ジクロロアセタート

Dichloroacetate anion

HCID 25975CAS 13425-80-4

基本情報

標準SMILES
O=C([O-])C(Cl)Cl
InChIKey
JXTHNDFMNIQAHM-UHFFFAOYSA-M
分子式
C2HCl2O2-
平均分子量
127.93 g/mol
単同位体質量
126.93590821

概要

Dichloroacetate is a monocarboxylic acid anion that is the conjugate base of dichloroacetic acid. It has a role as a geroprotector. It is functionally related to an acetate. It is a conjugate base of a dichloroacetic acid.

名称と識別子

優先名称
Dichloroacetate anion
IUPAC
2,2-dichloroacetate
現地名
ジクロロアセタート
英語名
Dichloroacetate
分子式
C2HCl2O2
分子量
0

名称と別名

Dichloroacetate13425-80-4DichloracetateDichloroacetate ionDichloroacetic acid ion(1-)CHEBI:28240DTXSID40158610Dichloroacetate anionRefChem:1083416DTXCID80811012,2-dichloroacetateBRN 3903873
名称をさらに表示
ジクロロアセタート
Ion Chromatography Standard: Dichloroacetate @ 500 microg/mL in H2OAcetic acid, 2,?2-?dichloro-?, ion(1-?); Acetic acid, dichloro-, ion(1-) (8CI,9CI); 2,2-Dichloroacetate; Dichloroacetate anion; Dichloroacetate ion; Dichloroacetate ion(1-)2q8hACETIC ACID, DICHLORO-, ION(1-)GTPL4518Method 300.1 Surrogate StandardBDBM50177027ACETICACID,DICHLORO-,ION(1-)

データベース識別子

CAS
13425-80-4
PubChem CID
25975
DTXSID
DTXSID40158610
ChEBI
CHEBI:28240
Nikkaji
J54.198B

物性

構造計算による物性

XLogP
1.8
極性表面積
40.1 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
6

安全と法規制

毒性情報

Health Effects · 1 件

Multiple independent studies demonstrate that DCA has the ability to alter normal carbohydrate metabolism. Dichloroacetic acid treatment results in a significant reduction in plasma levels of glucose, pyruvate, and lactate. Another consistent finding in DCA ingestion studies is a dose-related increase in liver size, generally accompanied (or caused) by an increase in glycogen deposition in the liver. There is an extensive and consistent data base demonstrating the reproductive toxicity of DCA in males and females. Neurologic symptoms and morphologic changes in the nervous system have been reported in humans, dogs, and rats. (L2086)

Exposure RoutesIngestion
Toxicity Summary · 1 件

The dichloroacetate ion stimulates the activity of the enzyme pyruvate dehydrogenase by inhibiting the enzyme pyruvate dehydrogenase kinase. Thus, it decreases lactate production by shifting the metabolism of pyruvate from fermentation towards oxidation in the mitochondria. (Wikipedia)

Carcinogen Classification2B, possibly carcinogenic to humans. (L135)
Toxicity DataORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg [Rabbit]

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Dichloroacetic acid is metabolized in the liver by oxidative dechlorination to yield glyoxylate, which can enter intermediary metabolism and either be oxidized to oxalate and excreted, converted to carbon dioxide, and/or incorporated into amino acids or other cellular molecules. (L2086)

用途と製造

Uses · 1 件

Dichloroacetic acid has shown promise as a potentially new class of anti-cancer medication, but has yet to complete clinical trials. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. As of October 2014, dichloroacetic acid was undergoing phase III clinical trials for cancer treatment (L2084) (Wikipedia). Dichloroacetic acid has undergone clinical trials for the treatment of lactic acidosis in humans, but the trials found no clinical benefit (Wikipedia). In 2014 Thomas E. Mallouk and colleagues published a new technique for the production of graphene by intercalation of graphite with non-oxidizing Brønsted acids including dichloroacetic acid, raising the prospect that dichloroacetic acid might be used in industrial graphene production in the future (L2085).

サプライヤー1 社

AccuStandard Inc[email protected]

補足説明

定義ChEBI: A monocarboxylic acid anion that is the conjugate base of dichloroacetic acid.

関連反応

2 件

関連ノート

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