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A8626

Sigma-Aldrich

Adenine

≥99%

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Synonym(s):
6-Aminopurine, Vitamin B4
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

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

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This Item
A2786A5665PHR1383
vibrant-m

A8626

Adenine

vibrant-m

A2786

Adenine

vibrant-m

A5665

Adenine

vibrant-m

PHR1383

Adenine

biological source

synthetic

biological source

synthetic

biological source

-

biological source

-

color

white to off-white

color

white to off-white

color

white to off-white

color

-

form

powder

form

powder

form

powder

form

-

storage temp.

room temp

storage temp.

room temp

storage temp.

-

storage temp.

2-8°C

solubility

0.5 M HCl: soluble 20 mg/mL, Grade III, colorless to faint yellow or tan

solubility

0.5 M HCl: soluble 20 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

0.5 M HCl: soluble 20 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

-

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.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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1152-M

Adenine

Cristiene Okabe et al.
American journal of physiology. Renal physiology, 305(2), F155-F163 (2013-05-10)
Adenine overload promotes intratubular crystal precipitation and interstitial nephritis. We showed recently that these abnormalities are strongly attenuated in mice knockout for Toll-like receptors-2, -4, MyD88, ASC, or caspase-1. We now investigated whether NF-κB activation also plays a pathogenic role
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
Energy transfer from adenosine triphosphate
Ross J
The Journal of Physical Chemistry B, 110(13), 6987-6990 (2006)
The prebiotic role of adenine: a critical analysis
Shapiro R
Origins of Life and Evolution of the Biosphere : the Journal of the International Society For the Study of the Origin of Life, 25(1-3), 83-98 (1995)
A novel approach to adenine-induced chronic kidney disease associated anemia in rodents
Rahman A, et al.
PLoS ONE, 13(2), e0192531-e0192531 (2018)

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