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7-Methylxanthine (PC001170)

Record Information
Version1.0
Creation date2018-05-02 11:57:37 UTC
Update date2018-05-04 14:25:57 UTC
FoodComEx IDPC001170
FoodDB RecordFDB001978
Chemical Information
Name7-Methylxanthine
Description7-Methylxanthine, also known as heteroxanthin, 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. 7-Methylxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). 7-Methylxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, 7-methylxanthine participates in a number of enzymatic reactions. In particular, 7-methylxanthine and formaldehyde can be biosynthesized from paraxanthine through the action of the enzyme cytochrome P450 1A2. In addition, 7-methylxanthine can be converted into 7-methyluric acid through the action of the enzyme xanthine dehydrogenase/oxidase. In humans, 7-methylxanthine is involved in caffeine metabolism. Outside of the human body, 7-Methylxanthine has been detected, but not quantified in, arabica coffee. This could make 7-methylxanthine a potential biomarker for the consumption of these foods.
CAS Number552-62-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2,6-Dihydroxy-7-methylpurineHMDB
3,7-dihydro-7-Methyl-1H-purine-2,6-dioneChEBI
3,7-Dihydro-7-methyl-1H-purine-2,6-dione, 9CIdb_source
7-Methyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
7-Methyl-7H-purine-2,6-diolHMDB
7-MethylxanthinChEBI
7-Methylxanthinedb_source
HeteroxanthinChEBI
Heteroxanthinedb_source
MethylxanthineHMDB
Chemical FormulaC6H6N4O2
IUPAC name7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)
InChI KeyPFWLFWPASULGAN-UHFFFAOYSA-N
Isomeric SMILESCN1C=NC2=C1C(=O)NC(=O)N2
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • Alkaloid or derivatives
  • Hydroxypyrimidine
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-0.89GASPARI,F & BONATI,M (1987)
Experimental Water SolubilityNot Available
Melting PointMp 380° dec.DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage Conditions-18°C
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
AKSci 8053AB
MetaSci HMDB0001991
Sigma-Aldrich HMDB0001991
Toronto Research Chemicals M338580