A8626

Sigma-Aldrich

Adenine

≥99%

Synonym(s):
Vitamin B4, 6-Aminopurine
Empirical Formula (Hill Notation):
C5H5N5
CAS Number:
Molecular Weight:
135.13
Beilstein/REAXYS Number:
5777
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51
Pricing and availability is not currently available.

biological source

synthetic

assay

≥99%

form

powder

application(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

Nc1ncnc2nHcnc12

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)

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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)

Packaging

1, 5, 25, 100 g in poly bottle
1 kg in poly bottle

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

22

Safety Statement

26-36

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

WGK 3

A novel approach to adenine-induced chronic kidney disease associated anemia in rodents
Rahman A, et al.
PLoS ONE, 13(2), e0192531-e0192531 (2018)
Energy transfer from adenosine triphosphate
Ross J
The Journal of Physical Chemistry B, 110(13), 6987-6990 (2006)
Adenine: an important drug scaffold for the design of antiviral agents
Wang C, et al.
Acta Pharmaceutica Sinica. B, 5(5), 431-441 (2015)
Toshihiro Kobayashi et al.
Analytical and bioanalytical chemistry, 406(5), 1365-1376 (2013-11-16)
To identify blood markers for early stages of chronic kidney disease (CKD), blood samples were collected from rats with adenine-induced CKD over 28 days. Plasma samples were subjected to metabolomic profiling by liquid chromatography-mass spectrometry, followed by multivariate analyses. In...
E M Ungerfeld et al.
Canadian journal of microbiology, 49(10), 650-654 (2003-12-10)
The inhibition of pyruvate oxidative decarboxylation as a means of decreasing ruminal methanogenesis in vitro was studied. In the first experiment, the addition of adenosine and adenine (with and without ribose) to ruminal batch cultures did not decrease methanogenesis. In...

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