4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

Base Information

• Chemical Name: 4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
• CAS No.: 2318-18-5
• Molecular Formula: C19H27 N O6
• Molecular Weight: 366.48
• European Community (EC) Number: 694-556-7
• DSSTox Substance ID: DTXSID40859716
• Wikidata: Q105031645,Q105031651
• Mol file: 2318-18-5.mol

Synonyms:neosenkirkine;senkirkine;senkirkine, (15E)-isomer

Chemical Property of 4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

Chemical Property:

• Vapor Pressure: 3.72E-17mmHg at 25°C
• Melting Point: 197°C
• Refractive Index: 1.5180 (estimate)
• Boiling Point: 604.9°Cat760mmHg
• PKA: 12.67±0.40(Predicted)
• Flash Point: 319.6°C
• PSA: 93.14000
• Density: 1.22g/cm³
• LogP: 0.94740
• Storage Temp.: ?20°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 365.18383758
• Heavy Atom Count: 26
• Complexity: 652

Purity/Quality:

99% ^*data from raw suppliers

Senkirkine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CC(C(C(=O)OCC2=CCN(CCC(C2=O)OC1=O)C)(C)O)C
• Description: A further hepatotoxiC alkaloid present in Senecio kirkii Hook, S. renardi and Nardosrnia laevigata. The base has [α]25D - 16° (c 1.89, MeOH) or[α]15D - 6.2° (c 1.91, CHCI3). It forms colourless plates when crystallized from either Me2CO or AcOEt and yields a picrate, m.p. 225.5-226°C and a picrolonate, m.p. 109- 110°C. The ultraviolet spectrum shows a single absorption maximum at 219 mp.. Several crystalline salts and derivatives are known, e.g. the aurichloride, m.p. 182.5-183.5°C; platinichloride, m.p. 196-7°C (dec.); bitartrate, m.p. 201°C; reineckate, m.p. 169-171°C; picrate, m.p. 225- 225.5°C; picrolonate, m.p. 138°C and the methiodide, m.p. 194-6°C (dec.). The O-acetate occurs naturally (q.v.) in Senecio kirkii.
• Uses: Senkirkine is a hepatotoxic pyrrolizidine alkaloid. Studies show that Senkirkine has carincogenic activity as it induced chromosomal aberrations in cultured mammalian cells as well as hepatic tumors in rats.

Technology Process of 4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

There total 1 articles about 4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ Senkirkine (2318-18-5,57194-70-4,60827-69-2)

Guidance literature:

Aus Senecio vernalis;

DOI:10.1021/ja00826a033

Reference yield:

senkirkine (2318-18-5) + acetyl chloride (75-36-5) → acetylsenkirkine (53092-44-7,60872-63-1,90364-91-3)

Guidance literature:

DOI:10.1039/jr9650002492

Downstream raw materials:

acetylsenkirkine