A modified pyrimidine
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5-(Hydroxymethyl)-2’-deoxycytidine

Item No. 18162

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2'-deoxy-5-(hydroxymethyl)-cytidine
CAS Number
7226-77-9
Molecular Formula
C10H15N3O5
Formula Weight
257.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
277 nm
SMILES
O=C1N([C@H]2C[C@H](O)[C@@H](CO)O2)C=C(CO)C(N)=N1
InChi Code
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
InChi Key
HMUOMFLFUUHUPE-XLPZGREQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $203

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    25 mg

    $462

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    Product 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.1 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.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Song, C.X., Szulwach, K.E., Fu, Y., et al. Selective chemical labeling reveals the genome-wide distribution of 5-hydroxymethylcytosine. Nat. Biotechnol. 29(1), 68-72 (2011).

    2. Le, T., Kim, K.P., Fan, G., et al. A sensitive mass-spectrometry method for simultaneous quantification of DNA methylation and hydroxymethylation levels in biological samples. Anal. Biochem. 412(2), 203-209 (2011).

    3. Clark, T.A., Lu, X., Luong, K., et al. Enhanced 5-methylcytosine detection in single-molecule, real-time sequencing via Tet1 oxidation. BMC Biol. 11(4), 1-10 (2013).

    4. Krais, A.M., Park, Y.J., Plass, C., et al. Determination of genomic 5-hydroxymethyl-2'-deoxycytidine in human DNA by capillary electrophoresis with laser induced fluorescence. Epigenetics 6(5), 560-565 (2011).