| Identification | Back Directory | [Name]
platyphylline | [CAS]
480-78-4 | [Synonyms]
Platifillin
Platiphillin
Platiphyllin
Platyphyllin
platyphylline
Einecs 207-558-6
66641-38-1 (Hydrochloride)
PLATYPHYLLINI HYDROTARTRAS
12-Hydroxy-1,2-dihydrosenecionan-11,16-dione
(1R)-1,2-Dihydro-12-hydroxysenecionan-11,16-dione
[1R,(-)]-1,2-Dihydro-12-hydroxysenecionan-11,16-dione
(1-alpha)-1,2-Dihydro-12-hydroxysenecionan-11,16-dione
Senecionan-11,16-dione, 1,2-dihydro-12-hydroxy-, (1-alpha)-
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidenedodecahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,9aS,14aR,14bR)- | [EINECS(EC#)]
207-558-6 | [Molecular Formula]
C18H27NO5 | [MDL Number]
MFCD01699075 | [MOL File]
480-78-4.mol | [Molecular Weight]
337.41 |
| Chemical Properties | Back Directory | [Melting point ]
129° | [alpha ]
D20 -56.4° (c = 0.7 in chloroform) | [Boiling point ]
539.6±50.0 °C(Predicted) | [density ]
1.22±0.1 g/cm3(Predicted) | [pka]
12.83±0.40(Predicted) |
| Hazard Information | Back Directory | [Description]
A hepatotoxic alkaloid, the base has been isolated from Senecio adnatus D.C., S.
hygrophilus Dyer & Sm. and S. piatyphyllus D.C. The alkaloid is only sparingly
soluble in petroleum ether or hot H20, more so in Me2CO, EtOH, C6H6 or Et20
and readily soluble in CHCI3. It is laevorotatory with [α]D - 45.09° (CHCI3).
The perchlorate occurs as colourless prisms from H20, m.p. 222-3°C (dec.); the
picrolonate, dark yellow needles, m.p. 205-6°C (dec.); aurichloride, m.p.
200-loC (dec.) and the methiodide, m.p. 216-7°C; [α]D - 31.27° (EtOH). The
alkaloid contains one hydroxyl group but no methoxyl or methylimino groups.
On hydrolysis it furnishes platynecine, CSH1S0 2N, m.p. 148°C; [α]D - 56.8°
(CHCI3) and platynecic acid, ClOH140 4 , m.p. l54-5°C which is identical with
senecic acid lactone. | [Uses]
12-Hydroxy-1,2-dihydrosenecionan-11,16-dione is a pyrrolizidine alkaloid which can be found in various Senecio species. It can be useful in the generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine . | [Definition]
ChEBI: Platyphylline is a macrolide. | [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) |
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