Adenin
9H-Purin-6-amine · Adenin · 6-AMINOPURINE · 7H-PURIN-6-AMINE · Ade · Vitamin B4 · ANE · Purin-6-amine
Identifikatoren & physikalische Daten
| CAS No. | 73-24-5 |
|---|---|
| Summenformel | C5H5N5 |
| Durchschnittliche Molmasse | 135,13 g/mol |
| Monoisotopische Masse | 135,05449516 g/mol |
| SMILES | Nc1ncnc2nc[nH]c12 |
| InChIKey | GFFGJBXGBJISGV-UHFFFAOYSA-N |
| PubChem CID | 190 |
| ChEMBL | CHEMBL1797130 |
| ChEBI | CHEBI:16708 |
| EC No. | 200-796-1 |
| DTXSID | DTXSID6022557 |
| Lokaler Name | Adenin |
Chemische & physikalische Eigenschaften
| XLogP | -0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 80,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 127 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | -0.09 |
| Löslichkeit | 1.03 mg/mL>20.3 [ug/mL] (The mean of the results at pH 7.4)0.5 M HCl: soluble20mg/mL, Grade III, colorless to faint yellow or tan0.5 g/L (20 ºC) |
| Schmelzpunkt | 360 °C>360 °C (lit.) |
| Physical Description | Solid |
| Ionization Efficiency | Positive2.882.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 4.15 (at 25 °C) |
| Collision Cross Section | 125.2 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID6022557]122.4 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]119 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]123.66 Ų [M+H]+ [CCS Type: TW125.1 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]127.9 Ų [M+H]+ [CCS Type: DTMethod: stepped-field] |
| Siedepunkt | 238.81°C (rough estimate) |
| Dichte | 1.3795 (rough estimate) |
| Brechungsindex | 1.7000 (estimate) |
| Flammpunkt | 220°C |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 4.12(at 25℃) |
| Aggregatzustand | Liquid or Solid |
| Farbe | Clear colorless to light yellow |
| Geruch | Odorless |
| Biologische Quelle | synthetic |
| Merck | 14,152 |
| BRN | 5777 |
| Henry-Konstante | 1.3×109 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Moisture-sensitive. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | 1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) |
| InChIKey | GFFGJBXGBJISGV-UHFFFAOYSA-N |
| SMILES | Nc1ncnc2[nH]cnc12 |
| LogP (Verteilungskoeffizient) | -0.090 |
| CAS Datenbank | 73-24-5(CAS DataBase Reference) |
| NIST chemische Informationen | Adenine(73-24-5) |
| EPA chemische Informationen | Adenine (73-24-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (96.8%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 349 reports by companies from 10 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Purin-6-amineStatus: Active Update: 17-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/25078Adenine: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1H-Purin-6-amine: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (96.8%) |
| Toxizitätsübersicht | Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose, and it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between reactions. In older literature, adenine was sometimes called Vitamin B4Not Available |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 8-10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29335990 |
| RTECS-Nr. | AU6125000 |
| R-Sätze (R) | 22-20/21/22 |
| Toxizität | LD50 orally in rats: 745 mg/kg (Philips) |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
adenine is one of the purine nitrogenous bases that composes DNA and RNA; composed of two carbon–nitrogen rings. Adenine bonds with thymine in DNA and with uracil in RNA (see base pairing rule); it is also a major component of other molecules such as adenosine triphosphate.
History
Adenine is one of the two purines found in DNA and RNA. The other is guanine. Adenine and guanine are called bases in reference to DNA and RNA. A nucleic acid base attached to ribose forms a ribonucleoside. Adenine combined with ribose produces the nucleoside adenosine.
Verwenden
Adenine is used as an active component of boron-deficient media to grow yeast in order to assess whether yeast growth is stimulated by boron. It is useful as a local antiseptic and vitamin B4. Further, it is used in the microbial determination of niacin. It is also employed as a food supplement for adult rats to investigate the effects of dietary adenine overload. In addition to this, it is used in the production of nucleotides of the nucleic acids.