メチルマロン酸
メチルマロン酸 · 2-メチルマロン酸 · α-メチルマロン酸 · 2-メチルプロパン二酸 · イソこはく酸 · メチルマロン酸(メチル-D3) · メチルマロン酸 溶液 · METHYLMALONIC ACID
識別子と物理属性
| CAS No. | 1215348-94-9 |
|---|---|
| 分子式 | C4H6O4 |
| 平均分子量 | 118.09 g/mol |
| 単同位体質量 | 118.02660867 g/mol |
| SMILES | CC(C(=O)O)C(=O)O |
| InChIKey | ZIYVHBGGAOATLY-UHFFFAOYSA-N |
| PubChem CID | 487 |
| ChEMBL | CHEMBL1232416 |
| ChEBI | CHEBI:30860 |
| EC No. | 208-219-5 |
| DTXSID | DTXSID00199549 |
| 現地名 | メチルマロン酸 |
化学・物理的性質
| XLogP | 0.1 |
|---|---|
| 極性表面積 | 74.6 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 2 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 103 |
| 溶解度 | 679000679.0 mg/mLDMSO（微量）、メタノール（微量）溶ける |
| 融点 | 135135 °C128-130 °C (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 3.12 (at 20 °C) |
| 沸点 | 272.71°C (rough estimate) |
| 密度 | 1.45 |
| 屈折率 | 1.4304 (estimate) |
| 引火点 | 2℃ |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 3.07, 5.76(at 25℃) |
| 色 | 白い |
| 比重 | 1.455 |
| pH | 3.23(1 mM solution)2.6(10 mM solution)2.05(100 mM solution) |
| BRN | 1756084 |
| InChI | 1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8) |
| InChIKey | ZIYVHBGGAOATLY-UHFFFAOYSA-N |
| SMILES | CC(C(O)=O)C(O)=O |
| CAS データベース | 516-05-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Methylmalonic acid(516-05-2) |
化学的特性
white crystalline powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 5.4% (3 of 56) of reports.WarningH315 (94.6%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (94.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (92.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 56 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 3 of 56 reports by companies.There are 5 notifications provided by 53 of 56 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (94.6%)Eye Irrit. 2 (94.6%)STOT SE 3 (92.9%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%) |
| 健康影響 | Chronically high levels of methylmalonic acid are associated with at least 5 inborn errors of metabolism including: Malonyl CoA decarboxylase deficiency, Malonic Aciduria, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Methylmalonic Aciduria and Methylmalonic Aciduria Due to Cobalamin-Related Disorders. |
| 毒性の概要 | Methylmalonic acid is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. Accumulation of Methylmalonic acid in the body has been shown to be toxic. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | OO1400000 |
| 輸送番号（UN） | UN 1648 3 / PGII |
| 税関コード | 29171900 |
| 危険文句（R） | 36/37/38-36-20/21/22-11 |
| 危険表示 | Xi,Xn,F |
| 安全措置（S） | 26-36/37-16 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
methylpropanedioic acid．C4H6O4(118.09)．CH3CH(COOH)2．メチルマロン酸は，二塩基酸の一種．プロピオン酸エチルと炭酸ジエチルとをナトリウムエトキシドの存在下で縮合したのち，加水分解すると得られる．結晶．融点135 ℃．pKa 3.06(25 ℃)．エタノール，エーテル，酢酸エチルに可溶，水，ベンゼンに難溶．加熱すると二酸化炭素を放出してプロピオン酸になる．メチルマロニルCoAの代謝異常を起こしたメチルマロン酸血症の患者の尿中に多量に排泄される．森北出版「化学辞典（第2版）
用途
有機合成原料。
使用
2-Methylpropanedioic acid binds with coenzyme A to form methylmalonyl-CoA, also a metabolic intermediate transformed to succinic acid (SA) by a vitamin B12-dependent catalytic step, and is broadly used as a clinical biomarker of functional vitamin B12 status.
一般的な説明
Methylmalonic acid is an indicator of vitamin B12 deficiency and methylmalonic acidemia. This Certified Spiking Solution is suitable for use in preparation of calibrators or controls in clinical and diagnostic testing using GC/MS or LC/MS.
製法・合成法
純化方法
The acid crystallises as the hydrate from water. [Beilstein 2 IV 1932.]