困難であるという欠点がある。On the other hand, nonionic surfactants such as Triton X-100 have a low critical micelle concentration, and also have the disadvantage that it is difficult to remove the surfactant by dialysis.
発明が解決しようとする課題
本発明は、室温で水に溶解し、かつ透析による脱離が可
能で、非イオン界面活性剤として有用な新規化合物を提
供することを目的としてなされたものである。Problems to be Solved by the Invention The purpose of the present invention is to provide a novel compound that is soluble in water at room temperature, can be desorbed by dialysis, and is useful as a nonionic surfactant.
課題を解決するための手段
本発明者らは、非イオン界面活性剤として有用な新規化
合物を開発するために種々研究を重ねた結果、特定のグ
リセリルエーテル系のものがその目的に適合することを
見出し、この知見に基づいて本発明をなすに至った。Means for Solving the Problems The present inventors have conducted various studies to develop new compounds useful as nonionic surfactants, and have found that a specific glyceryl ether type compound is suitable for the purpose. Based on this finding, the present invention has been made.
すなわち、本発明は、−最大
（式中、Ｒ１は炭素数５〜３０の炭化水素基、Ｒ１はＨ
１炭素数１〜４の炭化水素基又はヒドロキシ基を含む炭
化水素基、Ｘは炭素数１〜４の炭化水素基又はヒドロキ
シル基を含む炭化水素基である）で表わされるＮ−アシ
ルアミノアルキルグリセリルエーテル化合物を提供する
ものである。That is, the present invention provides - maximum (wherein R1 is a hydrocarbon group having 5 to 30 carbon atoms, R1 is H
N-acylaminoalkylglyceryl represented by a hydrocarbon group having 1 to 4 carbon atoms or a hydrocarbon group containing a hydroxyl group, where X is a hydrocarbon group having 1 to 4 carbon atoms or a hydrocarbon group containing a hydroxyl group It provides an ether compound.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の化合物におけるＲ１は炭素数５〜３０の炭化水
素基であり、このようなものとしては、例えばヘキシル
、ヘプチル、オクチル、ノニル、ウンデシル、ドデシル
、ラウリル、ミリスチル、パルミチル、セチル、エイコ
シル、シクロヘキシル、デカリルなどの飽和炭化水素基
、ヘキセニル、デセニル、オレイル、リノリル、リルニ
ル、リルイルなどの不飽和炭化水素基、ステロイド系の
脂環式化合物、アビエチン酸などのテルペン系化合物な
どを挙げることができる。これらの中で特にヘキシル、
ヘプチル、オクチル、ノニル、デシルなどのアルキル基
、オレイルなどのアルケニル基、アビエチルなどのテル
ペン系のものが好適である。R1 in the compound of the present invention is a hydrocarbon group having 5 to 30 carbon atoms, such as hexyl, heptyl, octyl, nonyl, undecyl, dodecyl, lauryl, myristyl, palmityl, cetyl, eicosyl, cyclohexyl. , saturated hydrocarbon groups such as decalyl, unsaturated hydrocarbon groups such as hexenyl, decenyl, oleyl, linolyl, lilunyl, and lylyl, steroidal alicyclic compounds, and terpene compounds such as abietic acid. Among these, especially hexyl,
Preferred are alkyl groups such as heptyl, octyl, nonyl, and decyl, alkenyl groups such as oleyl, and terpene groups such as abiethyl.
本発明の化合物におけるＲ７はＨ１炭素数１〜４の炭化
水素基又はヒドロキシアルキル基でアリ、このようなも
のとしては、例えば、メチル、エチル、プロピル、ブチ
ル、ヒドロキシメチル、２−ヒドロキシエチル、２−ヒ
ドロキシプロピノ呟２．３−ジヒドロキシブチルなどを
挙げることができる。これらの中で特にＨ１メチル、２
−ヒドロキシエチルが好適である。R7 in the compound of the present invention is a hydrocarbon group or a hydroxyalkyl group having 1 to 4 H1 carbon atoms, such as methyl, ethyl, propyl, butyl, hydroxymethyl, 2-hydroxyethyl, -Hydroxypropylene, 2,3-dihydroxybutyl, and the like. Among these, especially H1 methyl, 2
-Hydroxyethyl is preferred.
