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Seneciphylline

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Seneciphylline Basic information

Product Name:
Seneciphylline
Synonyms:
  • ALPHA-LONGILOBINE
  • SENECIPHYLLIN
  • (15cis)-12-Hydroxy-13,19-didehydrosenecionan-11,16-dione
  • 13,19-didehydro-12-hydroxysenecionan-11,16-dione
  • 16-dione,13,19-didehydro-12-hydroxy-senecionan-1
  • 16-dione,13,19-didehydro-12-hydroxy-senecionin-1
  • NSC 30622
  • oxy-6-methyl-5-methylene(1,6)dioxacyclodode///
CAS:
480-81-9
MF:
C18H23NO5
MW:
333.38
Mol File:
480-81-9.mol
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Seneciphylline Chemical Properties

Melting point:
217°C
alpha 
D -128° (chloroform)
Boiling point:
470.34°C (rough estimate)
Density 
1.2467 (rough estimate)
refractive index 
1.5740 (estimate)
storage temp. 
-20°C
solubility 
DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 0.1 mg/ml
form 
Solid
pka
12.43±0.20(Predicted)
color 
White to off-white
Stability:
Stable, but reacts with oxygen in the air. Incompatible with alkali, oxidizing agents. Store under inert gas.
LogP
0.810 (est)
CAS DataBase Reference
480-81-9
IARC
3 (Vol. 10, Sup 7) 1987
EPA Substance Registry System
Seneciphylline (480-81-9)
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Safety Information

Hazard Codes 
T
Risk Statements 
23/24/25-25
Safety Statements 
1-20-24/25-45
RIDADR 
1544
WGK Germany 
3
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
480-81-9(Hazardous Substances Data)
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Seneciphylline Usage And Synthesis

Description

Seneciphylline, a pyrrolizidine alkaloid, one of the main components of Chinese medicine herb Tusanqi, which is a reason of the hepatic sinusoidal obstruction syndrome (HSOS). In addition, experiments on rats have shown that seneciphylline had adverse effects on the development and organic morphodifferentiation of embryos, thus the pregnant people exposed to Hebra may get potential risk on the fetus.

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, Derived from the whole plant or root of Gynura segetum (Lour.) Merr (Ju Sanqi).

Uses

Seneciphylline is a minor constituent of S. jacobaea, which has been used as a medicinal herb in Europe. It has the effect of coagulation and hemostasis.
Seneciphylline is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells.

Application

Seneciphylline is a naturally occurring plant toxin, which is employed to defend the plant against herbivore and insect attacks.
Seneciphylline may be used as an analytical reference standard for the quantification of the analyte in feed samples and traditional Chinese herbal medicines using different chromatography techniques.

Definition

ChEBI: LSM-2853 is a citraconoyl group.

Air & Water Reactions

Reacts slowly with atmospheric oxygen. . Insoluble in water.

Reactivity Profile

SENECIPHYLLIN is readily hydrolyzed with alkali; SENECIPHYLLIN reacts readily with oxidizing agents .

Health Hazard

Seneciphylline and aflatoxin B. may be of greater importance as a cause of human disease than the presently known outbreaks of poisoning would indicate.
SYMPTOMS: Symptoms associated with this compound include abdominal pain, nausea and diarrhea, emaciation, intestinal edema and congestion of the liver. ACUTE/CHRONIC HAZARDS: Very toxic. (NTP, 1992)

Fire Hazard

Flash point data are not available for SENECIPHYLLIN, but SENECIPHYLLIN is probably combustible.

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