A8626

Adenine

≥99%

• Synonym(s): 6-Aminopurine, Vitamin B₄
• Empirical Formula (Hill Notation): C₅H₅N₅
• CAS Number: 73-24-5
• Molecular Weight: 135.13
• Beilstein: 5777
• EC Number: 200-796-1
• MDL number: MFCD00041790
• UNSPSC Code: 41106305
• PubChem Substance ID: 24891349
• NACRES: NA.51

Properties

• biological source: synthetic
• Assay: ≥99%
• form: powder
• technique(s): UV/Vis spectroscopy: suitable
• color: white to off-white
• mp: >360 °C (lit.)
• solubility: 0.5 M HCl: soluble 20 mg/mL, Grade III, colorless to faint yellow or tan
• storage temp.: room temp
• SMILES string: Nc1ncnc2[nH]cnc12
• InChI: 1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
• InChI key: GFFGJBXGBJISGV-UHFFFAOYSA-N
• Gene Information: human ... AKT1(207) , GSK3B(2932) , LCK(3932) , MAP3K1(4214) , MAPK14(1432) , MAPK8(5599) , MAPK9(5601) , MAPKAPK2(9261) , PRKACA(5566) , PRKCA(5578) , RAF1(5894) , ROCK2(9475) ; mouse ... Mapk1(26413) ; rat ... Camk2a(25400) , Mapk10(25272)

Description

General description

Adenine is a purine nucleobase. It is part of DNA, and RNA. Adenine is also a component of cofactors (NAD, FAD) and signaling molecules (cAMP).

Application

Adenine is suitable for use:

• as a component of boron-deficient media to grow yeast in order to assess whether yeast growth is stimulated by boron
• as a food supplement for adult rats to investigate the effects of dietary adenine overload
• as a nucleic acid base supplement in the basal media used to grow anaerobic Bacillus mojavensis and Bacillus subtilis in a study to show that DNA or deoxyribonucleosides are required for the anaerobic growth of these bacteria
• as an additive to investigate the effects of adenine on CH₄ production and on fermentation by ruminal batch cultures from nonlactating Holstein cows
• as a part of adenine diet in rats in a study to identify blood markers for early stages of adenine-induced chronic kidney disease (CKD)

Biochem/physiol Actions

Adenine is essential for many in vivo and in vitro biochemical processes. Adenine is converted to adenosine with ribose. On phosphorylation, it forms AMP, ADP and ATP. ATP is the energy currency of the cell and is required during cellular metabolism. Adenine is metabolized to is 2,8-dihydroxyadenine, which on accumulation in proximal tubules leads to the induction of chronic kidney disease (CKD) with severe anemia in rats. Adenine based derivatives elicit antiviral functionality against dsDNA viruses and are exploited for generating antiviral scaffolds.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves