Cas no 20764-61-8 (1,2,3,4,5-Penta-O-acetyl-β-D-fructose)

1,2,3,4,5-Penta-O-acetyl-β-D-fructose is a fully acetylated derivative of β-D-fructose, commonly utilized as an intermediate in carbohydrate chemistry and synthetic applications. The acetylation of hydroxyl groups enhances stability, making it suitable for storage and handling under standard laboratory conditions. This compound serves as a versatile precursor for glycosylation reactions, protecting-group strategies, and the synthesis of modified sugars or nucleosides. Its well-defined structure and high purity ensure reproducibility in research and industrial processes. The acetyl groups facilitate selective deprotection, enabling controlled functionalization for targeted molecular design. This derivative is particularly valuable in medicinal chemistry and glycobiology for probing sugar-based interactions or developing bioactive compounds.
1,2,3,4,5-Penta-O-acetyl-β-D-fructose structure
20764-61-8 structure
Product Name:1,2,3,4,5-Penta-O-acetyl-β-D-fructose
CAS No:20764-61-8
MF:C16H22O11
MW:390.339286327362
CID:910491
PubChem ID:348017
Update Time:2025-06-09

1,2,3,4,5-Penta-O-acetyl-β-D-fructose Chemical and Physical Properties

Names and Identifiers

    • .β.-d-fructopyranose Pentaacetate
    • 1,2,3,4,5-PENTA-O-ACETYL-B-D-FRUCTOSE
    • .beta.-D-Fructopyranose pentaacetate
    • 1,2,3,4,5-Penta-O-acetylhex-2-ulopyranose #
    • NSC407029
    • .beta.-D-Fructopyranose, pentaacetate
    • beta-D-Fructopyranose, pentaacetate
    • NSC-407029
    • 1,2,3,4,5-Penta-O-acetylhex-2-ulopyranose
    • Fructopyranose, pentaacetate, .beta.-D-
    • (2,3,4,5-tetraacetyloxyoxan-2-yl)methyl acetate
    • JTQZPXRNYVFCJI-UHFFFAOYSA-N
    • [2,3,4,5-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
    • 20764-61-8
    • DTXSID20942973
    • 1,2,3,4,5-Penta-O-acetyl-β-D-fructose
    • Inchi: 1S/C16H22O11/c1-8(17)22-7-16(27-12(5)21)15(26-11(4)20)14(25-10(3)19)13(6-23-16)24-9(2)18/h13-15H,6-7H2,1-5H3
    • InChI Key: JTQZPXRNYVFCJI-UHFFFAOYSA-N
    • SMILES: CC(OCC1(C(OC(=O)C)C(OC(=O)C)C(OC(=O)C)CO1)OC(=O)C)=O

Computed Properties

  • Exact Mass: 390.116
  • Monoisotopic Mass: 390.116
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 11
  • Complexity: 614
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 4
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.5
  • Topological Polar Surface Area: 141?2

Experimental Properties

  • Density: 1.31
  • Boiling Point: 430.6°C at 760 mmHg
  • Flash Point: 186.1°C
  • Refractive Index: 1.484

1,2,3,4,5-Penta-O-acetyl-β-D-fructose Pricemore >>

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Additional information on 1,2,3,4,5-Penta-O-acetyl-β-D-fructose

Comprehensive Overview of 1,2,3,4,5-Penta-O-acetyl-β-D-fructose (CAS No. 20764-61-8): Properties, Applications, and Innovations

1,2,3,4,5-Penta-O-acetyl-β-D-fructose (CAS No. 20764-61-8) is a highly specialized carbohydrate derivative that has garnered significant attention in the fields of organic chemistry, pharmaceuticals, and biotechnology. This compound, characterized by its fully acetylated fructose backbone, serves as a critical intermediate in the synthesis of complex sugars and bioactive molecules. Its unique structural properties make it indispensable for researchers exploring glycosylation reactions, carbohydrate chemistry, and drug delivery systems.

The growing interest in sugar-based therapeutics and natural product derivatives has propelled the demand for compounds like 1,2,3,4,5-Penta-O-acetyl-β-D-fructose. With the rise of green chemistry and sustainable synthesis methods, researchers are increasingly focusing on optimizing the production of such derivatives to minimize environmental impact. This aligns with the broader trend of biobased materials and renewable resources, which are dominating discussions in both academic and industrial circles.

One of the most frequently searched questions related to this compound is: "What are the applications of 1,2,3,4,5-Penta-O-acetyl-β-D-fructose in drug development?" The answer lies in its role as a protective group in carbohydrate chemistry. By acetylating the hydroxyl groups of fructose, this compound prevents unwanted side reactions during synthetic processes, enabling the precise construction of oligosaccharides and glycoconjugates. These molecules are pivotal in designing targeted therapies and vaccine adjuvants, addressing current healthcare challenges such as antimicrobial resistance and personalized medicine.

Another hot topic is the compound's utility in flavor and fragrance industries. As consumers gravitate toward natural sweeteners and clean-label ingredients, 1,2,3,4,5-Penta-O-acetyl-β-D-fructose serves as a precursor for modifying taste profiles and enhancing stability in food products. This application resonates with the booming market for functional foods and nutraceuticals, where innovation is driven by health-conscious consumer demands.

From a technical standpoint, the compound's solubility, stability, and reactivity are key attributes often explored in research. Its compatibility with various solvents and reagents makes it a versatile building block for enzymatic transformations and catalytic processes. Recent advancements in enzymatic deacetylation have further expanded its potential, offering greener alternatives to traditional chemical methods.

In summary, 1,2,3,4,5-Penta-O-acetyl-β-D-fructose (CAS No. 20764-61-8) is a multifaceted compound with applications spanning pharmaceuticals, food science, and biotechnology. Its relevance in contemporary research underscores the importance of carbohydrate engineering and sustainable chemistry, making it a subject of enduring interest for scientists and industry professionals alike.

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