A8626

Adenine

≥99%, synthetic, powder

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

Properties

• Product Name: Adenine, ≥99%
• InChI key: GFFGJBXGBJISGV-UHFFFAOYSA-N
• InChI: 1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
• SMILES string: Nc1ncnc2[nH]cnc12
• 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
• Quality Level: 200
• 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

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[1]
• as a food supplement for adult rats to investigate the effects of dietary adenine overload[2]
• 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[3]
• as an additive to investigate the effects of adenine on CH₄ production and on fermentation by ruminal batch cultures from nonlactating Holstein cows[4]
• 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)[5]

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.[6] ATP is the energy currency of the cell and is required during cellular metabolism.[7] 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.[8] Adenine based derivatives elicit antiviral functionality against dsDNA viruses and are exploited for generating antiviral scaffolds.

General description

Adenine is a purine nucleobase.[6] It is part of DNA,[6] and RNA.[9] Adenine is also a component of cofactors (NAD, FAD) and signaling molecules (cAMP).

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves