CAS 604-68-2

Penta-O-acetyl-α-D-glucopyranose

Description:

Penta-O-acetyl-α-D-glucopyranose is a derivative of glucose, specifically an acetylated form of α-D-glucopyranose. It is characterized by the presence of five acetyl groups attached to the hydroxyl (-OH) groups of the glucose molecule, which enhances its lipophilicity and stability compared to unmodified glucose. This compound is typically a white to off-white crystalline solid and is soluble in organic solvents such as chloroform and acetone, but less soluble in water due to the acetyl groups. Penta-O-acetyl-α-D-glucopyranose is often used in organic synthesis and carbohydrate chemistry as a protecting group for hydroxyl functionalities, facilitating various chemical reactions without interfering with the glucose structure. Its molecular formula reflects the modifications made to the glucose backbone, and it is commonly utilized in the synthesis of glycosides and other carbohydrate derivatives. Additionally, it may have applications in pharmaceuticals and biochemistry, particularly in studies involving glycosylation reactions.

Formula: C₁₆H₂₂O₁₁

InChI: InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16+/m1/s1

InChI key: InChIKey=LPTITAGPBXDDGR-LJIZCISZSA-N

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

Synonyms:

• 1,2,3,4,6-Penta-O-Acetyl-A-D-Glucopyranose
• 1,2,3,4,6-Penta-O-Acetyl-A-Glucopyranose
• 1,2,3,4,6-Penta-O-Acetyl-Alpha-D-Glucopyranose
• 1,2,3,4,6-Penta-O-Acetyl-Alpha-D-Glucose
• 1,2,3,4,6-Penta-O-Acetyl-Alpha-Glucopyranose
• 1,2,3,4,6-Penta-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranose
• 1,2,3,4,6-Pentaacetyl-Alpha-D-Glucose
• 1,2,3,4,6-Tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranoside
• 2,3,4,5,6-Penta-O-Acetyl-D-Glucose
• 2,3,4,6-Tetra-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranosyl acetate
• Alpha-D-Glucopyranose, Pentaacetate
• Alpha-Glucose Pentaacetate
• D-Glucose, 2,3,4,5,6-Pentaacetate
• Glucopyranose Pentaacetate
• Glucopyranose, Pentaacetate, Alpha-D-
• Glucopyranose, pentaacetate, α-<span class="text-smallcaps">D</span>-
• Glucose 2,3,4,5,6-Pentaacetate
• Glucose Pentaacetate
• NSC 119335
• NSC 9290
• Penta-O-acetyl-α-<span class="text-smallcaps">D</span>-glucopyranose
• Pentaacetyl-α-<span class="text-smallcaps">D</span>-glucopyranose
• Pentaacetyl-α-<span class="text-smallcaps">D</span>-glucose
• Α-D-Glucose Pentaacetate
• α-<span class="text-smallcaps">D</span>-Glucopyranose, 1,2,3,4,6-pentaacetate
• α-<span class="text-smallcaps">D</span>-Glucopyranose, pentaacetate
• α-<span class="text-smallcaps">D</span>-Glucopyranosyl pentaacetate
• α-<span class="text-smallcaps">D</span>-Glucose pentaacetate
• α-D-Glucopyranose, pentaacetate
• Glucopyranose, pentaacetate, α-D-

α-D-Glucose pentaacetate, 99%

CAS: 604-68-2

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Formula: C₁₆H₂₂O₁₁

Purity: 99%

Color and Shape: White, Powder

Molecular weight: 390.34

Ref: 02-B22137

a-D-Glucopyranose, pentaacetate

CAS: 604-68-2

Formula: C₁₆H₂₂O₁₁

Purity: 98%

Color and Shape: Solid

Molecular weight: 390.3393

Ref: IN-DA00IAOZ

α-D(+)-Glucose pentaacetate

CAS: 604-68-2

α-D(+)-Glucose pentaacetate

Purity: 98%

Molecular weight: 390.34g/mol

Ref: 54-OR1015495

α-D-Glucose Pentaacetate

CAS: 604-68-2

Formula: C₁₆H₂₂O₁₁

Purity: ≥ 98.0% (dried basis)

Color and Shape: White or almost white powder

Molecular weight: 390.34

Ref: 7W-GC4753

Penta-O-acetyl-α-D-glucopyranose

CAS: 604-68-2

Formula: C₁₆H₂₂O₁₁

Purity: >97.0%(GC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 390.34

Ref: 3B-G0225

α-D-Glucose Pentaacetate

Controlled Product

CAS: 604-68-2

Applications D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets. Only α-D-glucose pentaacetate caused an immediate increase in insulin output. The β-anomer of D-glucose pentaacetate first transiently inhibited insulin release, this initial effect being followed by a secondary rise in secretory rate.
References Carpinelli, A., et al.: Mol. Cell Endocrinol., 17, 103 (1980), Hellman, B., et al.: Diab. Metab., 20, 123 (1994), Malaisse, W., et al.: Int. J. Mol. Med., 2, 331 (1998), Sener, A., et al.: Mol. Gen. Metab., 64, 135 (1998),

Formula: C₁₆H₂₂O₁₁

Color and Shape: Neat

Molecular weight: 390.34

Ref: TR-G596495

1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose

CAS: 604-68-2

1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose is a chemical compound that is an ester of the sugar penta-O-acetyl-a-D-glucopyranose and acetic acid. It has been shown to inhibit the activity of a number of enzymes, including proteins such as phospholipases C and D and fatty acid synthetases. The 1,2,3,4,6-penta-O-acetyl analogues have been shown to be effective in inhibiting model systems for the pathogenesis of inflammatory bowel disease and cancer. The hydroxyl group on the sugar ring may be important for binding to these enzymes.

Formula: C₁₆H₂₂O₁₁

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 390.34 g/mol

Ref: 3D-MP05197

a-D-Glucopyranose pentaacetate

CAS: 604-68-2

Formula: C₁₆H₂₂O₁₁

Purity: 95%

Color and Shape: Solid

Molecular weight: 390.341

Ref: 10-F243070

a-D-Glucose Pentaacetate extrapure, 99%

CAS: 604-68-2

Formula: C₁₆H₂₂O₁₁

Purity: min. 99%

Color and Shape: White, Crystalline powder

Molecular weight: 390.35

Ref: SR-12419