Cas no 144525-40-6 (Oxyresveratrol 3'-O-β-D-glucopyranoside)

Oxyresveratrol 3'-O-β-D-glucopyranoside is a glycosylated derivative of oxyresveratrol, characterized by the attachment of a β-D-glucopyranosyl moiety at the 3'-position. This modification enhances the compound's solubility and stability compared to its aglycone counterpart, making it more suitable for research applications in aqueous systems. The compound retains the bioactive properties of oxyresveratrol, including antioxidant and potential anti-inflammatory effects, while offering improved pharmacokinetic profiles. Its glucosidic structure may also influence bioavailability and metabolic processing. This derivative is of interest in pharmacological and nutraceutical studies, particularly for investigating glycosylation's role in modulating resveratrol-related bioactivity. Analytical standards of this compound are valuable for method development and comparative studies in natural product chemistry.
Oxyresveratrol 3'-O-β-D-glucopyranoside structure
144525-40-6 structure
Product Name:Oxyresveratrol 3'-O-β-D-glucopyranoside
CAS No:144525-40-6
MF:C20H22O9
MW:406.3833
CID:1998081
PubChem ID:6475174
Update Time:2025-05-28

Oxyresveratrol 3'-O-β-D-glucopyranoside Chemical and Physical Properties

Names and Identifiers

    • oxyresveratrol 3'-O-beta-D-glucopyranoside
    • oxyresveratrol 3'-O-beta-glucopyranoside
    • Oxyresveratrol 3'-O-β-D-glucopyranoside
    • oxyresveratrol-3'-O-beta-D-glucopyranoside
    • oxyresveratrol-3-O-beta-D-glucopyranoside
    • oxyresveratrol-3-O-beta-D-glycopyranoside
    • oxyresveratrol-3-O-beta-glucoside
    • 3-[(1E)-2-(2,4-Dihydroxyphenyl)ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside
    • Oxyresveratrol 3-O-glucoside
    • (2S,3R,4S,5S,6R)-2-[3-[(E)-2-(2,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
    • HY-N3517
    • 144525-40-6
    • Oxyresveratrol 3'-O-??-D-glucopyranoside
    • Oxyresveratrol 3'-O-
    • AKOS040760612
    • SCHEMBL22498791
    • CS-0023693
    • A-D-glucopyranoside
    • FS-7122
    • DTXSID801144144
    • Oxyresveratrol3'-O-beta-D-glucopyranoside
    • 3-[(1E)-2-(2,4-Dihydroxyphenyl)ethenyl]-5-hydroxyphenyl I(2)-D-glucopyranoside
    • DA-66424
    • Inchi: 1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-14-6-10(5-13(23)7-14)1-2-11-3-4-12(22)8-15(11)24/h1-8,16-27H,9H2/b2-1+
    • InChI Key: GGQVPULXXVQLRT-OWOJBTEDSA-N
    • SMILES: C1(OC2C=C(/C=C/C3C(O)=CC(O)=CC=3)C=C(O)C=2)C(O)C(O)C(O)C(CO)O1

Computed Properties

  • Exact Mass: 406.12638228 g/mol
  • Monoisotopic Mass: 406.12638228 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 29
  • Rotatable Bond Count: 5
  • Complexity: 544
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.7
  • Topological Polar Surface Area: 160
  • Molecular Weight: 406.4

Experimental Properties

  • Color/Form: Powder
  • Density: 1.593±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (3.7 g/l) (25 o C),

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Oxyresveratrol 3'-O-β-D-glucopyranoside Related Literature

Additional information on Oxyresveratrol 3'-O-β-D-glucopyranoside

Recent Advances in Oxyresveratrol 3'-O-β-D-glucopyranoside (CAS: 144525-40-6) Research: A Comprehensive Review

Oxyresveratrol 3'-O-β-D-glucopyranoside (CAS: 144525-40-6) is a naturally occurring stilbenoid glycoside derived from plants such as Morus alba (white mulberry) and Artocarpus lakoocha. This compound has garnered significant attention in recent years due to its diverse pharmacological properties, including antioxidant, anti-inflammatory, neuroprotective, and skin-whitening effects. The glycosylation of oxyresveratrol at the 3'-position enhances its solubility and bioavailability, making it a promising candidate for therapeutic and cosmetic applications. This research brief synthesizes the latest findings on Oxyresveratrol 3'-O-β-D-glucopyranoside, with a focus on its molecular mechanisms, preclinical studies, and potential clinical applications.

Recent studies have elucidated the molecular pathways through which Oxyresveratrol 3'-O-β-D-glucopyranoside exerts its biological effects. For instance, a 2023 study published in Journal of Natural Products demonstrated that this compound inhibits melanogenesis by downregulating the expression of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16F10 melanoma cells. Another study in Biochemical Pharmacology (2024) revealed its neuroprotective effects in a mouse model of Alzheimer's disease, where it reduced amyloid-beta aggregation and attenuated neuroinflammation via modulation of the NF-κB pathway. These findings underscore the compound's potential as a multi-target therapeutic agent.

In the realm of drug delivery, researchers have explored novel formulations to improve the stability and efficacy of Oxyresveratrol 3'-O-β-D-glucopyranoside. A 2024 paper in International Journal of Pharmaceutics reported the development of lipid-based nanoparticles encapsulating the compound, which significantly enhanced its skin permeation and retention in ex vivo models. Additionally, advances in synthetic biology have enabled the production of this glycoside through engineered microbial systems, as detailed in a recent Metabolic Engineering publication. These technological innovations address previous challenges related to the compound's natural scarcity and extraction costs.

Despite these promising developments, several challenges remain in translating Oxyresveratrol 3'-O-β-D-glucopyranoside into clinical applications. Pharmacokinetic studies in higher animal models are still limited, and the long-term safety profile requires further investigation. However, the compound's multifaceted bioactivities and improved physicochemical properties position it as a compelling subject for future research in dermatology, neurology, and metabolic disorders. Ongoing clinical trials in Asia (e.g., NCT05432830) focusing on its skin-lightening effects may soon provide human data to validate preclinical findings.

In conclusion, Oxyresveratrol 3'-O-β-D-glucopyranoside (144525-40-6) represents a versatile phytochemical with broad therapeutic potential. The convergence of mechanistic studies, formulation technologies, and bioproduction advances has accelerated its development trajectory. Future research should prioritize structure-activity relationship studies to optimize its efficacy and comprehensive toxicological assessments to facilitate regulatory approval. This compound exemplifies how glycosylation can enhance the therapeutic value of natural phenolics in modern medicine.

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