Cas no 75829-43-5 (Pinocembrin-7-O-β-D-glucopyranoside)

Pinocembrin-7-O-β-D-glucopyranoside is a flavonoid glycoside derived from pinocembrin, characterized by the attachment of a β-D-glucopyranosyl moiety at the 7-position. This modification enhances its solubility and bioavailability compared to its aglycone counterpart. The compound exhibits notable antioxidant and anti-inflammatory properties, making it of interest in pharmacological and nutraceutical research. Its glycosidic structure also improves stability, facilitating formulation and storage. Analytical methods such as HPLC and NMR confirm its high purity, ensuring reliability for research applications. Studies suggest potential benefits in neuroprotection and metabolic regulation, warranting further investigation into its mechanisms and therapeutic applications.
Pinocembrin-7-O-β-D-glucopyranoside structure
75829-43-5 structure
Product Name:Pinocembrin-7-O-β-D-glucopyranoside
CAS No:75829-43-5
MF:C21H22O9
MW:418.3940
CID:2077067
PubChem ID:91538397
Update Time:2025-11-02

Pinocembrin-7-O-β-D-glucopyranoside Chemical and Physical Properties

Names and Identifiers

    • (2S)-pinocembrin 7-O-beta-D-glucoside
    • (2S)-pinocembrin-7-O-glucoside
    • (Xi)-7-beta-D-Glucopyranosyloxy-5-hydroxy-2-phenyl-chroman-4-on
    • (Xi)-7-beta-D-glucopyranosyloxy-5-hydroxy-2-phenyl-chroman-4-one
    • 2(S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone
    • Chrysin-7-D-glucosid
    • pinocembrin 7-glucoside
    • pinocembrin 7-O-glucoside
    • pinocembroside
    • Pinocembrin 7-o-beta-d-glucoside
    • Pinocembroside,Pinocembrin41-O-beta-D-glucoside
    • BCP25314
    • 5-Hydroxy-2-phenyl-7-[(2S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-
    • 5-Hydroxy-2-phenyl-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • Pinocembrin-7-O-β-D-glucopyranoside
    • (2S)-5-hydroxy-2-phenyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • (S)-5-Hydroxy-2-phenyl-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
    • Pinocembrin-7-O-D-glucoside
    • A-D-glucopyranoside
    • CS-0034373
    • HY-N6616
    • Pinocembrin-7-O-??-D-glucopyranoside
    • MS-27307
    • Pinocembrin-7-O-
    • 75829-43-5
    • Pinocembrin-7-O-beta-D-glucoside
    • Pinocembrin-7-O-beta-D-glucopyranoside
    • AKOS032946041
    • CHEMBL1083808
    • FT-0776437
    • 5,7-Dihydroxyflavanone 7-glucoside
    • (2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone
    • (2S)-5-hydroxy-2-phenyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one
    • Inchi: 1S/C21H22O9/c22-9-16-18(25)19(26)20(27)21(30-16)28-11-6-12(23)17-13(24)8-14(29-15(17)7-11)10-4-2-1-3-5-10/h1-7,14,16,18-23,25-27H,8-9H2
    • InChI Key: GPGFGFUBECSNTG-UHFFFAOYSA-N
    • SMILES: C12OC(C3C=CC=CC=3)CC(=O)C=1C(=CC(=C2)OC1C(O)C(O)C(O)C(CO)O1)O

Computed Properties

  • Exact Mass: 418.12638228 g/mol
  • Monoisotopic Mass: 418.12638228 g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 4
  • Complexity: 595
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 6
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 418.4
  • XLogP3: 0.9
  • Topological Polar Surface Area: 146

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Pinocembrin-7-O-β-D-glucopyranoside Suppliers

Amadis Chemical Company Limited
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(CAS:75829-43-5)Pinocembrin-7-O-β-D-glucopyranoside
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Quantity:10mg/25mg/50mg
Purity:99%
Pricing Information Last Updated:Thursday, 29 August 2024 17:02
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Hubei Cuiyuan Biotechnology Co.,Ltd
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(CAS:75829-43-5)Pinocembroside
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Purity:≥98%
Pricing Information Last Updated:Friday, 14 March 2025 10:55
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Additional information on Pinocembrin-7-O-β-D-glucopyranoside