本発明の化合物におけるＸとしては炭素数１〜４の炭化
水素基又はヒドロキシル基を含む炭化水素基であり、こ
のようなものとしてはジメチレン、トリメチレン、２−
ヒドロキシトリメチレン、テトラメチレン、２−ヒドロ
キシメチルジメチレン、２−メチルジメチレンなどを挙
げることができる。X in the compound of the present invention is a hydrocarbon group having 1 to 4 carbon atoms or a hydrocarbon group containing a hydroxyl group, such as dimethylene, trimethylene, 2-
Examples include hydroxytrimethylene, tetramethylene, 2-hydroxymethyldimethylene, and 2-methyldimethylene.
これらの中で特にジメチレン、２−ヒドロキシトリメチ
レンが好適である。Among these, dimethylene and 2-hydroxytrimethylene are particularly preferred.
本発明の一般式（１）で表わされる化合物は、例えば−
最大
％式％（）
（式中、Ｒよ、Ｘは上記と同じ意味を有する）で表わさ
れるアミンと、−最大
％式％（）
（式中、Ｒ１は上記と同じ意味を有する）で表わされる
酸クロリドを反応させた後、ツルケタール環を加水分解
することにより開環して容易に製造することができる。The compound represented by the general formula (1) of the present invention is, for example, -
an amine of the formula %(), in which R and X have the same meanings as above; After reacting the acid chloride, the turketal ring is hydrolyzed to open the ring.
発明の効果
本発明の新規化合物であるＮ−アシルアミノアルキルグ
リセリルエーテルは新規な非イオン界面活性剤として有
用であり、室温で水に溶解し、透析による界面活性剤の
脱離・除去が容易である上に、膜タンパク質可溶化剤と
しての基本的な性質、すなわち、
（ｉ） 油溶性物質の可溶化力がある、（ｉｉ）
タンパク質を変性させない、（ｉｉ） 臨界ミセル濃
度が高い、
（ｉｖ） 紫外部の光学的透過率がよい、（ｖ）
高純度で安定である
という優れた性能を有している。Effects of the Invention N-acylaminoalkylglyceryl ether, a novel compound of the present invention, is useful as a new nonionic surfactant, dissolves in water at room temperature, and can be easily desorbed and removed by dialysis. In addition, it has the basic properties as a membrane protein solubilizer, namely (i) it has the ability to solubilize oil-soluble substances, and (ii) it has the ability to solubilize oil-soluble substances.
Does not denature proteins, (ii) has a high critical micelle concentration, (iv) has good optical transmittance in ultraviolet light, (v)
It has excellent properties of high purity and stability.
実施例
次に実施例によって本発明をさらに詳細に説明するが、
本発明は、これらの例によってなんら限定されるもので
はない。EXAMPLES Next, the present invention will be explained in more detail by examples.
The present invention is not limited in any way by these examples.
実施例１
かくはん機、冷却器、温度計、滴下漏斗を取り付けた５
００ｍｆｆ１４つロ反応フラスコ中に４−（２’−アミ
ノエトキシメチル）−２，２−ジメチル−１，３−ジオ
キソラン１３．８９（０，０７９ｍｏｌ）とジエチルエ
ーテル３００＋ｌ１ｌｌを入れ、トリエチルアミン９．
６ｇ（０，０９Ｓｍｏｌ）を氷冷下でかきまぜながら加
えた。これに滴下漏斗よりオクタノイルクロリド１２．
８９（０，０７９１１１１１）を０．５時間で滴下し、
滴下終了後さらに１時間水冷下でかきまぜた。析出しＩ
；トリエチルアミン塩酸塩をろ別した後、減圧蒸留によ
り４−［２’−（Ｎ−オクタノイルアミノ）エトキシメ
チル］−２４−得た。ｂ、１１．１６０℃／ ｌ ＋＋
ｎＨ（。Example 1 5 equipped with stirrer, cooler, thermometer, and dropping funnel
13.89 (0,079 mol) of 4-(2'-aminoethoxymethyl)-2,2-dimethyl-1,3-dioxolane and 300+11 liter of diethyl ether were placed in a reaction flask containing 14 ml of triethylamine.
6 g (0.09 Smol) was added while stirring under ice cooling. Add 12.0 octanoyl chloride to this using a dropping funnel.
