1699-46-3

Basic information

• Product Name: (S)-Reticuline
• Synonyms: (S)-Reticuline 7-Isoquinolinol,1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl- (Related Reference);(RS)-Reticuline;1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol;(1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
• CAS NO: 1699-46-3
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.39
• Mol File: 1699-46-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 144 °C
• Boiling Point: 504.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.217±0.06 g/cm3(Predicted)
• PKA: 9.95±0.10(Predicted)
• CAS DataBase Reference: (S)-Reticuline(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Reticuline(1699-46-3)
• EPA Substance Registry System: (S)-Reticuline(1699-46-3)

Safety Data

• Hazardous Substances Data: 1699-46-3(Hazardous Substances Data)

Usage

General Description

(S)-Reticuline is a natural chemical compound found in various plants, including the opium poppy, and is involved in the biosynthesis of numerous alkaloids. It is a precursor for the synthesis of a variety of important natural products, such as morphine, codeine, and sanguinarine. (S)-Reticuline has also been identified as a key intermediate in the biosynthetic pathways for benzylisoquinoline alkaloids, which are compounds with diverse biological activities and pharmaceutical potential. Research on (S)-Reticuline continues to uncover its potential applications in medicine and drug development, making it an important target for biotechnological and synthetic efforts.

Upstream product

• 82841-66-5 1-(3-Hydroxy-4-methoxy-benzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline-4,7-diol 
• 13168-51-9 N-benzoyl-norreticuline 
• 1699-38-3 3-benzyloxy-4-methoxy-benzyl chloride 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 94707-57-0 N-<1,2-bis<3-(benzyloxy)-4-methoxyphenyl>ethyl>-N-methylamine 
• 94707-56-9 N-methyl-3-(benzyloxy)-4-methoxybenzaldimine 
• 72258-92-5 (+/-)-N-Formyl-N-norreticuline 
• 70614-67-4 1-(3-benzyloxy-4-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 50-00-0 formaldehyd 
• 1699-46-3 reticuline 
• 121-33-5 vanillin 
• 38171-33-4 2-(4-(benzyloxy)-3-methoxyphenyl)-N-methylethanamine 
• 1700-33-0 N-ethoxycarbonyl-4-benzyloxy-3-methoxyphenethylamine 
• 54313-33-6 2-(3-(benzyloxy)-4-methoxyphenyl)acetyl chloride 

Downstream Products

• 621-59-0 isovanillin 
• 72142-82-6 1,2-didehydrocoripallinium ion 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 16202-17-8 1,2-dehydroreticuline 
• 1049036-81-8 Salutaridin 
• 5164-93-2 isoboldine 
• 59419-31-7 (+/-)-<2',6',8-3H3>reticuline 
• 71610-34-9 (+/-)-reticuline N-oxide 
• 56435-41-7 yenhusomine 
• 32728-75-9 cavidine 
• 524-46-9 (+)-adlumine 
• 485-19-8 (R)-reticuline 
• 605-34-5 (S)-scoulerine 
• 483-45-4 S-(-)-coreximine 

Relevant articles and documents

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Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

Deracemisation of benzylisoquinoline alkaloids employing monoamine oxidase variants

Chemo-enzymatic deracemisation was applied to obtain the (S)-enantiomer of 1-benzylisoquinolines from the racemate in high isolated yield (up to 85%) and excellent optical purity (ee > 97%). The one-pot deracemisation protocol encompassed enantioselective oxidation by a monoamine oxidase (MAO-N) and concomitant reduction of the resulting iminium species by ammonia-borane. The challenge was the oxidation at the sterically demanding chiral centre. Recently developed variants of MAO-N, featuring an enlarged active-site pocket, turned out to be suitable biocatalysts for these substrates. In contrast to previous MAO-N variants, which preferentially converted the (S)-enantiomer, the MAO-N variant D11 used in the present study was found to oxidise all tested benzylisoquinoline substrates with (R)-enantiopreference. The structural determinants of enantioselectivity were investigated by means of protein-ligand docking simulations. The applicability of the deracemisation system was demonstrated on preparative scale (150 mg) for three benzylisoquinoline alkaloids (natural as well as non-natural), including the hypotensive and antispasmodic agent (S)-reticuline.