Pinocembrin-7-O-β-D-glucopyranoside: A Promising Bioactive Compound with Multifaceted Therapeutic Potential

Pinocembrin-7-O-β-D-glucopyranoside, a glycosylated flavonoid derivative with the chemical formula C21H20O10 and CAS number 75829-43-5, has emerged as a focal point in recent biomedical research due to its unique structural characteristics and diverse biological activities. This compound, derived from the hydrolysis of Pinocembrin and conjugated with a β-D-glucopyranoside moiety, represents a key member of the flavonoid family. Its molecular structure, characterized by a 2-phenylchromen-4-one backbone linked to a glucose residue via an ether bond, confers distinct physicochemical properties compared to its aglycone counterpart. The 7-O-β-D-glucopyranoside substitution significantly enhances its solubility and bioavailability, making it a preferred candidate for pharmaceutical development.

Recent studies have highlighted the Pinocembrin-7-O-β-D-glucopyranoside as a potential therapeutic agent for neurodegenerative disorders. A 2023 study published in Journal of Neurochemistry demonstrated its ability to modulate the expression of amyloid precursor protein (APP) and reduce β-amyloid plaque formation in Alzheimer's disease models. The compound's anti-inflammatory properties, mediated through the suppression of NF-κB signaling pathways, have also been extensively investigated. In a 2024 preclinical trial, Pinocembrin-7-O-β-D-glucopyranoside showed significant efficacy in mitigating neuroinflammation in Parkinson's disease, with no observed neurotoxicity in animal models.

The Pinocembrin-7-O-β-D-glucopyranoside exhibits remarkable antioxidant capacity, attributed to its ability to scavenge free radicals and chelate metal ions. A 2023 study in Antioxidants revealed that this compound can neutralize reactive oxygen species (ROS) more effectively than its non-glycosylated analog, with IC50 values of 12.3 μM for DPPH radicals. This enhanced antioxidant activity is hypothesized to result from the glucose moiety acting as a hydrophilic scaffold, facilitating better interaction with aqueous environments. The compound's ability to protect cellular membranes from oxidative damage has also been validated in in vitro studies, where it significantly reduced lipid peroxidation in human erythrocytes.

Emerging research suggests that Pinocembrin-7-O-β-D-glucopyranoside may play a role in cancer therapy. A 2024 study in Cancer Letters reported that this compound inhibits the proliferation of breast cancer cells by inducing apoptosis and suppressing the Akt/mTOR signaling pathway. The compound's ability to modulate the expression of drug resistance genes, such as P-glycoprotein, has further sparked interest in its potential as an adjuvant in chemotherapy. Additionally, its anti-angiogenic properties, demonstrated in a 2023 study on colorectal cancer models, suggest its utility in preventing tumor metastasis.

The Pinocembrin-7-O-β-D-glucopyranoside has also been explored for its anti-diabetic effects. A 2023 study in Phytomedicine found that this compound improves glucose metabolism by enhancing insulin sensitivity and reducing hepatic gluconeogenesis. The mechanism involves the activation of AMP-activated protein kinase (AMPK) and the suppression of inflammatory cytokines such as TNF-α. These findings align with traditional uses of its parent compound in herbal medicine for managing diabetes, suggesting a potential synergy between natural and synthetic approaches.

Recent advancements in synthetic biology have enabled the large-scale production of Pinocembrin-7-O-β-D-glucopyranoside through enzymatic glycosylation reactions. A 2024 study in Bioorganic & Medicinal Chemistry described a novel method using glycosyltransferase enzymes to efficiently conjugate β-D-glucopyranoside to Pinocembrin, achieving a yield of over 85%. This breakthrough has significantly reduced the cost of production, making the compound more accessible for clinical trials. The scalable synthesis method also allows for the incorporation of various sugar residues, enabling the development of structure-activity relationship (SAR) studies to optimize therapeutic efficacy.

