Hypoxanthine CAS No. 68-94-0

Product Description

Hypoxanthine is a naturally occurring purine derivative and a key intermediate in the purine metabolism pathway. It is a purine nucleobase with a characteristic bicyclic ring structure. In biological systems, hypoxanthine is formed during the breakdown of adenosine monophosphate (AMP) and can be converted to xanthine and then to uric acid by the enzyme xanthine oxidase. It also plays a crucial role in the nucleotide salvage pathway, where it is recycled back into nucleotides like inosine monophosphate (IMP) via the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRT). Hypoxanthine is rarely incorporated into DNA or RNA but can contribute to mutagenesis if mismatched. Medically, elevated hypoxanthine levels are associated with conditions like gout, hyperuricemia, and Lesch-Nyhan syndrome, a genetic disorder caused by HGPRT deficiency. It also serves as a biomarker for hypoxia, ischemia, and oxidative stress. In industrial and research settings, hypoxanthine is used in cell culture media, food science for flavor enhancement, and antioxidant research. It appears as a white to off-white crystalline powder, is slightly soluble in water, and soluble in alkali.

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Product Use & Characteristics

• Chemical Structure and Properties

  • Molecular Formula: C₅H₄N₄O

  • Molecular Weight: 136.11 g/mol

  • IUPAC Name: 1,7-dihydropurin-6-one

  • Structure: A purine base resembling adenine and guanine but with a keto group (=O) at position 6 instead of an amino group. Contains an imidazopyridine ring structure, a derivative of purine.

  • Appearance: White to off-white crystalline powder

  • Solubility: Slightly soluble in water, insoluble in organic solvents such as ethanol and ether, soluble in alkali

• Biological Role

  • Purine Metabolism: Formed during the breakdown of adenosine monophosphate (AMP) via deamination or from inosine. Converted to xanthine by the enzyme xanthine oxidase, then further to uric acid (in humans) or allantoin (in some animals).

  • Nucleotide Salvage Pathway: Hypoxanthine can be recycled back into nucleotides (e.g., IMP, inosine monophosphate) via the enzyme HGPRT (hypoxanthine-guanine phosphoribosyltransferase).

  • Genetic Code: Rarely incorporated into DNA/RNA but may pair with cytosine (C), thymine (T), or uracil (U), contributing to mutagenesis if mismatched.

  • Cell Injury Marker: Elevated levels of hypoxanthine can indicate hypoxia (low oxygen levels) in tissues, as it accumulates when ATP degradation is increased due to oxygen deprivation.

  • Nucleic Acid Constituent: Hypoxanthine can occasionally be found as a component of nucleic acids, particularly in the anticodon of transfer RNA (tRNA) in the form of its nucleoside, inosine.

  • Energy Metabolism: Hypoxanthine can modulate energy metabolism in cells, improving intestinal barrier function by increasing intracellular ATP levels.

  • Other Roles: Involved in cholesterol metabolism, cell apoptosis, and neural signaling.

Uses

• Medical and Clinical Significance

  • Gout & Hyperuricemia: Elevated hypoxanthine levels (due to enzyme deficiencies or increased catabolism) can lead to excess uric acid, causing gout or kidney stones.

  • Lesch-Nyhan Syndrome: A genetic disorder caused by HGPRT deficiency, leading to hypoxanthine accumulation, neurological dysfunction, and self-injurious behavior.

  • Biomarker: Elevated hypoxanthine in blood/urine may indicate hypoxia (oxygen deficiency), ischemia, or oxidative stress.

  • Diagnosis of Immunodeficiency Diseases: HGPRT deficiency can lead to Lesch-Nyhan syndrome, in which patients have impaired hypoxanthine utilization, leading to excessive production of uric acid and related neuropsychiatric symptoms.

  • Organ Preservation and Reperfusion Injury: In transplant medicine, the accumulation of hypoxanthine is considered a sign of ATP decomposition during ischemia, and during reperfusion, a large number of free radicals are produced through the xanthine oxidase system, causing oxidative stress damage.

• Industrial and Research Applications

  • Cell Culture: Used in selective culture media, such as HAT medium (containing hypoxanthine, aminopterin, and thymidine), for screening hybridoma cells. Also used in media for hybridoma and cancer cell studies.

  • Biochemical Research: Used in studies of purine metabolism, DNA synthesis and repair mechanisms, oxidative stress response, etc. Helps assess enzyme activity (e.g., HGPRT activity).

  • Diagnostics: Used as a biomarker for tissue hypoxia, ischemia, or oxidative stress.

  • Food Science: Found in meat/fish as a product of ATP degradation; contributes to flavor.

  • Antioxidant Research: Studied for potential protective effects against oxidative damage.

Safety and Handling

• Hazards: Generally considered of low toxicity.

• Handling: Handle with standard laboratory precautions.

• Storage: Store in a cool, dry place. Keep container tightly closed.

Synonyms

• 6-Hydroxypurine

• Purine-6-ol

• Hypoxanthin

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