基本情報
- 標準SMILES
O=c1[nH]c(=O)c2[nH]cnc2[nH]1- InChIKey
LRFVTYWOQMYALW-UHFFFAOYSA-N- 分子式
- C5H4N4O2
- 平均分子量
- 152.11 g/mol
- 単同位体質量
- 152.03342537
概要
9H-xanthine is an oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. It has a role as a Saccharomyces cerevisiae metabolite. It is a tautomer of a 7H-xanthine.
名称と識別子
- 優先名称
- Xanthine
- IUPAC
- 3,7-dihydropurine-2,6-dione
- 現地名
- キサンチン
- 英語名
- Xanthine
- 分子式
- C5H4N4O2
- 分子量
- 152.11
名称と別名
名称をさらに表示
データベース識別子
- CAS
69-89-6- PubChem CID
- 1188
- DTXSID
DTXSID4035120- ChEMBL
CHEMBL1424- ChEBI
CHEBI:17712- UNII
- 1AVZ07U9S7
- EC Number
- 200-718-6
- Nikkaji
- J2.371J
物性
構造計算による物性
- XLogP
- -0.7
- 極性表面積
- 86.9 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 217
実験および物理化学的性質
Physical Description
Solid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
124.36 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
129.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
124 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
130.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
137.3 Ų [M+H]+
物理化学的性質
- 融点
- 300 °C · 300 °C
- 沸点
- 274.55 °C · 274.55°C (rough estimate)
- 比重(密度)
- 1.5452 · 1.5452 (rough estimate)
- 蒸気密度
- 5.3 · 5.3 (vs air)
- 屈折率
- 1.85 · 1.8500 (estimate)
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- 4 OH: · NH4OH: 溶けやすい
- 酸解離定数(Pka)
- 9.95 · pKa 9.95 (Uncertain)
- 外見
- 粉
- 色
- 白色~やや黄色
- 臭い (Odor)
- 無臭
- 由来生物
- synthetic (organic)
- 水溶解度
- 水に可溶(0.067g/L)。
- 比熱容量
- 0.99 J/ · Cp(crystal): 0.99 J/(g·K), at 25℃
- Merck
- 14 · 14,10059
- BRN
- 8733 · 8733
- 化粧品成分の機能
- スキンコンディショニング
- InChI
- 1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
- InChIKey
- LRFVTYWOQMYALW-UHFFFAOYSA-N
- SMILES
- O=C1NC(=O)c2nc[nH]c2N1
- LogP
- -0.73 · -0.730
- CAS データベース
- 69 · 69-89-6(CAS DataBase Reference)
- NISTの化学物質情報
- Xanthine(69-89-6)
- EPAの化学物質情報
- Xanthine (69-89-6)
化学的性質
化学的特性White to off-white crystalline powder
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 3.7% (3 of 82) of reports.
Warning
H317 (85.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 82 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: 1H-Purine-2,6-dione, 3,7-dihydro-
1H-Purine-2,6-dione, 3,9-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Purine-2,6-dione, 3,9-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 09-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33594
1H-Purine-2,6-dione, 3,7-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
May cause irritation; [Alfa Aesar MSDS] An irritant that may cause severe eye irritation; May cause skin sensitization; [Sigma-Aldrich MSDS] PubMed search for (69-89-6[EC/RN Number]) AND (allergic or sensitizer or sensitization or dermatitis): no records supporting skin sensitization; [PubMed]
毒性情報
Treatment
Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of xanthine toxicity until normal kidney function can be restored. Acute Exposure: 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.
Health Effects
Chronically high concentrations of xanthine can lead to health problems such as renal failure and xanthine kidney stones, one of the rarest types of kidney stones. Chronically high levels of xanthine are associated with at least 4 inborn errors of metabolism including: Xanthinuria type I, Xanthuria type II, Molybdenium Cofactor Deficiency, and Xanthinuria.
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- ZD7700000
- hs_code
- 29335990
- risk_code
- 36-43-36/37/38
- 化審法
- (5)-1133
- hazard_code
- Xi
- safety_code
- 36/37-37/39-26
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/Metabolites
Xanthine is readily converted to uric acid. The enzyme xanthine oxidase makes uric acid from xanthine and hypoxanthine, which in turn are produced from other purines. In humans and higher primates, uric acid is the final oxidation (breakdown) product of purine metabolism and is excreted in urine.
用途と製造
Uses
Found in animal organs, yeast, potatoes, coffee beans, and tea; [Merck Index] A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed) [ChemIDplus]
Naturally produced by the body (endogenous).
応用分野
解説C5H4N4O2(152.12).プリン塩基の一種で,図のような互変異性がある.動物の肝臓,尿,またはイースト,バレイショ,コーヒー豆,紅茶などに含まれる.グアニンの硫酸溶液を亜硝酸ナトリウムで脱アミノ化すると得られる."板状結晶(水より再結晶).加熱すると一部昇華し,融解せずに300 ℃ 以上で分解する.水,エタノールに難溶,鉱酸に可溶,アンモニア水や水酸化ナトリウム溶液に可溶.生体内ではアデニン,ヒポキサンチンの酸化,グアニンの脱アミノ化により生成し,酸化酵素の作用で尿酸になる.[CAS 69-89-6]森北出版「化学辞典(第2版)
使用2,6-Dihydroxypurine was fund in animal organs, yeast, patatoes, coffee beans, tea. 2,6-Dihydroxypurine can be used to relax and widen certain breathing passages of the lungs. It is also found that a large number of derivatives have adenoside receptor antagonist properties.
一般的な説明Xanthine is a purine that can be produced in the purine metabolic pathway via different precursors:Guanine deamination by guanine deaminaseHypoxanthine conversion by xanthine oxidoreductase
使用用途キサンチンの使用用途として、組織低酸素症のマーカーとして使用できる可能性が示唆されています。また、キサンチン誘導体の中には、薬として使用されている物質もあります。 最近の研究で、虚血性障害により体内のキサンチン濃度が上昇する結果が報告されました。そのため、キサンチン濃度を測定し、組織内で酸素が不足しているかどうかを判定できる可能性が示唆されています。 さらに、キサンチン誘導体として、 (英: theobromine) や (英: caffeine) などが存在します。具体的に、カフェインは、鎮痛剤、眠気除去薬、風邪薬の材料の一部として使用可能です。
調製方法
純化方法The monohydrate separates in a microcrystalline form on slow acidification with acetic acid of a solution of xanthine in dilute NaOH. It is also precipitated by addition of conc NH3 to its solution in hot 2N HCl (charcoal). After washing with H2O and EtOH, it is dehydrated by heating above 125o. Its solubility in H2O is 1 in 14,000parts at 16o and 1 in 1,500parts of boiling H2O, and separates as plates . It has no m, but the perchlorate has m 262-264o [Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp252-253 1971, ISBN 0-471-38205-1]. [Beilstein 26 H 447, 26 I 131, 26 II 260, 26 III/IV 2327.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義本品は、次の化学式で表される有機化合物である。
定義A poisonous colorless crystalline organic compound that occurs in blood, coffee beans, potatoes, and urine. It is used as a chemical intermediate.
関連反応
関連ノート
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