(-)-Reticuline
Basic information
- CAS
3968-19-2- Standard SMILES
COc1ccc(C[C@@H]2c3cc(O)c(OC)cc3CCN2C)cc1O- InChIKey
BHLYRWXGMIUIHG-OAHLLOKOSA-N- Molecular formula
- C19H23NO4
- Average molar mass
- 329.4 g/mol
- Monoisotopic mass
- 329.16270821
Overview
(R)-reticuline is a reticuline. It is a conjugate base of a (R)-reticulinium(1+). It is an enantiomer of a (S)-reticuline.
Names & identifiers
- Preferred name
- (-)-Reticuline
- IUPAC
- (1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
- English name
- L-Reticuline
- Molecular formula
- C19H23NO4
- Molecular weight
- 329.39022
Names & synonyms
(R)-Reticuline3968-19-2(-)-reticuline(1R)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-olCHEBI:17428DTXSID80331501(1R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol(1R)-1,2,3,4-Tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-7-isoquinolinol(1R)-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-olRefChem:1049136DTXCID90282595
Show more names
(R)-Reticuline (>(R)-Reticuline (>80% ee)7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-, (1R)-
L-ReticulineR-RETICULINE(R)-(-)-reticuline(R)-Reticuline (>80% ee)A1A4H(1R)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-Isoquinolinol; (-)-Reticuline; (R)-(-)-Reticuline; L-Reticuline;(R)-N-methylnorreticulineCHEMBL401501
Database identifiers
- CAS
3968-19-2- PubChem CID
- 440586
- DTXSID
DTXSID80331501- ChEMBL
CHEMBL401501- ChEBI
CHEBI:17428- Nikkaji
- J471.974C
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 62.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 407
Physicochemical properties
- Melting point
- 200 °C · >200°C (dec.)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- color
- Pale Yellow to Yellow to Orange
Chemistry & industry
Applications
Uses(R)-Reticuline is the (R)-enantiomer of Reticuline, a tetrahydrobenzylisoquinoline alkaloid found in opium. (R)-Reticuline is converted into Salutaridine by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum
Additional notes
DefinitionChEBI: (R)-reticuline is a reticuline. It is a conjugate base of a (R)-reticulinium(1+). It is an enantiomer of a (S)-reticuline.
Related reactions
0 records
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Compound notes
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