尿酸

Uric Acid

HCID 1175CAS 69-93-2

基本情報

標準SMILES
O=c1[nH]c(=O)c2[nH]c(=O)[nH]c2[nH]1
InChIKey
LEHOTFFKMJEONL-UHFFFAOYSA-N
分子式
C5H4N4O3
平均分子量
168.11 g/mol
単同位体質量
168.02833999

概要

7,9-dihydro-1H-purine-2,6,8(3H)-trione is an oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a tautomer of a 2,6-dihydroxy-7,9-dihydro-8H-purin-8-one, a 9H-purine-2,6,8-triol, a 7H-purine-2,6,8-triol, a 1H-purine-2,6,8-triol and a 5,7-dihydro-1H-purine-2,6,8(9H)-trione.

名称と識別子

優先名称
Uric Acid
IUPAC
7,9-dihydro-3H-purine-2,6,8-trione
現地名
尿酸
英語名
Uric acid
分子式
C5H4N4O3
分子量
168.11

名称と別名

uric acid69-93-2urateLithic acid2,6,8-trioxypurine2,6,8-trihydroxypurine7,9-Dihydro-1H-purine-2,6,8(3H)-trione2,6,8-Trioxopurine1H-Purine-2,6,8-triol1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-Purine-2,6,8(1H,3H,9H)-trione7,9-dihydro-3H-purine-2,6,8-trione
名称をさらに表示
尿酸1,7-ジヒドロ-2-ヒドロキシ-6H-プリン-6,8(9H)-ジオン8-ヒドロキシキサンチン1H-プリン-2,6,8(3H,7H,9H)-トリオン7,9-ジヒドロ-1H-プリン-2,6,8(3H)-トリオントリケトプリン2,6,8-トリヒドロキシプリン9H-プリン-2,6,8-トリオール7H-プリン-2,6,8(1H,3H,9H)-トリオン尿酸 CRM6008‐A尿酸, 99%尿酸 CRM6008-aTRIKETOPURINEUric aciNSC 3975URIC OXIDEUricAcidGrURIC ACID(RG)
2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trioneUricum acidumIdelalisib metabolite m54trioxopurineDTXSID3042508NSC-3975268B43MJ25DTXCID1022508

データベース識別子

CAS
69-93-2
PubChem CID
1175
DTXSID
DTXSID3042508
ChEMBL
CHEMBL792
ChEBI
CHEBI:17775
UNII
268B43MJ25
EC Number
200-720-7
Nikkaji
J2.372H

物性

構造計算による物性

XLogP
-1.9
極性表面積
99.3 Ų
水素結合供与体数
4
水素結合受容体数
3
回転可能結合数
0
重原子数
12

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Purines
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning; Buffering
SpringerMaterials PropertiesCrystal structure
LogP-2.17
Solubility0.06 mg/mL

物理化学的性質

融点
300 °C · >300 °C (lit.)
沸点
297.02 °C · 297.02°C (rough estimate)
比重(密度)
1 · 1,9 g/cm3
屈折率
1.99 · 1.9900 (estimate)
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
水性ベース(少量、加温)
化学的性質 · 1 件

化学的特性Uric acid (C5H4O3N4) is a white solid that is insoluble in cold water, alcohol, or ether and sparingly soluble in hot water. It acts as a weak dibasic acid, creating two series of salts, with most being very slightly soluble in water (except for lithium urate, which is soluble).

安全と法規制

GHS分類

GHS Classification · 3 件

This chemical does not meet GHS hazard criteria for 96.8% (30 of 31) of all reports.

Not Classified

Aggregated GHS information provided per 31 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 3 件

Chemical: 1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-

Status: Active Update: 12-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23478

1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-: 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 SummaryMay cause irritation; Reproductive effects observed in rats; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified

安全データ

wgk
3
tsca
TSCA listed
rtecs
YU7050080
毒性
A nitrogenous end product and the principal excretory product of purine metabolism in mammals. In birds and reptiles, it is the principal end product of nitrogen metabolism in general. Defects in uric acid metabolism and excretion appear to be associated with a number of disease states, and it frequently occurs as a component of renal calculi. It has not been associated closely with toxic insults except in the case of lead poisoning. Lead causes an elevation in blood uric acid concentration (uric acidemia) and a decrease in uric acid excretion.
hs_code
29339900
risk_code
33-36/37/38

化学と産業

薬理情報

Pharmacodynamics · 1 件

Uric acid is a strong reducing agent (donates electrons) and an antioxidant. Normally in humans, one of the main antioxidants in plasma is uric acid. Several animal studies have found that animals given exogenous uric acid within 3 hours after a stroke had decreased infarct volume, improved neurologic function, and diminished inflammatory responses providing evidence for the neuroprotective effects of uric acid. In some early human studies, uric acid has so far shown similar neuroprotective effects, in both the cortex and subcortex areas, due to its antioxidant effects such as decreased lipid peroxidation, and there appears to be no significant toxicities.

