(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol CAS#: 485-19-8

ChemicalBook > Product Catalog > Natural Products > Alkaloids > (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol

(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol

Basic information Safety Supplier Related

(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol Basic information

Product Name:

(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol

Synonyms:

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

CAS:

485-19-8

MF:

C19H23NO4

MW:

329.39

EINECS:

207-611-3

Product Categories:

Amines
Aromatics
Chiral Reagents
Intermediates & Fine Chemicals
Pharmaceuticals

Mol File:

485-19-8.mol

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(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol Chemical Properties

Melting point:: 125-126°C
Boiling point:: 648.96°C (rough estimate)
Density: 1.4371 (rough estimate)
refractive index: 1.6800 (estimate)
storage temp.: Sealed in dry,2-8°C
solubility: Soluble in DMSO
pka: 9.95±0.10(Predicted)
form: Solid
color: Off-white to yellow
optical activity: +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

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(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

Reticulin 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.

Uses

Precursor of many aporphine and morphine-type alkaloids.

Definition

ChEBI: The (S)-enantiomer of reticuline.

in vivo

Reticuline (5, 10 and 20 mg/kg, i. v., randomly) injections produced an intense hypotension in normotensive rats. The hypotensive effect of Reticuline is probably due to a peripheral vasodilation in consequence of: 1) muscarinic stimulation and NOS activation in the vascular endothelium, 2) voltage-dependent Ca²⁺ channel blockade and/or 3) inhibition of Ca²⁺ release from norepinephrine-sensitive intracellular stores^[2].

IC 50

JAK2; STAT3; NF-κB; Human Endogenous Metabolite

(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-olSupplier

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