Dibenzo(f,h)pyrrolo(1,2-b)isoquinolin-14-ol, 9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-, cis-(+-)-
Basic information
- CAS
6799-27-5- Standard SMILES
COc1ccc2c3c(c4cc(OC)c(OC)cc4c2c1)CN1CCCC1C3O- InChIKey
LAWAARLALKUFQQ-AUSIDOKSSA-N- Molecular formula
- C23H25NO4
- Average molar mass
- 379.4 g/mol
- Monoisotopic mass
- 379.17835828
Names & identifiers
- Preferred name
- Dibenzo(f,h)pyrrolo(1,2-b)isoquinolin-14-ol, 9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-, cis-(+-)-
- IUPAC
- 3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-14-ol
- English name
- Tylophorinine
- Molecular formula
- C23H25NO4
- Molecular weight
- 379.45
Names & synonyms
(+-)-Pergularinine6799-27-5Dibenzo(f,h)pyrrolo(1,2-b)isoquinolin-14-ol, 9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-, cis-(+-)-SCHEMBL13222733TylophorinineDibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol, 9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-, (13aR,14S)-rel-
Database identifiers
- CAS
6799-27-5- PubChem CID
- 628305
- Nikkaji
- J1.999.647F
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 51.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 559
Physicochemical properties
- Melting point
- 248 · 248-9°C
- Boiling point
- 588.5 · 588.5±50.0 °C(Predicted)
- Density
- 1.31 · 1.31±0.1 g/cm3(Predicted)
- pka
- 13.48 · 13.48±0.20(Predicted)
Chemistry & industry
Applications
DescriptionAn alkaloid of Tylophora asthmatica, the base crystallizes as the hemihydrate, m.p. 232-3°C (dec.) and has[α]27D - 14.2° (c 1.76, CHCI3). The ultraviolet spectrum in MeOH has absorption maxima at 258, 287 and 340 Mu. The salts crystallize well, e.g. the hydrochloride, m.p. 257°C (dec.); nitrate, m.p. 240- 2°C; methiodide, m.p. 243-5°C (dec.) and the O-acetate, m.p. 222-3°C.
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