Thalistyline
Basic information
- CAS
62251-53-0- Standard SMILES
COc1ccc(C[C@H]2c3cc(OC)c(OC)c(OC)c3CC[N+]2(C)C)cc1Oc1ccc(C[C@H]2c3cc(OC)c4c(c3CCN2C)OCO4)cc1- InChIKey
UNLANLZLFACELM-LQJZCPKCSA-N- Molecular formula
- C41H49N2O8+
- Average molar mass
- 697.8 g/mol
- Monoisotopic mass
- 697.34889153
Names & identifiers
- Preferred name
- Thalistyline
- IUPAC
- (6S)-4-methoxy-6-[[4-[2-methoxy-5-[[(1S)-5,6,7-trimethoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium-1-yl]methyl]phenoxy]phenyl]methyl]-7-methyl-8,9-dihydro-6H-[1,3]dioxolo[4,5-f]isoquinoline
- English name
- thalistyline
- Molecular formula
- C41H49N2O8
- Molecular weight
- 0
Names & synonyms
Thalistyline62251-53-0DTXSID20211313RefChem:189080DTXCID20133804CHEMBL1187403(1S)-5,6,7-Trimethoxy-1-{[4-methoxy-3-(4-{[(6S)-4-methoxy-7-methyl-6,7,8,9-tetrahydro-2H-[1,3]dioxolo[4,5-f]isoquinolin-6-yl]methyl}phenoxy)phenyl]methyl}-2,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-2-iumIsoquinolinium, 1,2,3,4-tetrahydro-5,6,7-trimethoxy-1-((4-methoxy-3-(4-((5,6,7,8-tetrahydro-9-methoxy-6-methyl-1,3-diolo(4,5-g)isoquinolin-5-yl)methyl)phenoxy)phenyl)methyl)-2,2-dimethyl-, (S-(R*,R*))-(1S)-1,2,3,4-Tetrahydro-5,6,7-trimethoxy-1-[[4-methoxy-3-[4-[[(5S)-5,6,7,8-tetrahydro-9-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]methyl]phenoxy]phenyl]methyl]-2,2-dimethylisoquinolin-2-ium
Database identifiers
- CAS
62251-53-0- PubChem CID
- 162971
- DTXSID
DTXSID20211313- ChEMBL
CHEMBL1187403、CHEMBL501762
Properties
Computed structural properties
- XLogP
- 6.9
- Topological polar surface area
- 77.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 11
- Heavy atoms
- 51
- Formal charge
- 1
- Complexity
- 1,110
Chemistry & industry
Applications
DescriptionA quaternary bisbenzylisoquinoline alkaloid, thalistyline has been isolated from Thalictrum longistylum DC and T. podocarpum Hunb. grown in Columbia, South America. The base has been isolated as the chloride which forms needles from H20 with m.p. ISO-3°C and a specific rotation of [α]20D + 146° (c 0.1, MeOH). The ultraviolet spectrum of this salt has absorption maxima at 276 and 283 nm. The base has also been characterized as the crystalline iodide, m.p. 220-3°C (dec.) and methiodide, m.p. 266-8°C (dec.). Sodium-liquid ammonia cleavage gives an optically inactive phenolic base, C22H31NO4 as an oil and a phenolic base C18H21NO3 as colourless crystals, m.p. 221-2°C.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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