基本情報
- CAS
56-14-4- 標準SMILES
O=C([O-])CCC(=O)[O-]- InChIKey
KDYFGRWQOYBRFD-UHFFFAOYSA-L- 分子式
- C4H4O4-2
- 平均分子量
- 116.07 g/mol
- 単同位体質量
- 116.01205577
概要
Succinate(2-) is a dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxy groups of succinic acid. It has a role as a Saccharomyces cerevisiae metabolite and a human metabolite. It is a succinate, a dicarboxylic acid dianion and a C4-dicarboxylate. It is a conjugate base of a succinate(1-).
名称と識別子
- 優先名称
- Succinate
- IUPAC
- butanedioate
- 英語名
- ANION STANDARD - SUCCINATE
- 分子式
- C4H4O4-2
- 分子量
- 116.07216
名称と別名
名称をさらに表示
データベース識別子
- CAS
56-14-4- PubChem CID
- 160419
- DTXSID
DTXSID4036772- ChEBI
CHEBI:30031- UNII
- AJ326AG789
- EC Number
- 611-361-4
- Nikkaji
- J215.983J
物性
構造計算による物性
- XLogP
- 0.7
- 極性表面積
- 80.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 4
- 回転可能結合数
- 1
- 重原子数
- 8
- 形式電荷
- -2
- 複雑度
- 81.6
実験および物理化学的性質
安全と法規制
毒性情報
Treatment
EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Health Effects
At acute doses or exposures succinic acid is a skin irritant. Chronically high doses of succinate can lead to succinylation or succination of a variety of enzymes. Partial succinate dehydrogenase deficiency (15% to 50% of normal reference enzyme activity) in skeletal muscle leads to elevated succinate levels and causes mitochondrial myopathy with various symptoms, for example, brain involvement, cardiomyopathy, and/or exercise intolerance.
Toxicity Summary
Succinate can inhibit the activities of α-KG–dependent oxygenases (KDMs) and the TET family of 5-methlycytosine (5mC) hydroxylases. Succinate also mediates allosteric inhibition of hypoxia inducible factor (HIF) prolyl hydroxylases (PHDs). Inhibition of HIF PHDs leads to activation of HIF-mediated pseudohypoxic response, whereas inhibition of KDMs and TET family of 5mC hydroxylases causes epigenetic alterations that ultimately cause cancer. Succination of KEAP1 in FH deficiency results in the constitutive activation of the antioxidant defense pathway mediated by NRF2, conferring a reductive milieu that promotes cell proliferation. Succination of the Krebs cycle enzyme Aco2 impairs aconitase activity in Fh1-deficient MEFs. Succination also causes irreversible inactivation of glyceraldehyde-3-phosphate dehydrogenase (GAPDH).
化学と産業
薬理情報
用途と製造
Uses
Succinic acid is a precursor to some specialized polyesters. It is also a component of some alkyd resins. Succinic acid is used in the food and beverage industry, primarily as an acidity regulator. It is also sold as a food additive and dietary supplement, and is generally recognized as safe by the US FDA.
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補足説明
定義ChEBI: A dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxy groups of succinic acid.
関連反応
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