Grundinformationen
- 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
- 152,03342537
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
Weitere Namen anzeigen
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
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]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 300 °C · 300 °C
- Siedepunkt
- 274.55 °C · 274.55°C (rough estimate)
- Dichte
- 1.5452 · 1.5452 (rough estimate)
- Dampfdichte
- 5.3 · 5.3 (vs air)
- Brechungsindex
- 1.85 · 1.8500 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- 4 OH: · NH4OH: freely soluble
- pka
- 9.95 · pKa 9.95 (Uncertain)
- Aggregatzustand
- Powder
- Farbe
- White to slightly yellow
- Geruch (Odor)
- Odorless
- Biologische Quelle
- synthetic (organic)
- Wasserlöslichkeit
- Soluble in water(0.067g/L).
- Spezifische Wärmekapazität
- 0.99 J/ · Cp(crystal): 0.99 J/(g·K), at 25℃
- Merck
- 14 · 14,10059
- BRN
- 8733 · 8733
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONING
- 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 Datenbank
- 69 · 69-89-6(CAS DataBase Reference)
- NIST chemische Informationen
- Xanthine(69-89-6)
- EPA chemische Informationen
- Xanthine (69-89-6)
Sicherheit und Regulatorisches
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)
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]
Toxikologische Informationen
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.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29335990
- RTECS-Nr.
- ZD7700000
- risk_code
- 36-43-36/37/38
- hazard_code
- Xi
- safety_code
- 36/37-37/39-26
- Speicherklasse
- 11 - Combustible Solids
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.
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).
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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Ergänzende Hinweise
DefinitionA poisonous colorless crystalline organic compound that occurs in blood, coffee beans, potatoes, and urine. It is used as a chemical intermediate.
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