89 (0,07911111) was added dropwise over 0.5 hours,
After the addition was completed, the mixture was stirred for another hour under water cooling. Precipitation I
; After triethylamine hydrochloride was filtered off, 4-[2'-(N-octanoylamino)ethoxymethyl]-24- was obtained by distillation under reduced pressure. b, 11.160℃/l ++
nH(.
これをエタノール２００ｍＱに溶解し、Ｉ ＮＨＣｌｌ
ｌｏＧｍｌを加え、１０時間室温で放置後、ＮａＯ［１
水溶液で中和した。溶媒を減圧除去後、ジエチルエーテ
ル２００ｍ１ｌを加え、副生成物である食塩を分離し、
ジエチルエーテル溶液を氷冷すると、目的物であるＣ７
Ｂ、、ＣＯＮ肛！１２ｃＨ２０ｃＨｚｃ［１（Ｏｌｌ）
ＣｕｔＯＢの白色結晶が析出した。この結晶をろ別し、
冷ジエチルエーテル１００ｍ１！で洗浄後乾燥して白色
結晶１８９（収率８７％）を得た。融点は４５．０〜４
６，５°Ｃであった。分析結果を次に示す。This was dissolved in 200 mQ of ethanol, and INHCl
After adding loGml and leaving it at room temperature for 10 hours, NaO[1
Neutralized with aqueous solution. After removing the solvent under reduced pressure, 200ml of diethyl ether was added to separate the by-product common salt.
When the diethyl ether solution is ice-cooled, the target product C7
B, CON anus! 12cH20cHzc[1(Oll)
White crystals of CutOB were precipitated. Filter this crystal,
100ml of cold diethyl ether! After washing with water and drying, white crystals 189 (yield: 87%) were obtained. Melting point is 45.0-4
The temperature was 6.5°C. The analysis results are shown below.
’Ｈ−ＮＭＲ
測定条件：ａｉｎｃＤｃら、ＴＭＳ内部標準Ｓニー重線
、ｄ：二重線、ｔ：三重線、ｌ：多重線（以下同じ）
２．２（ｔ）、 ２ ［１（ＣＩｌ、Ｃ０ＮＢ）２．９
〜３．２（ブロードｌ）、 ２１！（−Ｏｉｌ）３．
３〜４．０（ａ）、 ９１（ＮｌｌｌＣＨｚ、０ＣＨＬ
、Ｃ靭Ｈ，ＣＨＬＯｉｌ）６．２（ｔ）、 Ｉ
ＨぐＮ旦）ＧＣ−ＭＳスペクトル
測定条件二使用カラム ウルトラ２（内径０．２１＋１
ｍ１長さ１５ｍ）、温度２００〜２７０°Ｃ／分、ディ
テクターインジェクション
温度２７０℃（以下同じ）
Ｅｌモード測定 トリメチルシリル化後のデータを次に
示す。'H-NMR measurement conditions: aincDc et al., TMS internal standard S knee doublet, d: doublet, t: triplet, l: multiplet (same below) 2.2 (t), 2 [1 (CIl, C0NB) 2.9
~3.2 (Broad l), 21! (-Oil)3.
3-4.0(a), 91(NlllCHHz, 0CHL
, C H, CHLOil)6.2(t), I
Column Ultra 2 (inner diameter 0.21 + 1) GC-MS spectrum measurement conditions
m1 length 15 m), temperature 200 to 270°C/min, detector injection temperature 270°C (the same applies hereinafter) El mode measurement The data after trimethylsilylation are shown below.
フラグメント フラグメント 相対強度イオンの構
造 イオンの分子量
５ｉ（ＣＨ３）ｘ ７３ １００Ｃ
ＨｚＯ５ｉ（ＣＨ３）ｘ １０３ １３
ＣｒＨ＋ｓＣＯ１２７２３
ＣＦ１１１５ＣＯＮＨＣＨ！−
十Ｂ
−Ｃｌ１ｔｚＯ５ｉ（ＣＨｓ）ｓ ２６０
１５Ｍ”−１５３９００，５
トリメチルシリル化後の分子量は４０５であった。また
、本発明の化合物の臨界ミセル濃度は５０ｍＭであり、
その濃度以上における表面張力値は３１ 、１ ｄｙａ
ｅ／ ｃｍであった（測定条件２３℃、以下同じ）。Fragment Fragment Relative intensity ion structure Ion molecular weight 5i (CH3) x 73 100C
HzO5i(CH3)x 103 13
CrH+sCO12723 CF1115CONHCH! - 10B -Cl1tzO5i(CHs)s 260
15M"-153900,5 The molecular weight after trimethylsilylation was 405. Also, the critical micelle concentration of the compound of the present invention was 50mM,
The surface tension value above that concentration is 31,1 dya
e/cm (measurement conditions: 23°C, same hereinafter).
