1-((3-Hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

HCID 10233

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Basic information

CAS: 485-19-8
Standard SMILES: COc1ccc(CC2c3cc(O)c(OC)cc3CCN2C)cc1O
InChIKey: BHLYRWXGMIUIHG-UHFFFAOYSA-N
Molecular formula: C19H23NO4
Average molar mass: 329.4 g/mol
Monoisotopic mass: 329.16270821

Names & identifiers

Preferred name: 1-((3-Hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
IUPAC: 1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
English name: (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol
Molecular formula: C19H23NO4
Molecular weight: 329.39

Names & synonyms

1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol1-((3-Hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-olRefChem:1053640DTXCID80810846DTXSID108620101699-46-3S-RETICULINE(RS)-Reticuline( inverted exclamation markA)-Reticuline1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-olDL-Reticuline(+/-)-Reticuline

Show more names

reticuline(S)-ReticulineReticuline (>90% ee)(S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol(1S)-1-[(3-hydroxy-4-methoxy-phenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol2-Methoxy-5-[[(1S)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline]-1-ylmethyl]phenol[1S,(+)]-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-, (1S)-[1S,(+)]-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinoline-7-ol

Compound NP-025371SCHEMBL147596orb1941190AKOS030627825EBC-611262FR763291-[(3-hydroxy-4-methoxy-phenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-olHY-135489

Database identifiers

CAS: 485-19-8
PubChem CID: 10233
ChEBI: CHEBI:26533
Nikkaji: J3.030.943J

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 62.2 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 4
Heavy atoms: 24
Formal charge: 0
Complexity: 407

Physicochemical properties

Melting point: 125 · 125-126°C
Boiling point: 648.96 °C · 648.96°C (rough estimate)
Density: 1.4371 · 1.4371 (rough estimate)
refractive index: 1.68 · 1.6800 (estimate)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Soluble in DMSO
pka: 9.95 · 9.95±0.10(Predicted)
form: Solid
color: Off-white to yellow
optical activity: 88.318 · +88.318 (c 0.21, ethanol)
InChI: InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
InChIKey: BHLYRWXGMIUIHG-HNNXBMFYSA-N
SMILES: [C@H]1(CC2=CC=C(OC)C(O)=C2)C2=C(C=C(OC)C(O)=C2)CCN1C
FDA UNII: 35 Z551WT4 · X35Z551WT4
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301+H311+H331-H315-H319
Precautionary statements: 501 · P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405

Safety & regulation

Safety data

Signal word: Danger
Symbol(GHS): GHS06
Hazard statements: H301+H311+H331-H315-H319
Precautionary statements: P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405

Chemistry & industry

Applications

UsesReticulin can be used to improve production of morphinan alkaloids, as well as its anti-inflammatory properties. It can also be used to lead scaffolds as PDE5A inhibitors and antihypertensives.

UsesPrecursor of many aporphine and morphine-type alkaloids.