Cas no 480-85-3 ((+)-Retronecine)

(+)-Retronecine is a pyrrolizidine alkaloid intermediate, recognized for its role in the biosynthesis of various bioactive compounds. Its stereospecific structure makes it valuable in synthetic chemistry and pharmacological research, particularly in studying hepatotoxic and antitumor agents. The compound's high purity and well-defined configuration ensure reproducibility in experimental applications. (+)-Retronecine is commonly utilized as a reference standard in analytical chemistry, aiding in the identification and quantification of related alkaloids. Its stability under controlled conditions further enhances its utility in laboratory settings. Researchers appreciate its consistent performance in mechanistic studies and its relevance in exploring plant-derived toxins. Proper handling is advised due to its potential toxicity.
(+)-Retronecine structure
(+)-Retronecine structure
Product Name:(+)-Retronecine
CAS No:480-85-3
MF:C8H13NO2
MW:155.194322347641
CID:331175
PubChem ID:329754139
Update Time:2025-08-02

(+)-Retronecine Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrrolizine-7-methanol,2,3,5,7a-tetrahydro-1-hydroxy-, (1R,7aR)-
    • Relronecine (7R)
    • (+)-Retronecine
    • (1R,7aR)-7-(Hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol
    • RETRONECINE
    • (1R,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol
    • NS00121945
    • CHEBI:8821
    • C06177
    • CS-0144131
    • SCHEMBL673883
    • ( )-Retronecine
    • UNII-2P5723M6II
    • (1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol
    • RETRONECINE [MI]
    • Q3933789
    • HY-N8419
    • 1H-Pyrrolizine-7-methanol, 2,3,5,7a-beta-tetrahydro-1-alpha-hydroxy-
    • InChI=1/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s
    • DTXSID401020156
    • 1ST160717
    • FS-6720
    • AKOS003672869
    • Retronecin
    • RETRONECINE [HSDB]
    • HSDB 3567
    • CCRIS 5776
    • Retronecine, analytical standard
    • MFCD01684783
    • 480-85-3
    • 2P5723M6II
    • Senecifolinene
    • 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1R-trans)-
    • Heliotridine
    • MDL: MFCD01684783
    • Inchi: 1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1
    • InChI Key: HJSJELVDQOXCHO-HTQZYQBOSA-N
    • SMILES: O[C@@H]1CCN2CC=C(CO)[C@@H]21

Computed Properties

  • Exact Mass: 155.09469
  • Monoisotopic Mass: 155.095
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 191
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 43.7A^2
  • XLogP3: -1.3

Experimental Properties

  • Color/Form: Powder
  • Density: 1.29
  • Melting Point: 119-120°
  • Boiling Point: 291.3°Cat760mmHg
  • Flash Point: 161.4°C
  • Refractive Index: 1.611
  • PSA: 43.7
  • LogP: -0.70820
  • Specific Rotation: 20D +4.95° (c = 0.58 in alc)

(+)-Retronecine Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • RTECS:VH7175000
  • HazardClass:6.1(b)
  • PackingGroup:III
  • Toxicity:LD50 i.v. in mice: 634.0 ±26.0 mg/kg (Harris)
  • Storage Condition:2-8°C

(+)-Retronecine Pricemore >>

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(+)-Retronecine Related Literature

Additional information on (+)-Retronecine

Exploring (+)-Retronecine (CAS No. 480-85-3): A Comprehensive Overview of Its Properties and Applications

(+)-Retronecine (CAS No. 480-85-3) is a naturally occurring pyrrolizidine alkaloid that has garnered significant attention in the fields of pharmacology, biochemistry, and natural product chemistry. This compound, characterized by its unique bicyclic structure, serves as a key intermediate in the biosynthesis of various bioactive alkaloids. Its molecular formula, C8H13NO2, and distinct stereochemistry make it a subject of interest for researchers exploring natural product synthesis and medicinal chemistry.

The growing interest in (+)-Retronecine is partly driven by its potential applications in drug discovery and phytochemical research. With the rise of plant-derived therapeutics, compounds like (+)-Retronecine are being studied for their role in the development of novel pharmaceuticals. Searches for "pyrrolizidine alkaloids benefits" and "natural alkaloids in medicine" reflect the public's curiosity about these compounds. Additionally, the compound's CAS No. 480-85-3 is frequently queried in scientific databases, underscoring its relevance in academic and industrial research.

One of the most intriguing aspects of (+)-Retronecine is its structural versatility. As a precursor to other alkaloids, it plays a critical role in the synthesis of complex molecules. Researchers investigating "alkaloid biosynthesis pathways" often highlight (+)-Retronecine as a model compound. Its ability to form esters with necic acids, for instance, has been a focal point in studies on plant defense mechanisms and ecological interactions. This aligns with the increasing demand for sustainable and eco-friendly bioactive compounds.

In recent years, the scientific community has also explored the pharmacological potential of (+)-Retronecine. While some pyrrolizidine alkaloids are known for their toxicity, controlled studies on (+)-Retronecine have revealed its utility in targeted therapeutic applications. Queries such as "safe uses of pyrrolizidine alkaloids" and "alkaloids in cancer research" demonstrate the public's interest in balancing efficacy and safety. This compound's role in enzyme inhibition and cell signaling pathways further underscores its importance in modern drug development.

From a technical standpoint, the isolation and characterization of (+)-Retronecine require advanced analytical techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. These methods ensure the purity and structural integrity of the compound, which is crucial for both research and industrial applications. The CAS No. 480-85-3 serves as a unique identifier in chemical databases, facilitating accurate data retrieval and collaboration among scientists.

The future of (+)-Retronecine research looks promising, particularly in the context of green chemistry and biotechnology. As the demand for sustainable and bio-based products grows, this compound could play a pivotal role in the development of eco-friendly pharmaceuticals and agricultural bioagents. Searches for "sustainable alkaloid production" and "biotech applications of plant alkaloids" highlight the evolving trends in this field.

In conclusion, (+)-Retronecine (CAS No. 480-85-3) stands as a fascinating example of nature's chemical ingenuity. Its structural complexity, biosynthetic significance, and potential therapeutic applications make it a valuable subject for ongoing research. Whether you're a scientist, student, or enthusiast, understanding this compound offers insights into the broader world of natural products and their transformative impact on science and medicine.

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