メチルマロン酸

Methylmalonic Acid

HCID 487CAS 1215348-94-9

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

Methylmalonic acid2-Methylmalonic acid516-05-22-Methylpropanedioic acidIsosuccinic acidmethylmalonatePropanedioic acid, methyl-1,1-Ethanedicarboxylic acidmethylpropanedioic acidMalonic acid, methyl-2-methyl-propanedioic acidCHEBI:30860
名称をさらに表示
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AI315327onic acidNSC 25201AI3 15327AI3-15327Methylmalonicisosuccinicacid
DTXSID001995498LL8S712J7NSC-25201Acid, MethylmalonicRefChem:818643DTXCID10122040208-219-5MFCD00002656

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

実験および物理化学的性質

Solubility · 2 件

679000

679.0 mg/mL

Melting Point · 2 件

135

135 °C

Physical DescriptionSolid
Dissociation Constants3.12 (at 20 °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

化学的性質

化学的特性white crystalline powder

安全と法規制

GHS分類

GHS Classification · 6 件

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 · 2 件

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 · 1 件

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 · 1 件

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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

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

化学と産業

薬理情報

Tissue LocationsKidney;Liver;Placenta
Cellular LocationsCytoplasm
Metabolite Pathways · 1 件

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

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
応用分野 · 4 件

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.]

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
補足説明 · 1 件

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

26 件

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