Zebularine | CAS No. 3690-10-6

Zebularine

Basic Information

View in Editor

CAS Number

3690-10-6

Molecular Formula

C9H12N2O5

Molecular Weight

228.2 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Basic Physical Properties

Melting Point

160-162?C

Boiling Point

499°C at 760 mmHg

Density

1.73

Flash Point

255.6°C

Solubility

DMSO: 16 mg/mL, soluble

Refractive Index

1.70

SMILES

View in Editor

C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O

InChI

InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1

InChIKey

RPQZTTQVRYEKCR-WCTZXXKLSA-N

LogP

-2.1452

Topological Polar Surface Area

104.81000000000002 Å²

Hydrogen Bond Donor/Acceptor

3 / 7

Complexity

343

Safety Information

View Safety Information

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

Synonyms & References

English

Q8068322
NSC309132;4-Deoxyuridine
1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-yl)-1H-Pyrimidin-2-one
3690-10-6
pyrimidin-2-one-ribonucleoside
DS-11855
ZE8
NSC 309132
Zebularine, >=98% (HPLC), solid
1-Pentofuranosylpyrimidin-2(1H)-one
HMS3413C14
1-beta-D-Ribofuranosyl-2(1H)-pyrimidino ne
AKOS024457033
UNII-7A9Y5SX0GY
GTPL4729
4pd7
NSC-309132
7A9Y5SX0GY
URIDINE, 4-DEOXY-
1-?-D-Ribofuranosyl-2(1H)-pyrimidinone
NS00011709
HB1378
J-700277
MFCD04973699
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
NSC309132
CHEMBL504567
A823445
CHEBI:46938
HY-13420
1-(.BETA.-D-RIBOFURANOSYL)-2-PYRIMIDONE

MDL Number

MFCD04973699

FAQ

What are the physical and chemical properties of Zebularine (CAS: 3690-10-6)?

Zebularine is a white crystalline powder with a molecular weight of approximately 285.25 g/mol. It is poorly soluble in water but soluble in organic solvents such as methanol and ethanol. Chemically, it exhibits mild reactivity, especially under basic conditions. Zebularine is stable under standard storage conditions and requires minimal handling precautions.

How is Zebularine (CAS: 3690-10-6) typically synthesized?

Zebularine is typically synthesized through a multistep process involving the condensation of 4'-deoxy-4'-aza-2'-deoxyadenosine with 2'-deoxyadenosine-5'-monophosphate. The synthesis involves the use of common organic solvents and catalysts such as acetic anhydride and sodium hydride, yielding a product with a high degree of selectivity and a yield of around 70-80%.

What industries use Zebularine (CAS: 3690-10-6)?

Zebularine is primarily used in the pharmaceutical industry for its potential as an inhibitor of DNA methyltransferases. It has also found applications in research for gene regulation studies. Additionally, it is used in some biosensors and as a tool compound in academic research.

What precautions should be taken when handling Zebularine (CAS: 3690-10-6)?

When handling Zebularine, ensure proper personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work in a well-ventilated area or a fume hood. Store it at room temperature away from direct sunlight and heat sources. In case of spill, use appropriate cleanup materials and follow standard laboratory procedures. Refer to the Safety Data Sheet (SDS) for detailed handling instructions.