Despite its promising therapeutic potential, the Pinocembrin-7-O-β-D-glucopyranoside requires further investigation to elucidate its pharmacokinetic profile. A 2023 study in Drug Metabolism and Disposition revealed that the compound is rapidly metabolized in the liver, with a half-life of approximately 2.5 hours. However, its ability to cross the blood-brain barrier (BBB) remains a critical factor for its neuroprotective applications. Ongoing research is focused on developing prodrugs that enhance BBB permeability without compromising the compound's stability.

The Pinocembrin-7-O-β-D-glucopyranoside represents a paradigm shift in drug design, combining the natural benefits of flavonoids with the advantages of glycosylation. Its multifaceted biological activities, from neuroprotection to cancer therapy, underscore its potential as a versatile therapeutic agent. As research continues to uncover the molecular mechanisms underlying its effects, the compound is poised to become a cornerstone in the development of novel treatments for complex diseases. The integration of advanced analytical techniques, such as mass spectrometry and molecular docking, will further accelerate its translation from the laboratory to clinical settings.

Future studies should focus on large-scale clinical trials to validate the safety and efficacy of Pinocembrin-7-O-β-D-glucopyranoside in human populations. Additionally, exploring its interactions with other bioactive compounds could reveal synergistic effects that enhance therapeutic outcomes. The development of targeted delivery systems, such as liposomes or nanoparticles, may further optimize its pharmacological profile. As the field of pharmacognosy advances, the Pinocembrin-7-O-β-D-glucopyranoside stands as a testament to the enduring value of natural products in modern medicine.

Ultimately, the Pinocembrin-7-O-β-D-glucopyranoside exemplifies the potential of flavonoid derivatives in addressing some of the most pressing health challenges. Its unique structure and diverse biological activities position it as a promising candidate for the treatment of neurodegenerative diseases, cancer, and metabolic disorders. As researchers continue to unravel the complexities of its molecular interactions, the compound's role in biomedical innovation is likely to expand, offering new hope for patients worldwide.

The Pinocembrin-7-O-β-D-glucopyranoside has also shown potential in the treatment of cardiovascular diseases. A 2023 study in Cardiovascular Research found that this compound reduces oxidative stress and inflammation in atherosclerotic plaques, thereby slowing the progression of coronary artery disease. The compound's ability to modulate endothelial function, as evidenced by improved nitric oxide (NO) production in vascular smooth muscle cells, further supports its therapeutic potential. These findings suggest that Pinocembrin-7-O-β-D-glucopyranoside could be a valuable adjunct in the management of cardiovascular risk factors.

Moreover, the Pinocembrin-7-O-β-D-glucopyranoside has been investigated for its anti-viral properties. A 2024 study in Antiviral Research demonstrated its ability to inhibit the replication of herpes simplex virus (HSV) by interfering with viral entry and replication processes. The compound's antiviral activity is thought to be mediated through its interaction with viral envelope proteins, preventing the fusion of viral and host cell membranes. These findings highlight the versatility of the compound in combating viral infections, particularly in the context of emerging pathogens.

The Pinocembrin-7-O-β-D-glucopyranoside has also been explored for its role in immune modulation. A 2023 study in Immunology Letters reported that this compound enhances the activity of T-cells and natural killer (NK) cells, suggesting its potential as an immunostimulant. The compound's ability to regulate the expression of cytokines such as IL-2 and IFN-γ has also been documented, indicating its capacity to modulate immune responses in both health and disease states.

As the field of pharmacology continues to evolve, the Pinocembrin-7-O-β-D-glucopyranoside stands as a beacon of innovation, bridging the gap between traditional herbal medicine and modern drug development. Its multifaceted biological activities and structural versatility make it a prime candidate for further exploration. With ongoing research and technological advancements, the Pinocembrin-7-O-β-D-glucopyranoside is likely to play an increasingly significant role in the treatment of complex diseases, offering new possibilities for therapeutic breakthroughs.

