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Cytosine β-D-arabinofuranoside hydrochloride

SIGMA/C6645 - crystalline

Synonym: 1-(β-D-Arabino­furanosyl)­cytosine hydrochloride; Ara-C hydrochloride; Arabinocytidine hydrochloride; Arabinosylcytosine hydrochloride; Cytarabine hydrochloride; Cytosine arabinoside hydrochloride

CAS Number: 69-74-9
Empirical Formula (Hill Notation): C9H13N3O5 · HCl
Molecular Weight: 279.68
EC Number: 200-713-9
MDL Number: MFCD00012839
Linear Formula: C9H13N3O5 · HCl
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-C6645-25MG 25 mg
 $56.10
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45-C6645-100MG 100 mg
 $75.60
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45-C6645-500MG 500 mg
 $267.00
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45-C6645-1G 1 g
 $412.00
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45-C6645-5G 5 g
 $1440.00
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: C6645-100MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: C6645-1G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: C6645-500MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: C6645-5G

 

assay ≥99% (HPLC)
biological source synthetic (inorganic)
form crystalline
InChI 1S/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1
InChI key KCURWTAZOZXKSJ-JBMRGDGGSA-N
mp 197-198 °C (lit.)
Quality Level 200 
SMILES string Cl[H].NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O
solubility water: 50 mg/mL, clear, colorless
storage temp. 2-8°C
Application: Cytosine β-D-arabinofuranoside hydrochloride has been used in fetal bovine serum supplemented Dulbecco′s modified eagle medium (FBS-DMEM) and B27/neurobasal-A medium to inhibit the growth of glial cells. It has also been used to inhibit astrocyte proliferation in embryonic spinal cord neurons.
Biochem/physiol Actions: Ara-C is phosphorylated to Ara-CTP and is incorporatee into DNA. It inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation, and ultimately induces apoptosis via the PKC signaling pathway. Does not inhibit RNA synthesis. Anti-leukemia agent.
Other Notes: 2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research 
Packaging: 1, 5 g in glass bottle
Packaging: 100, 500 mg in glass bottle
Packaging: 25 mg in poly bottle
Purity ≥99% (HPLC)
mp 197-198 °C (lit.)
Storage Temp. 2-8°C
UNSPSC 12352202

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