キサンチン
Xanthine
基本情報
- CAS
69-89-6- 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
- 152.03342538
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
xanthine69-89-62,6-Dihydroxypurine2,6-dioxopurineXanthinIsoxanthineXanthic oxidePseudoxanthine1H-Purine-2,6-diol9H-Purine-2,6-diol3,7-Dihydro-1H-purine-2,6-dione1H-Purine-2,6-dione, 3,7-dihydro-
名称をさらに表示
キサンチン1H-プリン-2,6(3H,7H)-ジオン6-ヒドロキシ-1H-プリン-2(9H)-オン9H-プリン-2,6-ジオール2,6-ジオキソプリン3,7-ジヒドロ-1H-プリン-2,6-ジオン9H-プリン-2,6(1H,3H)-ジオン7H-プリン-2,6(1H,3H)-ジオン1H-プリン-2,6-ジオール2,6-ジヒドロキシプリンキサンチン, 結晶, 99~100%Xan7H-xanthineDioxopurine1H-Purine-2,6(3H,7H)-dione
Purine-2,6-diol3,7-dihydropurine-2,6-dione2,6(1,3)-Purinedion3,9-dihydro-1H-purine-2,6-dione2,6-Dioxo-1,2,3,6-tetrahydropurine1H-Purine-2,6-dione, 3,9-dihydro-9H-Purine-2,6-(1H,3H)-dionePurine-2,6(1H,3H)-dione
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
Chemical ClassesNitrogen Compounds -> Purines
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP
-0.73
-0.73
Solubility0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)
Melting Point> 300 °C
Physical Description
Solid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]
Solid
Dissociation Constants7.53
Collision Cross Section
124.36 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
120.6 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)]
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
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)
REACH registered substance: Purine-2(3H),6(1H)-dione (EC: 200-718-6)
1H-Purine-2,6-dione, 3,7-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 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]
Hazard Classes and CategoriesSkin Sens. 1 (85.4%)
毒性情報
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.
Tissue LocationsBladder
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
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).
U.S. Production2023: <50,000 lb
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information1H-Purine-2,6-dione, 3,9-dihydro-: ACTIVE
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）
関連反応
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