実施例２
実施例１においてオクタノイルクロリドに代えてノナノ
イルクロリド１０ 、１ ｇ（ｏ、ｏｓｙモル）を用い
た以外は実施例１と同様にして目的物であるＣａＨｔ□
Ｃ０ＮＨＣＨｚＣ［１２０Ｃｆ［ｘＣＨ（ＯＨ）Ｃ［［
＊ＯＨの白色結晶１４９（収率８９％）を得た。融点は
５１〜５２℃であった。Example 2 The target product CaHt
C0NHHzC[120Cf[xCH(OH)C[[
*White crystals of OH 149 (yield: 89%) were obtained. The melting point was 51-52°C.
’Ｈ−ＮＭＲ
２，２（Ｌ）、 ２１１（Ｃ１ｌ、Ｃ０ＮＩＩ）２．９
〜３．２（ブロードｔ）、 ２Ｈ（−０す３．３〜４．
０（＋）、 ９Ｈ（Ｎ［１ＣＨＬ、ＯＣＲ，、Ｃ隻ｏｎ
、ｃｏ、ｏｎ）６．２（１）、 １Ｂ（ＮＨ）
ＧＣ−ＭＳスペクトル
Ｅｌモード測定 トリメチルシリル化後のデータを次に
示す。'H-NMR 2,2 (L), 211 (C1l, C0NII) 2.9
~3.2 (broad t), 2H (-0s3.3~4.
0(+), 9H(N[1CHL, OCR,, C ship on
, co, on) 6.2(1), 1B(NH) GC-MS spectrum El mode measurement The data after trimethylsilylation are shown below.
フラグメント ７ラグメント 相対強度イオンの構
造 イオンの分子量
−Ｓ＋（Ｃ１ｌｓ）ｓ ７３ １００
ＣＨ２０Ｓｉ（Ｃ１１３）ｓ １０３ １
２ＣａＨ＋ｙＣＯ１４１２５
ＣｓＨ＋ ｙｃＯＮＨｃＨｚ−
十Ｂ
−ＣＨｔＯ５ｉ（ＣＨｉ）ｘ ２７４
２１Ｍ”−１５４０４０，９
トリメチルシリル化後の分子量は４１９であった。また
、本発明の化合物の臨界ミセル濃度は１６ｍＭであり、
その濃度以上における表面張力値は３１ 、５ ｄｙｎ
ｅ／ ｃＩｌであった。Fragment 7 fragment Relative strength ion structure Molecular weight of ion -S+(C1ls)s 73 100
CH20Si(C113)s 103 1
2CaH+yCO14125 CsH+ ycONHcHz- 10B -CHtO5i(CHi)x 274
21M”-154040,9 The molecular weight after trimethylsilylation was 419. Also, the critical micelle concentration of the compound of the present invention was 16 mM,
The surface tension value above that concentration is 31,5 dyn
e/cIl.
実施例３
実施例１においてオクタノイルクロリドに代えてデカノ
イルクロリド１０．９９（０，０５７モル）を用いた以
外は実施例１と同様にして目的物であるＣ＊Ｈ＋ ５ｃ
ＯＮｆ［ｃ！１ｔｃＨ２０ｃＨｚｃＨ（ＯＨ）ＣＩｌｚ
ＯＨ（７）白色結晶１５９（収率９１％）を得た。融点
は６３．４〜６４．６℃であった。Example 3 The target product C*H+ 5c was prepared in the same manner as in Example 1 except that 10.99 (0,057 mol) of decanoyl chloride was used in place of octanoyl chloride in Example 1.
