522-99-6

Basic information

• Product Name: 1'-Isoemetine
• CAS NO: 522-99-6
• Molecular Formula: C₂₉H₄₀N₂O₄
• Molecular Weight: 480.648
• Mol File: 522-99-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 600.3°Cat760mmHg
• Flash Point: 316.9°C
• Density: 1.17g/cm³
• CAS DataBase Reference: 1'-Isoemetine(CAS DataBase Reference)
• NIST Chemistry Reference: 1'-Isoemetine(522-99-6)
• EPA Substance Registry System: 1'-Isoemetine(522-99-6)

Safety Data

• Hazardous Substances Data: 522-99-6(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 29700-91-2 <2S-<2α(S^*),3β,11β>>-3-ethyl-1,3,4,6,7,11b-hexahydro-10-hydroxy-2-(6-benzyloxy-7-methoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methyl-9-methoxy-2H-benzoquinolizine 
• 549-91-7 (-)-Protoemetine 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 
• 1357385-49-9 (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-3-vinyl-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline 
• 1357385-48-8 {(2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl}methanol 
• 1357385-46-6 methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 7344-78-7 (-)-protoemetinol 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 483-17-0 cephaeline 
• 14031-35-7 S-Adenosyl-L-methionine 
• 40752-81-6 rac-10,11,6',7'-tetramethoxy-emet-1'-ene 
• 6110-83-4 (+/-)-(3c-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2t-yl)-acetic acid-(3,4-dimethoxy-phenethylamide) 

Downstream Products

• 90-05-1 2-methoxy-phenol 
• 75-50-3 trimethylamine 
• 124600-15-3 2'-Benzoyl-10,11,6',7'-tetramethoxy-emetan 
• 106066-83-5 rac-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide 
• 483-18-1 emetine 
• 4764-20-9 4,5-dimethoxyphthalimide 
• 577-68-4 m-hemipinic acid 
• 106066-83-5 ent-10,11,6',7'-tetramethoxy-emetan-2'-carboxylic acid anilide 
• 1609-47-8 diethyl dicarbonate 
• 105-58-8 Diethyl carbonate 
• 483-19-2 emetine 
• 4594-02-9 nigellimine 

Relevant articles and documents

A Cyclopeptide and a Tetrahydroisoquinoline Alkaloid from Ophiorrhiza nutans

A new cyclopeptide, ophiorrhisine A (1), a new tetrahydroisoquinoline alkaloid, 7′,10-dide-O-methylcephaeline (2), two known β-carboline alkaloids, and four known tetrahydroisoquinoline alkaloids were isolated from Ophiorrhiza nutans (Rubiaceae). Compound 1 is a tetrapeptide possessing a 14-membered paracyclophane ring and a novel N,N,N-trimethyltyrosine residue in the side chain. The stereochemistry at the aryl-alkyl ether bond was different from that of other known 14-membered paracyclophanes. The structure of 2 was established by spectroscopic analysis and semisynthesis.

Molecular cloning of an O-methyltransferase from adventitious roots of carapichea ipecacuanha

Carapichea ipecacuanha produces various emetinetype alkaloids, known as ipecac alkaloids, which have long been used as expectorants, emetics, and amebicides. In this study, we isolated an O-methyltransferase cDNA from this medicinal plant. The encoded protein (CiOMT1) showed 98% sequence identity to IpeOMT2, which catalyzes the 7′-O-methylation of 7′-O- demethylcephaeline to form cephaeline at the penultimate step of emetine biosynthesis (Nomura and Kutchan, J. Biol. Chem., 285, 7722-7738 (2010)). Recombinant CiOMT1 showed both 7′-O-methylation and 6′-O-methylation activities at the last two steps of emetine biosynthesis. This indicates that small differences in amino acid residues are responsible for distinct regional methylation specificities between IpeOMT2 and CiOMT1, and that CiOMT1 might contribute to two sequential O-methylation steps from 7′-O- demethylcephaeline to emetine.

Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step

Catalytic asymmetric allylation of 3,4-dihydro-6,7-dimethoxyisoquinoline was carried out using allyltrimethoxysilane in the presence of Cu(I) and tol-BINAP. The allyl adduct thus obtained was transformed to a chiral synthetic intermediate for (-)-emetine in good yield. The procedure was applied to the total synthesis of ent-emetine.