基本情報
- 標準SMILES
CC(C(=O)O)C(=O)O- InChIKey
ZIYVHBGGAOATLY-UHFFFAOYSA-N- 分子式
- C4H6O4
- 平均分子量
- 118.09 g/mol
- 単同位体質量
- 118.02660867
名称と識別子
- 優先名称
- Methylmalonic Acid
- IUPAC
- 2-methylpropanedioic acid
- 現地名
- メチルマロン酸
- 英語名
- 2-Methylpropanedioic acid
- 分子式
- C4H6O4
- 分子量
- 118.09
名称と別名
名称をさらに表示
データベース識別子
- CAS
1215348-94-9、516-05-2- PubChem CID
- 487
- DTXSID
DTXSID00199549- ChEMBL
CHEMBL1232416- ChEBI
CHEBI:30860- UNII
- 8LL8S712J7
- EC Number
- 208-219-5、693-939-6
- Nikkaji
- J6.302I
物性
構造計算による物性
- XLogP
- 0.1
- 極性表面積
- 74.6 Ų
- 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
実験および物理化学的性質
Solubility
679000
679.0 mg/mL
Melting Point
135
135 °C
物理化学的性質
- 融点
- 128 · 128-130 °C (lit.)
- 沸点
- 272.71 °C · 272.71°C (rough estimate)
- 比重(密度)
- 1.45 · 1.45
- 屈折率
- 1.4304 · 1.4304 (estimate)
- 闪点
- 2 ℃ · 2℃
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- DMSO(微量)、メタノール(微量)
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 3.07 · 3.07, 5.76(at 25℃)
- 色
- 白い
- 比重
- 1.455 · 1.455
- PH
- 3.23 · 3.23(1 mM solution);2.6(10 mM solution);2.05(100 mM solution)
- 水溶解度
- 溶ける
- BRN
- 1756084 · 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 · 516-05-2(CAS DataBase Reference)
- NISTの化学物質情報
- Methylmalonic acid(516-05-2)
化学的性質
化学的特性white crystalline powder
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 5.4% (3 of 56) of reports.
Warning
H315 (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 exposure; Respiratory 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.
危険有害性情報
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%)
毒性情報
Health Effects
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.
Toxicity Summary
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.
安全データ
- wgk
- 3
- rtecs
- OO1400000
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29171900
- risk_code
- 36/37/38-36-20/21/22-11
- hazard_code
- Xi,Xn,F
- safety_code
- 26-36/37-16
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolite Pathways
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency;3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency;3-hydroxyisobutyric acid dehydrogenase deficiency;3-hydroxyisobutyric aciduria;3-Methylcrotonyl Coa Carboxylase Deficiency Type I;3-Methylglutaconic Aciduria Type I;3-Methylglutaconic Aciduria Type III;3-Methylglutaconic Aciduria Type IV;Beta-Ketothiolase Deficiency;Isobutyryl-coa dehydrogenase deficiency;Total 22 pathways, visit the HMDB page for details
用途と製造
応用分野
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.
調製方法
純化方法The acid crystallises as the hydrate from water. [Beilstein 2 IV 1932.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: Methylmalonic acid is a dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group. It has a role as a human metabolite. It is functionally related to a malonic acid. It is a conjugate acid of a methylmalonate(1-).
関連反応
関連ノート
読み込み中…