purin-6(1H)-one
Hypoxanthine
CAS: 68-94-0
Molecular Formula: C5H4N4O
purin-6(1H)-one - Names and Identifiers
| Name | Hypoxanthine |
| Synonyms | Hypoxanthine 9H-Purin-6-ol Hypoxanthinee purin-6(1H)-one 6-Hydroxypurine HYPOXANTHINE(RG) purine-6(1H)-one 3,7-dihydropurin-6-one HYPOXANTHINE ANHYDROUS 3,7-dihydro-6H-purin-6-one 1,7-Dihydro-6H-purin-6-one 3,5-dihydro-6H-purin-6-one Hypoxanthine 6-Hydroxypurine 6-HYDROXYPURINE(HYPOXANTHINE) |
| CAS | 68-94-0 |
| EINECS | 200-697-3 |
| InChI | InChI=1/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-3H,(H,6,7,8,9,10) |
| InChIKey | FDGQSTZJBFJUBT-UHFFFAOYSA-N |
purin-6(1H)-one - Physico-chemical Properties
| Molecular Formula | C5H4N4O |
| Molar Mass | 136.11 |
| Density | 1.4295 (rough estimate) |
| Melting Point | >300 °C (lit.) |
| Boling Point | 250.36°C (rough estimate) |
| Flash Point | 109.3°C |
| Water Solubility | practically insoluble |
| Solubility | DMSO : 10 mg/mL (73.47 mM; Need ultrasonic) |
| Vapor Presure | 0.0148mmHg at 25°C |
| Appearance | White powder |
| Color | Colorless to yellow to brown, darken on storage with no loss of purity |
| Odor | Odorless |
| Merck | 14,4869 |
| BRN | 5811 |
| pKa | 8.7(at 25℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.8500 (estimate) |
| MDL | MFCD00005725 |
| Physical and Chemical Properties | Melting point 250°C water-soluble practically insoluble |
| Use | As a raw material for mercaptopurine and azathioprine |
purin-6(1H)-one - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | UP0791000 |
| TSCA | Yes |
| HS Code | 29335990 |
| Hazard Note | Harmful |
| Toxicity | LD50 intraperitoneal in mouse: 750mg/kg |
purin-6(1H)-one - Reference Information
| Purine compound | Hypoxanthine is a common purine compound with high activity 6-hydroxyl functional group. Derivatives of hypoxanthine, such as 6-mercaptopurine, are important anti-tumor drugs and plant growth regulators. Because purine compounds have a wide range of biological activities and application value, people have a strong interest in the efficient synthesis of these compounds. Hypoxanthine and xanthine are widely found in animals and plants. Inosinic acid of its nucleotide is the precursor of purine nucleotide of nucleic acid. It is also the mother of caffeine. Hypoxanthine can be produced by adenine deamination through the action of adenine deaminase or nitrous acid, and it can also cause inosine to undergo phospholysis through nucleoside phosphorylase. hypoxanthine (hypoxanthine,Hx) is a metabolite of nucleosides and an important alkaloid purine, which participates in regulating some physiological functions of human body. Studies have found that Hx can promote lipolysis in mice and reduce body fat mass. The anti-obesity study results of Hx on nutritional obese mice showed that after 4 weeks of administration, Hx administration group could effectively reduce the body mass, total fat mass, Lee's index and fat coefficient of obese mice, and the difference between Hx low dose group and model group was the most obvious. |
| Biosynthesis | In most microorganisms, purine synthesis mainly includes de novo synthesis and remediation. The de novo synthesis pathway of purines is to synthesize hypoxanthine nucleotides (IMP) with 5-phosphate ribose pyrophosphate (PRPP) and glutamine as precursors through 10 steps. IMP is then converted into adenosine monophosphate (AMP) and guanosine monophosphate (GMP) through two branches respectively. At the same time, IMP can be further degraded to hypoxanthine. Although the de novo synthesis pathway of purine compounds has long been proven, the synthesis pathway is tightly regulated by different levels such as transcription repression, transcription attenuation, and substrate feedback inhibition, and it is difficult to accumulate in the natural state. The Zhao Guang research group of the bio-based materials group of Qingdao Energy Institute recently successfully realized the efficient synthesis of hypoxanthine in E. coli, and used transcriptomics and fluorescence quantitative PCR technology to analyze the synthesis and regulation mechanism of purine metabolic pathways. First of all, the accumulation of hypoxanthine was increased by nearly 10 times by removing the transcriptional repressive regulation of the regulatory protein PurR, mitigating the substrate feedback inhibition by the key enzyme site-directed mutation, improving the accumulation of purine synthesis precursors, and destroying the branch metabolic pathway of IMP. Hypoxanthine accumulation reached 791.54 mg/L at 5L fermentor level. However, during hypoxanthine fermentation, it was found that the accumulation of by-products acetic acid and xanthine was significant. In order to solve the problem of accumulation of by-products, the researchers of this research group found that the global regulatory factor ArcA has a good effect in the regulation of purine metabolism. The accumulation of acetic acid by-products is reduced from 8.40g/L to 1.21g/L, while hypoxanthine The yield reaches 1243 mg/L. |
| chemical properties | needle crystal. Melting point> 360 ℃. |
| Uses | Used as raw material for mercaptopurine and azathioprine Intermediate of anti-malignant tumor drug 6-mercaptopurine. |
| Production method | Ethyl cyanoacetate, sodium ethoxide, and thiourea are cycled to obtain 2-mercapto-4-amino-6-hydroxypyrimidine, and then nitrification, reduction, elimination, and cyclization to obtain 6-hydroxypurine. |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Last Update：2024-04-09 20:52:54
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