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

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

Uses

1. Used in Pharmaceutical Applications:
1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol is used as a pharmaceutical compound for its potential therapeutic properties. As a benzylisoquinoline alkaloid, it may exhibit various biological activities that can be harnessed for the development of new drugs.
2. Used in Research and Development:
In the field of research, 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol serves as a valuable compound for studying the structure-activity relationships of benzylisoquinoline alkaloids. This can lead to the discovery of new bioactive molecules with potential applications in medicine.
3. Used in Natural Product Chemistry:
In the study of natural products, 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol is used as a reference compound for comparing the chemical properties and biological activities of other related alkaloids found in plants.
4. Used in Drug Synthesis:
1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol can be used as a starting material or intermediate in the synthesis of more complex alkaloids or other bioactive compounds with potential pharmaceutical applications.
5. Used in Drug Delivery Systems:
Similar to gallotannin, 1α-(4-Hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6-methoxyisoquinoline-7-ol may also benefit from novel drug delivery systems to enhance its bioavailability and therapeutic outcomes. Researchers can explore the use of various organic and metallic nanoparticles as carriers for this alkaloid, aiming to improve its delivery and efficacy in targeted applications.

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 
• 486-39-5 Coclaurine 
• 14031-35-7 S-Adenosyl-L-methionine 
• 485-80-3 S-adenosyl-L-methionine 
• 132257-14-8 (+)-OO'-dibenzylcoclaurine hydrochloride 
• 1027417-45-3 C₄₄H₄₂Cl₆N₂O₁₀ 
• 248243-55-2 dinorthalidezine acetate 
• 248583-77-9 longiberine 
• 248279-26-7 O-ethyllongiberine 
• 11021-81-1 thalibrunine 
• 3422-42-2 (-)-coclaurine hydrochloride 
• 35596-93-1 (+)-di-O-bisbenzyl-N-methylcoclaurine 

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.

Isolation and characterization of two O-methyltransferases involved in benzylisoquinoline alkaloid biosynthesis in sacred lotus (Nelumbo nucifera)

Benzylisoquinoline alkaloids (BIAs) are a major class of plant metabolites with many pharmacological benefits. Sacred lotus (Nelumbo nucifera) is an ancient aquatic plant of medicinal value because of antiviral and immunomodulatory activities linked to its constituent BIAs. Although more than 30 BIAs belonging to the 1-benzylisoquinoline, aporphine, and bisbenzylisoquinoline structural subclasses and displaying a predominant R-enantiomeric conformation have been isolated from N. nucifera, its BIA biosynthetic genes and enzymes remain unknown. Herein, we report the isolation and biochemical characterization of two O-methyltransferases (OMTs) involved in BIA biosynthesis in sacred lotus. Five homologous genes, designated NnOMT1-5 and encoding polypeptides sharing >40% amino acid sequence identity, were expressed in Escherichia coli. Functional characterization of the purified recombinant proteins revealed that NnOMT1 is a regiospecific 1-benzylisoquinoline 6-O-methyltransferase (6OMT) accepting both Rand S-substrates, whereas NnOMT5 is mainly a 7-O-methyltransferase (7OMT), with relatively minor 6OMT activity and a strong stereospecific preference for S-enantiomers. Available aporphines were not accepted as substrates by either enzyme, suggesting that O-methylation precedes BIA formation from 1-benzylisoquinoline intermediates. Km values for NnOMT1 and NnOMT5 were 20 and 13 μM for (R,S)-norcoclaurine and (S)-N-methylcoclaurine, respectively, similar to those forOMTs from other BIA-producing plants. Organ-based correlations of alkaloid content,OMTactivity in crude extracts, andOMTgene expression supported physiological roles for NnOMT1 and NnOMT5 in BIA metabolism, occurring primarily in young leaves and embryos of sacred lotus. In summary, our work identifies two OMTs involved in BIA metabolism in the medicinal plant N. nucifera.

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.

Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors

Effects of derivatives of coclaurine (C), which mimic the 'eastern' or the nonquaternary halves of the alkaloids tetrandrine or d-tubocurarine, respectively, both of which are inhibitors of nicotinic acetylcholine receptors (nACh), were examined on recomb

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.

THE BIOSYNTHESIS OF THE ALKALOIDS OF CISSAMPELOS PAREIRA LINN

Tracer experimets show that the bisbenzylisoqunoline alkaloid,(S,R)-hayatidin (10) is stereospecifically biosynthesized in young Cissampelos pareira Linn plants by intermolecular oxidativ coupling of (S)-(5)-and (R)-(3)-N-methylcoclaurines whereas (R,R)-isochondrodendrine (14) and (R,R)-bebeerine (12) are formed in the plants by oxidative dimerization of (R)-N-methyl-coclaurine (3).

Absolute Configuration and Biosynthesis of Tiliacorine and Tiliacorinine

The incorporation of (+/-)-coclaurine, (+/-)-norcoclaurine, (+/-)-N-methylcoclaurine, and didehydro-N-methylcoclaurinium iodide into tiliacorinine and tiliacorine in Tiliacora racemosa Colebr. has been studied, and specific utilization of the (+/-)-N-meth

THE BIOSYNTHESIS OF THE ALKALOIDS OF CROTON SPARSIFLORUS MORONG

Incorporation of tyrosine, dopa, dopamine, 4-hydroxyphenylpyruvic acid, (+/-)-, norcoclaurine-1-carboxylic acid, -norcoclaurine, -coclaurine, and -N-methylcoclaurine into N-methylcrotsparine, N-methylcrotsparinine and N-methylsparsiflorine in Croton sparsiflorus Morong has been studied.The evidence supports the direct oxidative coupling of (+)-, and (-)-N-methylcoclaurines to give N-methylcrotsparine and N-methylcrotsparinine, respectively.Tracer experiment show that N-methylcrotsparine undergoes dienone-phenol rearrangement to give N-methylsparsiflorine.A doublelabelling experiment with (+/-)-Nmethylcoclaurine demonstrated that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion.The intermediacy of norcoclaurine-1-carboxylic acid and specific incorporation of dehydro-N-methylcoclaurinium salt into the bases have been demonstrated.

The Structure of Thalibrunine, a Reinvestigation and Revision

Evidence is presented that thalibrunine has structure 2 and is the 2'-hydroxy derivative of hernandezine.Ceric ammonium nitrate oxidation of thalibrunine acetate (3) gave 2-methoxy-4-acetoxy-4',5-diformyldiphenyl ether (6), which was also prepared synthet