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About This Item
Empirical Formula (Hill Notation):
C10H15N3O5
CAS Number:
Molecular Weight:
257.24
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
218-390-8
MDL number:
Product Name
5-Methylcytidine, ≥99%
InChI key
ZAYHVCMSTBRABG-JXOAFFINSA-N
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
SMILES string
CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N
assay
≥99%
form
powder
mp
212-215 °C (dec.) (lit.)
solubility
water: 25 mg/mL, clear, colorless
Quality Level
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Application
5-Methylcytidine has been used as a standard for deriving the calibration curve in reversed phase high performance liquid chromatography (RP-HPLC).
5-Methylcytidine is used in studies of DNA methylation processes (epigenetics).
Biochem/physiol Actions
5-Methylcytidine is an alkylated pyrimidine plays an important role enhancing the stacking in A- and B- helices of nucleic acid, results in increase of the melting temperature and improves thermal stability leading to structural stabilization.
General description
5-Methylcytidine is a component of RNA in Escherichia coli. It is present in the RNA of plant, animal and bacterial origin. It is one of the C derivative present in transfer RNA (tRNA).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Leonidas Chouliaras et al.
Neurobiology of aging, 33(8), 1672-1681 (2011-07-19)
Aberrant DNA methylation patterns have been linked to molecular and cellular alterations in the aging brain. Caloric restriction (CR) and upregulation of antioxidants have been proposed as interventions to prevent or delay age-related brain pathology. Previously, we have shown in
DNA Methyltransferases - Role and Function, 30-30 (2016)
Advances in Carbohydrate Chemistry, Volume 14, 291-291 (1959)
Maria Beatrice Bitonti et al.
Journal of experimental botany, 53(371), 1047-1054 (2002-04-25)
Chromatin organization, nuclear DNA methylation and endogenous zeatin localization were investigated in shoot apical meristems (SAM) during juvenile and adult phases of peach (Prunus persica (L.) Batsch). The aim was to examine the extent to which these parameters could discriminate
K Itoh et al.
Clinica chimica acta; international journal of clinical chemistry, 234(1-2), 37-45 (1995-01-31)
A monoclonal antibody against 5-methylcytidine was prepared and characterized. This antibody, termed AMC, was reactive with compounds that had 5-methylcytosine structure (i.e. 5-methyl-2'-deoxycytidine, 5-methylcytidine and 5-methylcytosine). AMC had the highest reactivity to 5-methyl-2'-deoxycytidine among reactive compounds and had no or
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