Adenine

• CAS: 73-24-5
• Catalog Number: ACM73245-1
• Category: Main Products
• Molecular Weight: 135.13 g/mol
• Molecular Formula: C5H5N5
• Description: Adenine, free base is a cytokinin that displays weak shoot proliferation and organogenesis relative to other adenine-based cytokinins.
• Synonyms: 6-Aminopurine; Vitamin B4
• IUPAC Name: 7H-purin-6-amine
• Canonical SMILES: C1=NC2=C(N1)C(=NC=N2)N
• InChI Key: GFFGJBXGBJISGV-UHFFFAOYSA-N
• Boiling Point: 553.5ºC at 760 mmHg
• Melting Point: >360°C(lit.)
• Flash Point: 220°C
• Density: 1.612 g/cm³
• Solubility: 1N KOH
• Appearance: White to Off-White Powder
• Application: Cytokinin
• Active Content: 95%
• EC Number: 200-796-1
• Exact Mass: 135.05400
• Form: Powder
• Hazard Statements: Xn,Xi
• Notes: Plant Tissue Culture Tested
• Packing Group: III
• Physical State: Solid
• Safety Description: 26-36
• Stability: Stable. Moisture-sensitive. Incompatible with strong oxidizing agents.
• Storage Temperature: 2 to 8 °C
• Supplemental Hazard Statements: H315-H319-H301
• Symbol: GHS06,GHS07
• WGK Germany: 3

Case Study

Stability Enhancement of Adenine via Adsorption onto Saponite under Simulated Hydrothermal Conditions

Ramírez-Vázquez L, et al. Planetary and Space Science, 2025, 264, 106151.

In this study, adenine was investigated for its stability in a prebiotic context by simulating hydrothermal impact-generated environments, using saponite as a geochemically relevant clay mineral. Given adenine's known thermal lability, experiments focused on its adsorption behavior and thermal degradation in the presence of saponite. Adsorption kinetics and isotherms revealed efficient adenine binding to saponite at acidic pH (3.5), achieving ~97% adsorption. Analytical techniques, including X-ray diffraction (XRD), X-ray fluorescence (XRF), Raman spectroscopy, ATR-FTIR, UV-vis spectrophotometry, and HPLC-UV chromatography, were employed to monitor the molecular interactions and confirm structural integrity. Thermolysis assays were conducted by heating aqueous adenine and adenine-saponite suspensions at 100-200 °C across a pH range of 3.5-8.9. The results demonstrated that saponite significantly retards adenine decomposition, suggesting a mineral-mediated stabilization mechanism.

Adenine-Assisted Synthesis of Phytic Acid-Doped Sulfonated Poly(ether ether ketone) Membranes for Acid Recovery

Jiang Z, et al. Chemical Engineering Science, 2025, 315, 121887.

Adenine was strategically utilized to modify sulfonated poly(ether ether ketone) (SPEEK), enabling the preparation of SPEEK-xA/IP6 membranes doped with phytic acid (IP6) for electrodialytic acid recovery. In the synthesis of SPEEK-40A, 7.50 g of SPEEK (17.03 mmol SO₃H) was dissolved in 75 mL DMSO and reacted with 3.04 g of CDI (18.73 mmol) at 60 °C for 3 hours to activate the sulfonic acid groups. Subsequently, 1.02 g of adenine (9.37 mmol) was added, and the reaction was continued for another 3 hours. After dialysis in deionized water for 72 hours to remove unreacted species, the product was evaporated and oven-dried at 60 °C for 24 hours, yielding 90-95%. The resulting adenine units acted as multifunctional crosslinking sites with IP6 and sulfonic groups, significantly enhancing membrane integrity. The SPEEK-40A/IP6 membrane demonstrated a proton flux of 2.16 mmol m⁻² s⁻¹ and H⁺/Fe²⁺ permselectivity of 58.5-1.72-fold higher than unmodified SPEEK and superior to commercial ASTOM membranes. These improvements are attributed to adenine's protonated structure, which facilitates transport and selectivity, confirming adenine's efficacy in fabricating high-performance membranes for acidic wastewater treatment.

UV-SERS Analysis of Adenine Adsorption on Cobalt Electrodes via Electrochemical Deposition

Remeikienė A, et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2025, 330, 125733.

In this study, adenine was investigated using ultraviolet surface-enhanced Raman spectroscopy (UV-SERS) to probe its adsorption behavior on electrochemically prepared cobalt electrodes. The cobalt substrate was fabricated by electrodeposition from aqueous CoSO₄ solution onto mechanically and chemically polished copper electrodes under negative potentials. The three-electrode system facilitated precise control of surface formation, yielding nanostructured Co surfaces optimized for UV-SERS enhancement at 325 nm excitation. Adenine solutions of varying concentrations, prepared in 0.1 M NaClO₄, were incubated on the cobalt surface under electrochemical polarization. UV-SERS spectra collected in situ revealed potential- and concentration-dependent vibrational features. Isotopic substitution (H₂O/D₂O) experiments were employed to confirm hydrogen bonding interactions and deduce adsorption orientation. Spectral analysis indicated that adenine predominantly adsorbs in its N9H tautomeric form, coordinating through the N7 atom of the imidazole ring and the exocyclic amino group. The ring plane aligns nearly perpendicular to the cobalt surface, facilitating strong molecule-metal interaction. This protocol underscores the utility of adenine as a model nucleobase for metal-interface studies and demonstrates the effectiveness of UV-SERS combined with electrochemically deposited cobalt electrodes for high-sensitivity molecular diagnostics and surface interaction profiling.

Synthetic Use

Upstream Synthesis Route 1

• 49721-45-1
• 77287-34-4

• 73-24-5

Reference: [1]Journal of the American Chemical Society,1949,vol. 71,p. 2246

Downstream Synthesis Route 1

• 75-03-6
• 73-24-5

• 2715-68-6
• 24309-36-2
• 43003-87-8

Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 3, p. 525 - 534

Downstream Synthesis Route 2

• 3083-77-0
• 73-24-5

• 5536-17-4

Reference: [1] Russian Journal of Bioorganic Chemistry, 2009, vol. 35, # 6, p. 739 - 745

Downstream Synthesis Route 3

• 73-24-5

• 2715-68-6

Reference: [1] Synthetic Communications, 1996, vol. 26, # 6, p. 1209 - 1221

Downstream Synthesis Route 4

• 73-24-5

• 68-94-0

Reference: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1889,vol. 13,p. 441

* For details of the synthesis route, please refer to the original source to ensure accuracy.