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

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

Used in Pharmaceutical Industry:
(S)-Norreticuline is used as a key intermediate in the synthesis of Erythrina alkaloids, which possess a wide range of pharmacological properties, including antitumor, antiviral, and anti-inflammatory activities. Its role in the production of these alkaloids makes it a valuable compound for the development of new drugs and therapies.
Used in Cosmetic Industry:
(S)-Norreticuline is used as a cell proliferation stimulant for promoting hair growth. Its ability to stimulate the proliferation of cultured cells from murine hair makes it a potential ingredient in hair growth promoting products, offering a natural alternative to synthetic compounds.

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 
• 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 
• 1108621-60-8 2-(2-(3-isopropoxy-4-methoxystyryl)-4-isopropoxy-5-methoxyphenyl)ethoxime 
• 1108621-45-9 1-(3-isopropoxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-7-isopropoxy-6-methoxyisoquinoline 
• 133343-26-7 (4R,5R)-4,5-Bis-(3-benzyloxy-4-methoxy-phenyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 133343-22-3 (4R,5R)-4,5-Bis-(3-benzyloxy-4-methoxy-phenyl)-[1,3,2]dioxathiolane 2-oxide 

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 
• 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 
• 18694-10-5 1-(3'-hydroxy-4'-methoxybenzyl)-6,7-dimethoxyisoquinoline 
• 72258-95-8 (+/-)-6'-Bromotetrahydropapaveroline-Hydrogen Bromide 
• 485-19-8 (R)-reticuline 
• 485-19-8 (+)-(S)-reticuline 
• 1699-46-3 reticuline 

Relevant articles and documents

Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products

Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

PHELLODENDRINE ANALOGS AND ALLERGY TYPE IV SUPPRESSOR CONTAINING THE SAME AS ACTIVE INGREDIENT

Phellodendrine analogs represented by general formula (I), wherein A represents the group (a); B represents hydrogen, lower alkyl or lower acyl, or alternatively A and B together with the adjacent nitrogen atom form a substituted 1,2,3,4-tetrahydroisoquinoline ring represented by general formula (II), R11, R12, R21, R22, R31 and R32 represent each hydrogen, hydroxyl or lower alkoxy; n1 represents a number of 0 to 2; n2 represents a number of 1 and 2; and m1 represents a number of 0 to 1, provided tsat when A represents the group (b), and n2 is 2, B is lower acyl, and that when A and B together form a substituted 1,2,3,4-tetrahydroisoquinoline ring, n1 is 1 and m1 is not 0. These analogs (I) and related compounds have an excellent activity of suppressing allergy type IV and hence are utilizable as a medicine efficacious against diseases wherein allergy type IV participates, such as chronic hepatitis, intractable asthma, nephrotic syndrome or rheumatism.

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.