Cas no 4449-55-2 (Warangalone)

Warangalone is a naturally occurring prenylated isoflavonoid compound, primarily derived from plants such as Millettia pinnata (Pongamia pinnata). It exhibits notable biological activities, including antioxidant, anti-inflammatory, and potential anticancer properties. Structurally, warangalone features a distinctive isoflavone backbone with a prenyl group, enhancing its lipophilicity and interaction with cellular targets. Its mechanism of action involves modulation of key signaling pathways, such as NF-κB and MAPK, contributing to its therapeutic potential. Warangalone is also studied for its role in metabolic regulation and neuroprotective effects. Due to its multifunctional bioactivity and natural origin, it is a promising candidate for pharmacological research and nutraceutical applications.
Warangalone structure
Warangalone structure
Product Name:Warangalone
CAS No:4449-55-2
MF:C25H24O5
MW:404.455067634583
CID:330516
PubChem ID:5379679
Update Time:2025-07-02

Warangalone Chemical and Physical Properties

Names and Identifiers

    • 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one,5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-buten-1-yl)-
    • Warangalone
    • 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one,5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl...
    • 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
    • Scandenolone
    • Scandenone
    • [ "Scandenone" ]
    • AKOS015896248
    • LMPK12050205
    • 5-Hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-g]chromen-6-one #
    • FT-0655477
    • A826605
    • 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(p-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
    • 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
    • HY-N1074
    • HGHOPAZIUPORIN-UHFFFAOYSA-N
    • DTXSID40196193
    • B0005-418142
    • XW161525
    • 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-2H,6H-pyrano[3,2-g]chromen-6-one
    • Warangalon
    • 2H,6H-Benzo(1,2-b:5,4-b')dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
    • CS-8196
    • NS00067919
    • SCHEMBL571534
    • 4449-55-2
    • CHEMBL458134
    • MS-26917
    • 2H,6H-Benzo(1,2-b:5,4-b')dipyran-6-one, 5-hydroxy-7-(p-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
    • DA-78948
    • DTXCID50118684
    • 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano(3,2-g)chromen-6-one
    • Inchi: 1S/C25H24O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)21(27)20-22(28)19(13-29-24(18)20)15-6-8-16(26)9-7-15/h5-9,11-13,26-27H,10H2,1-4H3
    • InChI Key: HGHOPAZIUPORIN-UHFFFAOYSA-N
    • SMILES: O1C2C(C=CC1(C)C)=C(C1C(C(C3C=CC(=CC=3)O)=COC=1C=2C/C=C(\C)/C)=O)O

Computed Properties

  • Exact Mass: 404.16200
  • Monoisotopic Mass: 404.162374
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 3
  • Complexity: 752
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 10
  • XLogP3: 5.9
  • Topological Polar Surface Area: 76

Experimental Properties

  • Color/Form: Yellow powder
  • Density: 1.258
  • Melting Point: 164-165 °C
  • Boiling Point: 627°Cat760mmHg
  • Flash Point: 216.7°C
  • Refractive Index: 1.627
  • PSA: 79.90000
  • LogP: 5.56410
  • Vapor Pressure: 0.2±0.4 mmHg at 25°C

Warangalone Security Information

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Warangalone Related Literature

Additional information on Warangalone

Introduction to Warangalone (CAS No. 4449-55-2)

Warangalone, a naturally occurring compound with the chemical name (1R,5S)-5-methyl-1-hydroxy-4-isopropenyl-7-octen-3-one, is a molecule of significant interest in the field of chemical biology and pharmaceutical research. Its unique structural features and biological activities have positioned it as a promising candidate for further investigation in various therapeutic applications. This compound, identified by its unique CAS No. 4449-55-2, has garnered attention due to its potential role in modulating biological pathways and its structural similarity to other bioactive natural products.

The molecular structure of Warangalone consists of a complex blend of functional groups, including hydroxyl, methyl, and isopropenyl substituents, which contribute to its diverse chemical reactivity. These features make it an intriguing subject for synthetic chemists and biochemists alike, as they offer opportunities for structural modifications and the development of novel derivatives with enhanced pharmacological properties.

Recent advancements in analytical chemistry have enabled more precise characterization of Warangalone, revealing insights into its stereochemistry and conformational dynamics. Techniques such as nuclear magnetic resonance (NMR) spectroscopy and X-ray crystallography have been instrumental in elucidating its three-dimensional structure, which is crucial for understanding its biological interactions. The stereochemical configuration of Warangalone, particularly the absolute configuration at the C1 and C5 positions, has been found to be critical for its biological activity.

In the realm of pharmacological research, Warangalone has shown promise as a potential therapeutic agent. Initial studies have highlighted its ability to interact with specific biological targets, including enzymes and receptors involved in inflammatory responses. The compound's structural motif resembles that of known bioactive molecules, suggesting that it may exert similar effects on cellular processes. For instance, preliminary in vitro experiments have indicated that Warangalone can modulate the activity of certain enzymes associated with inflammation, potentially making it a valuable candidate for developing anti-inflammatory drugs.

Moreover, the natural occurrence of Warangalone in specific plant species has sparked interest in its ecological roles. Research has suggested that this compound may serve as a defense mechanism against herbivores or pathogens, showcasing the intricate relationship between chemical diversity and ecological interactions. The discovery of such natural products often provides valuable inspiration for synthetic chemists aiming to develop new drugs with similar biological activities.

The synthesis of Warangalone remains a challenging yet fascinating endeavor for organic chemists. The complexity of its molecular framework necessitates innovative synthetic strategies to achieve high yields and enantiopurity. Recent reports have described novel synthetic routes that leverage asymmetric catalysis to construct the key stereocenters of the molecule efficiently. These advances not only contribute to the growing library of synthetic methodologies but also enhance our ability to produce sufficient quantities of Warangalone for further biological testing.

As our understanding of the biological significance of natural products continues to expand, compounds like Warangalone are likely to play an increasingly important role in drug discovery and development. The integration of interdisciplinary approaches, combining expertise from chemistry, biology, and pharmacology, will be essential in unlocking the full potential of this remarkable molecule. Future research directions may include exploring its mechanism of action in greater detail, identifying additional biological targets, and optimizing its pharmacokinetic properties for therapeutic use.

The journey from natural product discovery to clinical application is often long and arduous, but compounds like Warangalone highlight the enduring importance of exploring nature's chemical diversity. Each new discovery brings us closer to understanding the complex interplay between structure and function in biological systems, paving the way for innovative treatments and a deeper appreciation of the molecular basis of life.

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