ChemicalBook > CAS DataBase List > 5-(Hydroxymethyl)-2'-deoxycytidine

5-(Hydroxymethyl)-2'-deoxycytidine

Product Name
5-(Hydroxymethyl)-2'-deoxycytidine
CAS No.
7226-77-9
Chemical Name
5-(Hydroxymethyl)-2'-deoxycytidine
Synonyms
5-hmdC;5-Hydroxymethyl-dC;5-hydroxy methyl-2'-dC;5-Hydroxymethyl-2'-deoxycytidine;4-(HydroxyMethyl)-2'-deoxycytidine;2'-deoxy-5-(hydroxyMethyl)cytidine;2'-Deoxy-5-(hydroxymethyl)cytidine>Cytidine, 2'-deoxy-5-(hydroxyMethyl)-;5-hydroxymethyldeoxycytidine monophosphate;4-Amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(hydroxymethyl)pyrimidin-2(1H)-one
CBNumber
CB01327931
Molecular Formula
C10H15N3O5
Formula Weight
257.24
MOL File
7226-77-9.mol
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5-(Hydroxymethyl)-2'-deoxycytidine Property

Melting point:
205°C(lit.)
Boiling point:
575.0±60.0 °C(Predicted)
Density 
1.480 g/cm3
storage temp. 
Store at -20°C
solubility 
DMF: 5 mg/ml; DMSO: 20 mg/ml; PBS (pH 7.2): 10 mg/ml
form 
powder to crystal
pka
13.47±0.10(Predicted)
color 
White to Light yellow
λmax
274nm(H2O)(lit.)
InChI
InChI=1S/C10H15N3O5/c11-9-5(3-14)2-13(10(17)12-9)8-1-6(16)7(4-15)18-8/h2,6-8,14-16H,1,3-4H2,(H2,11,12,17)/t6-,7+,8+/m0/s1
InChIKey
HMUOMFLFUUHUPE-XLPZGREQSA-N
SMILES
OC[C@H]1O[C@@H](N2C=C(CO)C(N)=NC2=O)C[C@@H]1O
CAS DataBase Reference
7226-77-9
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Safety

HS Code 
2934.99.4400
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
D4220
Product name
2'-Deoxy-5-(hydroxymethyl)cytidine
Purity
>98.0%(T)
Packaging
50mg
Price
$192
Updated
2024/03/01
TCI Chemical
Product number
D4220
Product name
2'-Deoxy-5-(hydroxymethyl)cytidine
Purity
>98.0%(T)
Packaging
200mg
Price
$636
Updated
2024/03/01
Cayman Chemical
Product number
18162
Product name
5-(Hydroxymethyl)-2’-deoxycytidine
Purity
≥95%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
18162
Product name
5-(Hydroxymethyl)-2’-deoxycytidine
Purity
≥95%
Packaging
5mg
Price
$116
Updated
2024/03/01
Cayman Chemical
Product number
18162
Product name
5-(Hydroxymethyl)-2’-deoxycytidine
Purity
≥95%
Packaging
10mg
Price
$184
Updated
2024/03/01
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5-(Hydroxymethyl)-2'-deoxycytidine Chemical Properties,Usage,Production

Description

DNA methylation occurs mainly at the 5’-position of cytosine rings (5-methylcytosine) and occurs almost exclusively in CpG islands. Another epigenetic modification in DNA has been recently identified that involves hydroxymethylation of this same base (5-hydroxymethylcytosine), which potentially offers another level of transcriptional control. 5-(Hydroxymethyl)-2’-deoxycytidine is a modified pyrimidine that is capable of producing interstrand cross-links in double-stranded DNA and has been used to quantify DNA hydroxymethylation levels in biological samples.

Uses

5-(Hydroxymethyl)-2’-deoxycytidine is a modified pyrimidine that is capable of producing interstrand cross-links in double-stranded DNA and has been used to quantify DNA hydroxymethylation levels in biological samples.[Cayman Chemical]

Biological Functions

5-(hydroxymethyl)-2'-deoxycytidine (5-hmdC), the oxidative product from 5- (methyl)-2'-deoxycytidine (5-mdC) by TET protein, plays critical roles in a variety of physiological processes such as DNA demethylation, cellular differentiation, and epigenetic regulation, etc. In addition, 5-hmdC has also been demonstrated as a potential biomarker reflecting the diagnosis and prognosis of multiple diseases. Some studies have reported that the level of 5-hmdC significantly decreases in diversified cancers, which suggests its important role in tumor formation and development. In 2009, breakthrough studies found that the 5-hmdC is not the unique oxidative product of 5-mdC. 5-(hydroxymethyl)-2'-deoxycytidine is a crucial intermediate product of the DNA demethylation pathway, which can act as potential biomarkers reflecting the diagnosis and prognosis in multiple tumors. 5-hmdC in human urine is in the form of single deoxynucleosides produced by DNA degradation or metabolism, which can avoid digestion. 5-hmdC has been identified in human urine[1].

References

[1] Mengzhe Guo. “Enrichment and Quantitative Determination of 5-(Hydroxymethyl)-2′-deoxycytidine, 5-(Formyl)-2′-deoxycytidine, and 5-(Carboxyl)-2′-deoxycytidine in Human Urine of Breast Cancer Patients by Magnetic Hyper-Cross-Linked Microporous Polymers Based on Polyionic Liquid.” Analytical Chemistry 90 6 (2018): 3906–3913.

5-(Hydroxymethyl)-2'-deoxycytidine Preparation Products And Raw materials

Raw materials

Preparation Products

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5-(Hydroxymethyl)-2'-deoxycytidine Suppliers

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7226-77-9, 5-(Hydroxymethyl)-2'-deoxycytidineRelated Search:


  • 5-hydroxymethyldeoxycytidine monophosphate
  • 2'-deoxy-5-(hydroxyMethyl)cytidine
  • 4-(HydroxyMethyl)-2'-deoxycytidine
  • Cytidine, 2'-deoxy-5-(hydroxyMethyl)-
  • 5-Hydroxymethyl-dC
  • 4-Amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(hydroxymethyl)pyrimidin-2(1H)-one
  • 5-hydroxy methyl-2'-dC
  • 2'-Deoxy-5-(hydroxymethyl)cytidine&gt
  • 5-hmdC
  • 5-Hydroxymethyl-2'-deoxycytidine
  • 7226-77-9
  • Bases & Related Reagents
  • Carbohydrates & Derivatives
  • Heterocycles
  • Nucleotides