Cas no 476-33-5 (Homochelidonine)

Homochelidonine is a benzylisoquinoline alkaloid derived from certain plant species, notably within the Papaveraceae family. It shares structural similarities with chelidonine, exhibiting potential pharmacological properties, including antispasmodic and anti-inflammatory effects. Its mechanism of action is linked to interactions with cellular microtubules, which may contribute to its biological activity. Homochelidonine is of interest in research due to its potential applications in studying alkaloid biosynthesis and cytotoxicity. The compound is typically isolated via chromatographic techniques, ensuring high purity for analytical and experimental use. Its stability under controlled conditions makes it suitable for further biochemical and pharmacological investigations.
Homochelidonine structure
Homochelidonine structure
Product Name:Homochelidonine
CAS No:476-33-5
MF:C21H23NO5
MW:369.411026239395
CID:329916
PubChem ID:164609
Update Time:2025-10-21

Homochelidonine Chemical and Physical Properties

Names and Identifiers

    • [1,3]Benzodioxolo[5,6-c]phenanthridin-5-ol,4b,5,6,11b,12,13-hexahydro-1,2-dimethoxy-12-methyl-, (4bR,5S,11bS)-
    • (4bR,5S,11bS)-1,2-dimethoxy-12-methyl-5,6,11b,13-tetrahydro-4bH-[1,3]benzodioxolo[5,6-c]phenanthridin-5-ol
    • HOMOCHELIDONINE, A-(P)
    • EINECS 207-505-7
    • (1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDIN-5-OL, 4B,5,6,11B,12,13-HEXAHYDRO-1,2-DIMETHOXY-12-METHYL-, (4BR-(4Balpha,5beta,11Balpha))-
    • NORCHELIDONINE
    • Homochelidonine
    • Q27114075
    • (1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDIN-5-OL, 4B,5,6,11B,12,13-HEXAHYDRO-1,2-DIMETHOXY-12-METHYL-, (4BR,5S,11BS)-
    • HOMOCHELIDONINE, (+)-
    • NS00031711
    • DTXSID20197209
    • SCHEMBL13998253
    • HOMOCHELIDONINE [MI]
    • (1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDIN-5-OL, 4B,5,6,11B,12,13-HEXAHYDRO-1,2-DIMETHOXY-12-METHYL-, (4BR-(4B.ALPHA.,5.BETA.,11B.ALPHA.))-
    • A-ALLOCRYPTOPINE
    • 476-33-5
    • (+)-HOMOCHELIDONINE
    • (+/-)-Homochelidonine
    • .ALPHA.-HOMOCHELIDONINE
    • (4BR-(4balpha,5beta,11balpha))-4b,5,6,11b,12,13-hexahydro-1,2-dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridin-5-ol
    • DTXCID80119700
    • ZP901RX893
    • (4BR-(4B.ALPHA.,5.BETA.,11B.ALPHA.))-4B,5,6,11B,12,13-HEXAHYDRO-1,2-DIMETHOXY-12-METHYL(1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDIN-5-OL
    • alpha-Homochelidonine
    • UNII-ZP901RX893
    • CHEBI:31025
    • Inchi: 1S/C21H23NO5/c1-22-9-14-12(4-5-16(24-2)21(14)25-3)19-15(23)6-11-7-17-18(27-10-26-17)8-13(11)20(19)22/h4-5,7-8,15,19-20,23H,6,9-10H2,1-3H3/t15-,19-,20+/m0/s1
    • InChI Key: MADYLZJCRKUBIK-RYGJVYDSSA-N
    • SMILES: O[C@H]1CC2C=C3C(=CC=2[C@@H]2[C@H]1C1C=CC(=C(C=1CN2C)OC)OC)OCO3

Computed Properties

  • Exact Mass: 369.15800
  • Monoisotopic Mass: 369.158
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 2
  • Complexity: 547
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 60.4A^2
  • XLogP3: 2.3

Experimental Properties

  • Density: 1.294
  • Melting Point: 182°
  • Boiling Point: 521.3°C at 760 mmHg
  • Flash Point: 269.1°C
  • Refractive Index: 1.615
  • PSA: 60.39000
  • LogP: 2.55770
  • Specific Rotation: D +118° (alc)

Homochelidonine Pricemore >>

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Homochelidonine Related Literature

Additional information on Homochelidonine

Homochelidonine: A Comprehensive Overview

Homochelidonine (CAS No. 476-33-5) is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound, also referred to as homochelidonine, has been extensively studied for its unique properties and potential applications in various industries. Recent advancements in chemical synthesis and analytical techniques have shed new light on its structure, synthesis, and biological activity.

The chemical structure of homochelidonine is characterized by a complex arrangement of functional groups, which contribute to its distinctive reactivity and stability. Researchers have employed advanced spectroscopic methods, such as NMR and IR spectroscopy, to elucidate the precise arrangement of atoms within the molecule. These studies have revealed that homochelidonine exhibits a high degree of symmetry, which plays a crucial role in its physical and chemical properties.

One of the most notable aspects of homochelidonine is its biological activity. Recent studies have demonstrated that this compound possesses potent antioxidant properties, making it a promising candidate for use in pharmaceuticals and nutraceuticals. Furthermore, homochelidonine has been shown to exhibit anti-inflammatory effects, which could be harnessed in the development of novel therapeutic agents for chronic inflammatory diseases.

The synthesis of homochelidonine has also been a focal point of recent research efforts. Traditional methods involving multi-step reactions have been optimized to improve yield and reduce production costs. For instance, the use of microwave-assisted synthesis has been reported to significantly accelerate the formation of homochelidonine while maintaining high purity levels.

In terms of applications, homochelidonine finds utility in several industries. Its antioxidant properties make it a valuable ingredient in cosmetic formulations aimed at combating oxidative stress and skin aging. Additionally, homochelidonine has been explored for its potential as a food preservative due to its ability to inhibit lipid oxidation.

Recent collaborative efforts between academic institutions and industrial partners have further expanded our understanding of homochelidonine's therapeutic potential. Preclinical studies conducted on animal models have highlighted its efficacy in reducing oxidative damage in tissues, suggesting its potential role in treating conditions associated with oxidative stress, such as neurodegenerative diseases.

The environmental impact of homochelidonine production has also garnered attention from researchers and regulatory bodies. Efforts are underway to develop sustainable synthesis routes that minimize waste generation and reduce energy consumption. These initiatives align with global trends toward greener chemistry practices.

In conclusion, homochelidonine (CAS No. 476-33-5) stands out as a compound with multifaceted applications across various sectors. Its unique chemical properties, coupled with recent advancements in synthesis and application development, position it as a key player in future innovations within the chemical and pharmaceutical industries.

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