Skip to main content

Uridine

ADVERTISEMENT
Identification
Molecular formula
C9H12N2O6
CAS number
58-96-8
IUPAC name
1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
State
State

At room temperature, uridine is typically found in a solid state as a crystalline powder. It is highly stable under normal conditions and does not easily decompose or sublimate.

Melting point (Celsius)
162.00
Melting point (Kelvin)
435.15
Boiling point (Celsius)
720.00
Boiling point (Kelvin)
993.15
General information
Molecular weight
244.20g/mol
Molar mass
244.2040g/mol
Density
1.6780g/cm3
Appearence

Uridine appears as a white crystalline powder in its solid form. It is typically odorless and has a slightly sweet taste. It is often found in its crystalline form under laboratory conditions.

Comment on solubility

Solubility Insights

The compound 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione exhibits some intriguing characteristics regarding its solubility. Let’s delve into the factors affecting its ability to dissolve in various solvents:

  • Polarity: The presence of multiple hydroxyl (-OH) groups in its structure significantly enhances polarity, leading to increased solubility in polar solvents such as water.
  • Hydrogen Bonding: The -OH groups can form hydrogen bonds with water molecules, further facilitating solubility. This interaction is critical for compounds with similar functional groups.
  • Solvent Compatibility: Apart from water, this compound is likely to be soluble in other polar organic solvents (e.g., methanol, ethanol). However, it may show limited solubility in nonpolar solvents.
  • Crytallinity: If the molecular structure leads to high crystallinity, solubility may be reduced; thus, the methodology of synthesis can also impact solubility behavior.

Overall, the solubility of this compound is mainly influenced by its functional groups and molecular interactions with solvents. As stated, "like dissolves like," making it critical to choose an appropriate solvent that matches the compound's features for successful dissolution.

Interesting facts

Interesting Facts about 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

This compound is a significant member of the family of molecules that resemble nucleobases, which are the building blocks of nucleic acids. Its fascinating structure and functional properties make it a key area of research in fields ranging from medicinal chemistry to molecular biology.

Key Features:

  • Structural Diversity: The presence of a tetrahydrofuran ring adorned with multiple hydroxyl groups illustrates how small changes in molecular architecture can lead to significant impacts in biological activity.
  • Biosynthetic Relevance: Compounds like this one often appear in studies related to biochemical pathways, particularly those involved in ribonucleic acid (RNA) synthesis and modification.
  • Pharmacological Potential: Researchers focus on derivatives of this structure as potential candidates for therapeutic agents due to their ability to interact with biological targets at the molecular level.

Moreover, this compound embodies the concept of chirality in its stereochemistry. The specific configuration of the carbon atoms in the tetrahydrofuran moiety contributes to its biological function, allowing it to engage effectively with enzymes and receptors. As the renowned chemist Linus Pauling once said, "Life is not just a chemical reaction, but one that depends on the 3-dimensional arrangement of atoms."

In summary, the intricate design of 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione not only highlights its potential utility in medicine but also serves as an inspiring example of the beauty of chemical structures in biological systems.

Synonyms
3083-77-0
ARABINOFURANOSYLURACIL
Arauridine
1-beta-D-Arabinofuranosyluracil
Uracil arabinoside
Ara-U
Spongouridin
Uridine arabinoside
Uracil-beta-D-arabinofuranoside
Arabinosyluracil
1beta-D-Arabinofuranosyluracil
1-beta-D-Arabinofurnosyluracil
ZK0WMW5NQF
2,4(1H,3H)-Pyrimidinedione, 1-beta-D-arabinofuranosyl-
EINECS 221-386-9
BRN 0028749
Uracil, 1-beta-D-arabinofuranosyl-
DTXSID80184832
5-24-06-00136 (Beilstein Handbook Reference)
URACIL ARABINOSIDE [USP-RS]
NSC-68928
Uracil, 1-.beta.-D-arabinofuranosyl-
2,4(1H,3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-
1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Sponguridine
1-.BETA.-D-ARABINOFURANOSYL-2,4(1H,3H)-PYRIMIDINEDIONE
URACIL ARABINOSIDE (USP-RS)
Arabinoside, Uracil
Ara U
Uracil Arabinofuranoside
Arabinofuranoside, Uracil
1 beta D Arabinofuranosyl Uracil
1-beta-D-Arabinofuranosyl Uracil
1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidine-2,4-dione
Uracil, 1-beta-D-Arabinofuranosyl
DTXCID20107323
Uracil, 1-beta-D-arabinofuranosyl-(VAN)
Uracil, 1-beta-D-arabinofuranosyl-(VAN) (8CI)
1-BETA-D-ARABINOFURANOSYL-2,4(1H,3H)-PYRIMIDINEDIONE
1-(3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidine-2,4-dione
1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Spongouridine
Uracil 1-|A-D-arabinofuranoside
MFCD00065998
CHEBI:68346
1-b-D-Arabinofuranosyluracil
Spongouridine (VAN)
1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
1-beta-D-Arabinofuranosylpyrimidine-2,4(1H,3H)-dione (Uracil Arabinoside)
NSC 68928
1-beta-D-Arabinofuranosyl-(1H,3H)-pyrimidine-2,4-dione
UNII-ZK0WMW5NQF
Uracil, 1-beta-D-arabinofuranosyl- (VAN)
1-eta--rabinofuranosyluracl
1-?-D-Arabinofuranosyluracil
SCHEMBL359587
Uracil 1--D-arabinofuranoside
1-(b-D-Arabinofuranosyl)uracil
CHEMBL1092065
HY-N6652R
Uracil 1-??-D-arabinofuranoside
DRTQHJPVMGBUCF-CCXZUQQUSA-N
uracil-1-beta-D-arabinofuranoside
1-(beta-D-arabinofuranosyl)uracil
BCP29295
HY-N6652
HG1013
s4807
Uracil 1- beta -D-arabinofuranoside
AKOS015969693
CCG-266899
NA05962
1-| cent-D-ARABINOFURANOSYLURACIL
DS-14592
1-beta-D-Arabinofuranosyluracil (Standard)
CS-0083204
NS00076410
SW220050-1
Ara-U;Arauridine;Uracil 1-b-D-arabinofuranoside
1-(beta-D-arabinofuranosyl)-pyrimidin-2,4(3H)-dione
BRD-K32566431-001-01-4
Q27136843
2,4(1H,3H)-Pyrimidinedione, 1-|A-D-arabinofuranosyl-
Uracil 1-beta-D-arabinofuranoside, lymphoma antiproliferative
Uracil arabinoside, European Pharmacopoeia (EP) Reference Standard
Uracil arabinoside, United States Pharmacopeia (USP) Reference Standard