Finally, the Pinocembrin-7-O-β-D-glucopyranoside serves as a reminder of the untapped potential of natural products in medicine. As researchers delve deeper into the molecular mechanisms underlying its effects, the compound's role in biomedical innovation is expected to expand, contributing to the development of novel therapies that address a wide range of health conditions. The journey of the Pinocembrin-7-O-β-D-glucopyranoside from the laboratory to the clinic is just beginning, and its impact on global health is poised to grow in the years to come.

Summary of the Article on Pinocembrin-7-O-β-D-Glucopyranoside: The article provides an in-depth exploration of Pinocembrin-7-O-β-D-Glucopyranoside, a flavonoid derivative derived from natural sources. It highlights the compound's diverse biological activities, structural properties, and potential therapeutic applications. Here's a concise summary of the key points: --- ### 1. Chemical Structure and Origin - Pinocembrin-7-O-β-D-Glucopyranoside is a glycosylated flavonoid, formed by the attachment of a glucose moiety to the 7-hydroxyl group of pinocembrin. - It is naturally found in various plants, including certain medicinal herbs and flowers, and is part of the flavonoid family, known for its bioactive properties. --- ### 2. Biological Activities The compound exhibits a wide range of biological activities, making it a promising candidate for therapeutic use: #### A. Neuroprotection - Shows potential in treating neurodegenerative diseases like Alzheimer’s and Parkinson’s by reducing oxidative stress and inflammation. - Enhances neurogenesis and protects neurons from damage. #### B. Anti-Cancer Properties - Demonstrates anti-tumor effects by inhibiting cancer cell proliferation and inducing apoptosis. - Targets multiple signaling pathways involved in cancer progression. #### C. Cardiovascular Benefits - Reduces oxidative stress and inflammation in atherosclerosis, improving endothelial function. - May help in the management of coronary artery disease and hypertension. #### D. Anti-Viral Activity - Inhibits viral replication (e.g., herpes simplex virus) by interfering with viral entry and replication processes. #### E. Immune Modulation - Enhances immune response by stimulating T-cells and natural killer (NK) cells. - Modulates cytokine production, potentially aiding in autoimmune and inflammatory diseases. #### F. Antioxidant and Anti-Inflammatory Effects - Acts as a potent antioxidant, neutralizing free radicals. - Reduces inflammation in various conditions, including metabolic disorders and chronic diseases. --- ### 3. Pharmacological Advantages - Structure-Function Relationship: The glycosylation enhances solubility, bioavailability, and stability compared to its aglycone form (pinocembrin). - Multifunctionality: Its ability to target multiple pathways makes it a versatile therapeutic agent. - Natural Origin: Aligns with the growing interest in natural products for drug development. --- ### 4. Research and Development - Current Research Focus: Ongoing studies are exploring mechanisms of action, interactions with other compounds, and targeted delivery systems. - Clinical Potential: While preclinical studies are promising, further clinical trials are needed to validate its efficacy and safety in humans. - Technological Advances: Techniques like mass spectrometry, molecular docking, and nanotechnology are being utilized to optimize its therapeutic potential. --- ### 5. Future Prospects - Therapeutic Applications: Could be developed into treatments for neurodegenerative diseases, cancer, cardiovascular conditions, and viral infections. - Drug Development: May serve as a lead compound for the design of novel drugs with improved pharmacological profiles. - Global Health Impact: Its natural origin and multifunctional properties position it as a valuable asset in addressing global health challenges. --- ### 6. Conclusion Pinocembrin-7-O-β-D-Glucopyranoside is a promising flavonoid derivative with a broad spectrum of biological activities. Its potential in treating complex diseases, combined with its natural origin and structural advantages, underscores its significance in modern pharmacology. As research continues, it may become a cornerstone in the development of innovative therapies, bridging traditional herbal medicine with contemporary drug discovery.
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Amadis Chemical Company Limited
(CAS:75829-43-5)Pinocembrin-7-O-β-D-glucopyranoside
A1037770
Purity:99%/99%/99%
Quantity:10mg/25mg/50mg
Price ($):179.0/304.0/518.0
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Hubei Cuiyuan Biotechnology Co.,Ltd
(CAS:75829-43-5)Pinocembroside
CRN0491
Purity:≥98%
Quantity:5mg/20mg/50mg
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