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D-Glucuronic acid γ-lactone

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Identification
Molecular formula
C6H8O6
CAS number
32449-92-6
IUPAC name
(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one
State
State

The compound is typically in a solid state at room temperature.

Melting point (Celsius)
160.00
Melting point (Kelvin)
433.15
Boiling point (Celsius)
211.00
Boiling point (Kelvin)
484.15
General information
Molecular weight
176.13g/mol
Molar mass
176.1260g/mol
Density
1.6402g/cm3
Appearence

The compound appears as a white or off-white crystalline solid. It typically crystallizes in monoclinic prismatic forms and may appear slightly translucent depending on the level of purity.

Comment on solubility

Solubility of (3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one

The compound (3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one exhibits noteworthy solubility characteristics primarily due to its functional groups. The presence of multiple hydroxyl (-OH) groups significantly influences its interaction with water. Here are some key points regarding its solubility:

  • Highly Soluble in Water: The numerous hydroxyl functional groups enhance the compound's ability to form hydrogen bonds with water molecules, promoting solubility.
  • Polar Nature: The polar characteristics imparted by the hydroxyl groups mean that this molecule is more likely to dissolve in polar solvents rather than non-polar solvents.
  • Temperature Influence: As with many organic compounds, temperature can play a vital role in solubility. Generally, increased temperature can lead to increased solubility in water.
  • Miscibility: Due to its structure, this compound is expected to be more miscible with other polar solvents, such as alcohols and certain organic solvents that can participate in hydrogen bonding.

In summary, the solubility of (3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one can be classified as highly soluble in aqueous solutions, influenced predominantly by the arrangement and number of hydroxyl groups within its molecular structure.

Interesting facts

Interesting Facts about (3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one

(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one is a fascinating compound that showcases the complexity and beauty of organic chemistry. Often referred to as a sugar derivative, this compound is notable for its unique structural features and biological significance. Here are some intriguing facts:

  • Sugar Structure: This compound is part of the carbohydrate family due to its sugar-like structure, which includes multiple hydroxyl (-OH) groups that contribute to its reactivity and solubility.
  • Chirality: The stereochemistry of this compound is particularly interesting, with multiple stereocenters that influence its biological interactions. The designation of S for specific carbon atoms indicates the spatial arrangement of these groups, which is crucial for its biological function.
  • Biological Role: Compounds similar to this one play significant roles in various metabolic pathways. For instance, the presence of hydroxymethyl groups suggests its potential involvement in biological processes, such as serving as a substrate for enzymes.
  • Potential Applications: Due to its structural characteristics, this compound could be explored for potential applications in pharmaceuticals and biochemistry. It may serve as a precursor for synthesizing other biologically active molecules.
  • Research Relevance: Ongoing studies in organic synthesis and medicinal chemistry highlight compounds like (3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one as valuable targets for drug discovery and development.

This compound serves as a reminder of the intricate relationship between structure and function in chemistry. As research continues to evolve, compounds like this hold the potential to unlock new therapeutic avenues and enhance our understanding of biochemical processes.

Synonyms
1,4-Anhydro-D-Ara-onic
G26873TS
D-Arabinono-1,4-lactone
D-Arabino-1,4-lactone
D-Arabonolactone
2782-09-4
1,4-D-Arabinonolactone
(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
D-Arabonic acid-1,4-lactone
D-Arabinonic acid, gamma-lactone
42417-44-7
BRN 0082056
ARABINONIC ACID, gamma-LACTONE, D-
Arabinonic acid-1,4-lactone
SCHEMBL419845
CHEBI:16292
CUOKHACJLGPRHD-JJYYJPOSSA-
GEO-04321
AKOS040768084
MA31272
D-Arabino-1,4-lactone, >=95.0% (GC)
C00652
D-Arabino-1,4-lactone, >=97.0% (HPLC)
4-18-00-02260 (Beilstein Handbook Reference)
Q27101836
E6B670A8-4605-455A-B696-7C0B3A83D3E3
(3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-one
InChI=1/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4+/m1/s1
L-Arabinonic acid,2-amino-2,3,5-trideoxy-3-methyl-,g-lactone,hydrochloride(9ci)