Rodiasine
Basic information
- CAS
6391-64-6- Standard SMILES
COc1cc2c3cc1Oc1c(OC)c(OC)cc4c1[C@H](Cc1ccc(OC)c(c1)-c1cc(ccc1O)C[C@H]3N(C)CC2)N(C)CC4- InChIKey
HIQZXOFBXJICTD-IHLOFXLRSA-N- Molecular formula
- C38H42N2O6
- Average molar mass
- 622.7 g/mol
- Monoisotopic mass
- 622.30428706
Overview
Rodiasine is a bisbenzylisoquinoline alkaloid and an isoquinoline alkaloid fundamental parent.
Names & identifiers
- Preferred name
- Rodiasine
- IUPAC
- (1R,14S)-9,20,21,25-tetramethoxy-15,30-dimethyl-23-oxa-15,30-diazaheptacyclo[22.6.2.13,7.18,12.114,18.027,31.022,33]pentatriaconta-3(35),4,6,8,10,12(34),18,20,22(33),24,26,31-dodecaen-6-ol
- English name
- 7-O-Methylantioquine
- Molecular formula
- C38H42N2O6
- Molecular weight
- 622.75
Names & synonyms
Rodiasine6391-64-6CHEBI:8886DTXSID20331803(1R,14S)-9,20,21,25-tetramethoxy-15,30-dimethyl-23-oxa-15,30-diazaheptacyclo[22.6.2.13,7.18,12.114,18.027,31.022,33]pentatriaconta-3(35),4,6,8,10,12(34),18,20,22(33),24,26,31-dodecaen-6-ol(1R,14S)-9,20,21,25-tetramethoxy-15,30-dimethyl-23-oxa-15,30-diazaheptacyclo(22.6.2.13,7.18,12.114,18.027,31.022,33)pentatriaconta-3(35),4,6,8,10,12(34),18,20,22(33),24,26,31-dodecaen-6-olRefChem:179763DTXCID302828977-O-MethylantioquineC09624CHEMBL1170881Q7356764
Show more names
2H,16H-1,24-Etheno-6,10:11,15-dimethenopyrido[2',3':17,18]oxacycloeicosino[2,3,4-ij]isoquinolin-9-ol, 3,4,4a,5,16a,17,18,19-octahydro-12,21,22,26-tetramethoxy-4,17-dimethyl-, (4aR,16aS)-
Properties
Computed structural properties
- XLogP
- 6.4
- Topological polar surface area
- 72.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 1,000
Physicochemical properties
- Melting point
- 195 °C · 195 °C(Solv: ethanol (64-17-5))
- Boiling point
- 745.4 · 745.4±60.0 °C(Predicted)
- Density
- 1.195 · 1.195±0.06 g/cm3(Predicted)
- pka
- 9.86 · 9.86±0.20(Predicted)
Chemistry & industry
Applications
DescriptionThis bisbenzylisoquinoline alkaloid from Ocotea rodiaei was originally considered to have the formulae C36H4006N2 or C36H4406N2. When crystallized from EtOH it yields cubic crystals but from MeOH it forms slender needles. It has [α]18D + 134° (c 0.63, CHCI3) or + 157° (c 1.0, CHCI3). The ultraviolet spectrum in EtOH has absorption maxima at 233 and 285 ITlJ.1 with a shoulder at 292 mJ.1. The monohydrochloride forms cubic crystals from EtOH, m.p. 255-9°C (dec.); [α]D + 74° (c 1.0, H20); the dimethiodide, m.p. 321°C (dec.); [α]20D+ 68° (c 0.147, H20); the dimethochloride, m.p. 286°C (dec.); [α]D + 81.5° (c 0.98, H20) and the dimethopicrate, existing in two crystal forms, m.p. 180°C and 253°C respectively. Four methoxyl groups and one phenolic hydroxyl group are present, the alkaloid furnishing the O-methyl derivative, m.p. 172-3°C; [α]D + 85° (c 0.57, CHCI 3) which also yields crystalline salts, e.g. the hydrochloride, m.p. 232-6°C (dec.) and the dimethiodide, m.p. 294-8°C (dec.); [α]D + 47° (H20).
Additional notes
DefinitionChEBI: Rodiasine is an isoquinoline alkaloid fundamental parent and a bisbenzylisoquinoline alkaloid.
Related reactions
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Compound notes
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