Purin-2(3H),6(1H)-dion
Xanthine
Grundinformationen
- CAS
69-89-6- Standard-SMILES
O=c1[nH]c(=O)c2[nH]cnc2[nH]1- InChIKey
LRFVTYWOQMYALW-UHFFFAOYSA-N- Summenformel
- C5H4N4O2
- Durchschnittliche Molmasse
- 152,11 g/mol
- Monoisotopische Masse
- 152,03342538
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Xanthine
- IUPAC
- 3,7-dihydropurine-2,6-dione
- Lokaler Name
- Purin-2(3H),6(1H)-dion
- Englischer Name
- Xanthine
- Summenformel
- C5H4N4O2
- Molmasse
- 152.11
Namen und Synonyme
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-
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
69-89-6- PubChem CID
- 1188
- DTXSID
DTXSID4035120- ChEMBL
CHEMBL1424- ChEBI
CHEBI:17712- UNII
- 1AVZ07U9S7
- EC Number
- 200-718-6
- Nikkaji
- J2.371J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 86,9 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 217
Experimentelle und physikochemische Eigenschaften
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]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
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%)
Chemie und Industrie
Pharmakologische Informationen
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)
Verwendung und Herstellung
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
Anwendungen
Verwenden2,6-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.
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