フマル酸1-メチル
(E)-2-ブテン二酸1-メチル · trans-エチレン-1,2-ジカルボン酸モノメチル · フマル酸モノメチル · フマル酸水素1-メチル · フマル酸1-メチル · (E)-2-ブテン二酸水素1-メチル · フマル酸水素メチル · MONO-フマル酸メチル
識別子と物理属性
| CAS No. | 2756-87-8 |
|---|---|
| 分子式 | C5H6O4 |
| 平均分子量 | 130.1 g/mol |
| 単同位体質量 | 130.02660867 g/mol |
| SMILES | COC(=O)/C=C/C(=O)O |
| InChIKey | NKHAVTQWNUWKEO-NSCUHMNNSA-N |
| PubChem CID | 5369209 |
| ChEMBL | CHEMBL589586 |
| ChEBI | CHEBI:167450 |
| EC No. | 220-412-6 |
| DTXSID | DTXSID801016498 |
| 現地名 | フマル酸1-メチル |
化学・物理的性質
| XLogP | 0.4 |
|---|---|
| 極性表面積 | 63.6 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 3 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 147 |
| 医薬品 | Pharmaceuticals -> Metabolite of Dimethyl fumarate |
| SpringerMaterials Properties | Crystal structure |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| 融点 | 144-145 °C (lit.) |
| 沸点 | 250.0±23.0 °C(Predicted) |
| 密度 | 1.37 g/cm3 |
| 貯蔵条件 | 2-8°C |
| 溶解度 | クロロホルム（微量）、DMSO（微量）、メタノール（微量） |
| pKa（酸解離定数） | 3.40±0.10(Predicted) |
| 外観・状態 | 個体 |
| 色 | オフホワイト |
| InChI | InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+ |
| InChIKey | NKHAVTQWNUWKEO-NSCUHMNNSA-N |
| SMILES | C(OC)(=O)/C=C/C(O)=O |
| CAS データベース | 2756-87-8(CAS DataBase Reference) |
化学的特性
Off-White Solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 26.2% (37 of 141) of reports.DangerH318 (72.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)Aggregated GHS information provided per 141 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Status: Active Update: 23-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/29959 |
| Hazard Classes and Categories | Eye Dam. 1 (72.3%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Monomethyl fumarateAmbiguous-DILI-concern4Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29171900 |
| 危険文句（R） | 41 |
| 化審法 | (2)-1142 |
| 危険表示 | Xi |
| 安全措置（S） | 26-39 |
| 危険等級 | Eye Irrit. 2 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
Monomethyl fumarate (MMF), a bioactive metabolite of fumaric acid ester, is an immunotherapy for psoriasis that causes decreased production of Th1 cytokines and lymphocytopenia. Monomethyl fumarate was shown to decrease DC response to LPS and decreased IL-12p70 and IL-10 production.
使用
Monomethyl fumarate is used to treat the relapsing forms of multiple sclerosis (MS), including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease. This medicine will not cure MS, but it may slow some of the disabling effects and decrease the number of relapses of the disease.Fumaric Acid Monomethyl Ester is one of the most bioactive anti-psoriatic fumaric acid ester metabolite. Fumaric Acid Monomethyl Ester is potent nicotinic acid receptor agonist. Fumaric Acid Monomethy l Ester has also been shown to selectively stimulate of T helper 2 cytokine response.
製法・合成法
製造方法
Monomethyl fumarate was synthesized by maleic anhydride and methanol. monomethyl fumarate could inhibit the growth of mold, and the storage time of feed could be prolonged.