Xanthine

HCID 1188

Basic information

CAS
69-89-6
Standard SMILES
O=c1[nH]c(=O)c2[nH]cnc2[nH]1
InChIKey
LRFVTYWOQMYALW-UHFFFAOYSA-N
Molecular formula
C5H4N4O2
Average molar mass
152.11 g/mol
Monoisotopic mass
152.03342537

Overview

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.

Names & identifiers

Preferred name
Xanthine
IUPAC
3,7-dihydropurine-2,6-dione
English name
Xanthine
Molecular formula
C5H4N4O2
Molecular weight
152.11

Names & synonyms

xanthine69-89-62,6-Dihydroxypurine2,6-dioxopurineXanthinIsoxanthineXanthic oxide1H-Purine-2,6-diolPseudoxanthine9H-Purine-2,6-diol3,7-Dihydro-1H-purine-2,6-dione1H-Purine-2,6-dione, 3,7-dihydro-
Show more names
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

Database identifiers

CAS
69-89-6
PubChem CID
1188
DTXSID
DTXSID4035120
ChEMBL
CHEMBL1424
ChEBI
CHEBI:17712
UNII
1AVZ07U9S7
EC Number
200-718-6
Nikkaji
J2.371J

Properties

Computed structural properties

XLogP
-0.7
Topological polar surface area
86.9 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Purines
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP-0.73
Solubility0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)

Physicochemical properties

Melting point
300 °C · 300 °C
Boiling point
274.55 °C · 274.55°C (rough estimate)
Density
1.5452 · 1.5452 (rough estimate)
vapor density
5.3 · 5.3 (vs air)
refractive index
1.85 · 1.8500 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

Regulatory Information · 4 items

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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 item

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%)

Toxicology

Treatment · 1 item

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 · 1 item

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.

Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity SummaryXanthine is a poorly soluble compound. As a result high concentrations of serum xanthine can lead to the formation of kidney stones (xanthine kidney stones) which can, over the long term, induce kidney failure.
Signs and SymptomsMay lead to arthropathy, myopathy, crystal nephropathy, urolithiasis, or renal failure.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
ZD7700000
hs_code
29335990
risk_code
36-43-36/37/38

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

Uses · 2 items

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
Applications · 3 items

Uses2,6-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.

UsesXanthine and xanthine oxidase system can be used to produce superoxide radicals.

General DescriptionXanthine is a purine that can be produced in the purine metabolic pathway via different precursors:Guanine deamination by guanine deaminaseHypoxanthine conversion by xanthine oxidoreductase

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
浙江华方药业股份有限公司0576-84169890
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionA poisonous colorless crystalline organic compound that occurs in blood, coffee beans, potatoes, and urine. It is used as a chemical intermediate.

DefinitionXanthine: a purine base, C5H4N4O2,found in many organisms.

Related reactions

40 records

Compound notes

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