Cas no 5239-09-8 (β-Heptaacetylrutinose)

β-Heptaacetylrutinose is a chemically modified derivative of rutinose, characterized by the acetylation of all seven hydroxyl groups in its structure. This modification enhances its stability and solubility in organic solvents, making it a valuable intermediate in synthetic chemistry, particularly in glycosylation reactions. The acetyl groups provide protective functionality, allowing selective deprotection for further derivatization. Its well-defined structure and high purity make it suitable for research in carbohydrate chemistry, pharmaceutical development, and the synthesis of complex glycosides. The compound’s consistent performance and compatibility with standard purification techniques underscore its utility in controlled synthetic applications.
β-Heptaacetylrutinose structure
β-Heptaacetylrutinose structure
Product Name:β-Heptaacetylrutinose
CAS No:5239-09-8
MF:C26H36O17
MW:620.55385017395
CID:1577290
PubChem ID:78901
Update Time:2025-11-06

β-Heptaacetylrutinose Chemical and Physical Properties

Names and Identifiers

    • 6-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl)-β-D-glucose tetraacetate
    • 6-O-(2,3,4-Tri-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose tetraacetate
    • UNII-2OBJ2V67OI
    • 2OBJ2V67OI
    • RUTINOSE, HEPTAACETATE
    • D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 1,2,3,4-TETRAACETATE
    • .BETA.-D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, TETRAACETATE
    • 1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-deoxyhexopyranosyl)hexopyranose
    • [(2S,3S,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-3-yl] acetate
    • DTXSID90966803
    • Rutinose heptaacetylrutinose
    • EINECS 226-037-4
    • .BETA.-D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 1,2,3,4-TETRAACETATE
    • D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, TETRAACETATE
    • D-GLUCOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, TETRAACETATE
    • .BETA.-HEPTAACETYLRUTINOSE
    • RUTINOSE HEPTAACETYLRUTINOSE [MI]
    • 5239-09-8
    • RUTINOSE, HEPTAACETATE, .BETA.-
    • β-Heptaacetylrutinose
    • Inchi: 1S/C26H36O17/c1-10-19(36-11(2)27)21(38-13(4)29)23(40-15(6)31)25(35-10)34-9-18-20(37-12(3)28)22(39-14(5)30)24(41-16(7)32)26(43-18)42-17(8)33/h10,18-26H,9H2,1-8H3
    • InChI Key: LUCVIXHBPBCYCD-UHFFFAOYSA-N
    • SMILES: CC1C(OC(=O)C)C(OC(=O)C)C(OC(=O)C)C(OCC2C(OC(=O)C)C(OC(=O)C)C(OC(=O)C)C(OC(=O)C)O2)O1

Computed Properties

  • Exact Mass: 620.19524968g/mol
  • Monoisotopic Mass: 620.19524968g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 17
  • Heavy Atom Count: 43
  • Rotatable Bond Count: 17
  • Complexity: 1070
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.2
  • Topological Polar Surface Area: 212?2

β-Heptaacetylrutinose Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
H265230-50mg
β-Heptaacetylrutinose
5239-09-8
50mg
$586.00 2023-05-18
TRC
H265230-100mg
β-Heptaacetylrutinose
5239-09-8
100mg
$1143.00 2023-05-18
TRC
H265230-250mg
β-Heptaacetylrutinose
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250mg
$2520.00 2023-05-18
TRC
H265230-mg250
β-Heptaacetylrutinose
5239-09-8
mg250
$ 2090.00 2022-07-14

β-Heptaacetylrutinose Related Literature

Additional information on β-Heptaacetylrutinose

Recent Advances in the Study of β-Heptaacetylrutinose (CAS: 5239-09-8): Synthesis, Applications, and Pharmacological Potential

In recent years, β-Heptaacetylrutinose (CAS: 5239-09-8) has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This compound, a fully acetylated derivative of rutinose, serves as a crucial intermediate in the synthesis of various glycosides and flavonoid conjugates. Recent studies have explored its role in enhancing drug bioavailability, modulating biological pathways, and serving as a scaffold for novel drug design. This research brief aims to synthesize the latest findings on β-Heptaacetylrutinose, highlighting its chemical synthesis, biological activities, and emerging applications in medicine.

The synthesis of β-Heptaacetylrutinose has been optimized through innovative chemical and enzymatic approaches. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a high-yield, regioselective acetylation method using rutinose as the starting material, achieving over 90% purity. The process leverages mild reaction conditions and eco-friendly catalysts, addressing previous challenges related to scalability and environmental impact. Furthermore, advancements in enzymatic acetylation have enabled the production of β-Heptaacetylrutinose with enhanced stereochemical control, which is critical for its application in chiral drug development.

Pharmacological investigations have revealed that β-Heptaacetylrutinose exhibits promising bioactivity profiles. In vitro studies indicate its potential as an anti-inflammatory agent, with demonstrated inhibition of key pro-inflammatory cytokines such as TNF-α and IL-6. Additionally, its acetylated structure enhances membrane permeability, making it a valuable candidate for improving the delivery of poorly soluble drugs. Recent preclinical trials have explored its use in combination therapies for chronic inflammatory diseases, with preliminary results showing synergistic effects when co-administered with conventional therapeutics.

Beyond its therapeutic potential, β-Heptaacetylrutinose has found applications in nanotechnology and targeted drug delivery systems. Researchers have successfully conjugated this compound with nanoparticles to create hybrid carriers capable of site-specific drug release. A 2024 study in Advanced Drug Delivery Reviews highlighted its role in stabilizing lipid-based nanoparticles, thereby improving their circulatory half-life and reducing off-target effects. These innovations underscore the versatility of β-Heptaacetylrutinose in addressing contemporary challenges in drug formulation and delivery.

In conclusion, β-Heptaacetylrutinose (CAS: 5239-09-8) represents a multifaceted compound with broad implications for chemical biology and pharmaceutical sciences. Ongoing research continues to uncover its mechanistic underpinnings and expand its applications, from synthetic chemistry to clinical therapeutics. Future directions may include exploring its role in personalized medicine and further optimizing its synthetic pathways for industrial-scale production. As the field progresses, β-Heptaacetylrutinose is poised to play a pivotal role in the development of next-generation pharmaceuticals.

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