Mechanism of ActionThe exact mechanism of action for uric acid's antioxidant effects have not yet been elucidated.
Metabolism/MetabolitesIn higher primates and humans, the enzyme, uricase, is absent, and thus uric acid is not further metabolized and is excreted. In all other mammals, uric acid is metabolized by uricase to allantoin, which is then excreted.
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Absorption, Distribution and ExcretionUric acid is eliminated by the kidneys.
Tissue LocationsAdipose Tissue

用途と製造

UsesFound in the urine of all carnivores; [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
Use ClassificationCosmetics -> Skin conditioning; Buffering
General Manufacturing Information1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-: ACTIVE
応用分野 · 5 件

解説尿酸化学合成もされている."無味,無臭の白い細かい結晶.分解点400 ℃ 以上.d251.836.λmax 207,236,292 nm(ε 14200,9800,2600,pH 8).エーテルに不溶,水に難溶,アルカリ性水溶液に可溶.二価の弱酸で,水溶液に硝酸を加え,蒸発乾固し,アンモニア水を注ぐと赤紫色のムレキシドを生成する(検出反応).また,尿酸はリンタングステン酸を還元して青色を呈する.この反応は尿酸の定量に用いられる.

用途痛風患者では,尿酸の代謝障害のため尿酸の生成が異常に増加し,血液中の量が増大するだけでなく,関節や腎臓に尿酸が沈着する.プリンヌクレオシドなどの合成原料として用いられる.

天然物の起源Uric acid is found in the urine, blood, and muscle juices of carnivorous animals (herbivorous animals secrete hippuric acid), in the excrement of birds, serpents and insects, and is an oxidation product of the complex nitrogenous compounds of the animal organism.

使用Uric Acid is a heterocyclcic compound that is created when purine nucleotides are broken down of by the human body. High blood concetration of Uric Acid is known as hyperuricemia and is often associated with a wide range of disorders and medical conditions such as gout, diabetes and metabolic syndrome. Uric acid may be a marker of oxidative stress and may have a potential therapeutic role as an antioxidant.

使用用途尿酸は研究目的や医薬品用途で使用される物質です。 尿酸はもともと体内で産生される物質であり、血液中の尿酸の濃度 (尿酸値) は「高尿酸血症」の指標として用いられています。高尿酸血症は、体内で尿酸が腎臓から排泄されにくくなったり、尿酸が多く産生されたりすることでおきる病気です。プリン体 (動物性の食品に多く含まれる、プリン骨格を有する物質) を多く含む食品をたくさん摂取することも、病気の一因となります。 男性・女性ともに「尿酸値7.0ミリグラム/デシリットル超」が、高尿酸血症の基準です。一方、尿酸値が「2ミリグラム/デシリットル以下」の場合は一般に「低尿酸血症」と診断されます。低尿酸血症は、体内で尿酸が腎臓から排泄されやすくなったり、尿酸があまり産生されなくなったりすることで生じる病気です。

調製方法 · 1 件

純化方法Crystallise uric acid from hot distilled H2O (the solubility in H2O is 1part/39,000parts at 18o and 1part/2,000parts at 100o). It is best purified by dissolving in an alkaline solution and acidifying with dilute HCl and drying it at 100o in a vacuum. [Bergmann & Dikstein J Am Chem Soc 77 691 1955, Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp256-257 1971, ISBN 0-471-38205-1, Beilstein 26 H 513, 26 I 151, 26 II 293, 26 III/IV 2619.]

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補足説明

定義本品は、次の化学式で表される複素環式化合物である。

定義A nitrogen compound produced from purines. In certain animals (e.g. birds and reptiles), it is the main excretory product resulting from breakdown of amino acids. In humans, uric acid crystals in the joints are the cause of gout.

関連反応

10 件

関連ノート

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