Description

5-Methyl ara-C (CAS No. 6829-31-8) is a nucleoside analog with the molecular formula C₁₀H₁₅N₃O₅ and the IUPAC name 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one. This compound is a modified cytosine derivative where a methyl group is introduced at the 5-position of the pyrimidine ring, structurally related to arabinosylcytosine (ara-C). It is widely utilized in biochemical and pharmacological research, particularly in studies involving nucleoside metabolism, DNA synthesis inhibition, and anticancer mechanisms. 5-Methyl ara-C is supplied as a high-purity solid, rigorously tested for quality and stability, ensuring optimal performance in research applications. Store in a cool, dry environment to maintain integrity.

Properties

• CAS Number: 6829-31-8
• Complexity: 422
• IUPAC Name: 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidin-2-one
• InChI: InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7+,9-/m1/s1
• InChI Key: ZAYHVCMSTBRABG-JAGXHNFQSA-N
• Exact Mass: 257.10117059
• Molecular Formula: C10H15N3O5
• Molecular Weight: 257.24
• SMILES: CC1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
• Topological: 129
• Monoisotopic Mass: 257.10117059
• Synonyms: 6829-31-8, 1beta-D-Arabinofuranosyl-5-methylcytosine, 5-Methyl ara-C, 5-Methylarabinosylcytosine, NSC 96372, NSC 529544, 1 beta-D-arabinofuranosyl-5-methylcytosine, 2(1H)-Pyrimidinone, 4-amino-1-beta-D-arabinofuranosyl-5-methyl-, 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one, 4-Amino-1-beta-D-arabinofuranosyl-5-methyl-2(1H)-pyrimidinone, 4-Amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1H)-one, 1-?-D-Arabinofuranosyl-5-methylcytosine, SCHEMBL5953706, DTXSID101016978, 1-beta-D-Arabinofuranosyl-5-methylcytosine

Application

5-Methyl ara-C is primarily used in oncology research as a nucleoside analog to study its cytotoxic effects on rapidly dividing cells, particularly in leukemia models. It serves as a valuable tool for investigating DNA synthesis inhibition and the mechanisms of chemoresistance. Researchers also employ it in epigenetic studies due to its structural similarity to modified nucleosides involved in DNA methylation processes.

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