Adenine

Base Information

• Chemical Name: Adenine
• CAS No.: 73-24-5
• Deprecated CAS: 22051-90-7,42911-33-1,42911-34-2,520-75-2,66224-65-5,1000264-10-7,71660-29-2,71660-30-5,1233216-08-4,1000264-10-7,42911-33-1,42911-34-2,520-75-2,66224-65-5,71660-30-5
• Molecular Formula: C5H5N5
• Molecular Weight: 135.128
• Hs Code.: 2933.59
• European Community (EC) Number: 200-796-1
• NSC Number: 757793,14666
• UNII: JAC85A2161
• DSSTox Substance ID: DTXSID6022557
• Nikkaji Number: J5.257D
• Wikipedia: Adenine
• Wikidata: Q15277
• NCI Thesaurus Code: C206
• Metabolomics Workbench ID: 37038
• ChEMBL ID: CHEMBL226345
• Mol file: 73-24-5.mol

Synonyms:4, Vitamin B;Adenine;B 4, Vitamin;Vitamin B 4

Chemical Property of Adenine

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 0.00172mmHg at 25°C
• Melting Point: >360 °C(lit.)
• Refractive Index: 1.954
• Boiling Point: 553.491 °C at 760 mmHg
• PKA: 4.12(at 25℃)
• Flash Point: 322.71 °C
• PSA: 80.48000
• Density: 1.612 g/cm³
• LogP: 0.51630
• Storage Temp.: Store at RT.
• Solubility.: 0.5 M HCl: soluble20mg/mL, Grade III, colorless to faint yellow
• Water Solubility.: 0.5 g/L (20 ºC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 135.05449518
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

Adenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC2=NC=NC(=C2N1)N
• DNA Composition and Nano-structuring: Adenine (A) is one of the four nucleobases found in DNA, along with Thymine (T), Cytosine (C), and Guanine (G). DNA oligomers composed of these nucleobases possess precise nano-structuring capabilities. Adenine's role in DNA allows for facile sequence programmability and specific hybridization properties with complementary sequences.
• Chiral Assembly Structures: Adenine's specific hybridization properties enable the design of chiral assembly structures using DNA. Studies have utilized adenine's interaction with complementary sequences to assemble nanoparticles into tetrahedral pyramidal shapes with distinct chirality. By designing attached oligomer sequences on different nanoparticles, chiral assembly structures with four distinct constituent nanoparticles have been constructed.
• Surface Interaction with Gold: Adenine exhibits high affinity with gold surfaces, followed by Cytosine, Guanine, and Thymine. This nucleobase-dependent surface interaction allows for synthetic control of nanomaterials. The kinetics and dynamics of adenine's interaction with gold surfaces play a crucial role in inducing single-nanoparticle morphology control in both monometallic and bimetallic systems.
• Variations in Bacterial Viruses: In bacterial viruses, variations in DNA bases such as Adenine help them escape degradation by bacterial restriction enzymes. For example, in the genome of cyanophage S-2L, Adenine is completely replaced by diaminopurine (Z), which forms non鈥揂 watson-Crick base pairing with Thymine.
• Applications in Organic Electronics: Adenine, as a constituent of DNA and RNA polymers, exhibits favorable properties for applications in organic electronics. Adenine's low oxidation potential makes it suitable for redox reactions. Additionally, adenine has been used as an electron-blocking layer in organic light-emitting diodes (OLEDs), leading to performance enhancements in terms of current efficiency and external quantum efficiency.

Technology Process of Adenine

There total 63 articles about Adenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

sulfuric acid (7664-93-9) + water (7732-18-5) + 5'-Deoxy-5'-methylthioadenosine (2457-80-9) → S-methyl-5-thio-D-ribose (23656-67-9,23656-91-9) + 7H-purin-6-ylamine (73-24-5,71660-29-2,71660-30-5)

Guidance literature:

at 100 ℃; Hydrolysis;

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + water (7732-18-5) + 5'-Deoxy-5'-methylthioadenosine (2457-80-9) → S-methyl-5-thio-D-ribose (23656-67-9,23656-91-9) + 7H-purin-6-ylamine (73-24-5,71660-29-2,71660-30-5)

Guidance literature:

Reference yield:

NAD (53-84-9,66844-06-2) + water (7732-18-5) → nicotinamide (98-92-0,1255150-40-3) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + 7H-purin-6-ylamine (73-24-5,71660-29-2,71660-30-5) + adenosine 5'-diphosphate (58-64-0,905904-58-7)

Guidance literature:

Einwirkung von UV-Strahlen auf eine wss. Loesung vom pH 6.Irradiation;

DOI:10.1021/ja01160a506 DOI:10.1016/0006-3002(56)90399-7

upstream raw materials:

2-(methylthio)-7H-purin-6-amine

N-(4,6-diaminopyrimidin-5-yl)formamide

N-(4,6-diamino-pyrimidin-5-yl)-thioformamide

6-amino-3,7-dihydro-purine-2-thione

Downstream raw materials:

3-benzyloxymethyl-3H-purin-6-ylamine

9-benzyloxymethyl-9H-adenine

tert-butyl 2-(6-amino-9H-purin-9-yl)acetate

9-benzyl-9H-purin-6-ylamine

Refernces

• 1、 Sturm, Matthew B.,Schramm, Vern L.. "Detecting ricin: Sensitive luminescent assay for ricin A-chain ribosome depurination kinetics". . p. 2847 - 2853. Retrieved 2009.
• 2、 Liu, Jia,Cai, Zhuan-Yun,Sun, Wei-Xin,Wang, Jia-Zheng,Shen, Xiao-Ru,Zhan, Chao,Devasenathipathy, Rajkumar,Zhou, Jian-Zhang,Wu, De-Yin,Mao, Bing-Wei,Tian, Zhong-Qun. "Plasmonic Hot Electron-Mediated Hydrodehalogenation Kinetics on Nanostructured Ag Electrodes". supporting information. p. 17489 - 17498. Retrieved 2020/11/12.
• 3、 -. "Total chemical synthesis method of adenine". Paragraph 0017; 0020; 0024. . Retrieved 2017/08/29.