480-78-4

Basic information

• Product Name: platyphylline
• Synonyms: platyphylline;(1R)-1,2-Dihydro-12-hydroxysenecionan-11,16-dione;[1R,(-)]-1,2-Dihydro-12-hydroxysenecionan-11,16-dione;Platifillin;(1-alpha)-1,2-Dihydro-12-hydroxysenecionan-11,16-dione;66641-38-1 (Hydrochloride);Einecs 207-558-6;Platiphillin
• CAS NO: 480-78-4
• Molecular Formula: C18H27NO5
• Molecular Weight: 337.413
• EINECS: 207-558-6
• Mol File: 480-78-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 129°
• Boiling Point: 539.6°Cat760mmHg
• Flash Point: 280.1°C
• Appearance: /
• Density: 1.22g/cm³
• Refractive Index: 1.553
• PKA: 12.83±0.40(Predicted)
• CAS DataBase Reference: platyphylline(CAS DataBase Reference)
• NIST Chemistry Reference: platyphylline(480-78-4)
• EPA Substance Registry System: platyphylline(480-78-4)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 480-78-4(Hazardous Substances Data)

Usage

Description

Platyphylline is a hepatotoxic alkaloid that has been isolated from various Senecio species, including Senecio adnatus D.C., S. hygrophilus Dyer & Sm., and S. platyphyllus D.C. This alkaloid is sparingly soluble in petroleum ether or hot water, more soluble in Me2CO, EtOH, C6H6, or Et20, and readily soluble in CHCI3. Platyphylline is levorotational with a specific rotation of [α]D 45.09° (CHCI3). It contains one hydroxyl group but lacks methoxyl or methylimino groups. Upon hydrolysis, it yields platynecine (C9H15O2N) and platynecic acid (C10H14O4), which is identical to senecioic acid lactone.

Uses

1. Used in Pharmaceutical Industry:
Platyphylline is used as a hepatotoxic alkaloid for its potential applications in the development of pharmaceuticals targeting liver-related conditions. Its specific properties, such as solubility and the presence of a hydroxyl group, make it a candidate for further research and development in the pharmaceutical field.
2. Used in Chemical Research:
Platyphylline is used as a research compound for studying its chemical properties, such as solubility, rotation, and hydrolysis products. This information can be valuable for understanding the structure-activity relationships and potential applications of similar alkaloids.
3. Used in Toxicological Studies:
Due to its hepatotoxic nature, platyphylline can be used as a model compound in toxicological studies to investigate the mechanisms of liver toxicity and develop strategies for mitigating or preventing such effects.
4. Used in Natural Product Chemistry:
Platyphylline, being an alkaloid isolated from Senecio species, can be used in the study of natural products chemistry, focusing on the isolation, characterization, and potential biological activities of alkaloids from plant sources.
5. Used in Drug Development:
The hepatotoxic properties of platyphylline may be exploited in the development of drugs targeting specific liver diseases or conditions, provided that its toxicity can be controlled and managed effectively.

References

Orekhov, Tiedebel., Ber., 68,653 (1935) Orekhov, Konovalova, Tiedebel., ibid, 68, 1886 (1935) Orekhov, Tiedebel., J. Gen. Chern. USSR, 8,273 (1938) de Waal., Onderstepoort J., 15,251 (1940) Koekemoer, Warren., J. Chern. Soc., 63 (1955)

InChI:InChI=1/C18H27NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4,11,13-15,22H,5-10H2,1-3H3/b12-4-/t11-,13+,14+,15+,18+/m0/s1

Downstream Products

• 480-84-2 (-)-hastanecine 
• 57123-97-4 (7aR)-7t-benzoyloximethyl-(7ar)-hexahydro-pyrrolizin-1t-ol