2-ヒドロキシ-2-オキソアセタート

Oxalate

HCID 71081CAS 338-70-5

基本情報

標準SMILES
O=C([O-])C(=O)[O-]
InChIKey
MUBZPKHOEPUJKR-UHFFFAOYSA-L
分子式
C2O4-2
平均分子量
88.02 g/mol
単同位体質量
87.98075564

概要

Oxalate(2-) is a dicarboxylic acid dianion obtained by deprotonation of both carboxy groups of oxalic acid. It has a role as a plant metabolite and a human metabolite. It is an oxalate and a dicarboxylic acid dianion. It is a conjugate base of an oxalate(1-).

名称と識別子

優先名称
Oxalate
IUPAC
oxalate
現地名
2-ヒドロキシ-2-オキソアセタート
英語名
2-hydroxy-2-oxoacetate
分子式
C2HO4
分子量
0

名称と別名

oxalateRefChem:168786CHEBI:132952OxalatesOxalate Ionethanedioateoxalate(2-)Oxalic acid, ion(2-)Ethanedioic acid, ion(2-)338-70-5PQ7QG47K6Toxalate2-
名称をさらに表示
2-ヒドロキシ-1-オキシラト-1,2-エタンジオンカルボキシラトぎ酸2-ヒドロキシ-2-オキソ酢酸アニオン2-オキソ-2-ヒドロキシアセタート水素オキサラート2-ヒドロキシ-2-オキソアセタートしゅう酸水素アニオンHydrogen Oxalate2-hydroxy-2-oxoacetateCarboxylatoformic acid2-Oxo-2-hydroxyacetate2-Hydroxy-1-oxylato-1,2-ethanedionebis[3-(1,3-dioxoisoindol-2-yl)propyl]azaniumIon Chromatography Anion Std oxalate 1mg/mL (1000 ppm)Ion Chromatography Anion Std oxalate 0.2mg/mL (200 ppm)(3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-5-yl)methyl-methylazanium
oxalate dianion3mof2rk7OXALATE ION(2-)UNII-PQ7QG47K6TOXALATE (C2O42-)GTPL4538BDBM92964

データベース識別子

CAS
338-70-5
PubChem CID
71081
DTXSID
DTXSID901047254
ChEBI
CHEBI:30623
UNII
PQ7QG47K6T
Nikkaji
J215.990B

物性

構造計算による物性

XLogP
1
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
0
重原子数
6

安全と法規制

毒性情報

Treatment · 1 件

Acute Exposure: If oxalic acid is swallowed, immediately give the person water or milk, unless instructed otherwise by a health care provider. DO NOT give water or milk if the person is having symptoms (such as vomiting, convulsions, or a decreased level of alertness) that make it hard to swallow. If acute exposure occurs to the eyes, irrigate opened eyes for several minutes under running water. Chronic exposure: in some patients with primary hyperoxaluria type 1, pyridoxine treatment (vitamin B6) may decrease oxalate excretion and prevent kidney stone formation.

Health Effects · 1 件

Because it binds vital nutrients such as calcium, long-term consumption of foods high in oxalic acid can be problematic. Healthy individuals can safely consume such foods in moderation, but those with kidney disorders, gout, rheumatoid arthritis, or certain forms of chronic vulvar pain (vulvodynia) are typically advised to avoid foods high in oxalic acid or oxalates. The calcium oxalate precipitate (better known as kidney stones) obstruct the kidney tubules. Conversely, calcium supplements taken along with foods high in oxalic acid can cause calcium oxalate to precipitate out in the gut and drastically reduce the levels of oxalate absorbed by the body (by 97% in some cases.) Chronically high levels of oxalic acid are associated with at least 2 inborn errors of metabolism including: Type I primary hyperoxaluria and Primary hyperoxaluria. Oxalate stones in primary hyperoxaluria tend to be severe, resulting in relatively early kidney damage (before age 20), which impairs the excretion of oxalate leading to a further acceleration in accumulation of oxalate in the body. After the development of renal failure patients may develop oxalate deposits in the bones, joints and bone marrow. Severe cases may develop haematological problems such as anaemia and thrombocytopaenia. The deposition of oxalate in the body is sometimes called "oxalosis" to be distinguished from "oxaluria" which refers to oxalate in the urine.

Toxicity Summary · 1 件

The affinity of divalent metal ions is sometimes reflected in their tendency to form insoluble precipitates. Thus in the body, oxalic acid also combines with metals ions such as Ca2+, Fe2+, and Mg2+ to deposit crystals of the corresponding oxalates, which irritate the gut and kidneys. (2) Therefore the toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints. Ingestion of ethylene glycol results in oxalic acid as a metabolite that can also cause acute kidney failure.

Signs and SymptomsOxalic acid poisoning symptoms include weakness, burning in the mouth, death from cardiovascular collapse, on the respiratory system, throat – burning in the throat, abdominal pain, nausea, vomiting, diarrhea, convulsions, and coma.
Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)

化学と産業

薬理情報

Metabolism/MetabolitesOxalic acid is not metabolized but excreted in the urine.

用途と製造

Uses · 1 件

Oxalic acid and oxalates are abundantly present in many plants, most notably fat hen (lamb's quarters), sorrel, and Oxalis species. The root and/or leaves of rhubarb and buckwheat are listed being high in oxalic acid.[8] Other edible plants that contain significant concentrations of oxalic acid include—in decreasing order—star fruit (carambola), black pepper, parsley, poppy seed, amaranth, spinach, chard, beets, cocoa, chocolate, most nuts, most berries, and beans. (L618)

上流・下流製品情報

サプライヤー1 社

MolMall Sarl[email protected]

補足説明

定義ChEBI: A dicarboxylic acid dianion obtained by deprotonation of both carboxy groups of oxalic acid.

関連反応

278 件

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