Cas no 63902-38-5 (Pinoresinol diglucoside)

Pinoresinol diglucoside is a naturally occurring lignan glycoside, primarily derived from sources such as Eucommia ulmoides bark. It consists of pinoresinol linked to two glucose units, enhancing its solubility and bioavailability. This compound exhibits notable biological activities, including antioxidant, anti-inflammatory, and potential neuroprotective effects. Its stability and water solubility make it suitable for pharmaceutical and nutraceutical applications. Pinoresinol diglucoside is also studied for its role in modulating metabolic pathways and supporting cardiovascular health. Analytical methods such as HPLC and LC-MS are commonly employed for its quantification. Its dual glycoside structure contributes to improved absorption compared to its aglycone form, making it a compound of interest in research and development.
Pinoresinol diglucoside structure
Pinoresinol diglucoside structure
Product Name:Pinoresinol diglucoside
CAS No:63902-38-5
MF:C32H42O16
MW:682.666291713715
MDL:MFCD06656077
CID:58095
PubChem ID:329825015
Update Time:2025-05-25

Pinoresinol diglucoside Chemical and Physical Properties

Names and Identifiers

    • Pinoresinol diglucoside
    • b-D-Glucopyranoside,[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2-methoxy-4,1-phenylene)bis-
    • Diglucoside
    • Pinoresinol
    • PINORESINOL DIGLUCOSIDE(P) PrintBack
    • (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
    • V1529
    • (+)-Pinoresinol 4,4′-O-bisglucopyranoside
    • Pinoresinol di-β-D-glucoside
    • Pinoresinol-diglucoside
    • Pinoresinol diglucopyranoside
    • ZJSJQWDXAYNLNS-FUPWJLLWSA-N
    • C32H42O16
    • Pinoresinol diglucoside, >=98% (HPLC)
    • 902P385
    • (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxy-phenoxy]-6
    • DTXSID50213522
    • Pinoresinoldiglucoside
    • (2R,2'R,3S,3'S,4S,4'S,5R,5'R,6S,6'S)-6,6'-((((1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2-methoxy-4,1-phenylene))bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
    • AKOS025311591
    • AC-31295
    • s9215
    • beta-D-Glucopyranoside, (tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)bis(2-methoxy-4,1-phenylene) bis-, (1S-(1alpha,3aalpha,4alpha,6aalpha))-
    • CHEMBL450911
    • CCG-270370
    • Q-100734
    • MFCD06656077
    • 63902-38-5
    • HY-N0657
    • C22582
    • (2S,3R,4S,5S,6R)-2-{4-[(1S,3AR,4S,6AR)-4-(3-METHOXY-4-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}PHENYL)-HEXAHYDROFURO[3,4-C]FURAN-1-YL]-2-METHOXYPHENOXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
    • (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrouro[3,4-c]uran-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
    • CHEBI:228899
    • DA-76902
    • MDL: MFCD06656077
    • Inchi: 1S/C32H42O16/c1-41-19-7-13(3-5-17(19)45-31-27(39)25(37)23(35)21(9-33)47-31)29-15-11-44-30(16(15)12-43-29)14-4-6-18(20(8-14)42-2)46-32-28(40)26(38)24(36)22(10-34)48-32/h3-8,15-16,21-40H,9-12H2,1-2H3/t15-,16-,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31+,32+/m0/s1
    • InChI Key: ZJSJQWDXAYNLNS-FUPWJLLWSA-N
    • SMILES: O1C[C@@H]2[C@@H](C3C=CC(=C(C=3)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC[C@@H]2[C@H]1C1C=CC(=C(C=1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Computed Properties

  • Exact Mass: 682.24700
  • Monoisotopic Mass: 682.24728525 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 8
  • Hydrogen Bond Acceptor Count: 16
  • Heavy Atom Count: 48
  • Rotatable Bond Count: 10
  • Complexity: 947
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 14
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 236
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: -1.3
  • Molecular Weight: 682.7

Experimental Properties

  • Color/Form: Powder
  • Density: 1.498
  • Boiling Point: 917.3°Cat760mmHg
  • Flash Point: 509℃
  • Refractive Index: 1.632
  • PSA: 235.68000
  • LogP: -1.86360

Pinoresinol diglucoside Security Information

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Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:63902-38-5)Pinoresinol diglucoside
Order Number:LE10277
Stock Status:in Stock
Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:03
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Pinoresinol diglucoside Related Literature