ONf[c! 1tcH20cHzcH(OH)CIlz
OH(7) white crystals 159 (yield 91%) were obtained. The melting point was 63.4-64.6°C.
’Ｈ−ＮＭＲ
２，２（＋）、 ２Ｆ！（ｃｕＬｃｏＮａ）２．９〜３
．ｌ（ブロードＬ）、！Ｈ（−０［＋）３．３〜４．０
（＠）、 ９Ｈ（ＮＨＣＥＩｔ、ＯＣｆ！ｔ、ｃＨＯＨ
，Ｃｆ１ｔＯ１ｌ）６．２（＋）、 ｘｕ（賎）
ＧＣ−ＭＳスペクトル
Ｅｌモード測定 トリメチルシリル化後のデータを次に
示す。'H-NMR 2,2(+), 2F! (cuLcoNa)2.9~3
．． l (broad L),! H(-0[+)3.3~4.0
(@), 9H(NHCEIt, OCf!t, cHOH
, Cf1tO1l)6.2(+), xu (賎) GC-MS spectrum El mode measurement The data after trimethylsilylation are shown below.
フラグメント フラグメント 相対強度イオンの構
造 イオンの分子量
一３ｉ（Ｃｌ３）ｓ ７３ １００
−Ｃ［１ｚＯ５ｉ（Ｃ［１ｓ）ｓ １０３
１８Ｃ，ｌｌ、、ＣＯ−１５５２１
ｃｓｕ＋５ｃｏＮｕｃＬ−
十Ｈ
−〇■ｇＯ５ｉ（ＣＨ３）ｓ ２８８
１２Ｍゝ −１５４１８０，６
トリメチルシリル化後の分子量は４３３であった。また
、本発明の化合物の臨界ミセル濃度は６．２ｍＭであり
、その濃度以上における表面張力値は２７．５ｄｙｎ！
／ｃｍであった。Fragment Fragment Structure of relative strength ion Molecular weight of ion -3i (Cl3)s 73 100
-C[1zO5i(C[1s)s 103
18C,ll,,CO-15521 csu+5coNucL- 10H-〇■gO5i(CH3)s 288
12Mゝ-154180,6 The molecular weight after trimethylsilylation was 433. Furthermore, the critical micelle concentration of the compound of the present invention is 6.2 mM, and the surface tension value above that concentration is 27.5 dyn!
/cm.
実施例４
アビエチン酸１０９（０，０３３モル）とジシクロへキ
シルカルボジイミドａ 、 ｓ ９（０，０３３モル）
をテトラヒドロ７ラン２００ＩＩＩｆｆｉに溶解し水冷
下でかきまぜた。約１時間後に自製してくるので、これ
に滴下漏斗より４−（２’−アミノエトキシメチル）−
２，２−ジメチル−監、３−ジオキソラン５ 、８９（
Ｑ、Ｏ３３モル）を溶解したテトラヒドロフラン溶液５
０ｍ１ｌヲ約１時間で滴下し、室温で約５時間かきまぜ
た。反応終了後、副生じたジシクロヘキシル尿素をろ別
し、溶媒を減圧除去後エーテル１００ｍ１ｌを加え水冷
下に再結晶して、目的物である
Ｃ＋ｓ［１＊５ＣＯＮＨＣＨｚＣｆｌｔＯＣＩ１２ＣＨ
（０■）ｃｕ、ｏｎの白色結晶１２９（収率８７％）を
得た。Example 4 Abietic acid 109 (0,033 mol) and dicyclohexylcarbodiimide a, s 9 (0,033 mol)
was dissolved in Tetrahydro7ran 200IIIffi and stirred under water cooling. About 1 hour later, the homemade product will be prepared, and from the dropping funnel add 4-(2'-aminoethoxymethyl)-
2,2-dimethyl-monitor, 3-dioxolane 5, 89 (
Tetrahydrofuran solution 5 in which Q, O (3 mol) was dissolved
0ml/l was added dropwise over about 1 hour and stirred at room temperature for about 5 hours. After the completion of the reaction, the dicyclohexyl urea produced as a by-product was filtered out, and the solvent was removed under reduced pressure. Then, 100 ml of ether was added and recrystallized under water cooling to obtain the target product, C+s[1*5CONHCHzCfltOCI12CH
White crystals 129 (yield: 87%) of (0■) cu,on were obtained.
