13168-51-9

Basic information

• Product Name: norreticuline
• Synonyms: norreticuline;1-(3-Hydroxy-4-methoxybenzyl)-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline;1-(3-Hydroxy-4-methoxybenzyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline;1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-7-isoquinolinol;7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-Methoxyphenyl)Methyl]-6-Methoxy-
• CAS NO: 13168-51-9
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36
• Mol File: 13168-51-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 519.5°C at 760 mmHg
• Flash Point: 268°C
• Appearance: /
• Density: 1.234g/cm³
• Vapor Pressure: 2.06E-11mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: norreticuline(CAS DataBase Reference)
• NIST Chemistry Reference: norreticuline(13168-51-9)
• EPA Substance Registry System: norreticuline(13168-51-9)

Safety Data

• Hazardous Substances Data: 13168-51-9(Hazardous Substances Data)

Usage

Uses

Reticuline (R188500) analog. (S)-Norreticuline is the precursor for the biosynthesis of Erythrina alkaloids. (S)-Norreticuline and (S)-reticuline stimulated the proliferation of cultured cells from murine hair.

InChI:InChI=1/C18H21NO4/c1-22-17-4-3-11(8-15(17)20)7-14-13-10-16(21)18(23-2)9-12(13)5-6-19-14/h3-4,8-10,14,19-21H,5-7H2,1-2H3

Upstream product

• 1131-94-8 homoisovanillic acid 
• 57231-35-3 4',6-O,O-dimethylpapaveroline 
• 169834-50-8 N-benzyl-(N-nor)-reticuline 
• 135574-24-2 Benzoic acid (R)-((S)-2-benzoyl-7-benzyloxy-6-methoxy-1,2-dihydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester 
• 4781-58-2 (-)-Norreticuline 
• 1108621-53-9 4-isopropoxy-2-[2-(3-isopropoxy-4-methoxyphenyl)ethynyl]-5-methoxybenzaldehyde 
• 215715-43-8 β,β-dibromo-3-isopropoxy-4-methoxystyrene 
• 439585-86-1 4-ethynyl-2-isopropoxy-1-methoxybenzene 
• 56517-33-0 4-isopropoxy-2-bromo-5-methoxybenzaldehyde 
• 34123-66-5 O-isopropylisovanillin 
• 2538-98-9 4-isopropyloxy-3-methoxybenzaldehyde 
• 1108621-39-1 1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline-N-(2-methylallyloxide) 
• 1108621-37-9 (Z)-2-[2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxy-2-methylprop-2-en-1-amine 
• 1108621-35-7 (Z)-2-[-2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl]-N-hydroxyethanamine 

Downstream Products

• 81038-53-1 6'-Chloro-N-norreticuline 
• 58116-06-6 (+/-)-6'-Bromo-N-norreticuline 
• 94617-77-3 1-(3-Hydroxy-4-methoxybenzyl)-7-hydroxy-6-methoxy-3,4-dihydroisoquinoline N-oxide 
• 16659-88-4 (+/-)-Tetrahydropapaveroline hydrobromide 
• 56435-41-7 yenhusomine 
• 32728-75-9 cavidine 
• 524-46-9 (+)-adlumine 
• 72258-95-8 (+/-)-6'-Bromotetrahydropapaveroline-Hydrogen Bromide 
• 485-19-8 (R)-reticuline 
• 485-19-8 (+)-(S)-reticuline 
• 18694-10-5 1-(3'-hydroxy-4'-methoxybenzyl)-6,7-dimethoxyisoquinoline 
• 1699-46-3 reticuline 
• 88780-63-6 7-(tert-Butyl-dimethyl-silanyloxy)-1-(3-hydroxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 88780-62-5 7-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-benzyl]-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 

Relevant articles and documents

Aromatization of 1-benzyltetrahydroisoquinolines: Racemization of (-)-(S)-(N-nor)-reticuline

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The tandem cope-type hydroamination/[2,3]-rearrangement sequence: A strategy to favor the formation of intermolecular hydroamination products and enable difficult cyclizations

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Short-cut in the pomeranz-fritsch synthesis of 1-benzyl-isoquinolines; short and efficient syntheses of norrecticuline derivatives and of papaverine

A new methodology for the Pomeranz-Fritsch synthesis of 1-benzyl-1,2-dihydroisoquinolines avoiding pavine or isopavine troubles, has been developed. These intermediates could be reduced to their 1,2,3,4-tetrahydro congeners or aromatized to give isoquinolines, as it was demonstrated by the synthesis of some norrecticuline derivatives 4-7 and of papaverin 8.