symphytine
symphytine Basic information
- Product Name:
- symphytine
- Synonyms:
-
- symphytine
- 2-Butenoic acid, 2-methyl-, (1R,7aR)-7-[[(2S,3S)-2,3-dihydroxy-2-(1-methylethyl)-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (2E)-
- CAS:
- 22571-95-5
- MF:
- C20H31NO6
- MW:
- 381.46
- Mol File:
- 22571-95-5.mol
symphytine Chemical Properties
- Boiling point:
- 508.85°C (rough estimate)
- Density
- 1.2168 (rough estimate)
- refractive index
- 1.5614 (estimate)
- pka
- 12.59±0.29(Predicted)
- IARC
- 3 (Vol. 31, Sup 7) 1987
symphytine Usage And Synthesis
Description
This pyrrolizidine alkaloid occurs in the roots of Symphytum officinale Linn. and is difficult to crystallize. The above structure has been proposed on the basis of chemical degradation and spectroscopic evidence.
Uses
Symphytine is a pyrrolizidine alkaloid isolated from Symphytum officinale and has carcinogenicity[1].
Definition
ChEBI: A but-2-enoate ester obtained by formal condensation of the carboxy group of (2E)-2-methylbut-2-enoic acid with the 1-hydroxy group of (1R,7aR)-7-({[(2S,3S)-2,3-dihydroxy- -isopropylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol.
in vivo
Symphytine (intraperitoneal injection; 13 mg/kg; 330 days) leads to survival for more than 330 days after the start of injections. Four of 20 rats (20%) had liver tumors: three has hemangioendothelial sarcoma and 1 has liver cell adenoma[1].
| Animal Model: | Male inbred ACI rats[1] |
| Dosage: | 13 mg/kg |
| Administration: | Intraperitoneal injection; 330 days |
| Result: | Led to hepatic tumor in rats. |
References
Furuya, Araki., Chem. Pharm. Bull. (Tokyo), 16,2512 (1968)
Structure:
Furuya, Hikichi., Phytochem., 10, 2217 (1971)
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