’ＨＮＭＲ
測定条件： Ｋ１ｎＣＤ、Ｃ００Ｄ、 ＴＭＳ内部標準
２．２（Ｌ）、 ２■（Ｃ１ｌ、Ｃ０ＩＩＨ）３．３−
３．９（ｍ）、 ９Ｈ（ＮＨＣＬＬ、ＯＣＲ，、Ｃ隻Ｏ
Ｂ、Ｃ］Ｏ［ｌ）５．３（ｔ）、 １１１（ＣＬ−東−
Ｃ）５．７（ｓ）、 Ｉ Ｈ（Ｃ−ＣＨ＝ Ｃ）ＧＣ−
ＭＳスペクトル
ＥＩモード測定 トリメチルシリル化後のデータを次に
示す。'HNMR measurement conditions: K1nCD, C00D, TMS internal standard 2.2 (L), 2■ (C1l, C0IIH) 3.3-
3.9 (m), 9H (NHCLL, OCR, C ship O
B, C] O[l) 5.3 (t), 111 (CL-East-
C) 5.7(s), IH(C-CH=C)GC-
MS spectrum EI mode measurement Data after trimethylsilylation are shown below.
フラグメント ７ラグメント 相対強度イオンの構
造 イオンの分子量
−５ｉ（ＣＬ）３７３ １００
−ＣＨｔＯ５ｉ（ＣＬ）ｘ １０３ １
３Ｃ＋Ｊｚ□ＣＯ−２８５２７
Ｃ＋５ＨｚｔＣＯＮＨＣ［Ｉｚ−
＋■
−ＣＬＯ５ｉ（ＣＬ）ｘ ４１８ １２
Ｍ”−１５５４８０，４
トリメチルシリル化後の分子量は５６３であっｔこ。Fragment 7 Fragment Relative strength ion structure Molecular weight of ion -5i (CL) 373 100 -CHtO5i (CL) x 103 1
3C+Jz□CO-28527 C+5HztCONHC[Iz- +■ -CLO5i(CL)x 418 12
M''-155480,4 The molecular weight after trimethylsilylation was 563.
特許出願人 ライオン株式会社Patent applicant: Lion Corporation
Claims (1)
はＨ、炭素数１〜４の炭化水素基又はヒドロキシ基を含
む炭化水素基、Ｘは炭素数１〜４の炭化水素基又はヒド
ロキシル基を含む炭化水素基である）で表わされるＮ−
アシルアミノアルキルグリセリルエーテル化合物。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 is a hydrocarbon group having 5 to 30 carbon atoms, R_2
is H, a hydrocarbon group having 1 to 4 carbon atoms or a hydrocarbon group containing a hydroxyl group, and X is a hydrocarbon group having 1 to 4 carbon atoms or a hydrocarbon group containing a hydroxyl group.
Acylaminoalkyl glyceryl ether compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10118188A JPH01272563A (en) | 1988-04-23 | 1988-04-23 | N-acylaminoalkyl glyceryl ether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10118188A JPH01272563A (en) | 1988-04-23 | 1988-04-23 | N-acylaminoalkyl glyceryl ether compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01272563A true JPH01272563A (en) | 1989-10-31 |
Family
ID=14293821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10118188A Pending JPH01272563A (en) | 1988-04-23 | 1988-04-23 | N-acylaminoalkyl glyceryl ether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01272563A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5371252A (en) * | 1989-09-29 | 1994-12-06 | L'oreal | Triglycerol alkylcarbamates, their preparation and their use as emulsifying agents in cosmetic compositions in the form of wax microdispersions |
| EP0687723A1 (en) * | 1994-06-16 | 1995-12-20 | Unilever Plc | Fabric conditioning molecules derived from glycerol and betaine |
-
1988
- 1988-04-23 JP JP10118188A patent/JPH01272563A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5371252A (en) * | 1989-09-29 | 1994-12-06 | L'oreal | Triglycerol alkylcarbamates, their preparation and their use as emulsifying agents in cosmetic compositions in the form of wax microdispersions |
| EP0687723A1 (en) * | 1994-06-16 | 1995-12-20 | Unilever Plc | Fabric conditioning molecules derived from glycerol and betaine |
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