3423-07-2

Basic information

• Product Name: 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol
• Synonyms: (1S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-2-methyl-6-methoxyisoquinolin-7-ol;(1S)-1-[(4-Hydroxyphenyl)methyl]-2-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-ol;(S)-N-Methylcoclaurine;1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol;N-Methylcoclaurine;(1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
• CAS NO: 3423-07-2
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.36424
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3423-07-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 480.9°C at 760 mmHg
• Flash Point: 244.6°C
• Appearance: /
• Density: 1.214g/cm³
• Vapor Pressure: 7.14E-10mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol(3423-07-2)
• EPA Substance Registry System: 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol(3423-07-2)

Safety Data

• Hazardous Substances Data: 3423-07-2(Hazardous Substances Data)

Usage

Description

This alkaloid, obtained from Glaucium fimbrilligerum, belongs to the benzylisoquinoline class of bases. Chemical analysis and degradations show that it contains one methoxyl group and two phenolic hydroxyl groups in the molecule. The full structure given has been determined from spectroscopic studies.

Uses

(+)-S-N-methylcoclaurine is an structure analog of Coclaurine (C633550), a benzyltetrahydroisoquinoline alkaloid extracted from Magnolia salicifolia.

References

Yunusov, Israilov, Khim. Prir. Soedin., 10,538 (1974)

InChI:InChI=1/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m0/s1

Upstream product

• 518-34-3 Tetrandrin 
• 477-57-6 (+)-isotetrandrine 
• 50-00-0 formaldehyd 
• 3422-42-2 (-)-coclaurine hydrochloride 
• 11021-81-1 thalibrunine 
• 866952-11-6 7,12-O,O'-dibenzyl-N-methylcoclaurine 
• 35596-93-1 (+)-di-O-bisbenzyl-N-methylcoclaurine 
• 248279-26-7 O-ethyllongiberine 
• 486-39-5 Coclaurine 
• 248583-77-9 longiberine 
• 248243-55-2 dinorthalidezine acetate 
• 1027417-45-3 C₄₄H₄₂Cl₆N₂O₁₀ 
• 132257-14-8 (+)-OO'-dibenzylcoclaurine hydrochloride 
• 35596-93-1 (±)-7-(benzyloxy)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Longiberine and O-methyllongiberine, dimeric protoberberine-benzyl tetrahydroisoquinoline alkaloids from Thalictrum longistylum

Two benzyltetrahydroisoquinoline - protoberberine dimers, longiberine (1) and O-methyllongiberine (2): were isolated from the roots of Thalictrum longistylum and represent a new class of dimeric alkaloids. The structure of longiberine (1) was established by spectral and chemical methods. Reductive cleavage of O-ethyllongiberine (4) with Na/liquid NH3 yielded (+)-(S)-N- methylcoclaurine (5), which determined one-half of the dimer, and 1D and 2D NMR studies arranged the substituents on the protoberberine nucleus. Chemical conversion of thalidezine (6) to 1 via the O-acetyl N,N-didemethyl derivative 9, which was methylenated in the Mannich reaction and N-methylated by the Eschweiler-Clarke procedure, established the second asymmetric center as S and confirmed the ring size and the order of the substituents for 1. Methylation of 1 with diazomethane formed the O-methyl derivative 2, identical with the natural product.

Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase

Benzylisoquinoline alkaloids (BIAs) are a structurally diverse family of plant secondary metabolites, which have been exploited to develop analgesics, antibiotics, antitumor agents, and other therapeutic agents. Biosynthesis of BIAs proceeds via a common pathway from tyrosine to (S)-reticulene at which point the pathway diverges. Coclaurine N-methyltransferase (CNMT) is a key enzyme in the pathway to (S)-reticulene, installing the N-methyl substituent that is essential for the bioactivity of many BIAs. In this paper, we describe the first crystal structure of CNMT which, along with mutagenesis studies, defines the enzymes active site architecture. The specificity of CNMT was also explored with a range of natural and synthetic substrates as well as co-factor analogues. Knowledge from this study could be used to generate improved CNMT variants required to produce BIAs or synthetic derivatives.

ALKALOIDS OF DEHAASIA TRIANDRA

Separation of the basic fraction from Dehaasia triandra afforded two new bisbenzylisoquinoline alkaloids, dehatridine and dehatrine, along with six known alkaloids, isocorydine, corytuberine, atheroline, nantenine, obaberine and a quaternary aporphine alkaloid, xanthoplanine (5). - Keywords: Dehaasia triandra; Lauraceae; Iau-Guoo-Nan; bisbenzylisoquinoline alkaloids; dehatridine; dehatrine.