CAS 13265-84-4

D-glucal

Description:

D-glucal, with the CAS number 13265-84-4, is an organic compound classified as an aldohexose and is a derivative of glucose. It is characterized by its open-chain structure, which features a carbonyl group (aldehyde) at one end and multiple hydroxyl groups along the carbon chain. D-glucal is typically a white to off-white solid and is soluble in water due to its polar functional groups. This compound is known for its reactivity, particularly in glycosylation reactions, making it valuable in organic synthesis and carbohydrate chemistry. D-glucal can undergo various transformations, including oxidation and reduction, and can participate in cyclization reactions to form glycosides. Its structural features contribute to its biological significance, as it can serve as a precursor for more complex carbohydrates. Additionally, D-glucal's properties make it a subject of interest in research related to glycoproteins and other biomolecules.

Formula: C₆H₁₀O₄

InChI: InChI=1/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6+/m1/s1

InChI key: InChIKey=YVECGMZCTULTIS-PBXRRBTRSA-N

SMILES: C(O)[C@@H]1[C@@H](O)[C@H](O)C=CO1

Synonyms:

• (4xi)-1,5-anhydro-2-deoxy-D-threo-hex-1-enitol
• 1,5-Anhydro-2-deoxy-<span class="text-smallcaps">D</span>-arabino-hex-1-enitol
• 1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol
• <span class="text-smallcaps">D</span>-(+)-Glucal
• <span class="text-smallcaps">D</span>-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-
• <span class="text-smallcaps">D</span>-arabino-Hex-1-enopyranose, 1,2-dideoxy-
• D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-
• Glucal
• D-Glucal
• D-arabino-Hex-1-enopyranose, 1,2-dideoxy-
• (2R,3S,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol
• (2R)-3β,4α-Dihydroxy-3,4-dihydro-2H-pyran-2α-methanol
• (2R)-3,4-Dihydro-2α-(hydroxymethyl)-2H-pyran-3β,4α-diol
• 1,2-Didehydro-1,2-dideoxy-D-glucopyranose
• P-GLUCAL
• 1,5-Anhydro-2-deoxy-D-arabino-hexa-1-enitol
• 1,5-anhydro-2-deoxy-d-arabino-hex-1-enito

(2R,3S,4R)-2-(Hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol

CAS: 13265-84-4

Purity: 95.0%

Color and Shape: Solid

Molecular weight: 146.14199829101562

Ref: 10-F228374

D-Glucal

CAS: 13265-84-4

Formula: C₆H₁₀O₄

Purity: >97.0%(GC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 146.14

Ref: 3B-G0274

D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-

CAS: 13265-84-4

Formula: C₆H₁₀O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 146.1412

Ref: IN-DA0010YI

D-Glucal

CAS: 13265-84-4

Formula: C₆H₁₀O₄

Purity: ≥ 98.0%

Color and Shape: White to off-white or beige powder

Molecular weight: 146.14

Ref: 7W-GC9693

D-Glucal

CAS: 13265-84-4

D-Glucal

Purity: 98%

Molecular weight: 146.14g/mol

Ref: 54-BICL2293

D-Glucal

CAS: 13265-84-4

D-Glucal is a protonated d-glucal, which is a simple sugar. It reacts with the electron acceptor oxygen to form an oxidized product. This product can be reduced back to the original molecule by using a reducing agent, such as sodium borohydride or sodium dithionite. D-Glucal has been shown to inhibit the growth of tumor cells in mice that are resistant to other anticancer drugs. D-Glucal inhibits transcription and replication of DNA by binding to the DNA-dependent RNA polymerase and blocking its ability to transcribe messenger RNA (mRNA). The enzyme is also inhibited by glycosidic bond architectures that prevent it from binding to the DNA template strand. D-Glucal also has an effect on protein synthesis because it binds to proteins and prevents them from performing their normal functions.
D-Glucal has been used as a model system for studying cellular processes in mammalian cells, such as oxidation

Formula: C₆H₁₀O₄

Purity: Min. 98 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 146.14 g/mol

Ref: 3D-MG04732

D-Glucal

Controlled Product

CAS: 13265-84-4

Applications D-Glucal is an important building block for both solution- and solid-phase synthesis of oligosaccharides.
References Gilkes, N., et al.: J. Biol. Chem., 259, 10455 (1984), Street, I., et al.: Biochemistry, 31, 9970 (1992), Crout, D., et al.: Curr. Opin. Chem. Biol., 2, 98 (1998),

Formula: C₆H₁₀O₄

Color and Shape: Neat

Molecular weight: 146.14

Ref: TR-G412500