HuagongsheHuagongshe Chemistry Print Report · For research reference only
(1R,7aR)-7-({[2,3-dihydroxy-2-(1-methylethyl)butanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2E)-2-methylbut-2-enoate
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)-
![(1R,7aR)-7-({[2,3-dihydroxy-2-(1-methylethyl)butanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2E)-2-methylbut-2-enoate molecular structure](/img/chemical/5284460.png)
Identifiers & Physical Properties
| CAS No. | 22571-95-5 |
|---|---|
| Molecular formula | C20H31NO6 |
| Average molar mass | 381.5 g/mol |
| Monoisotopic mass | 381.21513771 g/mol |
| SMILES | C/C=C(\C)C(=O)O[C@@H]1CCN2CC=C(COC(=O)C(O)(C(C)C)C(C)O)[C@H]12 |
| InChIKey | MVWPTZQHBOWRTF-OEQXRFFVSA-N |
| PubChem CID | 5284460 |
| DTXSID | DTXSID1021297 |
Chemical & Physical Properties
| XLogP | 1.3 |
|---|---|
| Topological polar surface area | 96.3 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 7 |
| Rotatable bonds | 9 |
| Heavy atoms | 27 |
| Formal charge | 0 |
| Complexity | 640 |
| Boiling point | 508.85°C (rough estimate) |
| Density | 1.2168 (rough estimate) |
| Refractive index | 1.5614 (estimate) |
| pKa (acidity coefficient) | 12.59±0.29(Predicted) |
| FDA UNII | 3K8W67TIDS |
| IARC | 3 (Vol. 31, Sup 7) 1987 |
| UN transport number | 1544 |
| Hazard class | 6.1(b) |
| Packing group | III |
Safety & Regulations
| UN transport number | 1544 |
|---|---|
| Hazard class | 6.1(b) |
| Packing group | III |
Applications & Uses
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].