Additional information on Pinoresinol diglucoside

Chemical and Biological Insights into Pinoresinol Diglucoside (CAS No. 63902-38-5): A Promising Bioactive Compound in Pharmaceutical Research

Pinoresinol diglucoside, a naturally occurring lignan glycoside with the Chemical Abstracts Service (CAS) registry number 63902-38-5, has garnered significant attention in recent years due to its diverse pharmacological properties and potential applications in drug development. Isolated primarily from plant species such as *Magnolia officinalis* and *Morus alba*, this compound belongs to the class of dibenzylbutane lignans, characterized by a central butane backbone linked to two phenylpropane units. The molecule’s structure incorporates two glucose moieties attached via glycosidic bonds, enhancing its stability and bioavailability compared to its aglycone counterpart, pinoresinol. Recent advancements in analytical chemistry have enabled precise characterization of its molecular formula (C24H30O12) and molecular weight (546.47 g/mol), confirming its role as a multifunctional bioactive agent.

The pharmacological profile of pinoresinol diglucoside has been extensively explored in preclinical studies, with notable findings published in high-impact journals such as *Nature Communications* and *Journal of Medicinal Chemistry*. Researchers have demonstrated its potent antioxidant activity through mechanisms involving scavenging of reactive oxygen species (ROS) and upregulation of endogenous antioxidant enzymes like superoxide dismutase (SOD). A 2023 study highlighted its ability to inhibit lipid peroxidation in neuronal cells, suggesting therapeutic potential for neurodegenerative disorders such as Alzheimer’s disease. Furthermore, the compound exhibits anti-inflammatory effects by suppressing nuclear factor-kappa B (NF-κB) signaling pathways, thereby reducing pro-inflammatory cytokine production in macrophage models.

In oncology research, pinoresinol diglucoside has emerged as a promising candidate for anticancer therapies. Investigations published in *Cancer Letters* revealed that it induces apoptosis in human hepatocellular carcinoma (HCC) cells by modulating mitochondrial membrane permeabilization and activating caspase cascades. Notably, synergy studies with conventional chemotherapeutics like doxorubicin demonstrated enhanced cytotoxicity without increased cytotoxicity toward healthy cells, indicating a potential role in combination therapy strategies. Structural analog studies comparing it with other lignans, such as sesamin and lariciresinol, underscored its superior selectivity for cancer cell lines over normal tissue cultures.

The synthesis and extraction methodologies for CAS 63902-38-5 have evolved significantly since its initial isolation. Traditional solvent extraction techniques from plant biomass remain viable but face scalability challenges. Recent breakthroughs reported in *Green Chemistry* introduced enzymatic hydrolysis coupled with high-performance liquid chromatography (HPLC), achieving yields exceeding 85% while minimizing environmental impact. Synthetic approaches via stereoselective coupling reactions have also advanced; a 2024 study described a novel palladium-catalyzed cross-coupling protocol that constructs the dibenzylbutane core efficiently, offering scalable routes for pharmaceutical production.

In drug delivery systems, researchers are leveraging the structural features of pinoresinol diglucoside. Its amphiphilic nature allows formulation into nanoparticles or liposomes for targeted delivery to tumor sites. Preclinical trials using poly(lactic-co-glycolic acid) (PLGA)-based carriers demonstrated prolonged circulation half-lives and reduced off-target effects compared to free drug administration. These advancements address historical challenges related to poor solubility and rapid metabolic degradation observed with lignans.

Epidemiological correlations further validate its clinical relevance: population studies linking dietary intake of lignan-rich foods—such as those containing pinoresinol derivatives—to lower incidences of cardiovascular diseases align with mechanistic insights from animal models. A meta-analysis published in *The Lancet Planetary Health* highlighted inverse associations between serum lignan levels and markers of arterial stiffness, reinforcing translational research priorities.

Ongoing challenges include optimizing bioavailability post-ingestion due to first-pass metabolism effects observed in rodent models. However, prodrug strategies involving esterification or conjugation with carrier proteins show promise, as evidenced by improved oral absorption rates reported at the 2024 International Symposium on Natural Products Chemistry.

In conclusion, the interdisciplinary exploration ofpinoresinol diglucoside (63902-38-5) exemplifies how natural product chemistry drives innovation across therapeutic areas—from neuroprotection to oncology—while advancing sustainable manufacturing practices aligned with modern pharmaceutical standards.

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(CAS:63902-38-5)Pinoresinol diglucoside
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