オキサロ酢酸

Oxaloacetic Acid

HCID 970CAS 328-42-7
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基本情報

標準SMILES
O=C(O)CC(=O)C(=O)O
InChIKey
KHPXUQMNIQBQEV-UHFFFAOYSA-N
分子式
C4H4O5
平均分子量
132.07 g/mol
単同位体質量
132.00587323

概要

Oxaloacetic acid is an oxodicarboxylic acid that is succinic acid bearing a single oxo group. It has a role as a geroprotector and a metabolite. It is an oxo dicarboxylic acid and a C4-dicarboxylic acid. It is functionally related to a succinic acid. It is a conjugate acid of an oxaloacetate(2-).

名称と識別子

優先名称
Oxaloacetic Acid
IUPAC
2-oxobutanedioic acid
現地名
オキサロ酢酸
英語名
Oxaloacetic acid
分子式
C4H4O5
分子量
132.07

名称と別名

oxalacetic acidoxaloacetic acid328-42-72-Oxobutanedioic acidoxaloacetateKetosuccinic acidOxosuccinic acid2-Ketosuccinic acidButanedioic acid, oxo-Bioepg2-oxo-butanedioic acidketo-oxaloacetate
名称をさらに表示
オキサル酢酸3-オキソブタン二酸2-オキソこはく酸2-ケトこはく酸2-オキソブタン二酸α-ケトこはく酸オキソブタン二酸オキソこはく酸2-ケトブタン二酸ケトこはく酸オキザロ酢酸オキサル酢酸(シス型)オキサル酢酸, 98〜99%オキサル酢酸, 97%オキサロ酢酸2-OXOSUCCINIC ACIDOAAOXOBUTANEDIOIC ACIDoxalaceticNSC 77688NSC 2842052-OXOSUCCINICOXLACETIC ACID
DTXSID8021646NSC-776882F399MM81JDTXCID901646CHEBI:30744Acid, OxalaceticAcid, Oxaloacetic2 Ketosuccinic Acid

データベース識別子

CAS
328-42-7
PubChem CID
970
DTXSID
DTXSID8021646
ChEMBL
CHEMBL1794791
ChEBI
CHEBI:30744
UNII
2F399MM81J
EC Number
206-329-8
Nikkaji
J5.675H

物性

構造計算による物性

XLogP
-0.6
極性表面積
91.7 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
3
重原子数
9

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
Solubility134 mg/mL
Melting Point161 °C
Physical Description · 2 件

Off-white powder; [Alfa Aesar MSDS]

Solid

物理化学的性質

融点
161 °C · 161 °C (dec.)(lit.)
沸点
163.94 °C · 163.94°C (rough estimate)
比重(密度)
1.3067 · 1.3067 (rough estimate)
蒸気圧
0.003 Pa · 0.003Pa at 20℃
屈折率
1.4 · 1.4000 (estimate)
闪点
88 °C · 88°C

化学的性質

化学的特性off-white crystals

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H314 (88.5%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P321, P337+P317, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 61 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

Chemical: Butanedioic acid, oxo-

Status: Active Update: 14-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/22927

Butanedioic acid, oxo-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryCauses convulsions in acute intraperitoneal studies of mice; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] See Oxalic acid and Acetic acid.
Hazard Classes and CategoriesSkin Corr. 1B (88.5%)

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

安全データ

wgk
3
tsca
TSCA listed
ridadr
UN 3261 8/PG 2
hs_code
29183000
risk_code
34
hazard_code
C

化学と産業

薬理情報

Tissue LocationsLiver
Cellular LocationsMitochondria
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)

用途と製造

General Manufacturing InformationButanedioic acid, 2-oxo-: ACTIVE
応用分野 · 5 件

解説オキサロ酢酸,ケト酸の一種で，ケト形とエノール形の互変異性体がある．リンゴ酸を過マンガン酸カリウムあるいは硫酸鉄(Ⅱ)の存在下，過酸化水素で酸化するか，ジアセチル酒石酸無水物をピリジン酢酸塩で処理してヒドロキシマレイン酸無水物のピリジン塩をつくり，これを硫酸で加水分解すると得られる．結晶では完全にエノール形をしており，融点152 ℃ のシス形と184 ℃ のトランス形の2種類があり，いずれもエタノールに可溶．森北出版「化学辞典（第2版）

説明Oxaloacetic acid, also known as oxalacetic acid, is is an α-keto acid and a key component of cellular metabolism in its conjugate base form, oxaloacetate. Oxaloacetate reacts with acetyl-coenzyme A (acetyl-CoA; ) and water to form citrate in the first step of the citric acid cycle and is regenerated by oxidation of L-malate in the final step. It is an intermediate in gluconeogenesis that is formed in mitochondria via carboxylation of pyruvate and subsequently decarboxylated and phosphorylated to form phosphoenolpyruvate. It can be converted to aspartate via addition of an amino group from glutamate. Oxaloacetate (30 μmol/min per 100 g for 30 minutes, i.v.) reduces blood glutamate levels, severity of neurological dysfunction, and brain edema in a rat model of closed head injury.

使用Oxaloacetic acid is a substrate for malate dehydrogenase and oxaloacetate decarboxylase. It is an inhibitor of succinic dehydrogenase. It is four carbon dicarboxylic acid that is an intermediate in the citric acid cycle and glucogenesis.

一般的な説明Oxaloacetic acid is a dicarboxylic acid. It is an intermediate in the citric acid cycle. It is highly soluble in water and is present ubiquitously. It is produced in the mitochondria by the action of pyruvate carboxylase on pyruvate. Breakdown products of oxaloacetate includes malate, pyruvate and aspartic acid.

使用用途1. 医薬品 医薬品の原料として広く使用され、高血圧治療薬や抗てんかん薬にオキサロ酢酸が含まれていることがあります。オキサロ酢酸を体内に補充することで、肝機能障害や腎臓病などの疾患治療に役立つことが報告されています。また、抗酸化作用や抗がん作用もあるとされ、がん治療の補助的な治療薬として研究が進んでいます。 2. 化学反応の触媒 有機合成の反応において、アルキル化やアセトアセチル化などの反応触媒として使用されます。

調製方法

純化方法Crystallise it from boiling EtOAc, or from hot Me2CO/hot *C6H6. [Beilstein 3 IV 1808.]

上流・下流製品情報

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
補足説明 · 1 件

定義ChEBI: Oxaloacetic acid is an oxodicarboxylic acid that is succinic acid bearing a single oxo group. It has a role as a metabolite and a geroprotector. It is an oxo dicarboxylic acid and a C4-dicarboxylic acid. It is functionally related to a succinic acid. It is a conjugate acid of an oxaloacetate(2-).

関連反応

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