1,7-Dimethylxanthine - ≥97% , CAS No.611-59-6

CAS: 611-59-6 Cat. No.: P137297 Peso molecular: 180.16 Beilstein Registry Number: 197907 Número EC: 210-271-9

GRADE & PURITY ≥97%

Synonyms

Caffeine Impurity F | 1,7-dimethyl-3H-purine-2,6-dione | 1,7-dimethyl-Xanthine | NSC 400018 | p-Xanthine | paraxanthine | 1,7-Dimethyl-1H-purine-2,6(3H,7H)-dione | 3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dione

Storage

Room temperature

Shipped In

Normal

Descripción general

Product Describtion:

Paraxanthine is a metabolite of caffeine which functions as an adenosine receptor ligand and a PARP-1 inhibitor in pulmonary epithelial cells. Studies suggest that Paraxanthine is structurally similar to caffeine and possibly mediates the physiological effects of caffeine. Also Paraxanthine acts as a competitive phosphodiesterase inhibitor, which increases intracellular cAMP, activates PKA, inhibits TNF-α and leukotriene synthesis. In addition, Paraxanthine acts as a Na+/K+ ATPase enzymatic effector.

Product Application:

1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).

Specifications

Sinónimos

Caffeine Impurity F | 1, 7-dimethyl-3H-purine-2, 6-dione | 1, 7-dimethyl-Xanthine | NSC 400018 | p-Xanthine | paraxanthine | 1, 7-Dimethyl-1H-purine-2, 6(3H, 7H)-dione | 3, 7-Dihydro-1, 7-dimethyl-1H-purine-2, 6-dione

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥97%

Nombres e identificadores

• Pubchem Sid: 488179848
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179848
• Sonrisas canónicas: CN1C=NC2=C1C(=O)N(C(=O)N2)C
• IUPAC Name: 1,7-dimethyl-3H-purine-2,6-dione
• InChIKey: QUNWUDVFRNGTCO-UHFFFAOYSA-N
• INCHI: 1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
• Isómeros SMILES: CN1C=NC2=C1C(=O)N(C(=O)N2)C
• WGK Alemania: 1
• RTECS: RV9380000
• Peso molecular: 180.16
• Beilstein: 197907
• Reaxy-Rn: 197907
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=197907&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Imidazopyrimidines
      • Subclass Purines and purine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Imidazopyrimidines
• Subclass: Purines and purine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Xanthines
• Alternative Parents: 6-oxopurines Alkaloids and derivatives Pyrimidones Hydroxypyrimidines N-substituted imidazoles Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Xanthine - 6-oxopurine - Purinone - Alkaloid or derivatives - Pyrimidone - Hydroxypyrimidine - N-substituted imidazole - Pyrimidine - Imidazole - Azole - Heteroaromatic compound - Lactam - Azacycle - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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BLM Tchem Bloom syndrome protein (4248 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

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KPNB1 Tbio Importin subunit beta-1/Snurportin-1 (25097 Activities)

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Objetivos asociados (no humanos)

Hdac6 Histone deacetylase 6 (222 Activities)

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Escherichia coli (133304 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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nfo Endonuclease 4 (425 Activities)

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Adora2b Adenosine A2 receptor (1828 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in ethanol (0.6 mg/ml), 0.1N NaOH (2 mg/ml), water (1 mg/ml), and 1N NH4OH (49.00 - 51.00 mg/ml).
• Punto de inflamación (°F): 48.2 °F
• Punto de inflamación (°C): 9 °C
• Punto de fusión (°C): 298 °C
• Peso molecular: 180.160 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 180.065 Da
• Monoisotopic Mass: 180.065 Da
• Topological Polar Surface Area: 67.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 267.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Xiaoyun Jiang, Yongling Lu, Lishuang Lv.  (2020)  Trapping Acrolein by Theophylline/Caffeine and Their Metabolites from Green Tea and Coffee in Mice and Humans.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:33253558] [10.1021/acs.jafc.0c05483]