Xanthine
CAS number:69-89-6
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Molecular Formula:
C5H4N4O2
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Molecular Weight:
152.11g/mol
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Brief Introduction:
Xanthine is a purine derivative that plays a pivotal role as an intermediate in the metabolic breakdown of adenosine triphosphate (ATP), occurring naturally in various biological systems. Its accumulation, particularly post-mortem in muscle tissues, is directly correlated with the degradation of ATP and serves as a reliable biochemical indicator of freshness in fish and meat products. Beyond its significance in food quality assessment, xanthine is also of clinical interest due to its involvement in purine metabolism, with abnormal concentrations in body fluids associated with disorders such as hyperuricemia, gout, renal dysfunction, and perinatal asphyxia. In analytical applications, xanthine is frequently detected through biosensing technologies that leverage its oxidative transformation via xanthine oxidase, producing hydrogen peroxide as a measurable byproduct. Recent innovations have integrated enzyme-mimicking nanomaterials and metal-organic frameworks to enhance the sensitivity, stability, and selectivity of xanthine biosensors, thus expanding their utility in both food safety monitoring and biomedical diagnostics.
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Properities:
Molecular Structure Xanthine is a purine derivative with a structure consisting of two fused rings (a six-membered pyrimidine ring and a five-membered imidazole ring). [2] Tautomerism Xanthine exhibits two types of tautomerism: annular (proton migration between N7 and N9) and lactim-lactam (proton migration between N1, N3, and the carbonyl group at C2). [2] Substitution Sites Xanthine has multiple substitution sites: 1-, 3-, 7-, 8-, and 9-positions. [2] Natural Derivatives Common natural derivatives include caffeine, theophylline, theobromine, and paraxanthine. [2] Biological Role Xanthine and its derivatives are involved in purine metabolism and act as intermediates in the generation of GMP, GDP, and GTP. [2] Optical Properties Xanthine derivatives exhibit high birefringence with a refractive index difference (Δn ≈ 0.25) and a slow-axis refractive index (n ≈ 1.7). [1] Solubility Xanthine derivatives like caffeine, theophylline, and theobromine have poor water solubility due to strong inter-base hydrogen bonds and base stacking. [2] Metabolism Xanthine derivatives are metabolized through demethylation or other specific pathways depending on their structure. [2] Pharmacological Properties Xanthine derivatives are known for their bronchodilator, anti-inflammatory, anti-tumor, and antioxidant properties. [2] Detection Limit A colorimetric sensor based on PtRu bimetallic nanozyme has a detection limit of 8.92 nmol L⁻¹ for xanthine. [3]. Freshness Indicator Xanthine concentration increases with prolonged storage time in fish meat, making it a key indicator of freshness. [3] -
References:
[1] Surface-Guided Crystallization of Xanthine Derivatives for Optical Metamaterial Applications (Advanced Materials - 2023)
[2] Xanthine scaffold: scope and potential in drug development (Heliyon - 2018)
[3] High-performance colorimetric sensor based on PtRu bimetallic nanozyme for xanthine analysis (Food Chemistry: X - 2024)
Purines
Xanthine is a purine base and a derivative of hypoxanthine in purine metabolism.
Heterocyclic Compounds
Xanthine contains two nitrogen-containing rings, classifying it as a heterocyclic compound.
Oxopurines
Xanthine has two keto groups (at positions 2 and 6), making it a dioxopurine.
Tautomeric Compounds
Xanthine exhibits tautomerism between keto and enol forms under different pH conditions.
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